diff --git a/src/agent/modify.ts b/src/agent/modify.ts
index 514f012..59bf9ea 100644
--- a/src/agent/modify.ts
+++ b/src/agent/modify.ts
@@ -249,16 +249,14 @@ export async function updateConversationLLMConfig(
 
 export interface RecompileAgentSystemPromptOptions {
   dryRun?: boolean;
-  updateTimestamp?: boolean;
 }
 
-interface AgentSystemPromptRecompileClient {
-  agents: {
+interface ConversationSystemPromptRecompileClient {
+  conversations: {
     recompile: (
-      agentId: string,
+      conversationId: string,
       params: {
         dry_run?: boolean;
-        update_timestamp?: boolean;
       },
     ) => Promise<string>;
   };
@@ -268,22 +266,21 @@ interface AgentSystemPromptRecompileClient {
  * Recompile an agent's system prompt after memory writes so server-side prompt
  * state picks up the latest memory content.
  *
- * @param agentId - The agent ID to recompile
- * @param options - Optional dry-run/timestamp controls
+ * @param conversationId - The conversation whose prompt should be recompiled
+ * @param options - Optional dry-run control
  * @param clientOverride - Optional injected client for tests
  * @returns The compiled system prompt returned by the API
  */
 export async function recompileAgentSystemPrompt(
-  agentId: string,
+  conversationId: string,
   options: RecompileAgentSystemPromptOptions = {},
-  clientOverride?: AgentSystemPromptRecompileClient,
+  clientOverride?: ConversationSystemPromptRecompileClient,
 ): Promise<string> {
   const client = (clientOverride ??
-    (await getClient())) as AgentSystemPromptRecompileClient;
+    (await getClient())) as ConversationSystemPromptRecompileClient;
 
-  return client.agents.recompile(agentId, {
+  return client.conversations.recompile(conversationId, {
     dry_run: options.dryRun,
-    update_timestamp: options.updateTimestamp,
   });
 }
 
diff --git a/src/cli/App.tsx b/src/cli/App.tsx
index 725c8d7..7bf01cc 100644
--- a/src/cli/App.tsx
+++ b/src/cli/App.tsx
@@ -1701,10 +1701,12 @@ export default function App({
   const initProgressByAgentRef = useRef(
     new Map<string, { shallowCompleted: boolean; deepFired: boolean }>(),
   );
-  const systemPromptRecompileByAgentRef = useRef(
+  const systemPromptRecompileByConversationRef = useRef(
     new Map<string, Promise<void>>(),
   );
-  const queuedSystemPromptRecompileByAgentRef = useRef(new Set<string>());
+  const queuedSystemPromptRecompileByConversationRef = useRef(
+    new Set<string>(),
+  );
   const updateInitProgress = (
     forAgentId: string,
     update: Partial<{ shallowCompleted: boolean; deepFired: boolean }>,
@@ -9289,15 +9291,17 @@ export default function App({
                   const msg = await handleMemorySubagentCompletion(
                     {
                       agentId,
+                      conversationId: conversationIdRef.current,
                       subagentType: "init",
                       initDepth: "deep",
                       success,
                       error,
                     },
                     {
-                      recompileByAgent: systemPromptRecompileByAgentRef.current,
-                      recompileQueuedByAgent:
-                        queuedSystemPromptRecompileByAgentRef.current,
+                      recompileByConversation:
+                        systemPromptRecompileByConversationRef.current,
+                      recompileQueuedByConversation:
+                        queuedSystemPromptRecompileByConversationRef.current,
                       updateInitProgress,
                       logRecompileFailure: (message) =>
                         debugWarn("memory", message),
@@ -9476,15 +9480,17 @@ export default function App({
               const msg = await handleMemorySubagentCompletion(
                 {
                   agentId,
+                  conversationId: conversationIdRef.current,
                   subagentType: "init",
                   initDepth: "shallow",
                   success,
                   error,
                 },
                 {
-                  recompileByAgent: systemPromptRecompileByAgentRef.current,
-                  recompileQueuedByAgent:
-                    queuedSystemPromptRecompileByAgentRef.current,
+                  recompileByConversation:
+                    systemPromptRecompileByConversationRef.current,
+                  recompileQueuedByConversation:
+                    queuedSystemPromptRecompileByConversationRef.current,
                   updateInitProgress,
                   logRecompileFailure: (message) =>
                     debugWarn("memory", message),
@@ -9605,14 +9611,16 @@ ${SYSTEM_REMINDER_CLOSE}
               const msg = await handleMemorySubagentCompletion(
                 {
                   agentId,
+                  conversationId: conversationIdRef.current,
                   subagentType: "reflection",
                   success,
                   error,
                 },
                 {
-                  recompileByAgent: systemPromptRecompileByAgentRef.current,
-                  recompileQueuedByAgent:
-                    queuedSystemPromptRecompileByAgentRef.current,
+                  recompileByConversation:
+                    systemPromptRecompileByConversationRef.current,
+                  recompileQueuedByConversation:
+                    queuedSystemPromptRecompileByConversationRef.current,
                   updateInitProgress,
                   logRecompileFailure: (message) =>
                     debugWarn("memory", message),
@@ -9660,15 +9668,17 @@ ${SYSTEM_REMINDER_CLOSE}
               const msg = await handleMemorySubagentCompletion(
                 {
                   agentId,
+                  conversationId: conversationIdRef.current,
                   subagentType: "init",
                   initDepth: "deep",
                   success,
                   error,
                 },
                 {
-                  recompileByAgent: systemPromptRecompileByAgentRef.current,
-                  recompileQueuedByAgent:
-                    queuedSystemPromptRecompileByAgentRef.current,
+                  recompileByConversation:
+                    systemPromptRecompileByConversationRef.current,
+                  recompileQueuedByConversation:
+                    queuedSystemPromptRecompileByConversationRef.current,
                   updateInitProgress,
                   logRecompileFailure: (message) =>
                     debugWarn("memory", message),
diff --git a/src/cli/helpers/memorySubagentCompletion.ts b/src/cli/helpers/memorySubagentCompletion.ts
index 0ef282d..0aa42ef 100644
--- a/src/cli/helpers/memorySubagentCompletion.ts
+++ b/src/cli/helpers/memorySubagentCompletion.ts
@@ -12,13 +12,14 @@ export interface MemoryInitProgressUpdate {
 }
 
