diff --git a/src/Backend/AutopilotMonitor.Functions/Functions/GetRuleResultsFunction.cs b/src/Backend/AutopilotMonitor.Functions/Functions/GetRuleResultsFunction.cs
index d6dace29..32bae941 100644
--- a/src/Backend/AutopilotMonitor.Functions/Functions/GetRuleResultsFunction.cs
+++ b/src/Backend/AutopilotMonitor.Functions/Functions/GetRuleResultsFunction.cs
@@ -49,17 +49,17 @@ namespace AutopilotMonitor.Functions.Functions
                 try
                 {
                     var ruleEngine = new RuleEngine(_analyzeRuleService, _storageService, _logger);
-                    var newResults = await ruleEngine.AnalyzeSessionAsync(tenantId, sessionId);
+                    var freshResults = await ruleEngine.AnalyzeSessionAsync(tenantId, sessionId, reanalyze: true);
 
-                    foreach (var result in newResults)
+                    // Delete existing results so stale entries don't persist after re-analysis
+                    await _storageService.DeleteSessionRuleResultsAsync(tenantId, sessionId);
+
+                    foreach (var result in freshResults)
                     {
                         await _storageService.StoreRuleResultAsync(result);
                     }
 
-                    if (newResults.Count > 0)
-                    {
-                        _logger.LogInformation($"On-demand analysis for session {sessionId}: {newResults.Count} new issue(s) detected");
-                    }
+                    _logger.LogInformation($"On-demand re-analysis for session {sessionId}: {freshResults.Count} issue(s) detected");
                 }
                 catch (Exception ex)
                 {
diff --git a/src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.cs b/src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.cs
index 64259abb..7a46059c 100644
--- a/src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.cs
+++ b/src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.cs
@@ -25,8 +25,9 @@ namespace AutopilotMonitor.Functions.Services
         /// <summary>
         /// Evaluates ALL active analyze rules against the full session event stream.
         /// Called once at enrollment end or on-demand. Fetches events internally.
+        /// When reanalyze=true, all rules are re-evaluated regardless of existing results.
         /// </summary>
-        public async Task<List<RuleResult>> AnalyzeSessionAsync(string tenantId, string sessionId)
+        public async Task<List<RuleResult>> AnalyzeSessionAsync(string tenantId, string sessionId, bool reanalyze = false)
         {
             var results = new List<RuleResult>();
 
@@ -41,9 +42,18 @@ namespace AutopilotMonitor.Functions.Services
                     return results;
                 }
 
-                // Get existing rule results to avoid duplicates
-                var existingResults = await _storageService.GetRuleResultsAsync(tenantId, sessionId);
-                var existingRuleIds = new HashSet<string>(existingResults.Select(r => r.RuleId));
+                // On reanalyze: skip deduplication so all rules are re-evaluated from scratch
+                // On normal run: skip rules already evaluated to avoid duplicate storage
+                HashSet<string> existingRuleIds;
+                if (reanalyze)
+                {
+                    existingRuleIds = new HashSet<string>();
+                }
+                else
+                {
+                    var existingResults = await _storageService.GetRuleResultsAsync(tenantId, sessionId);
+                    existingRuleIds = new HashSet<string>(existingResults.Select(r => r.RuleId));
+                }
 
                 _logger.LogInformation($"Analyzing session {sessionId}: {allEvents.Count} events, {activeRules.Count} rules ({existingRuleIds.Count} already evaluated)");