diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/DesktopArrivalDetectorTests.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/DesktopArrivalDetectorTests.cs
new file mode 100644
index 00000000..6d94477e
--- /dev/null
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/DesktopArrivalDetectorTests.cs
@@ -0,0 +1,178 @@
+#nullable enable
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring
+{
+    /// <summary>
+    /// Unit tests for <see cref="DesktopArrivalDetector.IsExcludedUser"/>. Hybrid-User-Driven
+    /// session diagnosis (e58bcfdb-…, 2026-05-01) showed the detector treated the fooUser
+    /// OOBE shell as a real user desktop, firing DesktopArrived 6 s after agent start —
+    /// before the Hybrid reboot to the AD account ever happened. The exclusion now covers
+    /// the foouser@/autopilot@ Autopilot provisioning placeholders in both UPN and
+    /// DOMAIN\User shapes.
+    /// </summary>
+    public sealed class DesktopArrivalDetectorTests
+    {
+        // ---------------- Existing exclusions stay covered ----------------
+
+        [Theory]
+        [InlineData("SYSTEM")]
+        [InlineData("system")]
+        [InlineData("LOCAL SERVICE")]
+        [InlineData("NETWORK SERVICE")]
+        [InlineData("DefaultUser0")]
+        [InlineData("DefaultUser1")]
+        [InlineData("defaultuser0")]
+        [InlineData("DefaultUser42")]
+        public void System_and_default_users_are_excluded(string user)
+        {
+            Assert.True(DesktopArrivalDetector.IsExcludedUser(user));
+        }
+
+        [Theory]
+        [InlineData("NT AUTHORITY\\SYSTEM")]
+        [InlineData("WORKGROUP\\DefaultUser0")]
+        [InlineData("CONTOSO\\DefaultUser1")]
+        public void Domain_qualified_system_users_are_excluded(string user)
+        {
+            Assert.True(DesktopArrivalDetector.IsExcludedUser(user));
+        }
+
+        // ---------------- Real users are NOT excluded ----------------
+
+        [Theory]
+        [InlineData("alice")]
+        [InlineData("CONTOSO\\alice")]
+        [InlineData("alice@contoso.com")]
+        [InlineData("bob.smith@fabrikam.com")]
+        // Codex review 2026-05-01 (Finding 3): the bare-username matcher was tightened
+        // from prefix-match to exact-match, so the following real account shapes that
+        // *start with* "autopilot" or "foouser" must now stay through the gate. Reused
+        // by UserProfileResolver — incorrectly excluding these would resolve the wrong
+        // home directory.
+        [InlineData("CONTOSO\\autopilotadmin")]
+        [InlineData("CONTOSO\\autopilot.admin")]
+        [InlineData("FABRIKAM\\foouserservice")]
+        [InlineData("autopilotadmin")]
+        [InlineData("foouserservice")]
+        public void Real_users_are_not_excluded(string user)
+        {
+            Assert.False(DesktopArrivalDetector.IsExcludedUser(user));
+        }
+
+        // ---------------- New: Autopilot placeholder UPN form ----------------
+
+        [Theory]
+        [InlineData("foouser@fabrikam.onmicrosoft.com")]
+        [InlineData("FooUser@fabrikam.onmicrosoft.com")]
+        [InlineData("FOOUSER@example.com")]
+        [InlineData("autopilot@contoso.com")]
+        [InlineData("Autopilot@contoso.com")]
+        [InlineData("AUTOPILOT@contoso.com")]
+        public void Autopilot_placeholder_upn_is_excluded(string upn)
+        {
+            // Hybrid User-Driven OOBE shell runs explorer.exe under foouser@<tenant>;
+            // matching this prevents premature DesktopArrived firing on the foo desktop.
+            // UPN form is delegated to AadJoinInfo.IsPlaceholderUserEmail (prefix-match
+            // on the local-part, so any tenant domain works).
+            Assert.True(DesktopArrivalDetector.IsExcludedUser(upn));
+        }
+
+        // ---------------- New: Domain-qualified placeholder (exact bare-name match) ----------------
+
+        [Theory]
+        [InlineData("AzureAD\\foouser")]
+        [InlineData("WORKGROUP\\autopilot")]
+        [InlineData("AzureAD\\FooUser")]    // case-insensitive
+        [InlineData("AzureAD\\AUTOPILOT")]  // case-insensitive
+        [InlineData("foouser")]             // bare username (no domain prefix)
+        [InlineData("autopilot")]           // bare username (no domain prefix)
+        public void Domain_qualified_placeholder_is_excluded(string user)
+        {
+            // WMI Win32_Process.GetOwner sometimes returns DOMAIN\foouser instead of the
+            // UPN form. The bare-username match is now EXACT (Finding 3) — no prefix.
+            Assert.True(DesktopArrivalDetector.IsExcludedUser(user));
+        }
+
+        // ---------------- Edge cases ----------------
+
+        [Theory]
+        [InlineData(null)]
+        [InlineData("")]
+        public void Null_or_empty_is_excluded(string? user)
+        {
+            Assert.True(DesktopArrivalDetector.IsExcludedUser(user!));
+        }
+
+        [Fact]
+        public void Real_user_email_with_foouser_substring_is_NOT_excluded()
+        {
+            // Defense against false positives — UPN match goes through
+            // AadJoinInfo.IsPlaceholderUserEmail which anchors the local-part at start.
+            // "realfoouser@…" and "not-autopilot@…" must NOT trigger.
+            Assert.False(DesktopArrivalDetector.IsExcludedUser("realfoouser@contoso.com"));
+            Assert.False(DesktopArrivalDetector.IsExcludedUser("not-autopilot@contoso.com"));
+        }
+
+        [Fact]
+        public void Real_user_with_default_substring_anywhere_is_NOT_excluded()
+        {
+            Assert.False(DesktopArrivalDetector.IsExcludedUser("MyDefaultUser"));
+            // "DefaultUser" prefix-match: this WOULD trigger because the bare-username
+            // DefaultUser* code path is still prefix-based (Windows generates
+            // DefaultUser0/1/2/...). Documenting current behavior.
+            Assert.True(DesktopArrivalDetector.IsExcludedUser("DefaultUserBob"));
+        }
+
+        // ============================================================================
+        // ResetForRealUserSwitch (Pkt 5 — placeholder→real-user transition)
+        // ============================================================================
+
+        [Fact]
+        public void ResetForRealUserSwitch_does_not_throw_when_detector_is_stopped()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+            using var detector = new DesktopArrivalDetector(logger);
+
+            // Detector has not been Started — Reset must be safe regardless. The Hybrid
+            // reset path may fire before any explicit Start in test fixtures, and we
+            // never want host-wiring to crash the agent.
+            detector.ResetForRealUserSwitch();
+        }
+
+        [Fact]
+        public void ResetForRealUserSwitch_is_idempotent()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+            using var detector = new DesktopArrivalDetector(logger);
+
+            // Calling reset multiple times back-to-back must not leak timer instances or
+            // throw. The composition root currently invokes it once per real-user join,
+            // but the contract is still safe-to-repeat.
+            detector.ResetForRealUserSwitch();
+            detector.ResetForRealUserSwitch();
+            detector.ResetForRealUserSwitch();
+        }
+
+        [Fact]
+        public void ResetForRealUserSwitch_after_Stop_restarts_polling_path()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+            using var detector = new DesktopArrivalDetector(logger);
+
+            detector.Start();
+            detector.Stop();
+
+            // After Stop the polling timer is null. Reset must reinstate it without
+            // requiring a fresh Start call (the Hybrid reboot transition shouldn't have
+            // to rebuild the host).
+            detector.ResetForRealUserSwitch();
+        }
+    }
+}
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/HybridLoginPendingDetectorTests.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/HybridLoginPendingDetectorTests.cs
new file mode 100644
index 00000000..5ea0dfc1
--- /dev/null
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/HybridLoginPendingDetectorTests.cs
@@ -0,0 +1,253 @@
+#nullable enable
+using System;
+using System.Linq;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
+using AutopilotMonitor.Agent.V2.Core.Orchestration;
+using AutopilotMonitor.Agent.V2.Core.SignalAdapters;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Agent.V2.Core.Tests.Orchestration;
+using AutopilotMonitor.DecisionCore.Engine;
+using AutopilotMonitor.DecisionCore.Signals;
+using SharedEventTypes = AutopilotMonitor.Shared.Constants.EventTypes;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring
+{
+    /// <summary>
+    /// Tests for the single-shot Hybrid User-Driven login-pending detector. Single-shot
+    /// semantics, conditional emission, and cancel-on-real-user are the contracts that
+    /// matter — the detector exists explicitly to NOT add periodicity / timer sprawl.
+    /// </summary>
+    public sealed class HybridLoginPendingDetectorTests
+    {
+        private static readonly DateTime Fixed = new DateTime(2026, 5, 1, 14, 11, 0, DateTimeKind.Utc);
+
+        private sealed class Fixture : IDisposable
+        {
+            public TempDirectory Tmp { get; } = new TempDirectory();
+            public AgentLogger Logger { get; }
+            public AadJoinWatcher Watcher { get; }
+            public FakeSignalIngressSink Ingress { get; } = new FakeSignalIngressSink();
+            public VirtualClock Clock { get; } = new VirtualClock(Fixed);
+            public InformationalEventPost Post { get; }
+            // Adapter wires the watcher's AadUserJoined into a real AadUserJoinedLate signal —
+            // tests need it so TriggerFromTest("...") fires the watcher event the detector
+            // is subscribed to.
+            public AadJoinWatcherAdapter Adapter { get; }
+
+            public Fixture()
+            {
+                Logger = new AgentLogger(Tmp.Path, AgentLogLevel.Info);
+                Watcher = new AadJoinWatcher(Logger);
+                Post = new InformationalEventPost(Ingress, Clock);
+                Adapter = new AadJoinWatcherAdapter(Watcher, Ingress, Clock);
+            }
+
+            public void Dispose()
+            {
+                Adapter.Dispose();
+                Watcher.Dispose();
+                Tmp.Dispose();
+            }
+        }
+
+        private static FakeSignalIngressSink.PostedSignal? FindHybridLoginPending(FakeSignalIngressSink ingress) =>
+            ingress.Posted.FirstOrDefault(p =>
+                p.Kind == DecisionSignalKind.InformationalEvent
+                && p.Payload != null
+                && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var et)
+                && et == SharedEventTypes.HybridLoginPending);
+
+        // ============================================================================
+        // Single-shot emission path
+        // ============================================================================
+
+        [Fact]
+        public void Arm_then_TriggerFromTest_emits_hybrid_login_pending_with_warning_severity()
+        {
+            using var f = new Fixture();
+            using var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger, TimeSpan.FromMinutes(10));
+
+            detector.Arm();
+            detector.TriggerFromTest();
+
+            var info = FindHybridLoginPending(f.Ingress);
+            Assert.NotNull(info);
+            Assert.Equal("HybridLoginPendingDetector", info!.Payload![SignalPayloadKeys.Source]);
+            Assert.Equal("Warning", info.Payload[SignalPayloadKeys.Severity]);
+            Assert.Equal("true", info.Payload[SignalPayloadKeys.ImmediateUpload]);
+            Assert.Equal("10", info.Payload["delayMinutes"]);
+            Assert.Equal("timer_fired", info.Payload["reason"]);
+            Assert.Equal("true", info.Payload["isHybridJoin"]);
+            Assert.True(detector.HasFiredForTest);
+        }
+
+        [Fact]
+        public void TriggerFromTest_without_Arm_emits_nothing()
+        {
+            // Codex review 2026-05-01: contract tightened — emission requires a deliberate
+            // Arm(). The earlier behavior (emit-regardless) had a misleading test name and
+            // a fragile contract; production was safe only because Arm() was the sole timer
+            // creator. Now the guard is explicit so any future code path that bypasses Arm()
+            // can't silently produce a hybrid_login_pending event.
+            using var f = new Fixture();
+            using var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger);
+
+            detector.TriggerFromTest();
+
+            Assert.Null(FindHybridLoginPending(f.Ingress));
+            Assert.False(detector.HasFiredForTest);
+        }
+
+        [Fact]
+        public void Arm_is_idempotent()
+        {
+            using var f = new Fixture();
+            using var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger);
+
+            detector.Arm();
+            detector.Arm();
+            detector.Arm();
+
+            // No hybrid_login_pending fires from arming alone — arming just starts a timer.
+            Assert.Null(FindHybridLoginPending(f.Ingress));
+            Assert.True(detector.IsArmedForTest);
+        }
+
+        [Fact]
+        public void Multiple_TriggerFromTest_calls_emit_only_once()
+        {
+            using var f = new Fixture();
+            using var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger);
+
+            detector.Arm();
+            detector.TriggerFromTest();
+            detector.TriggerFromTest();
+            detector.TriggerFromTest();
+
+            // Single-shot — exactly one informational event regardless of how many times
+            // the timer logic is re-entered.
+            var matches = f.Ingress.Posted.Where(p =>
+                p.Kind == DecisionSignalKind.InformationalEvent
+                && p.Payload != null
+                && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var et)
+                && et == SharedEventTypes.HybridLoginPending).ToList();
+            Assert.Single(matches);
+        }
+
+        // ============================================================================
+        // Cancel-on-real-user path
+        // ============================================================================
+
+        [Fact]
+        public void RealUserJoined_before_TriggerFromTest_cancels_emission()
+        {
+            using var f = new Fixture();
+            using var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger);
+
+            detector.Arm();
+            detector.TriggerRealUserJoinedFromTest();
+            detector.TriggerFromTest();
+
+            Assert.True(detector.IsCancelledByRealUserForTest);
+            Assert.False(detector.HasFiredForTest);
+            Assert.Null(FindHybridLoginPending(f.Ingress));
+        }
+
+        [Fact]
+        public void RealUserJoined_before_Arm_short_circuits_Arm()
+        {
+            // The watcher could in principle see a real user before Arm() is called
+            // (composition-time race). The detector subscribes in its constructor so the
+            // _cancelledByRealUser flag is set early and Arm() respects it.
+            using var f = new Fixture();
+            using var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger);
+
+            detector.TriggerRealUserJoinedFromTest();
+            detector.Arm();
+            detector.TriggerFromTest();
+
+            Assert.True(detector.IsCancelledByRealUserForTest);
+            Assert.False(detector.IsArmedForTest);
+            Assert.False(detector.HasFiredForTest);
+            Assert.Null(FindHybridLoginPending(f.Ingress));
+        }
+
+        [Fact]
+        public void Placeholder_user_does_not_cancel_emission()
+        {
+            // Placeholder is the EXPECTED state at the time the detector arms — only the
+            // appearance of a REAL AAD user (not foouser/autopilot) should cancel.
+            // The detector subscribes to AadUserJoined (the real-user event) only — the
+            // placeholder pathway never fires that event, so we don't need to simulate it
+            // here; just verifying the timer fires through unchanged.
+            using var f = new Fixture();
+            using var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger);
+
+            detector.Arm();
+            // No TriggerRealUserJoinedFromTest() — only a placeholder appeared in JoinInfo.
+            detector.TriggerFromTest();
+
+            Assert.False(detector.IsCancelledByRealUserForTest);
+            Assert.True(detector.HasFiredForTest);
+            Assert.NotNull(FindHybridLoginPending(f.Ingress));
+        }
+
+        // ============================================================================
+        // Lifecycle / Dispose
+        // ============================================================================
+
+        [Fact]
+        public void Dispose_after_Arm_does_not_throw()
+        {
+            using var f = new Fixture();
+            var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger);
+            detector.Arm();
+            detector.Dispose();
+
+            // No emission expected — dispose ate the timer before it fired.
+            Assert.Null(FindHybridLoginPending(f.Ingress));
+        }
+
+        [Fact]
+        public void TriggerFromTest_after_Dispose_does_not_emit()
+        {
+            using var f = new Fixture();
+            var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger);
+            detector.Arm();
+            detector.Dispose();
+
+            detector.TriggerFromTest();
+
+            Assert.Null(FindHybridLoginPending(f.Ingress));
+        }
+
+        [Fact]
+        public void Ctor_null_args_throw()
+        {
+            using var f = new Fixture();
+            Assert.Throws<ArgumentNullException>(() => new HybridLoginPendingDetector(null!, f.Post, f.Logger));
+            Assert.Throws<ArgumentNullException>(() => new HybridLoginPendingDetector(f.Watcher, null!, f.Logger));
+            Assert.Throws<ArgumentNullException>(() => new HybridLoginPendingDetector(f.Watcher, f.Post, null!));
+        }
+
+        // ============================================================================
+        // Custom delay
+        // ============================================================================
+
+        [Fact]
+        public void Custom_delay_is_reflected_in_payload()
+        {
+            using var f = new Fixture();
+            using var detector = new HybridLoginPendingDetector(f.Watcher, f.Post, f.Logger, TimeSpan.FromMinutes(15));
+
+            detector.Arm();
+            detector.TriggerFromTest();
+
+            var info = FindHybridLoginPending(f.Ingress);
+            Assert.NotNull(info);
+            Assert.Equal("15", info!.Payload!["delayMinutes"]);
+        }
+    }
+}
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/SignalAdapters/AadJoinWatcherAdapterTests.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/SignalAdapters/AadJoinWatcherAdapterTests.cs
index 256afed7..dd25af7b 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/SignalAdapters/AadJoinWatcherAdapterTests.cs
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/SignalAdapters/AadJoinWatcherAdapterTests.cs
@@ -5,7 +5,9 @@ using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
 using AutopilotMonitor.Agent.V2.Core.SignalAdapters;
 using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
 using AutopilotMonitor.Agent.V2.Core.Tests.Orchestration;
+using AutopilotMonitor.DecisionCore.Engine;
 using AutopilotMonitor.DecisionCore.Signals;
+using SharedEventTypes = AutopilotMonitor.Shared.Constants.EventTypes;
 using Xunit;
 
 namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
@@ -43,15 +45,42 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
 
             adapter.TriggerFromTest("alice@contoso.com", "abcd1234");
 
-            var posted = Assert.Single(f.Ingress.Posted);
-            Assert.Equal(DecisionSignalKind.AadUserJoinedLate, posted.Kind);
-            Assert.Equal("AadJoinWatcher", posted.SourceOrigin);
-            Assert.Equal(EvidenceKind.Derived, posted.Evidence.Kind);
-            Assert.Equal("contoso.com", posted.Payload!["userDomain"]);
-            Assert.Equal("true", posted.Payload["hasThumbprint"]);
+            // Codex review 2026-05-01: dual-emission — decision signal + informational event.
+            var decisionSignal = f.Ingress.Posted.Single(p => p.Kind == DecisionSignalKind.AadUserJoinedLate);
+            Assert.Equal("AadJoinWatcher", decisionSignal.SourceOrigin);
+            Assert.Equal(EvidenceKind.Derived, decisionSignal.Evidence.Kind);
+            Assert.Equal("contoso.com", decisionSignal.Payload!["userDomain"]);
+            Assert.Equal("true", decisionSignal.Payload["hasThumbprint"]);
 
-            // PII guard: full email MUST NOT appear in payload.
-            Assert.DoesNotContain("alice@", string.Concat(posted.Payload.Values));
+            // PII guard: full email MUST NOT appear in either rail's payload.
+            Assert.DoesNotContain("alice@", string.Concat(decisionSignal.Payload.Values));
+        }
+
+        [Fact]
+        public void TriggerFromTest_also_emits_aad_user_joined_late_informational_event()
+        {
+            using var f = new Fixture();
+            using var adapter = new AadJoinWatcherAdapter(f.Watcher, f.Ingress, f.Clock);
+
+            adapter.TriggerFromTest("alice@contoso.com", "abcd1234");
+
+            // FailureSnapshotBuilder reads the Events table — without this rail it cannot
+            // see that the real AAD user was ever observed (HandleAadUserJoinedLateV1 is
+            // observation-only, no timeline effect). Snapshot would always say
+            // aadJoinState=placeholder/unknown.
+            var info = f.Ingress.Posted.Single(p =>
+                p.Kind == DecisionSignalKind.InformationalEvent
+                && p.Payload != null
+                && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var et)
+                && et == SharedEventTypes.AadUserJoinedLate);
+            Assert.Equal("AadJoinWatcher", info.Payload![SignalPayloadKeys.Source]);
+            Assert.Equal("true", info.Payload[SignalPayloadKeys.ImmediateUpload]);
+            Assert.Equal("Info", info.Payload[SignalPayloadKeys.Severity]);
+            Assert.Equal("contoso.com", info.Payload["userDomain"]);
+            Assert.Equal("true", info.Payload["hasThumbprint"]);
+
+            // PII guard: the message must not glue local-part to domain.
+            Assert.DoesNotContain("alice@", info.Payload[SignalPayloadKeys.Message]);
         }
 
         [Fact]
@@ -62,9 +91,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
 
             adapter.TriggerFromTest("bob@tailspin.com", "x");
 
-            var posted = f.Ingress.Posted.Single();
-            Assert.Equal(DecisionSignalKind.UserAadSignInComplete, posted.Kind);
-            Assert.Contains("Post-reboot", posted.Evidence.Summary);
+            var decisionSignal = f.Ingress.Posted.Single(p => p.Kind == DecisionSignalKind.UserAadSignInComplete);
+            Assert.Contains("Post-reboot", decisionSignal.Evidence.Summary);
+
+            // Part 2 mode also dual-emits the corresponding info event.
+            var info = f.Ingress.Posted.Single(p =>
+                p.Kind == DecisionSignalKind.InformationalEvent
+                && p.Payload != null
+                && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var et)
+                && et == SharedEventTypes.UserAadSignInComplete);
+            Assert.Equal("tailspin.com", info.Payload!["userDomain"]);
         }
 
         [Fact]
@@ -75,7 +111,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
 
             adapter.TriggerFromTest("user@example.org", "");
 
-            Assert.Equal("false", f.Ingress.Posted[0].Payload!["hasThumbprint"]);
+            var decision = f.Ingress.Posted.Single(p => p.Kind == DecisionSignalKind.AadUserJoinedLate);
+            Assert.Equal("false", decision.Payload!["hasThumbprint"]);
         }
 
         [Fact]
@@ -86,11 +123,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
 
             adapter.TriggerFromTest("no-at-sign", "x");
 
-            Assert.Equal("unknown", f.Ingress.Posted[0].Payload!["userDomain"]);
+            var decision = f.Ingress.Posted.Single(p => p.Kind == DecisionSignalKind.AadUserJoinedLate);
+            Assert.Equal("unknown", decision.Payload!["userDomain"]);
         }
 
         [Fact]
-        public void Duplicate_trigger_is_deduplicated()
+        public void Duplicate_trigger_is_deduplicated_on_both_rails()
         {
             using var f = new Fixture();
             using var adapter = new AadJoinWatcherAdapter(f.Watcher, f.Ingress, f.Clock);
@@ -98,7 +136,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
             adapter.TriggerFromTest("alice@contoso.com", "x");
             adapter.TriggerFromTest("alice@contoso.com", "x");
 
-            Assert.Single(f.Ingress.Posted);
+            // Exactly one decision signal + one informational event for the real-user
+            // path (fire-once semantics on _fired).
+            Assert.Single(f.Ingress.Posted, p => p.Kind == DecisionSignalKind.AadUserJoinedLate);
+            Assert.Single(
+                f.Ingress.Posted,
+                p => p.Kind == DecisionSignalKind.InformationalEvent
+                    && p.Payload != null
+                    && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var et)
+                    && et == SharedEventTypes.AadUserJoinedLate);
+            Assert.Equal(2, f.Ingress.Posted.Count);
         }
 