 type RecompileAgentSystemPromptFn = (
-  agentId: string,
+  conversationId: string,
   options?: RecompileAgentSystemPromptOptions,
 ) => Promise<string>;
 
 export type MemorySubagentCompletionArgs =
   | {
       agentId: string;
+      conversationId: string;
       subagentType: "init";
       initDepth: MemoryInitDepth;
       success: boolean;
@@ -26,6 +27,7 @@ export type MemorySubagentCompletionArgs =
     }
   | {
       agentId: string;
+      conversationId: string;
       subagentType: "reflection";
       initDepth?: never;
       success: boolean;
@@ -33,8 +35,8 @@ export type MemorySubagentCompletionArgs =
     };
 
 export interface MemorySubagentCompletionDeps {
-  recompileByAgent: Map<string, Promise<void>>;
-  recompileQueuedByAgent: Set<string>;
+  recompileByConversation: Map<string, Promise<void>>;
+  recompileQueuedByConversation: Set<string>;
   updateInitProgress: (
     agentId: string,
     update: Partial<MemoryInitProgressUpdate>,
@@ -51,7 +53,8 @@ export async function handleMemorySubagentCompletion(
   args: MemorySubagentCompletionArgs,
   deps: MemorySubagentCompletionDeps,
 ): Promise<string> {
-  const { agentId, subagentType, initDepth, success, error } = args;
+  const { agentId, conversationId, subagentType, initDepth, success, error } =
+    args;
   const recompileAgentSystemPromptFn =
     deps.recompileAgentSystemPromptImpl ?? recompileAgentSystemPrompt;
   let recompileError: string | null = null;
@@ -67,25 +70,23 @@ export async function handleMemorySubagentCompletion(
     }
 
     try {
-      let inFlight = deps.recompileByAgent.get(agentId);
+      let inFlight = deps.recompileByConversation.get(conversationId);
 
       if (!inFlight) {
         inFlight = (async () => {
           do {
-            deps.recompileQueuedByAgent.delete(agentId);
-            await recompileAgentSystemPromptFn(agentId, {
-              updateTimestamp: true,
-            });
-          } while (deps.recompileQueuedByAgent.has(agentId));
+            deps.recompileQueuedByConversation.delete(conversationId);
+            await recompileAgentSystemPromptFn(conversationId, {});
+          } while (deps.recompileQueuedByConversation.has(conversationId));
         })().finally(() => {
           // Cleanup runs only after the shared promise settles, so every
           // concurrent caller awaits the same full recompile lifecycle.
-          deps.recompileQueuedByAgent.delete(agentId);
-          deps.recompileByAgent.delete(agentId);
+          deps.recompileQueuedByConversation.delete(conversationId);
+          deps.recompileByConversation.delete(conversationId);
         });
-        deps.recompileByAgent.set(agentId, inFlight);
+        deps.recompileByConversation.set(conversationId, inFlight);
       } else {
-        deps.recompileQueuedByAgent.add(agentId);
+        deps.recompileQueuedByConversation.add(conversationId);
       }
 
