diff --git a/packages/app/src/components/composer-actions.test.ts b/packages/app/src/components/composer-actions.test.ts
index 3067c52cf..9c385cee2 100644
--- a/packages/app/src/components/composer-actions.test.ts
+++ b/packages/app/src/components/composer-actions.test.ts
@@ -189,6 +189,7 @@ function createFakeStream(initialHead: Map<string, StreamItem[]> = new Map()): F
   const fake: FakeStream = {
     head: new Map(initialHead),
     tail: new Map(),
+    getTail: (agentId) => fake.tail.get(agentId),
     getHead: (agentId) => fake.head.get(agentId),
     setHead: (updater) => {
       fake.head = updater(fake.head);
diff --git a/packages/app/src/components/composer-actions.ts b/packages/app/src/components/composer-actions.ts
index 82e27fc9b..539717419 100644
--- a/packages/app/src/components/composer-actions.ts
+++ b/packages/app/src/components/composer-actions.ts
@@ -9,7 +9,13 @@ import {
   userAttachmentsOnly,
 } from "@/attachments/workspace-attachment-utils";
 import { splitComposerAttachmentsForSubmit } from "@/components/composer-attachments";
-import { generateMessageId, type StreamItem } from "@/types/stream";
+import {
+  appendOptimisticUserMessageToStream,
+  buildOptimisticUserMessage,
+  generateMessageId,
+  type StreamItem,
+  type UserMessageItem,
+} from "@/types/stream";
 import type { PickedImageAttachmentInput } from "@/hooks/image-attachment-picker";
 
 export interface QueuedComposerMessage {
@@ -49,6 +55,7 @@ export interface ComposerCancelClient {
 }
 
 export interface AgentStreamWriter {
+  getTail: (agentId: string) => StreamItem[] | undefined;
   getHead: (agentId: string) => StreamItem[] | undefined;
   setHead: (updater: (prev: Map<string, StreamItem[]>) => Map<string, StreamItem[]>) => void;
   setTail: (updater: (prev: Map<string, StreamItem[]>) => Map<string, StreamItem[]>) => void;
@@ -130,15 +137,13 @@ export async function dispatchComposerAgentMessage(
 ): Promise<void> {
   const wirePayload = splitComposerAttachmentsForSubmit(input.attachments);
   const messageId = generateMessageId();
-  const userMessage: StreamItem = {
-    kind: "user_message",
+  const userMessage = buildOptimisticUserMessage({
     id: messageId,
     text: input.text,
     timestamp: new Date(),
-    optimistic: true,
-    ...(wirePayload.images.length > 0 ? { images: wirePayload.images } : {}),
-    ...(wirePayload.attachments.length > 0 ? { attachments: wirePayload.attachments } : {}),
-  };
+    images: wirePayload.images,
+    attachments: wirePayload.attachments,
+  });
   appendUserMessageToStream(input.agentId, userMessage, input.stream);
   const imagesData = await input.encodeImages(wirePayload.images);
   await input.client.sendAgentMessage(input.agentId, input.text, {
@@ -150,23 +155,29 @@ export async function dispatchComposerAgentMessage(
 
 function appendUserMessageToStream(
   agentId: string,
-  userMessage: StreamItem,
+  userMessage: UserMessageItem,
   stream: AgentStreamWriter,
 ): void {
-  const head = stream.getHead(agentId);
-  if (head && head.length > 0) {
+  const result = appendOptimisticUserMessageToStream({
+    tail: stream.getTail(agentId) ?? [],
+    head: stream.getHead(agentId) ?? [],
+    message: userMessage,
+    placement: "active-head",
+  });
+  if (result.changedHead) {
     stream.setHead((prev) => {
       const next = new Map(prev);
-      next.set(agentId, [...(prev.get(agentId) ?? []), userMessage]);
+      next.set(agentId, result.head);
+      return next;
+    });
+  }
+  if (result.changedTail) {
+    stream.setTail((prev) => {
+      const next = new Map(prev);
+      next.set(agentId, result.tail);
       return next;
     });
-    return;
   }
-  stream.setTail((prev) => {
-    const next = new Map(prev);
-    next.set(agentId, [...(prev.get(agentId) ?? []), userMessage]);
-    return next;
-  });
 }
 