         [Fact]
@@ -109,5 +156,130 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
             Assert.Throws<ArgumentNullException>(() => new AadJoinWatcherAdapter(f.Watcher, null!, f.Clock));
             Assert.Throws<ArgumentNullException>(() => new AadJoinWatcherAdapter(f.Watcher, f.Ingress, null!));
         }
+
+        // ============================================================================
+        // Placeholder path (Hybrid completion-gap fix, 2026-05-01)
+        // ============================================================================
+
+        [Fact]
+        public void TriggerPlaceholderFromTest_emits_aad_placeholder_user_detected_informational_event()
+        {
+            using var f = new Fixture();
+            using var adapter = new AadJoinWatcherAdapter(f.Watcher, f.Ingress, f.Clock);
+
+            adapter.TriggerPlaceholderFromTest("foouser@fabrikam.onmicrosoft.com");
+
+            var info = f.Ingress.Posted.Single(p => p.Kind == DecisionSignalKind.InformationalEvent);
+            Assert.Equal(SharedEventTypes.AadPlaceholderUserDetected, info.Payload![SignalPayloadKeys.EventType]);
+            Assert.Equal("AadJoinWatcher", info.Payload[SignalPayloadKeys.Source]);
+            Assert.Equal("true", info.Payload[SignalPayloadKeys.ImmediateUpload]);
+            Assert.Equal("foouser", info.Payload["placeholderType"]);
+            Assert.Equal("fabrikam.onmicrosoft.com", info.Payload["userDomain"]);
+            Assert.Contains("registryKey", info.Payload.Keys);
+
+            // PII guard: the local part of the email must not appear (only domain).
+            Assert.DoesNotContain("foouser@", info.Payload[SignalPayloadKeys.Message]);
+        }
+
+        [Fact]
+        public void TriggerPlaceholderFromTest_classifies_autopilot_placeholder()
+        {
+            using var f = new Fixture();
+            using var adapter = new AadJoinWatcherAdapter(f.Watcher, f.Ingress, f.Clock);
+
+            adapter.TriggerPlaceholderFromTest("autopilot@contoso.com");
+
+            var info = f.Ingress.Posted.Single(p => p.Kind == DecisionSignalKind.InformationalEvent);
+            Assert.Equal("autopilot", info.Payload!["placeholderType"]);
+            Assert.Equal("contoso.com", info.Payload["userDomain"]);
+        }
+
+        [Fact]
+        public void Duplicate_placeholder_trigger_is_deduplicated()
+        {
+            using var f = new Fixture();
+            using var adapter = new AadJoinWatcherAdapter(f.Watcher, f.Ingress, f.Clock);
+
+            adapter.TriggerPlaceholderFromTest("foouser@example.com");
+            adapter.TriggerPlaceholderFromTest("foouser@example.com");
+            adapter.TriggerPlaceholderFromTest("foouser@example.com");
+
+            Assert.Single(f.Ingress.Posted, p => p.Kind == DecisionSignalKind.InformationalEvent);
+        }
+
+        [Fact]
+        public void Placeholder_and_real_user_emit_separate_signals_independently()
+        {
+            using var f = new Fixture();
+            using var adapter = new AadJoinWatcherAdapter(f.Watcher, f.Ingress, f.Clock);
+
+            adapter.TriggerPlaceholderFromTest("foouser@fabrikam.com");
+            adapter.TriggerFromTest("alice@fabrikam.com", "abcd");
+
+            // 3 posts total after Codex review 2026-05-01 dual-emission:
+            //   - placeholder informational event
+            //   - real-user decision signal (AadUserJoinedLate)
+            //   - real-user informational event (aad_user_joined_late)
+            Assert.Equal(3, f.Ingress.Posted.Count);
+            Assert.Single(f.Ingress.Posted, p =>
+                p.Kind == DecisionSignalKind.InformationalEvent
+                && p.Payload != null
+                && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var et1)
+                && et1 == SharedEventTypes.AadPlaceholderUserDetected);
+            Assert.Single(f.Ingress.Posted, p => p.Kind == DecisionSignalKind.AadUserJoinedLate);
+            Assert.Single(f.Ingress.Posted, p =>
+                p.Kind == DecisionSignalKind.InformationalEvent
+                && p.Payload != null
+                && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var et2)
+                && et2 == SharedEventTypes.AadUserJoinedLate);
+        }
+
+        // ============================================================================
+        // onRealUserJoined callback (Pkt 5 — DesktopArrivalDetector reset wiring)
+        // ============================================================================
+
+        [Fact]
+        public void Real_user_join_invokes_onRealUserJoined_callback_exactly_once()
+        {
+            using var f = new Fixture();
+            int invocations = 0;
+            using var adapter = new AadJoinWatcherAdapter(
+                f.Watcher, f.Ingress, f.Clock,
+                onRealUserJoined: () => invocations++);
+
+            adapter.TriggerFromTest("alice@contoso.com", "x");
+            adapter.TriggerFromTest("alice@contoso.com", "x"); // dedup — callback must not fire twice
+
+            Assert.Equal(1, invocations);
+        }
+
+        [Fact]
+        public void Placeholder_does_not_invoke_onRealUserJoined_callback()
+        {
+            using var f = new Fixture();
+            int invocations = 0;
+            using var adapter = new AadJoinWatcherAdapter(
+                f.Watcher, f.Ingress, f.Clock,
+                onRealUserJoined: () => invocations++);
+
+            adapter.TriggerPlaceholderFromTest("foouser@example.com");
+
+            Assert.Equal(0, invocations);
+        }
+
+        [Fact]
+        public void Throwing_onRealUserJoined_callback_does_not_break_signal_post()
+        {
+            using var f = new Fixture();
+            using var adapter = new AadJoinWatcherAdapter(
+                f.Watcher, f.Ingress, f.Clock,
+                onRealUserJoined: () => throw new InvalidOperationException("boom"));
+
+            // The signal post completes BEFORE the callback fires — even if the callback
+            // throws, the decision signal must already be on the bus.
+            adapter.TriggerFromTest("alice@contoso.com", "x");
+
+            Assert.Single(f.Ingress.Posted, p => p.Kind == DecisionSignalKind.AadUserJoinedLate);
+        }
     }
 }
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/DesktopArrivalDetector.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/DesktopArrivalDetector.cs
index 8063dd45..14c85400 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/DesktopArrivalDetector.cs
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/DesktopArrivalDetector.cs
@@ -67,6 +67,38 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
             _pollingTimer = null;
         }
 
+        /// <summary>
+        /// Resets desktop-arrival tracking after a placeholder→real-user transition (Hybrid
+        /// User-Driven completion-gap fix, 2026-05-01). Used by the composition root when
+        /// <see cref="AadJoinWatcher.AadUserJoined"/> fires for a real user — the previous
+        /// fooUser desktop the detector observed is invalidated, and polling restarts so the
+        /// AD-user desktop after the Hybrid reboot is detected as the actual real desktop.
+        /// <para>
+        /// Idempotent: safe to call multiple times. No-op if the detector already fired
+        /// after the reset (a subsequent real-user join after a real-user desktop is also
+        /// idempotent because the polling timer is restarted regardless and the next match
+        /// against IsExcludedUser will short-circuit on the still-valid desktop).
+        /// </para>
+        /// </summary>
+        public void ResetForRealUserSwitch()
+        {
+            _logger.Info("DesktopArrivalDetector: reset for real-user switch (placeholder→real user transition)");
+
+            // Drop any prior arrival state — subsequent polls must re-evaluate the current
+            // explorer.exe owner against IsExcludedUser anew.
+            _desktopArrived = false;
+            _excludedUserTraced = false;
+
+            // Restart polling. Dispose any existing timer first to avoid leaking ticks
+            // from an already-running schedule.
+            _pollingTimer?.Dispose();
+            _pollingTimer = new Timer(
+                PollForDesktop,
+                null,
+                TimeSpan.FromSeconds(5),
+                TimeSpan.FromSeconds(PollingIntervalSeconds));
+        }
+
         private void PollForDesktop(object state)
         {
             if (_desktopArrived)
@@ -179,14 +211,23 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
 
         /// <summary>
         /// Returns true if the user name matches any excluded system/service account.
-        /// Handles both "User" and "DOMAIN\User" formats.
-        /// Also matches the pattern DefaultUser* (case-insensitive).
+        /// Handles "User", "DOMAIN\User", and UPN ("user@domain") formats.
+        /// Also matches the patterns DefaultUser* and the Autopilot provisioning placeholders
+        /// foouser@* / autopilot@* (case-insensitive). The placeholder match prevents the
+        /// fooUser OOBE shell on Hybrid User-Driven enrollments from being treated as a
+        /// real user desktop.
         /// </summary>
         internal static bool IsExcludedUser(string fullUserName)
         {
             if (string.IsNullOrEmpty(fullUserName))
                 return true;
 
+            // UPN form (user@domain) — delegate to the same placeholder oracle the
+            // AadJoinWatcher uses, so the foouser@/autopilot@ list stays in one place.
+            if (fullUserName.IndexOf('@') >= 0
+                && AadJoinInfo.IsPlaceholderUserEmail(fullUserName))
+                return true;
+
             // Extract just the username part (after backslash if present)
             var userName = fullUserName;
             var backslashIndex = fullUserName.LastIndexOf('\\');
@@ -204,6 +245,20 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
             if (userName.StartsWith("DefaultUser", StringComparison.OrdinalIgnoreCase))
                 return true;
 
+            // DOMAIN\foouser / DOMAIN\autopilot — the WMI GetOwner call sometimes returns a
+            // synthetic local-machine domain instead of the UPN. EXACT match the bare
+            // username here (not prefix), so legitimate real accounts like
+            // CONTOSO\autopilotadmin or DOMAIN\foouserservice stay through the gate.
+            // Codex review 2026-05-01 (Finding 3): the previous prefix match was too broad
+            // and reused via UserProfileResolver, which would have resolved to the wrong
+            // user profile for any account starting with "autopilot" or "foouser".
+            // The UPN form (foouser@*, autopilot@*) is still handled above by
+            // AadJoinInfo.IsPlaceholderUserEmail — that path is what covers the
+            // real-world Autopilot placeholders (foouser@<tenant>.onmicrosoft.com).
+            if (string.Equals(userName, "foouser", StringComparison.OrdinalIgnoreCase)
+                || string.Equals(userName, "autopilot", StringComparison.OrdinalIgnoreCase))
+                return true;
+
             return false;
         }
 
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/HybridLoginPendingDetector.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/HybridLoginPendingDetector.cs
new file mode 100644
index 00000000..8347a3d1
--- /dev/null
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/HybridLoginPendingDetector.cs
@@ -0,0 +1,157 @@
+#nullable enable
+using System;
+using System.Collections.Generic;
+using System.Threading;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Orchestration;
+using AutopilotMonitor.Shared.Models;
+using SharedConstants = AutopilotMonitor.Shared.Constants;
+
+namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
+{
+    /// <summary>
+    /// Single-shot detector for the Hybrid User-Driven completion-gap (2026-05-01 trigger:
+    /// session e58bcfdb-3e68-4f23-a3c2-437429ca9e78). After a Hybrid AAD-Join reboot the
+    /// agent restarts and waits for the user to log in with their real AD/AAD account
+    /// (which replaces the foouser/autopilot placeholder in JoinInfo). When that login is
+    /// overdue the agent today goes silent until the backend 5-h watchdog fires; this
+    /// detector emits a <c>hybrid_login_pending</c> warning event after a short single-shot
+    /// timer so the operator sees an explicit "stuck waiting for AD login" signal in the
+    /// timeline.
+    /// <para>
+    /// Conditions checked at <see cref="Arm"/>: composition root must have already
+    /// confirmed a) post-reboot, b) <c>isHybridJoin == true</c>. The detector itself only
+    /// owns the timer + <see cref="AadJoinWatcher.AadUserJoined"/> cancel-path. No polling.
+    /// No periodicity. Fires at most once per agent process.
+    /// </para>
+    /// </summary>
+    internal sealed class HybridLoginPendingDetector : IDisposable
+    {
+        internal const int DefaultDelayMinutes = 10;
+        internal const string SourceLabel = "HybridLoginPendingDetector";
+
+        private readonly AadJoinWatcher _watcher;
+        private readonly InformationalEventPost _post;
+        private readonly AgentLogger _logger;
+        private readonly TimeSpan _delay;
+        private readonly object _lock = new object();
+
+        private Timer? _timer;
+        private bool _armed;
+        private bool _fired;
+        private bool _cancelledByRealUser;
+        private int _disposed;
+
+        internal HybridLoginPendingDetector(
+            AadJoinWatcher watcher,
+            InformationalEventPost post,
+            AgentLogger logger,
+            TimeSpan? delay = null)
+        {
+            _watcher = watcher ?? throw new ArgumentNullException(nameof(watcher));
+            _post = post ?? throw new ArgumentNullException(nameof(post));
+            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
+            _delay = delay ?? TimeSpan.FromMinutes(DefaultDelayMinutes);
+
+            // Subscribe up-front so a real-user join that arrives BEFORE Arm() is still
+            // recorded — _cancelledByRealUser short-circuits any later Arm() call.
+            _watcher.AadUserJoined += OnAadUserJoined;
+        }
+
+        /// <summary>
+        /// Starts the single-shot timer. Idempotent — repeated calls after the first arm
+        /// are no-ops. Has no effect if the watcher already saw a real AAD user (the
+        /// arming was racy and the cancel won), or if the detector already fired.
+        /// </summary>
+        public void Arm()
+        {
+            lock (_lock)
+            {
+                if (_disposed != 0) return;
+                if (_armed || _fired) return;
+                if (_cancelledByRealUser)
+                {
+                    _logger.Info("HybridLoginPendingDetector: arm requested but real AAD user already joined — skipped");
+                    return;
+                }
+
+                _armed = true;
+                _logger.Info(
+                    $"HybridLoginPendingDetector: armed — will emit hybrid_login_pending in {_delay.TotalMinutes:F0} min if real AAD user has not joined by then");
+
+                _timer = new Timer(OnTimer, null, _delay, Timeout.InfiniteTimeSpan);
+            }
+        }
+
+        public void Dispose()
+        {
+            if (Interlocked.Exchange(ref _disposed, 1) == 1) return;
+            try { _watcher.AadUserJoined -= OnAadUserJoined; } catch { }
+            lock (_lock)
+            {
+                _timer?.Dispose();
+                _timer = null;
+            }
+        }
+
+        // Test seam — bypasses the timer schedule. Same lock + state guards as the real path.
+        internal void TriggerFromTest() => OnTimer(null);
+
+        // Test seam — synthesises an AadUserJoined arrival without going through the
+        // watcher's private event-raise path. The watcher's events can only be invoked from
+        // inside the watcher class, so production unit tests have no way to observe the
+        // detector's cancel-on-real-user behavior otherwise.
+        internal void TriggerRealUserJoinedFromTest() =>
+            OnAadUserJoined(this, new AadUserJoinedEventArgs("test@example.com", "test-thumbprint"));
+
+        internal bool IsArmedForTest { get { lock (_lock) { return _armed; } } }
+        internal bool IsCancelledByRealUserForTest { get { lock (_lock) { return _cancelledByRealUser; } } }
+        internal bool HasFiredForTest { get { lock (_lock) { return _fired; } } }
+
+        private void OnTimer(object? state) => EmitInternal(reason: "timer_fired");
+
+        private void OnAadUserJoined(object sender, AadUserJoinedEventArgs e)
+        {
+            lock (_lock)
+            {
+                _cancelledByRealUser = true;
+                if (!_armed || _fired) return;
+
+                _timer?.Dispose();
+                _timer = null;
+                _logger.Info("HybridLoginPendingDetector: cancelled — real AAD user joined before timeout");
+            }
+        }
+
+        private void EmitInternal(string reason)
+        {
+            lock (_lock)
+            {
+                // _armed guard (Codex review 2026-05-01): production is safe because the
+                // timer is only created in Arm(), but explicit guard makes the contract
+                // unambiguous — emission requires a deliberate Arm(), full stop.
+                if (!_armed || _fired || _cancelledByRealUser || _disposed != 0) return;
+                _fired = true;
+                _timer?.Dispose();
+                _timer = null;
+            }
+
+            var data = new Dictionary<string, string>(StringComparer.Ordinal)
+            {
+                ["delayMinutes"] = ((int)_delay.TotalMinutes).ToString(),
+                ["reason"] = reason,
+                ["isHybridJoin"] = "true",  // armed only when composition root verified this
+            };
+
+            _post.Emit(
+                eventType: SharedConstants.EventTypes.HybridLoginPending,
+                source: SourceLabel,
+                message: $"Hybrid AAD Join: {(int)_delay.TotalMinutes} min after reboot still no real AD user — login overdue (placeholder still active in JoinInfo)",
+                severity: EventSeverity.Warning,
+                immediateUpload: true,
+                data: data);
+
+            _logger.Warning("HybridLoginPendingDetector: emitted hybrid_login_pending warning");
+        }
+    }
+}
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/DefaultComponentFactory.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/DefaultComponentFactory.cs
index 8d4dbd54..6ea8962e 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/DefaultComponentFactory.cs
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/DefaultComponentFactory.cs
@@ -69,6 +69,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
 
