refactor(cli): move /system upgrade hint into thinking tips (#1411)

Co-authored-by: Letta Code <noreply@letta.com>

src/cli/App.tsx

@@ -981,8 +981,9 @@ export default function App({
     setAgentState((prev) => (prev ? { ...prev, name } : prev));
   }, []);
 
-  // Check if the current agent would benefit from switching to the default prompt
-  const shouldShowDefaultPromptTip = useCallback(() => {
+  // Check if the current agent would benefit from switching to the default prompt.
+  // Used to conditionally include the /system tip in streaming tip rotation.
+  const includeSystemPromptUpgradeTip = useMemo(() => {
     if (!agentState?.id || !agentState.system) return false;
     const memMode = settingsManager.isMemfsEnabled(agentState.id)
       ? "memfs"
@@ -3079,8 +3080,6 @@ export default function App({
         ? `Resuming conversation with **${agentName}**`
         : `Starting new conversation with **${agentName}**`;
 
-      const showPromptTip = shouldShowDefaultPromptTip();
-
       // Command hints - vary based on agent state:
       // - Resuming: show /new (they may want a fresh conversation)
       // - New session + unpinned: show /pin (they should save their agent)
@@ -3092,9 +3091,6 @@ export default function App({
             "→ **/new**       start a new conversation",
             "→ **/init**      initialize your agent's memory",
             "→ **/remember**  teach your agent",
-            ...(showPromptTip
-              ? ["→ **/system**    upgrade to the latest default prompt"]
-              : []),
           ]
         : isPinned
           ? [
@@ -3103,9 +3099,6 @@ export default function App({
               "→ **/memory**    view your agent's memory",
               "→ **/init**      initialize your agent's memory",
               "→ **/remember**  teach your agent",
-              ...(showPromptTip
-                ? ["→ **/system**    upgrade to the latest default prompt"]
-                : []),
             ]
           : [
               "→ **/agents**    list all agents",
@@ -3113,9 +3106,6 @@ export default function App({
               "→ **/pin**       save + name your agent",
               "→ **/init**      initialize your agent's memory",
               "→ **/remember**  teach your agent",
-              ...(showPromptTip
-                ? ["→ **/system**    upgrade to the latest default prompt"]
-                : []),
             ];
 
       // Build status lines with optional release notes above header
@@ -3151,7 +3141,6 @@ export default function App({
     agentProvenance,
     resumedExistingConversation,
     releaseNotes,
-    shouldShowDefaultPromptTip,
   ]);
 
   // Fetch llmConfig when agent is ready
@@ -13075,9 +13064,6 @@ If using apply_patch, use this exact relative patch path: ${applyPatchRelativePa
           ? `Starting new conversation with **${agentName}**`
           : "Creating a new agent";
 
-      // Only show prompt tip for existing agents, not brand new ones
-      const showPromptTip = continueSession && shouldShowDefaultPromptTip();
-
       // Command hints - for pinned agents show /memory, for unpinned show /pin
       const commandHints = isPinned
         ? [
@@ -13086,9 +13072,6 @@ If using apply_patch, use this exact relative patch path: ${applyPatchRelativePa
             "→ **/memory**    view your agent's memory",
             "→ **/init**      initialize your agent's memory",
             "→ **/remember**  teach your agent",
-            ...(showPromptTip
-              ? ["→ **/system**    upgrade to the latest default prompt"]
-              : []),
           ]
         : [
             "→ **/agents**    list all agents",
@@ -13096,9 +13079,6 @@ If using apply_patch, use this exact relative patch path: ${applyPatchRelativePa
             "→ **/pin**       save + name your agent",
             "→ **/init**      initialize your agent's memory",
             "→ **/remember**  teach your agent",
-            ...(showPromptTip
-              ? ["→ **/system**    upgrade to the latest default prompt"]
-              : []),
           ];
 
       // Build status lines with optional release notes above header
@@ -13133,7 +13113,6 @@ If using apply_patch, use this exact relative patch path: ${applyPatchRelativePa
     agentState,
     refreshDerived,
     releaseNotes,
-    shouldShowDefaultPromptTip,
   ]);
 
   const liveTrajectorySnapshot =
@@ -13511,6 +13490,7 @@ If using apply_patch, use this exact relative patch path: ${applyPatchRelativePa
                 tokenCount={trajectoryTokenDisplay}
                 elapsedBaseMs={liveTrajectoryElapsedBaseMs}
                 thinkingMessage={thinkingMessage}
+                includeSystemPromptUpgradeTip={includeSystemPromptUpgradeTip}
                 onSubmit={onSubmit}
                 onBashSubmit={handleBashSubmit}
                 bashRunning={bashRunning}

src/cli/components/InputRich.tsx

@@ -477,6 +477,7 @@ const StreamingStatus = memo(function StreamingStatus({
   tokenCount,
   elapsedBaseMs,
   thinkingMessage,
+  includeSystemPromptUpgradeTip,
   agentName,
   interruptRequested,
   networkPhase,
@@ -488,6 +489,7 @@ const StreamingStatus = memo(function StreamingStatus({
   tokenCount: number;
   elapsedBaseMs: number;
   thinkingMessage: string;
+  includeSystemPromptUpgradeTip: boolean;
   agentName: string | null | undefined;
   interruptRequested: boolean;
   networkPhase: "upload" | "download" | "error" | null;
@@ -529,7 +531,6 @@ const StreamingStatus = memo(function StreamingStatus({
   const [shimmerOffset, setShimmerOffset] = useState(-3);
   const [elapsedMs, setElapsedMs] = useState(0);
   const [tipMessage, setTipMessage] = useState("");
-  const tipInitializedRef = useRef(false);
   const streamStartRef = useRef<number | null>(null);
 