 export interface QueueComposerMessageInput {
diff --git a/packages/app/src/components/composer.tsx b/packages/app/src/components/composer.tsx
index c52330b36..8ec2e2af5 100644
--- a/packages/app/src/components/composer.tsx
+++ b/packages/app/src/components/composer.tsx
@@ -1029,6 +1029,7 @@ export function Composer({
         throw new Error("Host is not connected");
       }
       const stream: AgentStreamWriter = {
+        getTail: (id) => useSessionStore.getState().sessions[serverId]?.agentStreamTail?.get(id),
         getHead: (id) => useSessionStore.getState().sessions[serverId]?.agentStreamHead?.get(id),
         setHead: (updater) => setAgentStreamHead(serverId, updater),
         setTail: (updater) => setAgentStreamTail(serverId, updater),
diff --git a/packages/app/src/contexts/session-context.tsx b/packages/app/src/contexts/session-context.tsx
index 3544a54a3..6d54f6fb0 100644
--- a/packages/app/src/contexts/session-context.tsx
+++ b/packages/app/src/contexts/session-context.tsx
@@ -13,6 +13,7 @@ import {
   type ProcessTimelineResponseOutput,
   type TimelineReducerSideEffect,
 } from "@/timeline/session-stream-reducers";
+import { useCreateFlowStore } from "@/stores/create-flow-store";
 import { TIMELINE_FETCH_PAGE_SIZE } from "@/timeline/timeline-fetch-policy";
 import type { AgentAttachment, SessionOutboundMessage } from "@server/shared/messages";
 import { parseServerInfoStatusPayload } from "@server/shared/messages";
@@ -375,6 +376,7 @@ function finalizeTimelineApplication(input: {
   }
   if (shouldMarkAuthoritativeHistoryApplied) {
     setAgentAuthoritativeHistoryApplied(serverId, agentId, true);
+    useCreateFlowStore.getState().clearByAgent({ serverId, agentId });
   }
   if (result.initResolution === "resolve") {
     resolveInitDeferred(initKey);
diff --git a/packages/app/src/hooks/use-agent-screen-state-machine.test.ts b/packages/app/src/hooks/use-agent-screen-state-machine.test.ts
index f4148f49c..b4e304e9b 100644
--- a/packages/app/src/hooks/use-agent-screen-state-machine.test.ts
+++ b/packages/app/src/hooks/use-agent-screen-state-machine.test.ts
@@ -57,13 +57,12 @@ function createAgentWithStatus({ id, status }: { id: string; status: Agent["stat
 function createBaseInput(): AgentScreenMachineInput {
   return {
     agent: null,
-    placeholderAgent: null,
+    continuity: { kind: "none" },
     missingAgentState: { kind: "idle" },
     isConnected: true,
     isArchivingCurrentAgent: false,
     isHistorySyncing: false,
     needsAuthoritativeSync: false,
-    shouldUseOptimisticStream: false,
     hasHydratedHistoryBefore: false,
   };
 }
@@ -298,8 +297,7 @@ describe("deriveAgentScreenViewState", () => {
     const memory = createBaseMemory();
     const input: AgentScreenMachineInput = {
       ...createBaseInput(),
-      placeholderAgent: createAgent("draft-agent"),
-      shouldUseOptimisticStream: true,
+      continuity: { kind: "optimistic-create", agent: createAgent("draft-agent") },
     };
 