         private ImeLogHost? _imeLogHost;
         private EspAndHelloHost? _espAndHelloHost;
+        private AadJoinHost? _aadJoinHost;
         private Transport.Telemetry.ITelemetrySpool? _telemetrySpool;
 
         /// <summary>
@@ -84,6 +85,14 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
         /// </summary>
         internal EspAndHelloHost? EspAndHelloHost => _espAndHelloHost;
 
+        /// <summary>
+        /// Exposes the <see cref="AadJoinHost"/> so the runtime host can arm the Hybrid
+        /// User-Driven login-pending detector after observing a reboot-kill on a Hybrid-AAD
+        /// device (2026-05-01 completion-gap fix). Returns <c>null</c> before
+        /// <see cref="CreateCollectorHosts"/> has been called.
+        /// </summary>
+        internal AadJoinHost? AadJoinHost => _aadJoinHost;
+
         /// <summary>
         /// Exposes the IME tracker's package-state list to peripheral consumers such as the
         /// <c>FinalStatusBuilder</c> in M4.6.β. Returns <c>null</c> before
@@ -178,9 +187,18 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
                 stateDirectory: _stateDirectory);
             hosts.Add(_espAndHelloHost);
 
-            hosts.Add(new DesktopArrivalHost(logger, ingress, clock));
+            // Hybrid User-Driven completion-gap fix (2026-05-01): the AadJoinHost notifies
+            // the DesktopArrivalHost when a real AAD user replaces the foouser/autopilot
+            // placeholder, so the detector resets and re-evaluates after the Hybrid reboot
+            // instead of staying latched on the foo desktop. Order matters — DesktopArrivalHost
+            // must exist before AadJoinHost so the callback target is available.
+            var desktopArrivalHost = new DesktopArrivalHost(logger, ingress, clock);
+            hosts.Add(desktopArrivalHost);
 
-            hosts.Add(new AadJoinHost(logger, ingress, clock));
+            _aadJoinHost = new AadJoinHost(
+                logger, ingress, clock,
+                onRealUserJoined: desktopArrivalHost.RequestResetForRealUserSwitch);
+            hosts.Add(_aadJoinHost);
 
             // Single-rail refactor (plan §5.8) — DeviceInfoCollector existed in V2.Core but had
             // no host so the Device-Details UI block was empty in V2 sessions (V1-Parity Issue #2).
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/AadJoinHost.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/AadJoinHost.cs
index 8ef9af85..1de89e15 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/AadJoinHost.cs
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/AadJoinHost.cs
@@ -1,4 +1,5 @@
 #nullable enable
+using System;
 using System.Threading;
 using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
@@ -13,20 +14,43 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
 
         private readonly AadJoinWatcher _watcher;
         private readonly AadJoinWatcherAdapter _adapter;
+        private readonly HybridLoginPendingDetector _hybridLoginPendingDetector;
         private int _disposed;
 
-        public AadJoinHost(AgentLogger logger, ISignalIngressSink ingress, IClock clock)
+        public AadJoinHost(
+            AgentLogger logger,
+            ISignalIngressSink ingress,
+            IClock clock,
+            Action? onRealUserJoined = null)
         {
             _watcher = new AadJoinWatcher(logger);
-            _adapter = new AadJoinWatcherAdapter(_watcher, ingress, clock);
+            _adapter = new AadJoinWatcherAdapter(_watcher, ingress, clock, onRealUserJoined: onRealUserJoined);
+            _hybridLoginPendingDetector = new HybridLoginPendingDetector(
+                watcher: _watcher,
+                post: new InformationalEventPost(ingress, clock),
+                logger: logger);
         }
 
         public void Start() => _watcher.Start();
         public void Stop() => _watcher.Stop();
 
+        /// <summary>
+        /// Composition-root entry point for the Hybrid User-Driven completion-gap fix
+        /// (2026-05-01). Only call when both prerequisites hold: a) the prior agent process
+        /// was killed by an OS reboot (<c>previousExitType=reboot_kill</c>), b) the
+        /// Autopilot profile is Hybrid AAD Join (<c>isHybridJoin=true</c>). The detector
+        /// itself enforces single-shot semantics + cancel-on-real-user — repeated calls or
+        /// late calls after a real user joined are safe no-ops.
+        /// </summary>
+        public void ArmHybridLoginPendingDetector() => _hybridLoginPendingDetector.Arm();
+
+        // Test seam — exposes the detector for unit tests in the V2.Core.Tests project.
+        internal HybridLoginPendingDetector HybridLoginPendingDetectorForTest => _hybridLoginPendingDetector;
+
         public void Dispose()
         {
             if (Interlocked.Exchange(ref _disposed, 1) == 1) return;
+            try { _hybridLoginPendingDetector.Dispose(); } catch { }
             try { _adapter.Dispose(); } catch { }
             try { _watcher.Dispose(); } catch { }
         }
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/DesktopArrivalHost.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/DesktopArrivalHost.cs
index 39969198..12643d57 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/DesktopArrivalHost.cs
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/DesktopArrivalHost.cs
@@ -24,6 +24,15 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
         public void Start() => _detector.Start();
         public void Stop() => _detector.Stop();
 
+        /// <summary>
+        /// Resets desktop-arrival tracking after a placeholder→real-user transition
+        /// (Hybrid User-Driven completion-gap fix, 2026-05-01). Wired by the composition
+        /// root through <see cref="AadJoinHost"/>'s <c>onRealUserJoined</c> callback so the
+        /// fooUser desktop the detector observed during foo-OOBE is invalidated and polling
+        /// restarts to detect the AD-user desktop after the Hybrid reboot.
+        /// </summary>
+        public void RequestResetForRealUserSwitch() => _detector.ResetForRealUserSwitch();
+
         public void Dispose()
         {
             if (Interlocked.Exchange(ref _disposed, 1) == 1) return;
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core/SignalAdapters/AadJoinWatcherAdapter.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core/SignalAdapters/AadJoinWatcherAdapter.cs
index 9516c78e..6f95180f 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2.Core/SignalAdapters/AadJoinWatcherAdapter.cs
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core/SignalAdapters/AadJoinWatcherAdapter.cs
@@ -5,50 +5,70 @@ using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
 using AutopilotMonitor.Agent.V2.Core.Orchestration;
 using AutopilotMonitor.DecisionCore.Engine;
 using AutopilotMonitor.DecisionCore.Signals;
+using AutopilotMonitor.Shared.Models;
+using SharedConstants = AutopilotMonitor.Shared.Constants;
 
 namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
 {
     /// <summary>
-    /// Adapter for <see cref="AadJoinWatcher"/> → <see cref="DecisionSignalKind.AadUserJoinedLate"/>
-    /// (Part 1) or <see cref="DecisionSignalKind.UserAadSignInComplete"/> (Part 2). Plan §2.1a / §2.2.
-    /// <para>
-    /// Only the <c>AadUserJoined</c>-Event (real user, non-placeholder) ist Decision-relevant
-    /// und wird als Signal emittiert. <c>PlaceholderUserDetected</c> ist diagnostisch
-    /// (transienter Provisioning-Account) und wird aktuell nicht als Decision-Signal
-    /// weitergereicht — bei Bedarf später als Event-Timeline-Entry emittierbar.
-    /// </para>
+    /// Adapter for <see cref="AadJoinWatcher"/>:
+    /// <list type="bullet">
+    /// <item><description><see cref="AadJoinWatcher.AadUserJoined"/> →
+    ///   <see cref="DecisionSignalKind.AadUserJoinedLate"/> (Part 1) or
+    ///   <see cref="DecisionSignalKind.UserAadSignInComplete"/> (Part 2). Plan §2.1a / §2.2.</description></item>
+    /// <item><description><see cref="AadJoinWatcher.PlaceholderUserDetected"/> → emits a
+    ///   <c>aad_placeholder_user_detected</c> informational event for backend timeline
+    ///   visibility (Hybrid User-Driven completion-gap fix, 2026-05-01). NOT a decision signal —
+    ///   the engine has no <see cref="DecisionSignalKind"/> for placeholder presence and the
+    ///   placeholder is expected to be replaced by a real user.</description></item>
+    /// </list>
     /// </summary>
     internal sealed class AadJoinWatcherAdapter : IDisposable
     {
+        private const string SourceLabel = "AadJoinWatcher";
+
         private readonly AadJoinWatcher _watcher;
         private readonly ISignalIngressSink _ingress;
         private readonly IClock _clock;
+        private readonly InformationalEventPost _post;
+        private readonly Action? _onRealUserJoined;
         private readonly bool _part2Mode;
         private bool _fired;
+        private bool _placeholderFired;
 
         public AadJoinWatcherAdapter(
             AadJoinWatcher watcher,
             ISignalIngressSink ingress,
             IClock clock,
-            bool part2Mode = false)
+            bool part2Mode = false,
+            Action? onRealUserJoined = null)
         {
             _watcher = watcher ?? throw new ArgumentNullException(nameof(watcher));
             _ingress = ingress ?? throw new ArgumentNullException(nameof(ingress));
             _clock = clock ?? throw new ArgumentNullException(nameof(clock));
+            _post = new InformationalEventPost(ingress, clock);
             _part2Mode = part2Mode;
+            _onRealUserJoined = onRealUserJoined;
 
             _watcher.AadUserJoined += OnAadUserJoined;
+            _watcher.PlaceholderUserDetected += OnPlaceholderUserDetected;
         }
 
         public void Dispose()
         {
             _watcher.AadUserJoined -= OnAadUserJoined;
+            _watcher.PlaceholderUserDetected -= OnPlaceholderUserDetected;
         }
 
         private void OnAadUserJoined(object sender, AadUserJoinedEventArgs e) => EmitInternal(e.UserEmail, e.Thumbprint);
 
+        private void OnPlaceholderUserDetected(object sender, AadPlaceholderUserDetectedEventArgs e) =>
+            EmitPlaceholderInternal(e.UserEmail);
+
         internal void TriggerFromTest(string userEmail, string thumbprint) => EmitInternal(userEmail, thumbprint);
 
