diff --git a/src/Agent/AutopilotMonitor.Agent.Core.Tests/Tracking/CompletionStateMachineTests.cs b/src/Agent/AutopilotMonitor.Agent.Core.Tests/Tracking/CompletionStateMachineTests.cs
index acd71c8d..57d497ce 100644
--- a/src/Agent/AutopilotMonitor.Agent.Core.Tests/Tracking/CompletionStateMachineTests.cs
+++ b/src/Agent/AutopilotMonitor.Agent.Core.Tests/Tracking/CompletionStateMachineTests.cs
@@ -1072,5 +1072,64 @@ namespace AutopilotMonitor.Agent.Core.Tests.Tracking
         {
             Assert.False(EnrollmentCompletionState.EspActive.IsWaiting());
         }
+
+        // ===== SECTION 5: Drift regression tests =====
+        // Repro for session 1fda3b0a-e586-4980-bc90-491e4e8ca870:
+        // ESP phase events were not persisted before reboot, so SM was restored with
+        // espEverSeen=false. Subsequent esp_exiting + desktop_arrived must not complete
+        // the SM prematurely — the ProcessTrigger snapshot sync lifts the missing flags
+        // from the context (the authoritative tracker state).
+
+        [Fact]
+        public void Drift_RestoredWithoutEspEverSeen_EspExitingSyncsFromContext()
+        {
+            var sm = new CompletionStateMachine();
+            sm.RestoreState(EnrollmentCompletionState.Idle,
+                espEverSeen: false, espFinalExitSeen: false, desktopArrived: false,
+                isWaitingForHello: false, isWaitingForEspSettle: false, deferredSource: null);
+
+            // ctx says ESP was seen (real tracker is the source of truth).
+            // Hello policy IS configured but not yet completed — must wait, not complete.
+            var ctx = DefaultContext(
+                lastEspPhase: "AccountSetup",
+                isHelloPolicyConfigured: true,
+                isHelloCompleted: false);
+            ctx.EspEverSeen = true;
+            ctx.EspFinalExitSeen = false;
+
+            var result = sm.ProcessTrigger("esp_exiting", ctx);
+
+            Assert.True(result.Transitioned);
+            Assert.NotEqual(EnrollmentCompletionState.Completed, sm.CurrentState);
+            Assert.False(result.ShouldEmitEnrollmentComplete);
+            Assert.True(sm.EspEverSeen, "SM must lift _espEverSeen from ctx via the sync block");
+            Assert.True(sm.EspFinalExitSeen, "esp_exiting Path A must mark final exit");
+        }
+
+        [Fact]
+        public void Drift_RestoredWithoutEspEverSeen_DesktopArrivedRoutesToEspBlocking()
+        {
+            // The exact scenario from session 1fda3b0a-e586-4980-bc90-491e4e8ca870 at 06:05:41:
+            // SM restored with espEverSeen=false, but ctx says ESP IS active.
+            // Pre-fix: SM took the "no ESP" else branch and reached Completed.
+            // Post-fix: sync block lifts _espEverSeen from ctx, SM correctly routes to
+            // DesktopArrivedEspBlocking.
+            var sm = new CompletionStateMachine();
+            sm.RestoreState(EnrollmentCompletionState.Idle,
+                espEverSeen: false, espFinalExitSeen: false, desktopArrived: false,
+                isWaitingForHello: false, isWaitingForEspSettle: false, deferredSource: null);
+
+            var ctx = DefaultContext(
+                isHelloPolicyConfigured: true,
+                isHelloCompleted: false);
+            ctx.EspEverSeen = true;
+            ctx.EspFinalExitSeen = false;
+
+            var result = sm.ProcessTrigger("desktop_arrived", ctx);
+
+            Assert.NotEqual(EnrollmentCompletionState.Completed, sm.CurrentState);
+            Assert.Equal(EnrollmentCompletionState.DesktopArrivedEspBlocking, sm.CurrentState);
+            Assert.False(result.ShouldEmitEnrollmentComplete);
+        }
     }
 }
diff --git a/src/Agent/AutopilotMonitor.Agent.Core/Monitoring/Tracking/CompletionStateMachine.cs b/src/Agent/AutopilotMonitor.Agent.Core/Monitoring/Tracking/CompletionStateMachine.cs
index 865de651..ad1157b1 100644
--- a/src/Agent/AutopilotMonitor.Agent.Core/Monitoring/Tracking/CompletionStateMachine.cs
+++ b/src/Agent/AutopilotMonitor.Agent.Core/Monitoring/Tracking/CompletionStateMachine.cs
@@ -181,6 +181,20 @@ namespace AutopilotMonitor.Agent.Core.Monitoring.Tracking
 
             lock (_lock)
             {
+                // Sync internal signal flags from the authoritative tracker snapshot.
+                // Monoton false→true: these signals are stable-once-seen. The single
+                // intentional reset (HandleEspResumed clearing _espFinalExitSeen) runs
+                // AFTER this sync inside its own switch case, so it remains the last writer.
+                // Without this, the SM can drift from the tracker (e.g. when
+                // _stateData.EspEverSeen=true was set in memory but Save() hadn't run
+                // before a reboot — restore loads false and downstream guards misfire).
+                if (ctx != null)
+                {
+                    if (ctx.EspEverSeen)      _espEverSeen = true;
+                    if (ctx.EspFinalExitSeen) _espFinalExitSeen = true;
+                    if (ctx.DesktopArrived)   _desktopArrived = true;
+                }
+
                 // Terminal states: no transitions allowed
                 if (_currentState.IsTerminal())
                     return TransitionResult.NoTransition;
diff --git a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
index 4524e19e..45b0f829 100644
--- a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
+++ b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
@@ -1 +1 @@
-984
+987