     const result = deriveAgentScreenViewState({ input, memory });
@@ -335,8 +333,7 @@ describe("deriveAgentScreenViewState", () => {
     const input: AgentScreenMachineInput = {
       ...createBaseInput(),
       agent: createAgentWithStatus({ id: "agent-1", status: "idle" }),
-      placeholderAgent: createAgent("agent-1"),
-      shouldUseOptimisticStream: true,
+      continuity: { kind: "optimistic-create", agent: createAgent("agent-1") },
       needsAuthoritativeSync: true,
       isHistorySyncing: true,
       hasHydratedHistoryBefore: false,
@@ -347,14 +344,14 @@ describe("deriveAgentScreenViewState", () => {
 
     expect(ready.source).toBe("optimistic");
     expect(ready.agent.status).toBe("running");
+    expect(ready.sync).toEqual({ status: "catching_up", ui: "silent" });
   });
 
   it("keeps optimistic flow non-blocking while transitioning to authoritative stream", () => {
     const initialMemory = createBaseMemory();
     const optimisticInput: AgentScreenMachineInput = {
       ...createBaseInput(),
-      placeholderAgent: createAgent("draft-agent"),
-      shouldUseOptimisticStream: true,
+      continuity: { kind: "optimistic-create", agent: createAgent("draft-agent") },
     };
 
     const optimistic = deriveAgentScreenViewState({
@@ -382,8 +379,7 @@ describe("deriveAgentScreenViewState", () => {
     const input: AgentScreenMachineInput = {
       ...createBaseInput(),
       agent: createAgentWithStatus({ id: "agent-1", status: "idle" }),
-      placeholderAgent: createAgent("agent-1"),
-      shouldUseOptimisticStream: true,
+      continuity: { kind: "optimistic-create", agent: createAgent("agent-1") },
     };
 
     const result = deriveAgentScreenViewState({ input, memory });
@@ -402,14 +398,12 @@ describe("deriveAgentScreenViewState", () => {
       {
         ...createBaseInput(),
         agent: createAgentWithStatus({ id: "agent-1", status: "idle" }),
-        placeholderAgent: createAgent("agent-1"),
-        shouldUseOptimisticStream: true,
+        continuity: { kind: "optimistic-create", agent: createAgent("agent-1") },
       },
       {
         ...createBaseInput(),
         agent: createAgentWithStatus({ id: "agent-1", status: "running" }),
-        placeholderAgent: createAgent("agent-1"),
-        shouldUseOptimisticStream: true,
+        continuity: { kind: "optimistic-create", agent: createAgent("agent-1") },
       },
       {
         ...createBaseInput(),
@@ -431,8 +425,7 @@ describe("deriveAgentScreenViewState", () => {
     const input: AgentScreenMachineInput = {
       ...createBaseInput(),
       agent: createAgentWithStatus({ id: "agent-1", status: "initializing" }),
-      placeholderAgent: createAgent("agent-1"),
-      shouldUseOptimisticStream: true,
+      continuity: { kind: "optimistic-create", agent: createAgent("agent-1") },
     };
 
     const result = deriveAgentScreenViewState({ input, memory });
@@ -447,8 +440,7 @@ describe("deriveAgentScreenViewState", () => {
     const input: AgentScreenMachineInput = {
       ...createBaseInput(),
       agent: createAgentWithStatus({ id: "agent-1", status: "running" }),
-      placeholderAgent: createAgent("agent-1"),
-      shouldUseOptimisticStream: true,
+      continuity: { kind: "optimistic-create", agent: createAgent("agent-1") },
     };
 
     const result = deriveAgentScreenViewState({ input, memory });
@@ -463,8 +455,7 @@ describe("deriveAgentScreenViewState", () => {
     const input: AgentScreenMachineInput = {
       ...createBaseInput(),
       agent: createAgentWithStatus({ id: "agent-1", status: "error" }),
-      placeholderAgent: createAgent("agent-1"),
-      shouldUseOptimisticStream: true,
+      continuity: { kind: "optimistic-create", agent: createAgent("agent-1") },
     };
 
     const result = deriveAgentScreenViewState({ input, memory });
@@ -479,8 +470,7 @@ describe("deriveAgentScreenViewState", () => {
     const input: AgentScreenMachineInput = {
       ...createBaseInput(),
       agent: createAgentWithStatus({ id: "agent-1", status: "closed" }),
-      placeholderAgent: createAgent("agent-1"),
-      shouldUseOptimisticStream: true,
+      continuity: { kind: "optimistic-create", agent: createAgent("agent-1") },
     };
 