+        internal void TriggerPlaceholderFromTest(string userEmail) => EmitPlaceholderInternal(userEmail);
+
         private void EmitInternal(string userEmail, string thumbprint)
         {
             if (_fired) return;
@@ -67,7 +87,7 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
             _ingress.Post(
                 kind: kind,
                 occurredAtUtc: _clock.UtcNow,
-                sourceOrigin: "AadJoinWatcher",
+                sourceOrigin: SourceLabel,
                 evidence: new Evidence(
                     kind: EvidenceKind.Derived,
                     identifier: "aad-join-watcher-v1",
@@ -79,6 +99,61 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
                         ["registryKey"] = @"HKLM\SYSTEM\CurrentControlSet\Control\CloudDomainJoin\JoinInfo",
                     }),
                 payload: payload);
+
+            // Codex review 2026-05-01 — also dual-emit as informational event.
+            // HandleAadUserJoinedLateV1 / Part 2 handler in DecisionEngine.Classic is
+            // observation-only (no timeline effect), so without this dual-emission the
+            // backend Events table never sees the real-user join. FailureSnapshotBuilder
+            // (and any other event-stream consumer) needs this anchor to correctly classify
+            // aadJoinState=real_user. Same PII-safe payload shape as the decision signal.
+            var infoEventType = _part2Mode
+                ? SharedConstants.EventTypes.UserAadSignInComplete
+                : SharedConstants.EventTypes.AadUserJoinedLate;
+            var infoMessage = _part2Mode
+                ? $"Post-reboot AAD user sign-in detected (domain={payload["userDomain"]})"
+                : $"Late AAD user join detected (domain={payload["userDomain"]})";
+            _post.Emit(
+                eventType: infoEventType,
+                source: SourceLabel,
+                message: infoMessage,
+                severity: EventSeverity.Info,
+                immediateUpload: true,
+                data: payload,
+                occurredAtUtc: _clock.UtcNow);
+
+            // Pkt 5 — notify the composition root that a real AAD user has appeared, so the
+            // DesktopArrivalDetector can be reset for the AD-user-after-Hybrid-reboot case.
+            // Fire AFTER the decision signal so reducer-state ordering remains the canonical source.
+            try { _onRealUserJoined?.Invoke(); }
+            catch { /* callback is best-effort — never let host wiring break the signal post */ }
+        }
+
+        private void EmitPlaceholderInternal(string userEmail)
+        {
+            if (_placeholderFired) return;
+            _placeholderFired = true;
+
+            // Hybrid User-Driven OOBE: foouser@/autopilot@ is the transient provisioning account.
+            // Emit a backend-timeline event so operators can see "Foo phase active" — gives the
+            // diagnose path an explicit anchor when the real-user join is overdue.
+            var placeholderType = ClassifyPlaceholder(userEmail);
+            var data = new Dictionary<string, string>(StringComparer.Ordinal)
+            {
+                ["userDomain"] = ExtractDomain(userEmail),
+                ["placeholderType"] = placeholderType,
+                ["registryKey"] = @"HKLM\SYSTEM\CurrentControlSet\Control\CloudDomainJoin\JoinInfo",
+            };
+
+            // PII-friendly message: placeholderType + domain reported separately so the
+            // local-part of the email is never glued to the domain in the message string.
+            _post.Emit(
+                eventType: SharedConstants.EventTypes.AadPlaceholderUserDetected,
+                source: SourceLabel,
+                message: $"Autopilot provisioning placeholder detected (type={placeholderType}, domain={data["userDomain"]}) — waiting for real AAD user join",
+                severity: EventSeverity.Info,
+                immediateUpload: true,
+                data: data,
+                occurredAtUtc: _clock.UtcNow);
         }
 
         private static string ExtractDomain(string email)
@@ -87,5 +162,13 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
             var at = email.IndexOf('@');
             return at >= 0 && at + 1 < email.Length ? email.Substring(at + 1) : "unknown";
         }
+
+        private static string ClassifyPlaceholder(string email)
+        {
+            if (string.IsNullOrEmpty(email)) return "unknown";
+            if (email.StartsWith("foouser@", StringComparison.OrdinalIgnoreCase)) return "foouser";
+            if (email.StartsWith("autopilot@", StringComparison.OrdinalIgnoreCase)) return "autopilot";
+            return "unknown";
+        }
     }
 }
diff --git a/src/Agent/AutopilotMonitor.Agent.V2/Runtime/AgentRuntimeHost.cs b/src/Agent/AutopilotMonitor.Agent.V2/Runtime/AgentRuntimeHost.cs
index b2de0375..1fd2fb03 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2/Runtime/AgentRuntimeHost.cs
+++ b/src/Agent/AutopilotMonitor.Agent.V2/Runtime/AgentRuntimeHost.cs
@@ -6,6 +6,7 @@ using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime;
 using AutopilotMonitor.Agent.V2.Core.Orchestration;
 using AutopilotMonitor.Agent.V2.Core.Runtime;
+using AutopilotMonitor.Agent.V2.Core.Security;
 using AutopilotMonitor.Agent.V2.Core.Termination;
 using AutopilotMonitor.DecisionCore.Classifiers;
 using AutopilotMonitor.DecisionCore.Engine;
@@ -333,6 +334,22 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                         if (string.Equals(previousExit?.ExitType, "reboot_kill", StringComparison.OrdinalIgnoreCase))
                         {
                             LifecycleEmitters.PostSystemRebootObserved(orchestrator.IngressSink, previousExit, logger);
+
+                            // Hybrid User-Driven completion-gap fix (2026-05-01): the reboot is the
+                            // expected switch from foouser/autopilot OOBE to the real AD account.
+                            // If the user never logs in we go silent until the 5-h backend watchdog;
+                            // arm a single-shot 10-min detector that emits hybrid_login_pending
+                            // once if the AAD user join is overdue. Cancelled when AadJoinWatcher
+                            // sees the real user. Only armed for actual Hybrid devices — non-Hybrid
+                            // reboots don't have the placeholder→real-user flow that motivates this.
+                            if (!isWhiteGloveResume && EnrollmentRegistryDetector.DetectHybridJoin())
+                            {
+                                try { componentFactory.AadJoinHost?.ArmHybridLoginPendingDetector(); }
+                                catch (Exception ex)
+                                {
+                                    logger.Warning($"ArmHybridLoginPendingDetector threw: {ex.Message}");
+                                }
+                            }
                         }
 
                         // V2 race-fix follow-up (10c8e0bf review, 2026-04-27) —
diff --git a/src/Agent/AutopilotMonitor.Agent.V2/buildcounter.txt b/src/Agent/AutopilotMonitor.Agent.V2/buildcounter.txt
index 2596e4ad..9b5dddac 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2/buildcounter.txt
+++ b/src/Agent/AutopilotMonitor.Agent.V2/buildcounter.txt
@@ -1 +1 @@
-520
+541
diff --git a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
index d729899c..39ccce40 100644
--- a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
+++ b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
@@ -1 +1 @@
-1235
+1240
diff --git a/src/Backend/AutopilotMonitor.Functions.Tests/FailureSnapshotBuilderTests.cs b/src/Backend/AutopilotMonitor.Functions.Tests/FailureSnapshotBuilderTests.cs
new file mode 100644
index 00000000..c3be7ab5
--- /dev/null
+++ b/src/Backend/AutopilotMonitor.Functions.Tests/FailureSnapshotBuilderTests.cs
@@ -0,0 +1,350 @@
+using System;
+using System.Collections.Generic;
+using AutopilotMonitor.Functions.Services;
+using AutopilotMonitor.Shared.Models;
+using Newtonsoft.Json.Linq;
+
+namespace AutopilotMonitor.Functions.Tests;
+
+/// <summary>
+/// Tests for the failure-state snapshot built when the maintenance 5h-timeout sweep
+/// graduates a session to Failed (Hybrid User-Driven completion-gap fix, 2026-05-01).
+/// The snapshot is the single point of post-mortem context for stuck sessions, so the
+/// shape contract has to be stable: schemaVersion, missingSignals list, and the lifecycle
+/// anchors all need to round-trip cleanly. Tests focus on the diagnostic value: would an
+/// operator looking at the snapshot for session e58bcfdb-… understand what went wrong?
+/// </summary>
+public class FailureSnapshotBuilderTests
+{
+    private static readonly DateTime Now = new DateTime(2026, 5, 1, 18, 45, 31, DateTimeKind.Utc);
+
+    private static EnrollmentEvent Event(string type, DateTime ts, string? message = null,
+        Dictionary<string, object>? data = null) => new()
+        {
+            EventType = type,
+            Timestamp = ts,
+            Source = "test",
+            Message = message ?? type,
+            Data = data!,
+        };
+
+    [Fact]
+    public void Build_returns_null_for_empty_event_list()
+    {
+        Assert.Null(FailureSnapshotBuilder.Build(null, Now));
+        Assert.Null(FailureSnapshotBuilder.Build(Array.Empty<EnrollmentEvent>(), Now));
+    }
+
+    [Fact]
+    public void Build_carries_schemaVersion_and_generation_metadata()
+    {
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("agent_started", Now.AddHours(-5)),
+        }, Now);
+
+        Assert.NotNull(json);
+        var obj = JObject.Parse(json!);
+        Assert.Equal(FailureSnapshotBuilder.CurrentSchemaVersion, (int)obj["schemaVersion"]!);
+        Assert.NotNull(obj["generatedAtUtc"]);
+        Assert.Equal(1, (int)obj["eventCount"]!);
+    }
+
+    [Fact]
+    public void Build_extracts_last_esp_phase_from_esp_phase_changed_events()
+    {
+        var t0 = Now.AddHours(-5);
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("esp_phase_changed", t0.AddSeconds(1),
+                data: new Dictionary<string, object> { ["espPhase"] = "DeviceSetup" }),
+            Event("esp_phase_changed", t0.AddSeconds(3),
+                data: new Dictionary<string, object> { ["espPhase"] = "AccountSetup" }),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.Equal("AccountSetup", (string?)obj["lastEspPhase"]);
+        Assert.NotNull(obj["lastEspPhaseAtUtc"]);
+    }
+
+    [Fact]
+    public void Build_records_desktop_arrival_with_timestamp()
+    {
+        var t = Now.AddHours(-5).AddSeconds(7);
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("desktop_arrived", t),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.True((bool)obj["desktopArrived"]!);
+        Assert.NotNull(obj["desktopArrivedAtUtc"]);
+    }
+
+    [Fact]
+    public void Build_records_hello_policy_disabled_state()
+    {
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("hello_policy_detected", Now.AddHours(-4),
+                data: new Dictionary<string, object> { ["helloEnabled"] = "false" }),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.True((bool)obj["helloPolicyDetected"]!);
+        Assert.False((bool)obj["helloPolicyEnabled"]!);
+    }
+
+    // ============================================================================
+    // AAD join-state classification
+    // ============================================================================
+
+    [Fact]
+    public void Build_classifies_placeholder_state_from_aad_placeholder_event()
+    {
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("aad_placeholder_user_detected", Now.AddHours(-4),
+                data: new Dictionary<string, object> { ["placeholderType"] = "foouser" }),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.Equal("placeholder", (string?)obj["aadJoinState"]);
+    }
+
+    [Fact]
+    public void Build_classifies_real_user_state_from_aad_user_joined_late()
+    {
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("aad_user_joined_late", Now.AddHours(-3)),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.Equal("real_user", (string?)obj["aadJoinState"]);
+    }
+
+    [Fact]
+    public void Build_aad_user_join_slot_is_satisfied_by_part_1_event()
+    {
+        // Codex review 2026-05-01 (Finding 1): the dual-emitted informational event
+        // is what makes this work. Before the fix, AadJoinWatcherAdapter only posted
+        // a DecisionSignal — HandleAadUserJoinedLateV1 emits no timeline effect, so
+        // the Events table never held an aad_user_joined_late row. The snapshot then
+        // always marked it missing AND classified aadJoinState as placeholder/unknown
+        // even on healthy real-user joins.
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("aad_user_joined_late", Now.AddHours(-3)),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        var missing = obj["missingSignals"]!.ToObject<List<string>>()!;
+        Assert.DoesNotContain("aad_user_join", missing);          // slot satisfied
+        Assert.DoesNotContain("aad_user_joined_late", missing);   // literal must never appear
+    }
+
+    [Fact]
+    public void Build_aad_user_join_slot_is_satisfied_by_part_2_event()
+    {
+        // Codex review 2026-05-01 (Finding 4): Part 2 (post-reboot user sign-in) emits
+        // user_aad_signin_complete instead of aad_user_joined_late. Both must satisfy
+        // the same conceptual slot — analog to hello_terminal admitting any of the
+        // four Hello terminal event types. Without the new branch, every healthy Part-2
+        // session would falsely list aad_user_joined_late as missing.
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("user_aad_signin_complete", Now.AddHours(-3)),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.Equal("real_user", (string?)obj["aadJoinState"]);
+
+        var missing = obj["missingSignals"]!.ToObject<List<string>>()!;
+        Assert.DoesNotContain("aad_user_join", missing);              // slot satisfied
+        Assert.DoesNotContain("aad_user_joined_late", missing);       // literal must never appear
+        Assert.DoesNotContain("user_aad_signin_complete", missing);   // ditto
+    }
+
+    [Fact]
+    public void Build_aad_user_join_slot_is_listed_missing_when_neither_part_event_present()
+    {
+        // The trigger session e58bcfdb saw no real-user join at all — the slot must
+        // be reported missing. Bare event list (just agent_started) keeps the test
+        // focused on the slot logic; the e58bcfdb-replay test below covers the
+        // realistic full anchor set.
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("agent_started", Now.AddHours(-5)),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        var missing = obj["missingSignals"]!.ToObject<List<string>>()!;
+        Assert.Contains("aad_user_join", missing);
+    }
+
+    [Fact]
+    public void Build_falls_back_to_aad_join_status_isFooUser_when_only_that_is_present()
+    {
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("aad_join_status", Now.AddHours(-4),
+                data: new Dictionary<string, object> { ["isFooUser"] = "true" }),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.Equal("placeholder", (string?)obj["aadJoinState"]);
+    }
+
+    [Fact]
+    public void Build_real_user_event_overrides_earlier_placeholder()
+    {
+        // The temporal pattern in Hybrid User-Driven: foo desktop appears (placeholder),
+        // reboot, real user signs in (real_user). Snapshot should report the LATEST state.
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("aad_placeholder_user_detected", Now.AddHours(-5)),
+            Event("aad_user_joined_late", Now.AddHours(-3)),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.Equal("real_user", (string?)obj["aadJoinState"]);
+    }
+
+    // ============================================================================
+    // Reboot + Hybrid context
+    // ============================================================================
+
+    [Fact]
+    public void Build_records_reboot_observation_and_hybrid_flag()
+    {
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("autopilot_profile", Now.AddHours(-5),
+                data: new Dictionary<string, object> { ["isHybridJoin"] = "true", ["enrollmentType"] = "v1" }),
+            Event("system_reboot_detected", Now.AddHours(-4)),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.True((bool)obj["rebootObserved"]!);
+        Assert.True((bool)obj["isHybridJoin"]!);
+        Assert.Equal("v1", (string?)obj["enrollmentType"]);
+    }
+
+    // ============================================================================
+    // Missing-signal computation — the diagnostic core of the snapshot
+    // ============================================================================
+
+    [Fact]
+    public void Build_lists_missing_signals_for_e58bcfdb_style_session()
+    {
+        // Replays the canonical anchors from session e58bcfdb-… (the trigger session for
+        // this fix). Confirms the snapshot would have surfaced exactly the gaps we
+        // identified in the diagnosis: no esp_exiting, no hello terminal, no
+        // aad_user_joined_late, no enrollment_complete.
+        var t0 = new DateTime(2026, 5, 1, 13, 45, 31, DateTimeKind.Utc);
+        var nowAtTimeout = t0.AddHours(5);
+
+        var events = new[]
+        {
+            Event("agent_started", t0),
+            Event("autopilot_profile", t0.AddSeconds(1),
+                data: new Dictionary<string, object> { ["isHybridJoin"] = "true", ["enrollmentType"] = "v1" }),
+            Event("esp_phase_changed", t0.AddSeconds(2),
+                data: new Dictionary<string, object> { ["espPhase"] = "DeviceSetup" }),
+            Event("aad_join_status", t0.AddSeconds(2),
+                data: new Dictionary<string, object> { ["isFooUser"] = "true" }),
+            Event("esp_phase_changed", t0.AddSeconds(3),
+                data: new Dictionary<string, object> { ["espPhase"] = "AccountSetup" }),
+            Event("desktop_arrived", t0.AddSeconds(6)),
+            Event("system_reboot_detected", t0.AddMinutes(25).AddSeconds(53)),
+        };
+
+        var json = FailureSnapshotBuilder.Build(events, nowAtTimeout);
+        var obj = JObject.Parse(json!);
+
+        var missing = obj["missingSignals"]!.ToObject<List<string>>()!;
+        Assert.Contains("esp_exiting", missing);
+        Assert.Contains("hello_policy_detected", missing);
+        Assert.Contains("hello_terminal", missing);
+        Assert.Contains("aad_user_join", missing);  // conceptual slot — Part 1 OR Part 2
+        Assert.Contains("enrollment_complete", missing);
+
+        // Things the session DID see should NOT be in the missing list.
+        Assert.DoesNotContain("esp_phase_changed", missing);
+        Assert.DoesNotContain("desktop_arrived", missing);
+
+        // Slot label is the conceptual name; the literal Part 1 / Part 2 event-type
+        // names must NOT appear directly in missingSignals (that would double-count).
+        Assert.DoesNotContain("aad_user_joined_late", missing);
+        Assert.DoesNotContain("user_aad_signin_complete", missing);
+
+        // High-level diagnostic fields render correctly.
+        Assert.Equal("AccountSetup", (string?)obj["lastEspPhase"]);
+        Assert.True((bool)obj["desktopArrived"]!);
+        Assert.True((bool)obj["rebootObserved"]!);
+        Assert.True((bool)obj["isHybridJoin"]!);
+        Assert.Equal("placeholder", (string?)obj["aadJoinState"]);
+    }
+
+    [Fact]
+    public void Build_treats_any_hello_terminal_as_satisfying_the_slot()
+    {
+        // hello_terminal is the conceptual slot — any of {completed, failed, blocked, skipped}
+        // satisfies it. Tested with hello_skipped which is the most common Hybrid path.
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("hello_skipped", Now.AddHours(-4)),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        var missing = obj["missingSignals"]!.ToObject<List<string>>()!;
+        Assert.DoesNotContain("hello_terminal", missing);
+    }
+
+    // ============================================================================
+    // Timing / stale silence
+    // ============================================================================
+
+    [Fact]
+    public void Build_computes_silenceMinutes_from_last_event_to_now()
+    {
+        var t = Now.AddHours(-3); // last event was 3h ago
+        var json = FailureSnapshotBuilder.Build(new[] { Event("agent_started", t) }, Now);
+
+        var obj = JObject.Parse(json!);
+        var silence = (int)obj["silenceMinutes"]!;
+        Assert.InRange(silence, 179, 181);
+    }
+
+    [Fact]
+    public void Build_handles_unsorted_input_via_secondary_sort()
+    {
+        // The contract says events come sorted, but the builder defensively re-sorts.
+        var t0 = Now.AddHours(-5);
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            Event("esp_phase_changed", t0.AddSeconds(3),
+                data: new Dictionary<string, object> { ["espPhase"] = "AccountSetup" }),
+            Event("esp_phase_changed", t0.AddSeconds(1),
+                data: new Dictionary<string, object> { ["espPhase"] = "DeviceSetup" }),
+        }, Now);
+
+        var obj = JObject.Parse(json!);
+        Assert.Equal("AccountSetup", (string?)obj["lastEspPhase"]);
+    }
+
+    [Fact]
+    public void Build_tolerates_events_with_null_or_missing_data()
+    {
+        // Events stored before the Data field was added still have to parse cleanly.
+        var json = FailureSnapshotBuilder.Build(new[]
+        {
+            new EnrollmentEvent { EventType = "agent_started", Timestamp = Now.AddHours(-5), Source = "test", Data = null! },
+        }, Now);
+
+        Assert.NotNull(json);
+        var obj = JObject.Parse(json!);
+        Assert.Equal(1, (int)obj["eventCount"]!);
+    }
+}
diff --git a/src/Backend/AutopilotMonitor.Functions/DataAccess/TableStorage/TableSessionRepository.cs b/src/Backend/AutopilotMonitor.Functions/DataAccess/TableStorage/TableSessionRepository.cs
index af609be1..27cbc8e3 100644
--- a/src/Backend/AutopilotMonitor.Functions/DataAccess/TableStorage/TableSessionRepository.cs
+++ b/src/Backend/AutopilotMonitor.Functions/DataAccess/TableStorage/TableSessionRepository.cs
@@ -49,11 +49,13 @@ namespace AutopilotMonitor.Functions.DataAccess.TableStorage
             DateTime? latestEventTimestamp = null, bool? isPreProvisioned = null,
             bool? isUserDriven = null, DateTime? resumedAt = null,
             DateTime? stalledAt = null, bool clearStalledAt = false, bool clearFailureReason = false,
-            string? failureSource = null, string? adminMarkedAction = null)
+            string? failureSource = null, string? adminMarkedAction = null,
+            string? failureSnapshotJson = null)
             => _storage.UpdateSessionStatusAsync(tenantId, sessionId, status,
                 currentPhase, failureReason, completedAt, earliestEventTimestamp,
                 latestEventTimestamp, isPreProvisioned, isUserDriven, resumedAt,
-                stalledAt, clearStalledAt, clearFailureReason, failureSource, adminMarkedAction);
+                stalledAt, clearStalledAt, clearFailureReason, failureSource, adminMarkedAction,
+                failureSnapshotJson);
 