       await inFlight;
@@ -95,7 +96,7 @@ export async function handleMemorySubagentCompletion(
           ? recompileFailure.message
           : String(recompileFailure);
       deps.logRecompileFailure?.(
-        `Failed to recompile system prompt after ${subagentType} subagent for ${agentId}: ${recompileError}`,
+        `Failed to recompile system prompt after ${subagentType} subagent for ${agentId} in conversation ${conversationId}: ${recompileError}`,
       );
     }
   }
diff --git a/src/tests/agent/recompile-system-prompt.test.ts b/src/tests/agent/recompile-system-prompt.test.ts
index c7945eb..ff624a1 100644
--- a/src/tests/agent/recompile-system-prompt.test.ts
+++ b/src/tests/agent/recompile-system-prompt.test.ts
@@ -4,11 +4,11 @@ import { recompileAgentSystemPrompt } from "../../agent/modify";
 describe("recompileAgentSystemPrompt", () => {
   test("calls the Letta agent recompile endpoint with mapped params", async () => {
     const agentsRecompileMock = mock(
-      (_agentId: string, _params?: Record<string, unknown>) =>
+      (_conversationId: string, _params?: Record<string, unknown>) =>
         Promise.resolve("compiled-system-prompt"),
     );
     const client = {
-      agents: {
+      conversations: {
         recompile: agentsRecompileMock,
       },
     };
@@ -16,7 +16,6 @@ describe("recompileAgentSystemPrompt", () => {
     const compiledPrompt = await recompileAgentSystemPrompt(
       "agent-123",
       {
-        updateTimestamp: true,
         dryRun: true,
       },
       client,
@@ -25,7 +24,6 @@ describe("recompileAgentSystemPrompt", () => {
     expect(compiledPrompt).toBe("compiled-system-prompt");
     expect(agentsRecompileMock).toHaveBeenCalledWith("agent-123", {
       dry_run: true,
-      update_timestamp: true,
     });
   });
 });
diff --git a/src/tests/cli/memory-subagent-recompile-wiring.test.ts b/src/tests/cli/memory-subagent-recompile-wiring.test.ts
index 07dbbf7..09c3fc8 100644
--- a/src/tests/cli/memory-subagent-recompile-wiring.test.ts
+++ b/src/tests/cli/memory-subagent-recompile-wiring.test.ts
@@ -3,7 +3,7 @@ import type { RecompileAgentSystemPromptOptions } from "../../agent/modify";
 import { handleMemorySubagentCompletion } from "../../cli/helpers/memorySubagentCompletion";
 
 const recompileAgentSystemPromptMock = mock(
-  (_agentId: string, _opts?: RecompileAgentSystemPromptOptions) =>
+  (_conversationId: string, _opts?: RecompileAgentSystemPromptOptions) =>
     Promise.resolve("compiled-system-prompt"),
 );
 
@@ -33,13 +33,14 @@ describe("memory subagent recompile handling", () => {
     const message = await handleMemorySubagentCompletion(
       {
         agentId: "agent-init-1",
+        conversationId: "conv-init-1",
         subagentType: "init",
         initDepth: "shallow",
         success: true,
       },
       {
-        recompileByAgent: new Map(),
-        recompileQueuedByAgent: new Set(),
+        recompileByConversation: new Map(),
+        recompileQueuedByConversation: new Set(),
         recompileAgentSystemPromptImpl: recompileAgentSystemPromptMock,
         updateInitProgress: (agentId, update) => {
           progressUpdates.push({
@@ -60,10 +61,8 @@ describe("memory subagent recompile handling", () => {
       },
     ]);
     expect(recompileAgentSystemPromptMock).toHaveBeenCalledWith(
-      "agent-init-1",
-      {
-        updateTimestamp: true,
-      },
+      "conv-init-1",
+      {},
     );
   });
 
@@ -74,11 +73,11 @@ describe("memory subagent recompile handling", () => {
       .mockImplementationOnce(() => firstDeferred.promise)
       .mockImplementationOnce(() => secondDeferred.promise);
 
-    const recompileByAgent = new Map<string, Promise<void>>();
-    const recompileQueuedByAgent = new Set<string>();
+    const recompileByConversation = new Map<string, Promise<void>>();
+    const recompileQueuedByConversation = new Set<string>();
     const deps = {
-      recompileByAgent,
-      recompileQueuedByAgent,
+      recompileByConversation,
+      recompileQueuedByConversation,
       recompileAgentSystemPromptImpl: recompileAgentSystemPromptMock,
       updateInitProgress: () => {},
     };
@@ -86,6 +85,7 @@ describe("memory subagent recompile handling", () => {
     const first = handleMemorySubagentCompletion(
       {
         agentId: "agent-shared",
+        conversationId: "conv-shared",
         subagentType: "reflection",
         success: true,
       },
@@ -94,6 +94,7 @@ describe("memory subagent recompile handling", () => {
     const second = handleMemorySubagentCompletion(
       {
         agentId: "agent-shared",
+        conversationId: "conv-shared",
         subagentType: "reflection",
         success: true,
       },
@@ -102,6 +103,7 @@ describe("memory subagent recompile handling", () => {
     const third = handleMemorySubagentCompletion(
       {
         agentId: "agent-shared",
+        conversationId: "conv-shared",
         subagentType: "reflection",
         success: true,
       },
@@ -109,14 +111,14 @@ describe("memory subagent recompile handling", () => {
     );
 