     const result = deriveAgentScreenViewState({ input, memory });
diff --git a/packages/app/src/hooks/use-agent-screen-state-machine.ts b/packages/app/src/hooks/use-agent-screen-state-machine.ts
index 5a9875e2f..be254a6a3 100644
--- a/packages/app/src/hooks/use-agent-screen-state-machine.ts
+++ b/packages/app/src/hooks/use-agent-screen-state-machine.ts
@@ -24,19 +24,26 @@ export type AgentScreenMissingState =
 
 export interface AgentScreenMachineInput {
   agent: AgentScreenAgent | null;
-  placeholderAgent: AgentScreenAgent | null;
   missingAgentState: AgentScreenMissingState;
   isConnected: boolean;
   isArchivingCurrentAgent: boolean;
   isHistorySyncing: boolean;
   needsAuthoritativeSync: boolean;
-  shouldUseOptimisticStream: boolean;
+  continuity: AgentScreenContinuity;
   hasHydratedHistoryBefore: boolean;
 }
 
+export type AgentScreenContinuity =
+  | { kind: "none" }
+  | { kind: "optimistic-create"; agent: AgentScreenAgent };
+
+function hasOptimisticCreateContinuity(input: AgentScreenMachineInput): boolean {
+  return input.continuity.kind === "optimistic-create";
+}
+
 function shouldBlockInitialAuthoritativeReadyState(input: AgentScreenMachineInput): boolean {
   return (
-    !input.shouldUseOptimisticStream &&
+    !hasOptimisticCreateContinuity(input) &&
     !input.hasHydratedHistoryBefore &&
     (input.needsAuthoritativeSync || input.isHistorySyncing)
   );
@@ -93,8 +100,7 @@ function updateInitialSyncFailureMemory(args: {
 
 function shouldUseOptimisticCreateFlowAgent(input: AgentScreenMachineInput): boolean {
   return (
-    input.shouldUseOptimisticStream &&
-    Boolean(input.placeholderAgent) &&
+    input.continuity.kind === "optimistic-create" &&
     (!input.agent || input.agent.status === "initializing" || input.agent.status === "idle")
   );
 }
@@ -104,29 +110,31 @@ function resolveCandidateAgent(args: {
   useOptimisticCreateFlowAgent: boolean;
 }): AgentScreenAgent | null {
   const { input, useOptimisticCreateFlowAgent } = args;
-  if (input.agent && useOptimisticCreateFlowAgent && input.placeholderAgent) {
-    return { ...input.agent, status: input.placeholderAgent.status };
+  const continuityAgent =
+    input.continuity.kind === "optimistic-create" ? input.continuity.agent : null;
+  if (input.agent && useOptimisticCreateFlowAgent && continuityAgent) {
+    return { ...input.agent, status: continuityAgent.status };
   }
-  return input.agent ?? input.placeholderAgent;
+  return input.agent ?? continuityAgent;
 }
 
 function resolveAgentScreenSource(args: {
   useOptimisticCreateFlowAgent: boolean;
   hasAgent: boolean;
-  shouldUseOptimisticStream: boolean;
+  hasOptimisticCreateContinuity: boolean;
 }): "authoritative" | "optimistic" | "stale" {
   if (args.useOptimisticCreateFlowAgent) return "optimistic";
   if (args.hasAgent) return "authoritative";
-  if (args.shouldUseOptimisticStream) return "optimistic";
+  if (args.hasOptimisticCreateContinuity) return "optimistic";
   return "stale";
 }
 
