Improve chat title generation

Author: ericdallo

CHANGELOG.md

@@ -2,6 +2,8 @@
 
 ## Unreleased
 
+- Improve chat title quality on 3rd-message retitle by filtering tool calls, tool results, reasoning and flag entries from the history passed to the title LLM, and by respecting the last compact marker.
+
 ## 0.128.0
 
 - Add `eca-desktop` as an official client in docs and landing page.

resources/prompts/title.md

@@ -23,3 +23,9 @@ Output: Single line, ≤30 chars, no explanations.
 "refactor user service" → Refactoring user service
 "why is app.js failing" → Analyzing app.js failure
 "implement rate limiting" → Implementing rate limiting
+
+Conversation:
+  user: "why is app.js failing"
+  assistant: "Looks like a missing env var in the loader."
+  user: "add a guard and default it to dev"
+→ Guarding app.js loader env var

src/eca/features/chat.clj

@@ -576,7 +576,8 @@
         (when generate-title?
           (let [title-past-messages (when retitle?
                                      (->> (get-in db [:chats chat-id :messages] [])
-                                          (filterv #(not= "reason" (:role %)))))]
+                                          shared/messages-after-last-compact-marker
+                                          (filterv #(contains? #{"user" "assistant"} (:role %)))))]
             (future* config
               (when-let [{:keys [output-text]} (llm-api/sync-prompt!
                                                 {:provider provider

test/eca/features/chat_test.clj

@@ -262,24 +262,58 @@
             "Should NOT call sync-prompt! on second message")
         (is (= "Title 1" (get-in (h/db) [:chats chat-id :title])))
 
+        ;; Inject noisy entries into history before the retitle fires, to
+        ;; exercise the role/content cleanup applied to :past-messages.
+        (swap! (h/db*) update-in [:chats chat-id :messages]
+               (fnil into [])
+               [{:role "reason" :content "internal thoughts"}
+                {:role "tool_call" :content {:name "read_file"}}
+                {:role "tool_call_output" :content "file contents"}
+                {:role "flag" :content {:text "ui-only"}}])
+
         ;; Message 3: should re-generate title with full conversation context
         (h/reset-messenger!)
         (prompt-with-title! {:message "And add tests" :chat-id chat-id} {:sync-prompt-mock sync-mock})
         (is (= 2 (count @sync-prompt-calls*))
             "Should call sync-prompt! again on third message")
         (is (= "Title 2" (get-in (h/db) [:chats chat-id :title])))
-        (let [retitle-call (second @sync-prompt-calls*)]
+        (let [retitle-call (second @sync-prompt-calls*)
+              past-roles (into #{} (map :role) (:past-messages retitle-call))]
           (is (= 1 (count (:user-messages retitle-call)))
               "Third message title should pass only current user message")
           (is (seq (:past-messages retitle-call))
-              "Third message title should include chat history as past-messages"))
+              "Third message title should include chat history as past-messages")
+          (is (= #{"user" "assistant"} past-roles)
+              "Past messages should be cleaned of tool_call, tool_call_output, reason and flag entries"))
 
         ;; Message 4: should NOT re-generate title
         (h/reset-messenger!)
         (prompt-with-title! {:message "One more thing" :chat-id chat-id} {:sync-prompt-mock sync-mock})
         (is (= 2 (count @sync-prompt-calls*))
             "Should NOT call sync-prompt! after third message"))))
 
+  (testing "retitle respects the last compact marker, dropping pre-compaction history"
+    (h/reset-components!)
+    (let [sync-prompt-calls* (atom [])
+          call-count* (atom 0)
+          sync-mock (fn [params]
+                      (swap! sync-prompt-calls* conj params)
+                      {:output-text (str "Title " (swap! call-count* inc))})]
+      (let [{:keys [chat-id]} (prompt-with-title! {:message "Help me debug"} {:sync-prompt-mock sync-mock})]
+        (h/reset-messenger!)
+        (prompt-with-title! {:message "Also refactor" :chat-id chat-id} {:sync-prompt-mock sync-mock})
+
+        ;; Insert a compact_marker so earlier history is treated as pre-compaction
+        ;; and must not reach the title LLM.
+        (swap! (h/db*) update-in [:chats chat-id :messages]
+               (fnil conj []) {:role "compact_marker" :content {:auto? false}})
+
+        (h/reset-messenger!)
+        (prompt-with-title! {:message "And add tests" :chat-id chat-id} {:sync-prompt-mock sync-mock})
+        (let [retitle-call (second @sync-prompt-calls*)]
+          (is (empty? (:past-messages retitle-call))
+              "Past messages before the compact marker should be dropped from title context")))))
+
   (testing "manual rename suppresses automatic re-titling"
     (h/reset-components!)
     (let [sync-prompt-calls* (atom [])