         public Task<bool> QueueServerActionAsync(string tenantId, string sessionId, ServerAction action)
             => _storage.QueueServerActionAsync(tenantId, sessionId, action);
diff --git a/src/Backend/AutopilotMonitor.Functions/Services/FailureSnapshotBuilder.cs b/src/Backend/AutopilotMonitor.Functions/Services/FailureSnapshotBuilder.cs
new file mode 100644
index 00000000..848546f8
--- /dev/null
+++ b/src/Backend/AutopilotMonitor.Functions/Services/FailureSnapshotBuilder.cs
@@ -0,0 +1,234 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using AutopilotMonitor.Shared.Models;
+using Newtonsoft.Json;
+
+namespace AutopilotMonitor.Functions.Services
+{
+    /// <summary>
+    /// Builds a compact JSON snapshot of "what we last knew about the session" at the
+    /// moment the maintenance watchdog times it out. Hybrid User-Driven completion-gap
+    /// fix (2026-05-01 trigger: session e58bcfdb-3e68-4f23-a3c2-437429ca9e78). Today's
+    /// 5h-timeout failure reason is just the literal string "Session timed out after 5
+    /// hours" — that gives operators no insight into where the session was stuck. This
+    /// builder walks the session's events and extracts the canonical lifecycle anchors
+    /// (last ESP phase, desktop arrival, Hello policy, AAD-join state, network state,
+    /// reboot observation) plus a list of MISSING signals so the snapshot answers
+    /// "why did this not complete?" at a glance.
+    /// <para>
+    /// The shape is intentionally flat and small (≤ ~1 KB JSON typical) so it fits in a
+    /// single Sessions-table column without strangling Storage costs. Schema is versioned
+    /// so the Web UI can render forward-compatibly.
+    /// </para>
+    /// </summary>
+    public static class FailureSnapshotBuilder
+    {
+        public const int CurrentSchemaVersion = 1;
+
+        // Canonical signals we expect to have seen by the time a healthy session completes.
+        // Missing entries are surfaced in the snapshot under "missingSignals". Some entries
+        // are conceptual slots that admit multiple concrete event types (see special-case
+        // branches in Build): "hello_terminal" is satisfied by any Hello terminal event,
+        // and "aad_user_join" by either the Part 1 (aad_user_joined_late) or Part 2
+        // (user_aad_signin_complete) real-user event.
+        private static readonly string[] CanonicalCompletionSignals =
+        {
+            "esp_phase_changed",
+            "esp_exiting",
+            "desktop_arrived",
+            "hello_policy_detected",
+            "hello_provisioning_completed", // OR _failed / _blocked / _skipped — emitted as "hello_terminal" slot
+            "aad_user_joined_late",         // OR user_aad_signin_complete — emitted as "aad_user_join" slot
+            "enrollment_complete",
+        };
+
+        /// <summary>
+        /// Build a snapshot from a session's chronological event list. Returns
+        /// <c>null</c> when the input is empty (caller should write nothing rather than
+        /// the literal "{}"). All inputs are tolerated — missing/malformed event data is
+        /// recorded as "unknown" rather than causing the maintenance pass to throw.
+        /// </summary>
+        public static string? Build(IReadOnlyList<EnrollmentEvent>? events, DateTime nowUtc)
+        {
+            if (events == null || events.Count == 0)
+                return null;
+
+            // Events arrive sorted by Sequence (ascending) per ISessionRepository contract.
+            // Defensive copy + secondary sort by Timestamp keeps the snapshot stable even
+            // if the caller passes an unsorted list.
+            var ordered = events.OrderBy(e => e.Timestamp).ToList();
+
+            var seenTypes = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
+            foreach (var evt in ordered) seenTypes.Add(evt.EventType ?? "");
+
+            // ---- Last ESP phase (from esp_phase_changed events) ------------------------
+            string? lastEspPhase = null;
+            DateTime? lastEspPhaseAt = null;
+            foreach (var evt in ordered)
+            {
+                if (string.Equals(evt.EventType, "esp_phase_changed", StringComparison.OrdinalIgnoreCase))
+                {
+                    lastEspPhase = TryGetDataString(evt, "espPhase") ?? lastEspPhase;
+                    lastEspPhaseAt = evt.Timestamp;
+                }
+            }
+
+            // ---- Desktop arrival -------------------------------------------------------
+            var desktopArrivedEvt = ordered.FirstOrDefault(e =>
+                string.Equals(e.EventType, "desktop_arrived", StringComparison.OrdinalIgnoreCase));
+            var desktopArrived = desktopArrivedEvt != null;
+            DateTime? desktopArrivedAt = desktopArrivedEvt?.Timestamp;
+
+            // ---- Hello policy ----------------------------------------------------------
+            var helloPolicyEvt = ordered.FirstOrDefault(e =>
+                string.Equals(e.EventType, "hello_policy_detected", StringComparison.OrdinalIgnoreCase));
+            bool? helloPolicyEnabled = null;
+            if (helloPolicyEvt != null)
+            {
+                var raw = TryGetDataString(helloPolicyEvt, "helloEnabled");
+                if (bool.TryParse(raw, out var parsed)) helloPolicyEnabled = parsed;
+            }
+
+            // ---- AAD join state — placeholder vs real user vs unknown ------------------
+            // Sources (newest wins):
+            //   - aad_placeholder_user_detected → placeholder
+            //   - aad_user_joined_late          → real_user (Part 1 path)
+            //   - user_aad_signin_complete      → real_user (Part 2 path; future)
+            //   - aad_join_status               → fallback heuristic via isFooUser flag
+            string aadJoinState = "unknown";
+            DateTime? aadJoinStateAt = null;
+            foreach (var evt in ordered)
+            {
+                var et = evt.EventType ?? "";
+                if (string.Equals(et, "aad_placeholder_user_detected", StringComparison.OrdinalIgnoreCase))
+                {
+                    aadJoinState = "placeholder";
+                    aadJoinStateAt = evt.Timestamp;
+                }
+                else if (string.Equals(et, "aad_user_joined_late", StringComparison.OrdinalIgnoreCase)
+                         || string.Equals(et, "user_aad_signin_complete", StringComparison.OrdinalIgnoreCase))
+                {
+                    aadJoinState = "real_user";
+                    aadJoinStateAt = evt.Timestamp;
+                }
+                else if (aadJoinState == "unknown"
+                         && string.Equals(et, "aad_join_status", StringComparison.OrdinalIgnoreCase))
+                {
+                    var isFoo = TryGetDataString(evt, "isFooUser");
+                    if (bool.TryParse(isFoo, out var foo))
+                    {
+                        aadJoinState = foo ? "placeholder" : "real_user";
+                        aadJoinStateAt = evt.Timestamp;
+                    }
+                }
+            }
+
+            // ---- Reboot observed -------------------------------------------------------
+            var rebootEvt = ordered.FirstOrDefault(e =>
+                string.Equals(e.EventType, "system_reboot_detected", StringComparison.OrdinalIgnoreCase));
+            var rebootObserved = rebootEvt != null;
+
+            // ---- Hybrid-join hint from autopilot_profile / enrollment_type_detected ----
+            bool? isHybridJoin = null;
+            string? enrollmentType = null;
+            foreach (var evt in ordered)
+            {
+                var et = evt.EventType ?? "";
+                if (string.Equals(et, "autopilot_profile", StringComparison.OrdinalIgnoreCase)
+                    || string.Equals(et, "enrollment_facts_observed", StringComparison.OrdinalIgnoreCase))
+                {
+                    var hybridRaw = TryGetDataString(evt, "isHybridJoin");
+                    if (bool.TryParse(hybridRaw, out var h)) isHybridJoin = h;
+                    enrollmentType ??= TryGetDataString(evt, "enrollmentType");
+                }
+                else if (enrollmentType == null
+                         && string.Equals(et, "enrollment_type_detected", StringComparison.OrdinalIgnoreCase))
+                {
+                    enrollmentType = TryGetDataString(evt, "enrollmentType");
+                }
+            }
+
+            // ---- Last network state ----------------------------------------------------
+            string? lastNetworkState = null;
+            for (var i = ordered.Count - 1; i >= 0; i--)
+            {
+                if (string.Equals(ordered[i].EventType, "network_state_change", StringComparison.OrdinalIgnoreCase))
+                {
+                    lastNetworkState = ordered[i].Message;
+                    break;
+                }
+            }
+
+            // ---- Timing facts ----------------------------------------------------------
+            var lastEventAt = ordered[ordered.Count - 1].Timestamp;
+            var silenceMinutes = (int)Math.Max(0, (nowUtc - lastEventAt).TotalMinutes);
+
+            // ---- Missing canonical signals --------------------------------------------
+            var missing = new List<string>();
+            foreach (var sig in CanonicalCompletionSignals)
+            {
+                if (sig == "hello_provisioning_completed")
+                {
+                    // Treat any Hello terminal as satisfying this slot.
+                    if (!seenTypes.Contains("hello_provisioning_completed")
+                        && !seenTypes.Contains("hello_provisioning_failed")
+                        && !seenTypes.Contains("hello_provisioning_blocked")
+                        && !seenTypes.Contains("hello_skipped"))
+                    {
+                        missing.Add("hello_terminal");
+                    }
+                }
+                else if (sig == "aad_user_joined_late")
+                {
+                    // Codex review 2026-05-01: Part 1 (Classic / WhiteGlove) emits
+                    // aad_user_joined_late; Part 2 (post-reboot user sign-in) emits
+                    // user_aad_signin_complete. Both satisfy the same conceptual slot.
+                    // Without this branch, every healthy Part-2 session would falsely
+                    // list aad_user_joined_late as missing even though aadJoinState
+                    // is correctly classified as real_user above.
+                    if (!seenTypes.Contains("aad_user_joined_late")
+                        && !seenTypes.Contains("user_aad_signin_complete"))
+                    {
+                        missing.Add("aad_user_join");
+                    }
+                }
+                else if (!seenTypes.Contains(sig))
+                {
+                    missing.Add(sig);
+                }
+            }
+
+            var snapshot = new
+            {
+                schemaVersion = CurrentSchemaVersion,
+                generatedAtUtc = nowUtc.ToString("o"),
+                eventCount = ordered.Count,
+                lastEventAtUtc = lastEventAt.ToString("o"),
+                silenceMinutes,
+                lastEspPhase,
+                lastEspPhaseAtUtc = lastEspPhaseAt?.ToString("o"),
+                desktopArrived,
+                desktopArrivedAtUtc = desktopArrivedAt?.ToString("o"),
+                helloPolicyDetected = helloPolicyEvt != null,
+                helloPolicyEnabled,
+                aadJoinState,
+                aadJoinStateAtUtc = aadJoinStateAt?.ToString("o"),
+                rebootObserved,
+                isHybridJoin,
+                enrollmentType,
+                lastNetworkState,
+                missingSignals = missing,
+            };
+
+            return JsonConvert.SerializeObject(snapshot, Formatting.None);
+        }
+
+        private static string? TryGetDataString(EnrollmentEvent evt, string key)
+        {
+            if (evt?.Data == null) return null;
+            if (!evt.Data.TryGetValue(key, out var raw) || raw == null) return null;
+            return raw.ToString();
+        }
+    }
+}
diff --git a/src/Backend/AutopilotMonitor.Functions/Services/MaintenanceService.cs b/src/Backend/AutopilotMonitor.Functions/Services/MaintenanceService.cs
index 75b733bf..38f7ec4b 100644
--- a/src/Backend/AutopilotMonitor.Functions/Services/MaintenanceService.cs
+++ b/src/Backend/AutopilotMonitor.Functions/Services/MaintenanceService.cs
@@ -274,11 +274,31 @@ namespace AutopilotMonitor.Functions.Services
 