 function resolveCatchingUpUi(args: {
-  shouldUseOptimisticStream: boolean;
+  hasOptimisticCreateContinuity: boolean;
   hasHydratedHistoryBefore: boolean;
   hadInitialSyncFailure: boolean;
 }): "overlay" | "silent" {
-  if (args.shouldUseOptimisticStream) return "silent";
+  if (args.hasOptimisticCreateContinuity) return "silent";
   if (args.hasHydratedHistoryBefore) return "silent";
   if (args.hadInitialSyncFailure) return "silent";
   return "overlay";
@@ -147,7 +155,7 @@ function resolveAgentScreenSync(args: {
     return {
       status: "catching_up",
       ui: resolveCatchingUpUi({
-        shouldUseOptimisticStream: input.shouldUseOptimisticStream,
+        hasOptimisticCreateContinuity: hasOptimisticCreateContinuity(input),
         hasHydratedHistoryBefore: input.hasHydratedHistoryBefore,
         hadInitialSyncFailure,
       }),
@@ -227,7 +235,7 @@ export function deriveAgentScreenViewState({
   const source = resolveAgentScreenSource({
     useOptimisticCreateFlowAgent,
     hasAgent: Boolean(input.agent),
-    shouldUseOptimisticStream: input.shouldUseOptimisticStream,
+    hasOptimisticCreateContinuity: hasOptimisticCreateContinuity(input),
   });
 
   const sync = resolveAgentScreenSync({
diff --git a/packages/app/src/hooks/use-draft-agent-create-flow.ts b/packages/app/src/hooks/use-draft-agent-create-flow.ts
index 3286b1240..1c92c9454 100644
--- a/packages/app/src/hooks/use-draft-agent-create-flow.ts
+++ b/packages/app/src/hooks/use-draft-agent-create-flow.ts
@@ -2,7 +2,9 @@ import { useCallback, useMemo, useReducer } from "react";
 import type { ComposerAttachment } from "@/attachments/types";
 import { splitComposerAttachmentsForSubmit } from "@/components/composer-attachments";
 import { useCreateFlowStore } from "@/stores/create-flow-store";
+import { useSessionStore } from "@/stores/session-store";
 import {
+  buildOptimisticUserMessage,
   generateMessageId,
   type StreamItem,
   type UserMessageImageAttachment,
@@ -110,6 +112,9 @@ export function useDraftAgentCreateFlow<TDraftAgent, TCreateResult>({
   const updatePendingAgentId = useCreateFlowStore((state) => state.updateAgentId);
   const markPendingCreateLifecycle = useCreateFlowStore((state) => state.markLifecycle);
   const clearPendingCreateAttempt = useCreateFlowStore((state) => state.clear);
+  const appendOptimisticUserMessageToAgentStream = useSessionStore(
+    (state) => state.appendOptimisticUserMessageToAgentStream,
+  );
 
   const formErrorMessage = machine.tag === "draft" ? machine.errorMessage : "";
   const isSubmitting = machine.tag === "creating";
@@ -128,19 +133,13 @@ export function useDraftAgentCreateFlow<TDraftAgent, TCreateResult>({
     }
 
     return [
-      {
-        kind: "user_message",
+      buildOptimisticUserMessage({
         id: machine.attempt.clientMessageId,
         text: machine.attempt.text,
         timestamp: machine.attempt.timestamp,
-        optimistic: true,
-        ...(machine.attempt.images && machine.attempt.images.length > 0
-          ? { images: machine.attempt.images }
-          : {}),
-        ...(machine.attempt.attachments && machine.attempt.attachments.length > 0
-          ? { attachments: machine.attempt.attachments }
-          : {}),
-      },
+        images: machine.attempt.images,
+        attachments: machine.attempt.attachments,
+      }),
     ];
   }, [machine]);
 