   useEffect(() => {
@@ -583,15 +584,9 @@ const StreamingStatus = memo(function StreamingStatus({
 
   useEffect(() => {
     if (streaming && visible) {
-      if (!tipInitializedRef.current) {
-        setTipMessage(getRandomThinkingTip());
-        tipInitializedRef.current = true;
-      }
-      return;
+      setTipMessage(getRandomThinkingTip({ includeSystemPromptUpgradeTip }));
     }
-
-    tipInitializedRef.current = false;
-  }, [streaming, visible]);
+  }, [streaming, visible, includeSystemPromptUpgradeTip]);
 
   const estimatedTokens = charsToTokens(tokenCount);
   const totalElapsedMs = elapsedBaseMs + elapsedMs;
@@ -724,6 +719,7 @@ export function Input({
   tokenCount,
   elapsedBaseMs = 0,
   thinkingMessage,
+  includeSystemPromptUpgradeTip = true,
   onSubmit,
   onBashSubmit,
   bashRunning = false,
@@ -766,6 +762,7 @@ export function Input({
   tokenCount: number;
   elapsedBaseMs?: number;
   thinkingMessage: string;
+  includeSystemPromptUpgradeTip?: boolean;
   onSubmit: (message?: string) => Promise<{ submitted: boolean }>;
   onBashSubmit?: (command: string) => Promise<void>;
   bashRunning?: boolean;
@@ -1713,6 +1710,7 @@ export function Input({
         tokenCount={tokenCount}
         elapsedBaseMs={elapsedBaseMs}
         thinkingMessage={thinkingMessage}
+        includeSystemPromptUpgradeTip={includeSystemPromptUpgradeTip}
         agentName={agentName}
         interruptRequested={interruptRequested}
         networkPhase={networkPhase}

src/cli/helpers/thinkingMessages.ts

@@ -43,6 +43,9 @@ const THINKING_VERBS = [
   "internalizing",
 ] as const;
 
+export const SYSTEM_PROMPT_UPGRADE_TIP =
+  "Use /system to upgrade to the latest default prompt.";
+
 export const THINKING_TIPS = [
   "Use /remember [instructions] to remember something from the conversation.",
   "Use /palace to inspect your agent's memory palace.",
@@ -51,6 +54,11 @@ export const THINKING_TIPS = [
   "Use /init to initialize (or re-init) your agent's memory.",
 ] as const;
 
+const THINKING_TIPS_WITH_SYSTEM_UPGRADE = [
+  ...THINKING_TIPS,
+  SYSTEM_PROMPT_UPGRADE_TIP,
+];
+
 type ThinkingVerb = (typeof THINKING_VERBS)[number];
 
 const PAST_TENSE_VERBS: Record<ThinkingVerb, string> = {
@@ -103,11 +111,6 @@ function getRandomVerb(): string {
   return THINKING_VERBS[index] ?? "thinking";
 }
 
-function getRandomTip(): string {
-  const index = Math.floor(Math.random() * THINKING_TIPS.length);
-  return THINKING_TIPS[index] ?? "";
-}
-
 // Get a random thinking verb phrase (e.g., "is thinking", "is processing")
 export function getRandomThinkingVerb(): string {
   return `is ${getRandomVerb()}`;
@@ -131,6 +134,16 @@ export function getRandomThinkingMessage(agentName?: string | null): string {
   return verb.charAt(0).toUpperCase() + verb.slice(1);
 }
 
-export function getRandomThinkingTip(): string {
-  return getRandomTip();
+export function getRandomThinkingTip(options?: {
+  includeSystemPromptUpgradeTip?: boolean;
+}): string {
+  const tipPool =
+    (options?.includeSystemPromptUpgradeTip ?? true)
+      ? THINKING_TIPS_WITH_SYSTEM_UPGRADE
+      : THINKING_TIPS;
+  if (tipPool.length === 0) {
+    return "";
+  }
+  const index = Math.floor(Math.random() * tipPool.length);
+  return tipPool[index] ?? "";
 }

src/tests/cli/thinkingMessages.test.ts

@@ -2,6 +2,7 @@ import { describe, expect, test } from "bun:test";
 import {
   getRandomThinkingMessage,
   getRandomThinkingTip,
+  SYSTEM_PROMPT_UPGRADE_TIP,
   THINKING_TIPS,
 } from "../../cli/helpers/thinkingMessages";
 
@@ -54,4 +55,12 @@ describe("Thinking messages", () => {
     expect(tip.length).toBeGreaterThan(0);
     expect((THINKING_TIPS as readonly string[]).includes(tip)).toBe(true);
   });
+
+  test("can exclude /system upgrade tip from the selection pool", () => {
+    const tips = Array.from({ length: 50 }, () =>
+      getRandomThinkingTip({ includeSystemPromptUpgradeTip: false }),
+    );
+
+    expect(tips.every((tip) => tip !== SYSTEM_PROMPT_UPGRADE_TIP)).toBe(true);
+  });
 });