                         foreach (var session in stalledSessions)
                         {
+                            // Hybrid User-Driven completion-gap fix (2026-05-01): before
+                            // graduating the session to terminal Failed, build a compact
+                            // snapshot of "what we last knew" so operators don't have to
+                            // scroll through hundreds of events to reconstruct where the
+                            // session was stuck. Best-effort — a snapshot read failure
+                            // must never block the timeout transition itself.
+                            string? snapshotJson = null;
+                            try
+                            {
+                                var sessionEvents = await _sessionRepo.GetSessionEventsAsync(
+                                    session.TenantId, session.SessionId, maxResults: 1000);
+                                snapshotJson = FailureSnapshotBuilder.Build(sessionEvents, now);
+                            }
+                            catch (Exception snapEx)
+                            {
+                                _logger.LogWarning(snapEx,
+                                    $"Failed to build failure snapshot for session {session.SessionId}; proceeding with timeout transition without snapshot");
+                            }
+
                             await _sessionRepo.UpdateSessionStatusAsync(
                                 session.TenantId,
                                 session.SessionId,
                                 SessionStatus.Failed,
-                                failureReason: $"Session timed out after {timeoutHours} hours (started at {session.StartedAt:yyyy-MM-dd HH:mm:ss} UTC)"
+                                failureReason: $"Session timed out after {timeoutHours} hours (started at {session.StartedAt:yyyy-MM-dd HH:mm:ss} UTC)",
+                                failureSnapshotJson: snapshotJson
                             );
                             sessionCount++;
                         }
diff --git a/src/Backend/AutopilotMonitor.Functions/Services/TableStorageService.Sessions.cs b/src/Backend/AutopilotMonitor.Functions/Services/TableStorageService.Sessions.cs
index 4ca7a755..bbd5ffb4 100644
--- a/src/Backend/AutopilotMonitor.Functions/Services/TableStorageService.Sessions.cs
+++ b/src/Backend/AutopilotMonitor.Functions/Services/TableStorageService.Sessions.cs
@@ -249,7 +249,8 @@ namespace AutopilotMonitor.Functions.Services
                 GeoLoc = entity.GetString("GeoLoc") ?? string.Empty,
                 PlatformScriptCount = SafeGetInt32(entity, "PlatformScriptCount") ?? 0,
                 RemediationScriptCount = SafeGetInt32(entity, "RemediationScriptCount") ?? 0,
-                ExcessiveEventsAlerted = entity.GetBoolean("ExcessiveEventsAlerted") ?? false
+                ExcessiveEventsAlerted = entity.GetBoolean("ExcessiveEventsAlerted") ?? false,
+                FailureSnapshotJson = entity.GetString("FailureSnapshotJson") ?? string.Empty
             };
         }
 
@@ -963,7 +964,7 @@ namespace AutopilotMonitor.Functions.Services
         /// back to the session's LastEventAt and only to UtcNow as a last resort, so DurationSeconds
         /// reflects when the session went silent rather than when the operator clicked the button.
         /// </param>
-        public async Task<bool> UpdateSessionStatusAsync(string tenantId, string sessionId, SessionStatus status, EnrollmentPhase? currentPhase = null, string? failureReason = null, DateTime? completedAt = null, DateTime? earliestEventTimestamp = null, DateTime? latestEventTimestamp = null, bool? isPreProvisioned = null, bool? isUserDriven = null, DateTime? resumedAt = null, DateTime? stalledAt = null, bool clearStalledAt = false, bool clearFailureReason = false, string? failureSource = null, string? adminMarkedAction = null)
+        public async Task<bool> UpdateSessionStatusAsync(string tenantId, string sessionId, SessionStatus status, EnrollmentPhase? currentPhase = null, string? failureReason = null, DateTime? completedAt = null, DateTime? earliestEventTimestamp = null, DateTime? latestEventTimestamp = null, bool? isPreProvisioned = null, bool? isUserDriven = null, DateTime? resumedAt = null, DateTime? stalledAt = null, bool clearStalledAt = false, bool clearFailureReason = false, string? failureSource = null, string? adminMarkedAction = null, string? failureSnapshotJson = null)
         {
             SecurityValidator.EnsureValidGuid(tenantId, nameof(tenantId));
             SecurityValidator.EnsureValidGuid(sessionId, nameof(sessionId));
@@ -1109,6 +1110,16 @@ namespace AutopilotMonitor.Functions.Services
                         update["FailureReason"] = failureReason;
                     }
 
+                    // Persist the failure-state snapshot when provided. Only the maintenance
+                    // 5h-timeout path supplies this today (Hybrid User-Driven completion-gap
+                    // fix, 2026-05-01); other terminal paths leave the field untouched, which
+                    // is fine — null/empty means "no snapshot available" and the UI falls back
+                    // to the existing FailureReason rendering.
+                    if (status == SessionStatus.Failed && !string.IsNullOrEmpty(failureSnapshotJson))
+                    {
+                        update["FailureSnapshotJson"] = failureSnapshotJson;
+                    }
+
                     // Record the origin of a Failed status (agent / rule:<id> / manual). When the caller
                     // passes null we leave the existing value untouched — concurrent updates from different
                     // sources shouldn't stomp on each other's attribution.
@@ -1307,6 +1318,11 @@ namespace AutopilotMonitor.Functions.Services
                             if (status == SessionStatus.Failed && !string.IsNullOrEmpty(failureReason))
                                 forceUpdate["FailureReason"] = failureReason;
 
+                            // Mirror the FailureSnapshotJson from the regular path so the
+                            // force-merge fallback never silently drops the snapshot.
+                            if (status == SessionStatus.Failed && !string.IsNullOrEmpty(failureSnapshotJson))
+                                forceUpdate["FailureSnapshotJson"] = failureSnapshotJson;
+
                             if (isPreProvisioned.HasValue)
                                 forceUpdate["IsPreProvisioned"] = isPreProvisioned.Value;
 
@@ -1862,7 +1878,8 @@ namespace AutopilotMonitor.Functions.Services
                 GeoLoc = entity.GetString("GeoLoc") ?? string.Empty,
                 PlatformScriptCount = SafeGetInt32(entity, "PlatformScriptCount") ?? 0,
                 RemediationScriptCount = SafeGetInt32(entity, "RemediationScriptCount") ?? 0,
-                ExcessiveEventsAlerted = entity.GetBoolean("ExcessiveEventsAlerted") ?? false
+                ExcessiveEventsAlerted = entity.GetBoolean("ExcessiveEventsAlerted") ?? false,
+                FailureSnapshotJson = entity.GetString("FailureSnapshotJson") ?? string.Empty
             };
         }
 
diff --git a/src/Shared/AutopilotMonitor.Shared/Constants.cs b/src/Shared/AutopilotMonitor.Shared/Constants.cs
index 560697a3..70796e89 100644
--- a/src/Shared/AutopilotMonitor.Shared/Constants.cs
+++ b/src/Shared/AutopilotMonitor.Shared/Constants.cs
@@ -231,6 +231,19 @@ namespace AutopilotMonitor.Shared
 
