diff --git a/src/Backend/AutopilotMonitor.Functions.Tests/RuleEngineDataPathResolverTests.cs b/src/Backend/AutopilotMonitor.Functions.Tests/RuleEngineDataPathResolverTests.cs
new file mode 100644
index 00000000..a88f9b04
--- /dev/null
+++ b/src/Backend/AutopilotMonitor.Functions.Tests/RuleEngineDataPathResolverTests.cs
@@ -0,0 +1,111 @@
+using System.Text.Json;
+using AutopilotMonitor.Functions.Services;
+
+namespace AutopilotMonitor.Functions.Tests;
+
+/// <summary>
+/// Unit tests for the dot-path resolver inside <see cref="RuleEngine.GetDataFieldValue"/>.
+/// Exercises both nested <c>Dictionary&lt;string,object&gt;</c> and <see cref="JsonElement"/>
+/// payload shapes — both occur in production depending on whether the event came in via
+/// the in-process emitter (typed sidecar) or was rehydrated from Table Storage JSON.
+/// </summary>
+public class RuleEngineDataPathResolverTests
+{
+    [Fact]
+    public void TryFlatLookup_LiteralKeyWithDot_StillResolves()
+    {
+        // Pre-existing v1 events used keys like "scan_summary.critical_cves" with a literal
+        // dot. The flat lookup must keep working so legacy rules don't break.
+        var data = new Dictionary<string, object>
+        {
+            ["scan_summary.critical_cves"] = 7,
+        };
+
+        var ok = RuleEngine.TryFlatLookup(data, "scan_summary.critical_cves", out var value);
+
+        Assert.True(ok);
+        Assert.Equal("7", value);
+    }
+
+    [Fact]
+    public void TryFlatLookup_CaseInsensitive()
+    {
+        var data = new Dictionary<string, object> { ["FailedSubcategories"] = "Certificates,VPN" };
+
+        var ok = RuleEngine.TryFlatLookup(data, "failedsubcategories", out var value);
+
+        Assert.True(ok);
+        Assert.Equal("Certificates,VPN", value);
+    }
+
+    [Fact]
+    public void ResolveDotPath_NestedDictionary_ReturnsLeafScalar()
+    {
+        var data = new Dictionary<string, object>
+        {
+            ["scan_summary"] = new Dictionary<string, object>
+            {
+                ["critical_cves"] = 3,
+                ["overall_risk"] = "high",
+            },
+        };
+
+        Assert.Equal("3", RuleEngine.ResolveDotPath(data, "scan_summary.critical_cves"));
+        Assert.Equal("high", RuleEngine.ResolveDotPath(data, "scan_summary.overall_risk"));
+    }
+
+    [Fact]
+    public void ResolveDotPath_NestedJsonElement_ReturnsLeafScalar()
+    {
+        // Events read back from Table Storage hit the resolver as JsonElement subtrees.
+        var json = """{"scan_summary":{"critical_cves":5,"kev_matches":2,"overall_risk":"critical"}}""";
+        using var doc = JsonDocument.Parse(json);
+        var data = new Dictionary<string, object>
+        {
+            ["scan_summary"] = doc.RootElement.GetProperty("scan_summary").Clone(),
+        };
+
+        Assert.Equal("5", RuleEngine.ResolveDotPath(data, "scan_summary.critical_cves"));
+        Assert.Equal("2", RuleEngine.ResolveDotPath(data, "scan_summary.kev_matches"));
+        Assert.Equal("critical", RuleEngine.ResolveDotPath(data, "scan_summary.overall_risk"));
+    }
+
+    [Fact]
+    public void ResolveDotPath_CaseInsensitiveAtEachLevel()
+    {
+        var data = new Dictionary<string, object>
+        {
+            ["Scan_Summary"] = new Dictionary<string, object>
+            {
+                ["Critical_CVEs"] = 4,
+            },
+        };
+
+        Assert.Equal("4", RuleEngine.ResolveDotPath(data, "scan_summary.critical_cves"));
+    }
+
+    [Fact]
+    public void ResolveDotPath_MissingPath_ReturnsNull()
+    {
+        var data = new Dictionary<string, object>
+        {
+            ["scan_summary"] = new Dictionary<string, object> { ["critical_cves"] = 1 },
+        };
+
+        Assert.Null(RuleEngine.ResolveDotPath(data, "scan_summary.missing"));
+        Assert.Null(RuleEngine.ResolveDotPath(data, "missing.critical_cves"));
+    }
+
+    [Fact]
+    public void ResolveDotPath_DescendIntoScalar_ReturnsNull()
+    {
+        // Path traverses past a scalar — must not throw, must return null so the rule
+        // misses cleanly instead of stringifying an unrelated value.
+        var data = new Dictionary<string, object>
+        {
+            ["scan_summary"] = "not-an-object",
+        };
+
+        Assert.Null(RuleEngine.ResolveDotPath(data, "scan_summary.critical_cves"));
+    }
+}
diff --git a/src/Backend/AutopilotMonitor.Functions/Services/EventIngestProcessor.cs b/src/Backend/AutopilotMonitor.Functions/Services/EventIngestProcessor.cs
index 29661fde..cfdf0a9e 100644
--- a/src/Backend/AutopilotMonitor.Functions/Services/EventIngestProcessor.cs
+++ b/src/Backend/AutopilotMonitor.Functions/Services/EventIngestProcessor.cs
@@ -344,6 +344,24 @@ namespace AutopilotMonitor.Functions.Services
                                     "{Prefix} Vulnerability correlation complete (async, whiteGlovePart={Part})",
                                     capturedPrefix, capturedWhiteGlovePart?.ToString() ?? "none");
 