     expect(recompileAgentSystemPromptMock).toHaveBeenCalledTimes(1);
-    expect(recompileByAgent.has("agent-shared")).toBe(true);
-    expect(recompileQueuedByAgent.has("agent-shared")).toBe(true);
+    expect(recompileByConversation.has("conv-shared")).toBe(true);
+    expect(recompileQueuedByConversation.has("conv-shared")).toBe(true);
 
     firstDeferred.resolve("compiled-system-prompt");
     await Promise.resolve();
 
     expect(recompileAgentSystemPromptMock).toHaveBeenCalledTimes(2);
-    expect(recompileByAgent.has("agent-shared")).toBe(true);
+    expect(recompileByConversation.has("conv-shared")).toBe(true);
 
     secondDeferred.resolve("compiled-system-prompt");
 
@@ -134,7 +136,47 @@ describe("memory subagent recompile handling", () => {
     expect(thirdMessage).toBe(
       "Reflected on /palace, the halls remember more now.",
     );
-    expect(recompileByAgent.size).toBe(0);
-    expect(recompileQueuedByAgent.size).toBe(0);
+    expect(recompileByConversation.size).toBe(0);
+    expect(recompileQueuedByConversation.size).toBe(0);
+  });
+
+  test("does not coalesce recompiles across different conversations for same agent", async () => {
+    const deps = {
+      recompileByConversation: new Map<string, Promise<void>>(),
+      recompileQueuedByConversation: new Set<string>(),
+      recompileAgentSystemPromptImpl: recompileAgentSystemPromptMock,
+      updateInitProgress: () => {},
+    };
+
+    const [firstMessage, secondMessage] = await Promise.all([
+      handleMemorySubagentCompletion(
+        {
+          agentId: "agent-shared",
+          conversationId: "conv-a",
+          subagentType: "reflection",
+          success: true,
+        },
+        deps,
+      ),
+      handleMemorySubagentCompletion(
+        {
+          agentId: "agent-shared",
+          conversationId: "conv-b",
+          subagentType: "reflection",
+          success: true,
+        },
+        deps,
+      ),
+    ]);
+
+    expect(firstMessage).toBe(
+      "Reflected on /palace, the halls remember more now.",
+    );
+    expect(secondMessage).toBe(
+      "Reflected on /palace, the halls remember more now.",
+    );
+    expect(recompileAgentSystemPromptMock).toHaveBeenCalledTimes(2);
+    expect(recompileAgentSystemPromptMock).toHaveBeenCalledWith("conv-a", {});
+    expect(recompileAgentSystemPromptMock).toHaveBeenCalledWith("conv-b", {});
   });
 });
diff --git a/src/tests/cli/task-notification-flush.test.ts b/src/tests/cli/task-notification-flush.test.ts
index 4208756..f529b1b 100644
--- a/src/tests/cli/task-notification-flush.test.ts
+++ b/src/tests/cli/task-notification-flush.test.ts
@@ -143,7 +143,7 @@ describe("background onComplete → flush wiring in App.tsx", () => {
     const onCompleteIdx = source.indexOf("onComplete:", initBlock);
     expect(onCompleteIdx).toBeGreaterThan(-1);
 
-    const onCompleteWindow = source.slice(onCompleteIdx, onCompleteIdx + 900);
+    const onCompleteWindow = source.slice(onCompleteIdx, onCompleteIdx + 1600);
     expect(onCompleteWindow).toContain("await handleMemorySubagentCompletion(");
     expect(onCompleteWindow).toContain("appendTaskNotificationEvents(");
   });
@@ -157,7 +157,7 @@ describe("background onComplete → flush wiring in App.tsx", () => {
     const onCompleteIdx = source.indexOf("onComplete:", reflectionBlock);
     expect(onCompleteIdx).toBeGreaterThan(-1);
 
-    const onCompleteWindow = source.slice(onCompleteIdx, onCompleteIdx + 700);
+    const onCompleteWindow = source.slice(onCompleteIdx, onCompleteIdx + 1400);
     expect(onCompleteWindow).toContain("await handleMemorySubagentCompletion(");
     expect(onCompleteWindow).toContain("appendTaskNotificationEvents(");
   });