             // TEMPORARY: shadow SM rollout verification — remove when CompletionStateMachine is promoted to primary
             public const string ShadowDiscrepancy         = "shadow_discrepancy";
+
+            // Hybrid User-Driven enrollment observability (V2 — Hybrid completion gaps, 2026-05-01).
+            // Pure observability — never consumed by the DecisionEngine, no DecisionSignalKind wired up.
+            public const string AadPlaceholderUserDetected = "aad_placeholder_user_detected"; // foouser@/autopilot@ first appearance in JoinInfo
+            public const string HybridLoginPending         = "hybrid_login_pending";          // Hybrid: 10 min after reboot still placeholder, real AD login overdue
+
+            // Real-user join — companion to AadPlaceholderUserDetected. The DecisionEngine consumes
+            // these as DecisionSignalKind only (HandleAadUserJoinedLateV1 is observation-only and
+            // emits no timeline effect), so the AadJoinWatcherAdapter dual-emits them as
+            // informational events too. Without this the FailureSnapshotBuilder cannot tell that
+            // the real AAD user was ever observed (Codex review 2026-05-01).
+            public const string AadUserJoinedLate          = "aad_user_joined_late";         // Real user replaces placeholder mid-session (Part 1 path)
+            public const string UserAadSignInComplete      = "user_aad_signin_complete";     // Real user signs in post-reboot (Part 2 path)
         }
 
         // -----------------------------------------------------------------------
diff --git a/src/Shared/AutopilotMonitor.Shared/DataAccess/ISessionRepository.cs b/src/Shared/AutopilotMonitor.Shared/DataAccess/ISessionRepository.cs
index 294075f3..f367d81f 100644
--- a/src/Shared/AutopilotMonitor.Shared/DataAccess/ISessionRepository.cs
+++ b/src/Shared/AutopilotMonitor.Shared/DataAccess/ISessionRepository.cs
@@ -27,7 +27,8 @@ namespace AutopilotMonitor.Shared.DataAccess
             DateTime? latestEventTimestamp = null, bool? isPreProvisioned = null,
             bool? isUserDriven = null, DateTime? resumedAt = null,
             DateTime? stalledAt = null, bool clearStalledAt = false, bool clearFailureReason = false,
-            string? failureSource = null, string? adminMarkedAction = null);
+            string? failureSource = null, string? adminMarkedAction = null,
+            string? failureSnapshotJson = null);
         Task IncrementSessionEventCountAsync(
             string tenantId, string sessionId, int increment,
             DateTime? earliestEventTimestamp = null, DateTime? latestEventTimestamp = null,
diff --git a/src/Shared/AutopilotMonitor.Shared/Models/SessionApiModels.cs b/src/Shared/AutopilotMonitor.Shared/Models/SessionApiModels.cs
index 29b5946f..5161402e 100644
--- a/src/Shared/AutopilotMonitor.Shared/Models/SessionApiModels.cs
+++ b/src/Shared/AutopilotMonitor.Shared/Models/SessionApiModels.cs
@@ -298,6 +298,18 @@ namespace AutopilotMonitor.Shared.Models
         /// on long-dead sessions.
         /// </summary>
         public DateTime? PendingActionsQueuedAt { get; set; }
+
+        /// <summary>
+        /// Compact JSON snapshot of "last known session state" written by the maintenance
+        /// 5h-timeout sweep when a session graduates to terminal Failed (Hybrid User-Driven
+        /// completion-gap fix, 2026-05-01). Captures the canonical lifecycle anchors —
+        /// last ESP phase, desktop arrival, Hello policy, AAD-join state, missing signals —
+        /// so operators don't have to scroll through hundreds of events to reconstruct
+        /// where a stuck session was when the watchdog fired. Empty / null on
+        /// healthy-completion paths and on sessions that predate the field. Built by
+        /// <see cref="AutopilotMonitor.Functions.Services.FailureSnapshotBuilder"/>.
+        /// </summary>
+        public string FailureSnapshotJson { get; set; } = string.Empty;
     }
 
     /// <summary>
diff --git a/src/Web/autopilot-monitor-web/app/sessions/[sessionId]/components/FailureSnapshotBlock.tsx b/src/Web/autopilot-monitor-web/app/sessions/[sessionId]/components/FailureSnapshotBlock.tsx
new file mode 100644
index 00000000..51d2c6fe
--- /dev/null
+++ b/src/Web/autopilot-monitor-web/app/sessions/[sessionId]/components/FailureSnapshotBlock.tsx
@@ -0,0 +1,133 @@
+"use client";
+
+import { useState } from "react";
+
+/**
+ * Renders the maintenance-built failure snapshot when present (Hybrid User-Driven
+ * completion-gap fix, 2026-05-01). The backend writes the JSON only on the 5h-timeout
+ * graduation path, so this block is hidden for healthy completions and for sessions
+ * that predate the field. The shape is best-effort — unknown fields are tolerated;
+ * legacy snapshots without `schemaVersion` simply render the fields they do carry.
+ */
+interface FailureSnapshot {
+  schemaVersion?: number;
+  generatedAtUtc?: string;
+  eventCount?: number;
+  lastEventAtUtc?: string;
+  silenceMinutes?: number;
+  lastEspPhase?: string | null;
+  lastEspPhaseAtUtc?: string | null;
+  desktopArrived?: boolean;
+  desktopArrivedAtUtc?: string | null;
+  helloPolicyDetected?: boolean;
+  helloPolicyEnabled?: boolean | null;
+  aadJoinState?: string;
+  aadJoinStateAtUtc?: string | null;
+  rebootObserved?: boolean;
+  isHybridJoin?: boolean | null;
+  enrollmentType?: string | null;
+  lastNetworkState?: string | null;
+  missingSignals?: string[];
+}
+
+export default function FailureSnapshotBlock({ failureSnapshotJson }: { failureSnapshotJson?: string }) {
+  const [expanded, setExpanded] = useState(false);
+
+  if (!failureSnapshotJson || failureSnapshotJson.trim().length === 0) return null;
+
+  let snapshot: FailureSnapshot | null = null;
+  try {
+    snapshot = JSON.parse(failureSnapshotJson) as FailureSnapshot;
+  } catch {
+    // Invalid JSON — render the raw string in a debug fallback so operators can still
+    // copy/paste it into a JSON formatter offline. No exception bubbles up to break
+    // the surrounding card.
+    return (
+      <div className="mt-4 p-3 rounded-lg bg-rose-50 border border-rose-200 text-sm text-rose-800">
+        <strong>Failure Snapshot (raw):</strong>
+        <pre className="mt-2 text-xs font-mono whitespace-pre-wrap break-all">{failureSnapshotJson}</pre>
+      </div>
+    );
+  }
+
+  const missing = snapshot.missingSignals ?? [];
+
+  return (
+    <div className="mt-4 rounded-lg bg-rose-50 border border-rose-200 text-sm text-rose-900">
+      <button
+        type="button"
+        className="w-full flex items-center justify-between px-3 py-2 text-left font-semibold"
+        onClick={() => setExpanded((e) => !e)}
+        aria-expanded={expanded}
+      >
+        <span className="flex items-center gap-2">
+          <svg className="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+            <path strokeLinecap="round" strokeLinejoin="round" strokeWidth={2} d="M12 9v2m0 4h.01m-6.938 4h13.856c1.54 0 2.502-1.667 1.732-2.5L13.732 4c-.77-.833-1.964-.833-2.732 0L4.082 16.5c-.77.833.192 2.5 1.732 2.5z" />
+          </svg>
+          Failure Snapshot {snapshot.silenceMinutes !== undefined && <span className="font-normal">(agent went silent {snapshot.silenceMinutes} min before timeout)</span>}
+        </span>
+        <svg className={`w-4 h-4 transition-transform ${expanded ? "rotate-180" : ""}`} fill="none" stroke="currentColor" viewBox="0 0 24 24">
+          <path strokeLinecap="round" strokeLinejoin="round" strokeWidth={2} d="M19 9l-7 7-7-7" />
+        </svg>
+      </button>
+      {expanded && (
+        <div className="px-3 pb-3 pt-1 space-y-2">
+          <div className="grid grid-cols-1 sm:grid-cols-2 gap-x-4 gap-y-1.5">
+            <SnapshotItem label="Last ESP phase" value={snapshot.lastEspPhase ?? "—"} sub={snapshot.lastEspPhaseAtUtc ?? undefined} />
+            <SnapshotItem label="Desktop arrived" value={fmtBool(snapshot.desktopArrived)} sub={snapshot.desktopArrivedAtUtc ?? undefined} />
+            <SnapshotItem label="Hello policy" value={fmtHelloPolicy(snapshot)} />
+            <SnapshotItem label="AAD join state" value={snapshot.aadJoinState ?? "unknown"} sub={snapshot.aadJoinStateAtUtc ?? undefined} />
+            <SnapshotItem label="Reboot observed" value={fmtBool(snapshot.rebootObserved)} />
+            <SnapshotItem label="Hybrid AAD join" value={snapshot.isHybridJoin === null || snapshot.isHybridJoin === undefined ? "unknown" : fmtBool(snapshot.isHybridJoin)} />
+            <SnapshotItem label="Enrollment type" value={snapshot.enrollmentType ?? "unknown"} />
+            <SnapshotItem label="Event count" value={snapshot.eventCount?.toString() ?? "—"} />
+            {snapshot.lastNetworkState && (
+              <SnapshotItem label="Last network state" value={snapshot.lastNetworkState} className="sm:col-span-2" />
+            )}
+          </div>
+          {missing.length > 0 && (
+            <div className="pt-2">
+              <div className="text-xs font-semibold text-rose-800 mb-1">Missing canonical signals at timeout:</div>
+              <div className="flex flex-wrap gap-1.5">
+                {missing.map((sig) => (
+                  <span key={sig} className="inline-flex items-center px-2 py-0.5 text-xs font-mono rounded bg-white border border-rose-300 text-rose-800">
+                    {sig}
+                  </span>
+                ))}
+              </div>
+            </div>
+          )}
+          {snapshot.generatedAtUtc && (
+            <div className="text-xs text-rose-700 pt-1">
+              Snapshot generated {new Date(snapshot.generatedAtUtc).toLocaleString()}
+              {snapshot.schemaVersion !== undefined && <> · schema v{snapshot.schemaVersion}</>}
+            </div>
+          )}
+        </div>
+      )}
+    </div>
+  );
+}
+
+function SnapshotItem({ label, value, sub, className }: { label: string; value: React.ReactNode; sub?: string; className?: string }) {
+  return (
+    <div className={className}>
+      <div className="text-xs font-semibold text-rose-800">{label}</div>
+      <div className="text-sm text-rose-900 break-words">{value}</div>
+      {sub && <div className="text-[11px] text-rose-700 font-mono">{sub}</div>}
+    </div>
+  );
+}
+
+function fmtBool(v: boolean | undefined | null) {
+  if (v === true) return "yes";
+  if (v === false) return "no";
+  return "unknown";
+}
+
+function fmtHelloPolicy(s: FailureSnapshot): string {
+  if (!s.helloPolicyDetected) return "not detected";
+  if (s.helloPolicyEnabled === true) return "detected (enabled)";
+  if (s.helloPolicyEnabled === false) return "detected (disabled)";
+  return "detected";
+}
diff --git a/src/Web/autopilot-monitor-web/app/sessions/[sessionId]/components/SessionInfoCard.tsx b/src/Web/autopilot-monitor-web/app/sessions/[sessionId]/components/SessionInfoCard.tsx
index 9b58076e..23a22ecd 100644
--- a/src/Web/autopilot-monitor-web/app/sessions/[sessionId]/components/SessionInfoCard.tsx
+++ b/src/Web/autopilot-monitor-web/app/sessions/[sessionId]/components/SessionInfoCard.tsx
@@ -2,6 +2,7 @@
 
 import { useState } from "react";
 import { Session } from "@/types";
+import FailureSnapshotBlock from "./FailureSnapshotBlock";
 
 interface SessionInfoCardProps {
   session: Session;
@@ -81,6 +82,7 @@ export default function SessionInfoCard({ session, enrollmentDuration, displaySt
           </span>
         </div>
       )}
+      <FailureSnapshotBlock failureSnapshotJson={session.failureSnapshotJson} />
     </div>
   );
 }
diff --git a/src/Web/autopilot-monitor-web/types/session.ts b/src/Web/autopilot-monitor-web/types/session.ts
index 71cd7945..c8aaf4fa 100644
--- a/src/Web/autopilot-monitor-web/types/session.ts
+++ b/src/Web/autopilot-monitor-web/types/session.ts
@@ -33,4 +33,12 @@ export interface Session {
   geoCountry?: string;
   geoRegion?: string;
   geoCity?: string;
+  /**
+   * Compact JSON snapshot of "last known session state" written by the maintenance
+   * 5h-timeout sweep when a session graduates to terminal Failed (Hybrid User-Driven
+   * completion-gap fix, 2026-05-01). Empty for healthy completions and sessions that
+   * predate the field. The detail page renders a collapsible "Failure Snapshot" block
+   * when populated.
+   */
+  failureSnapshotJson?: string;
 }