diff --git a/pkg/agent/loop.go b/pkg/agent/loop.go
index 6341cbb4c..bb2bf9ef0 100644
--- a/pkg/agent/loop.go
+++ b/pkg/agent/loop.go
@@ -1555,6 +1555,7 @@ func (al *AgentLoop) askSideQuestion(
 	var channel, chatID, senderID, senderDisplayName string
 	var media []string
 	var activeSkills []string
+	var history []providers.Message
 	var summary string
 	if opts != nil {
 		channel = opts.Channel
@@ -1570,13 +1571,14 @@ func (al *AgentLoop) askSideQuestion(
 				Budget:     agent.ContextWindow,
 				MaxTokens:  agent.MaxTokens,
 			}); err == nil && resp != nil {
+				history = resp.History
 				summary = resp.Summary
 			}
 		}
 	}
 
 	messages := agent.ContextBuilder.BuildMessages(
-		nil,
+		history,
 		summary,
 		question,
 		media,
diff --git a/pkg/agent/loop_test.go b/pkg/agent/loop_test.go
index 28aef5679..cc53d8a7a 100644
--- a/pkg/agent/loop_test.go
+++ b/pkg/agent/loop_test.go
@@ -286,8 +286,12 @@ func TestProcessMessage_BtwCommandRunsWithoutPersistingHistory(t *testing.T) {
 	if len(provider.lastMessages) == 0 {
 		t.Fatal("provider did not receive any messages")
 	}
-	if len(provider.lastMessages) != 2 {
-		t.Fatalf("provider messages len = %d, want 2 (system + user, no history)", len(provider.lastMessages))
+	if len(provider.lastMessages) != 4 {
+		t.Fatalf("provider messages len = %d, want 4 (system + prior history + user)", len(provider.lastMessages))
+	}
+
+	if !reflect.DeepEqual(provider.lastMessages[1:3], initialHistory) {
+		t.Fatalf("provider history = %#v, want %#v", provider.lastMessages[1:3], initialHistory)
 	}
 
 	lastMessage := provider.lastMessages[len(provider.lastMessages)-1]