diff --git a/src/Infrastructure/BotSharp.Abstraction/Rules/IRuleCriteriaEvaluator.cs b/src/Infrastructure/BotSharp.Abstraction/Rules/IRuleCriteriaEvaluator.cs
index 4f14ee622..e5f39aeb1 100644
--- a/src/Infrastructure/BotSharp.Abstraction/Rules/IRuleCriteriaEvaluator.cs
+++ b/src/Infrastructure/BotSharp.Abstraction/Rules/IRuleCriteriaEvaluator.cs
@@ -18,6 +18,10 @@ public interface IRuleCriteriaEvaluator
     /// Evaluate the criteria for a single agent's rule.
     /// </summary>
     /// <param name="agent">The agent whose rule is being considered</param>
+    /// <param name="agentRule">
+    /// The rule being considered. An agent can carry more than one rule on the same trigger, so the
+    /// evaluator is handed the one under evaluation rather than resolving it from the agent itself.
+    /// </param>
     /// <param name="trigger">The rule trigger</param>
     /// <param name="context">The per-request criteria context</param>
     /// <returns>
@@ -25,5 +29,5 @@ public interface IRuleCriteriaEvaluator
     /// or null when the evaluator could not produce an answer (missing script/template,
     /// failed execution, error).
     /// </returns>
-    Task<bool?> EvaluateAsync(Agent agent, IRuleTrigger trigger, RuleCriteriaContext context);
+    Task<bool?> EvaluateAsync(Agent agent, AgentRule agentRule, IRuleTrigger trigger, RuleCriteriaContext context);
 }
diff --git a/src/Infrastructure/BotSharp.Core.Rules/Criteria/Code/CodeCriteriaEvaluator.cs b/src/Infrastructure/BotSharp.Core.Rules/Criteria/Code/CodeCriteriaEvaluator.cs
index 31a712944..618c2140e 100644
--- a/src/Infrastructure/BotSharp.Core.Rules/Criteria/Code/CodeCriteriaEvaluator.cs
+++ b/src/Infrastructure/BotSharp.Core.Rules/Criteria/Code/CodeCriteriaEvaluator.cs
@@ -25,7 +25,7 @@ public CodeCriteriaEvaluator(
 
     public string Type => BuiltInRuleCriteria.PythonScript;
 
-    public async Task<bool?> EvaluateAsync(Agent agent, IRuleTrigger trigger, RuleCriteriaContext context)
+    public async Task<bool?> EvaluateAsync(Agent agent, AgentRule agentRule, IRuleTrigger trigger, RuleCriteriaContext context)
     {
         var settings = context.Options.GetData<CodeCriteriaSettings>() ?? new();
         var provider = settings.CodeProcessor ?? BuiltInCodeProcessor.PyInterpreter;
diff --git a/src/Infrastructure/BotSharp.Core.Rules/Criteria/Llm/LlmCriteriaEvaluator.cs b/src/Infrastructure/BotSharp.Core.Rules/Criteria/Llm/LlmCriteriaEvaluator.cs
index 839c740fa..6aaab0844 100644
--- a/src/Infrastructure/BotSharp.Core.Rules/Criteria/Llm/LlmCriteriaEvaluator.cs
+++ b/src/Infrastructure/BotSharp.Core.Rules/Criteria/Llm/LlmCriteriaEvaluator.cs
@@ -30,17 +30,16 @@ public LlmCriteriaEvaluator(
 
     public string Type => BuiltInRuleCriteria.Llm;
 
-    public async Task<bool?> EvaluateAsync(Agent agent, IRuleTrigger trigger, RuleCriteriaContext context)
+    public async Task<bool?> EvaluateAsync(Agent agent, AgentRule agentRule, IRuleTrigger trigger, RuleCriteriaContext context)
     {
         var settings = context.Options.GetData<LlmCriteriaSettings>() ?? new();
-        var rule = agent.Rules.FirstOrDefault(x => x.TriggerName.IsEqualTo(trigger.Name));
 
         // The Rules agent hosts the criteria-check template by default.
         var agentId = !string.IsNullOrWhiteSpace(settings.AgentId) ? settings.AgentId! : BuiltInAgentId.RulesInterpreter;
         var templateName = !string.IsNullOrWhiteSpace(settings.TemplateName)
                         ? settings.TemplateName! : (agentId == BuiltInAgentId.RulesInterpreter ? DefaultTemplateName : $"{trigger.Name}_criteria");
 