+                                // Synthetic `vulnerability_report` event so analyze rules can
+                                // match against `scan_summary.*` fields. The full report stays in
+                                // the VulnerabilityReports table — this event carries only the
+                                // summary slice that rule conditions need.
+                                await EmitVulnerabilityReportEventAsync(
+                                    capturedTenantId, capturedSessionId, capturedPrefix, reportData, phaseLabel);
+
+                                // Re-evaluate analyze rules now that the synth event is in the
+                                // table. The end-of-session analysis at the top of ProcessEventsAsync
+                                // is triggered by classification.CompletionEvent and may finish
+                                // before this vulnerability task does — without this re-analyze,
+                                // vulnerability-driven rules (ANALYZE-ID-003) miss their evidence.
+                                // Uses reanalyze=false: rules with stored results are skipped, so
+                                // there's no duplicate-result risk if the initial run already saw
+                                // the synth event in a tight race.
+                                await ReanalyzeAfterVulnerabilityEmitAsync(
+                                    capturedTenantId, capturedSessionId, capturedPrefix);
+
                                 var findings = reportData.ContainsKey("findings")
                                     ? reportData["findings"] as List<Dictionary<string, object>>
                                     : null;
@@ -478,6 +496,105 @@ namespace AutopilotMonitor.Functions.Services
             };
         }
 
+        /// <summary>
+        /// Stores a synthetic <c>vulnerability_report</c> event after a successful scan so analyze
+        /// rules can fire on the same event-stream surface as agent-emitted events. Carries only
+        /// <c>scan_summary</c> + <c>reportAvailable</c> + <c>phase</c>; the full per-CVE list lives
+        /// in the <c>VulnerabilityReports</c> table (read separately by the report API).
+        /// </summary>
+        private async Task EmitVulnerabilityReportEventAsync(
+            string tenantId,
+            string sessionId,
+            string sessionPrefix,
+            Dictionary<string, object> reportData,
+            string? phaseLabel)
+        {
+            try
+            {
+                var scanSummary = reportData.TryGetValue("scan_summary", out var summaryObj)
+                    && summaryObj is Dictionary<string, object> summaryDict
+                    ? summaryDict
+                    : new Dictionary<string, object>();
+
+                var overallRisk = scanSummary.TryGetValue("overall_risk", out var riskObj)
+                    ? riskObj?.ToString()
+                    : null;
+
+                var data = new Dictionary<string, object>(StringComparer.Ordinal)
+                {
+                    ["scan_summary"] = scanSummary,
+                    ["reportAvailable"] = true,
+                    ["phase"] = phaseLabel ?? "single",
+                };
+
+                var evt = new EnrollmentEvent
+                {
+                    TenantId = tenantId,
+                    SessionId = sessionId,
+                    EventType = "vulnerability_report",
+                    Severity = MapVulnerabilityRiskToSeverity(overallRisk),
+                    Source = "VulnerabilityCorrelationService",
+                    Phase = EnrollmentPhase.Unknown,
+                    Message = $"Vulnerability scan complete (risk={overallRisk ?? "unknown"}).",
+                    Timestamp = DateTime.UtcNow,
+                    Data = data,
+                };
+
+                await _sessionRepo.StoreEventsBatchAsync(new List<EnrollmentEvent> { evt });
+            }
+            catch (Exception ex)
+            {
+                _logger.LogWarning(ex,
+                    "{Prefix} vulnerability_report synth-event emit failed (non-fatal)", sessionPrefix);
+            }
+        }
+
+        /// <summary>
+        /// Runs <see cref="RuleEngine.AnalyzeSessionAsync"/> after the vulnerability synth event
+        /// has been persisted, so vulnerability-driven rules (e.g. ANALYZE-ID-003) can match
+        /// even when the initial enrollment-end analysis completed before the async correlation
+        /// finished. Skips rules that already have stored results — no duplicates.
+        /// </summary>
+        private async Task ReanalyzeAfterVulnerabilityEmitAsync(
+            string tenantId,
+            string sessionId,
+            string sessionPrefix)
+        {
+            try
+            {
+                var ruleEngine = new RuleEngine(_analyzeRuleService, _ruleRepo, _sessionRepo, _logger);
+                var outcome = await ruleEngine.AnalyzeSessionAsync(tenantId, sessionId);
+
+                foreach (var result in outcome.Results)
+                {
+                    await _ruleRepo.StoreRuleResultAsync(result);
+                }
+
+                if (outcome.Results.Count > 0)
+                {
+                    _logger.LogInformation(
+                        "{Prefix} Vulnerability re-analysis: {Count} additional rule result(s)",
+                        sessionPrefix, outcome.Results.Count);
+
+                    await _signalRNotification.NotifyRuleResultsAvailableAsync(
+                        tenantId, sessionId, outcome.Results.Count);
+                }
+            }
+            catch (Exception ex)
+            {
+                _logger.LogWarning(ex,
+                    "{Prefix} Vulnerability re-analysis failed (async, non-fatal)", sessionPrefix);
+            }
+        }
+
+        private static EventSeverity MapVulnerabilityRiskToSeverity(string? overallRisk) =>
+            (overallRisk ?? string.Empty).ToLowerInvariant() switch
+            {
+                "critical" => EventSeverity.Critical,
+                "high"     => EventSeverity.Error,
+                "medium"   => EventSeverity.Warning,
+                _          => EventSeverity.Info,
+            };
     }
 