-        var input = BuildInput(rule?.CriteriaConfig, settings);
+        var input = BuildInput(agentRule.CriteriaConfig, settings);
         var msg = $"rule trigger ({trigger.Name}) llm criteria (agent {agentId}, template {templateName}).";
 
         try
diff --git a/src/Infrastructure/BotSharp.Core.Rules/Engines/RuleEngine.cs b/src/Infrastructure/BotSharp.Core.Rules/Engines/RuleEngine.cs
index 697fdaeab..f6b906bc8 100644
--- a/src/Infrastructure/BotSharp.Core.Rules/Engines/RuleEngine.cs
+++ b/src/Infrastructure/BotSharp.Core.Rules/Engines/RuleEngine.cs
@@ -44,33 +44,41 @@ public async Task<IEnumerable<string>> Triggered(IRuleTrigger trigger, string te
         var filteredAgents = agents.Items.Where(x => x.Rules.Exists(r => r.TriggerName.IsEqualTo(trigger.Name) && !x.Disabled)).ToList();
         foreach (var agent in filteredAgents)
         {
-            var rule = agent.Rules.FirstOrDefault(x => x.TriggerName.IsEqualTo(trigger.Name) && !x.Disabled);
-            if (rule == null)
+            var rules = agent.Rules.Where(x => x.TriggerName.IsEqualTo(trigger.Name) && !x.Disabled).ToList();
+            if (rules.IsNullOrEmpty())
             {
                 continue;
             }
 
-            // The rule's own mode wins over the mode carried on the trigger options, so an agent can
-            // pick how its criteria is judged without the caller knowing.
-            var evaluator = ResolveCriteriaEvaluator(rule.CriteriaConfig?.Mode) ?? criteriaEvaluator;
-            if (evaluator != null && options?.Criteria != null)
+            foreach (var rule in rules)
             {
-                var criteriaContext = new RuleCriteriaContext
+                if (rule == null)
                 {
-                    Options = options.Criteria,
-                    States = states
-                };
+                    continue;
+                }
 
-                var isTriggered = await EvaluateCriteria(evaluator, agent, trigger, criteriaContext);
-                if (!isTriggered)
+                // The rule's own mode wins over the mode carried on the trigger options, so an agent can
+                // pick how its criteria is judged without the caller knowing.
+                var evaluator = ResolveCriteriaEvaluator(rule.CriteriaConfig?.Mode) ?? criteriaEvaluator;
+                if (evaluator != null && options?.Criteria != null)
                 {
-                    continue;
+                    var criteriaContext = new RuleCriteriaContext
+                    {
+                        Options = options.Criteria,
+                        States = states
+                    };
+
+                    var isTriggered = await EvaluateCriteria(evaluator, agent, rule, trigger, criteriaContext);
+                    if (!isTriggered)
+                    {
+                        continue;
+                    }
                 }
-            }
 
-            var msg = !string.IsNullOrWhiteSpace(rule.Message) ? rule.Message : text;
-            var convId = await SendMessageToAgent(agent, trigger, text, msg, states);
-            newConversationIds.Add(convId);
+                var msg = !string.IsNullOrWhiteSpace(rule.Message) ? rule.Message : text;
+                var convId = await SendMessageToAgent(agent, trigger, text, msg, states);
+                newConversationIds.Add(convId);
+            }
         }
 
         return newConversationIds;
@@ -96,10 +104,11 @@ public async Task<IEnumerable<string>> Triggered(IRuleTrigger trigger, string te
     private async Task<bool> EvaluateCriteria(
         IRuleCriteriaEvaluator evaluator,
         Agent agent,
+        AgentRule agentRule,
         IRuleTrigger trigger,
         RuleCriteriaContext context)
     {
-        var isTriggered = await evaluator.EvaluateAsync(agent, trigger, context);
+        var isTriggered = await evaluator.EvaluateAsync(agent, agentRule, trigger, context);
         if (isTriggered != null)
         {
             return isTriggered.Value;
@@ -118,7 +127,7 @@ private async Task<bool> EvaluateCriteria(
         }
 
         _logger.LogInformation($"Rule criteria evaluator ({evaluator.Type}) returned no result, falling back to llm for agent ({agent.Name}) and trigger ({trigger.Name}).");
-        return await llmEvaluator.EvaluateAsync(agent, trigger, context) ?? false;
+        return await llmEvaluator.EvaluateAsync(agent, agentRule, trigger, context) ?? false;
     }
     #endregion