     /// <summary>
diff --git a/src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.ConditionEvaluators.cs b/src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.ConditionEvaluators.cs
index 7373fa0d..4f1bc077 100644
--- a/src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.ConditionEvaluators.cs
+++ b/src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.ConditionEvaluators.cs
@@ -1,3 +1,4 @@
+using System.Text.Json;
 using System.Text.RegularExpressions;
 using AutopilotMonitor.Shared.Models;
 using Microsoft.Extensions.Logging;
@@ -318,18 +319,94 @@ namespace AutopilotMonitor.Functions.Services
             if (dataField.Equals("message", StringComparison.OrdinalIgnoreCase))
                 return evt.Message;
 
-            // Check in Data dictionary
-            if (evt.Data.TryGetValue(dataField, out var value))
-                return value?.ToString();
+            // Flat lookup first — preserves the legacy contract for keys that contain a
+            // literal dot (e.g. v1 events that wrote "scan_summary.critical_cves" as a
+            // single key) and is the cheap path for the common case.
+            if (TryFlatLookup(evt.Data, dataField, out var flat))
+                return flat;
 
-            // Try case-insensitive lookup
-            var key = evt.Data.Keys.FirstOrDefault(k => k.Equals(dataField, StringComparison.OrdinalIgnoreCase));
-            if (key != null)
-                return evt.Data[key]?.ToString();
+            // Dot-path traversal for nested Dictionary<string,object> / JsonElement values.
+            // Used by rules that target a structured payload (e.g. `scan_summary.kev_matches`
+            // when the emitter wrote `scan_summary` as a nested dict).
+            if (dataField.IndexOf('.') >= 0)
+                return ResolveDotPath(evt.Data, dataField);
 
             return null;
         }
 
+        internal static bool TryFlatLookup(Dictionary<string, object> data, string key, out string? value)
+        {
+            if (data.TryGetValue(key, out var raw))
+            {
+                value = raw?.ToString();
+                return true;
+            }
+            var hit = data.Keys.FirstOrDefault(k => k.Equals(key, StringComparison.OrdinalIgnoreCase));
+            if (hit != null)
+            {
+                value = data[hit]?.ToString();
+                return true;
+            }
+            value = null;
+            return false;
+        }
+
+        internal static string? ResolveDotPath(Dictionary<string, object> root, string path)
+        {
+            var parts = path.Split('.');
+            object? current = root;
+            foreach (var part in parts)
+            {
+                if (current == null) return null;
+
+                switch (current)
+                {
+                    case IDictionary<string, object> dict:
+                        if (!dict.TryGetValue(part, out var next))
+                        {
+                            var hit = dict.Keys.FirstOrDefault(k => k.Equals(part, StringComparison.OrdinalIgnoreCase));
+                            if (hit == null) return null;
+                            next = dict[hit];
+                        }
+                        current = next;
+                        break;
+
+                    case JsonElement jel when jel.ValueKind == JsonValueKind.Object:
+                        if (jel.TryGetProperty(part, out var prop))
+                        {
+                            current = prop;
+                        }
+                        else
+                        {
+                            // Case-insensitive fallback for JsonElement.
+                            JsonElement? found = null;
+                            foreach (var p in jel.EnumerateObject())
+                            {
+                                if (p.Name.Equals(part, StringComparison.OrdinalIgnoreCase))
+                                {
+                                    found = p.Value;
+                                    break;
+                                }
+                            }
+                            if (found == null) return null;
+                            current = found.Value;
+                        }
+                        break;
+
+                    default:
+                        // Scalar reached before path was exhausted — no descent possible.
+                        return null;
+                }
+            }
+
+            return current switch
+            {
+                null => null,
+                JsonElement jel => jel.ValueKind == JsonValueKind.String ? jel.GetString() : jel.ToString(),
+                _ => current.ToString(),
+            };
+        }
+
         private bool MatchesOperator(string fieldValue, string op, string compareValue)
         {
             switch (op?.ToLower())