@@ -228,6 +227,19 @@ export function useDraftAgentCreateFlow<TDraftAgent, TCreateResult>({
 
         if (createResult.agentId) {
           updatePendingAgentId({ draftId, agentId: createResult.agentId });
+          appendOptimisticUserMessageToAgentStream(
+            pendingServerId,
+            createResult.agentId,
+            buildOptimisticUserMessage({
+              id: attempt.clientMessageId,
+              text: attempt.text,
+              timestamp: attempt.timestamp,
+              images: attempt.images,
+              attachments: attempt.attachments,
+            }),
+            { placement: "tail", skipIfUserMessageExists: true },
+          );
+          markPendingCreateLifecycle({ draftId, lifecycle: "sent" });
         }
 
         await onCreateSuccess({ result: createResult.result, attempt });
@@ -241,6 +253,7 @@ export function useDraftAgentCreateFlow<TDraftAgent, TCreateResult>({
       }
     },
     [
+      appendOptimisticUserMessageToAgentStream,
       clearPendingCreateAttempt,
       createRequest,
       draftId,
diff --git a/packages/app/src/panels/agent-panel.tsx b/packages/app/src/panels/agent-panel.tsx
index 57f0409ef..a8604eae0 100644
--- a/packages/app/src/panels/agent-panel.tsx
+++ b/packages/app/src/panels/agent-panel.tsx
@@ -27,6 +27,7 @@ import { useAgentInitialization } from "@/hooks/use-agent-initialization";
 import { useAgentInputDraft, type AgentInputDraft } from "@/hooks/use-agent-input-draft";
 import {
   type AgentScreenAgent,
+  type AgentScreenContinuity,
   type AgentScreenMissingState,
   type AgentScreenViewState,
   useAgentScreenStateMachine,
@@ -60,7 +61,6 @@ import type { StreamItem } from "@/types/stream";
 import { getInitDeferred, getInitKey } from "@/utils/agent-initialization";
 import { derivePendingPermissionKey, normalizeAgentSnapshot } from "@/utils/agent-snapshots";
 import type { WorkspaceFileOpenRequest } from "@/workspace/file-open";
-import { mergePendingCreateImages } from "@/utils/pending-create-images";
 import { navigateToAgent } from "@/utils/navigate-to-agent";
 import { deriveSidebarStateBucket } from "@/utils/sidebar-agent-state";
 import { buildDraftAgentSetup, type ClientSlashCommand } from "@/client-slash-commands";
@@ -313,8 +313,22 @@ const EMPTY_PENDING_PERMISSIONS = new Map<string, PendingPermission>();
 const EMPTY_PENDING_PERMISSION_LIST: PendingPermission[] = [];
 
 type RouteBottomAnchorRequest = ReturnType<typeof deriveRouteBottomAnchorRequest>;
-type PendingCreateByDraftId = ReturnType<typeof useCreateFlowStore.getState>["pendingByDraftId"];
-type PendingCreateAttempt = PendingCreateByDraftId[string];
+
+function findActiveCreateHandoff(input: {
+  pendingByDraftId: ReturnType<typeof useCreateFlowStore.getState>["pendingByDraftId"];
+  serverId: string;
+  agentId?: string;
+}): boolean {
+  if (!input.agentId) {
+    return false;
+  }
+  return Object.values(input.pendingByDraftId).some(
+    (pending) =>
+      pending.lifecycle === "sent" &&
+      pending.serverId === input.serverId &&
+      pending.agentId === input.agentId,
+  );
+}
 
 function toErrorMessage(error: unknown): string {
   if (error instanceof Error) {
@@ -327,27 +341,6 @@ function isNotFoundErrorMessage(message: string): boolean {
   return /agent not found|not found/i.test(message);
 }
 
-function findPendingCreateForPanel(input: {
-  pendingByDraftId: PendingCreateByDraftId;
-  serverId: string;
-  agentId?: string;
-}): PendingCreateAttempt | null {
-  if (!input.agentId) {
-    return null;
-  }
-  const values = Object.values(input.pendingByDraftId);
-  for (const entry of values) {
-    if (
-      entry.lifecycle === "active" &&
-      entry.serverId === input.serverId &&
-      entry.agentId === input.agentId
-    ) {
-      return entry;
-    }
-  }
-  return null;
-}
-
 type AgentLookupState =
   | { tag: "idle" }
   | { tag: "loading" }
@@ -630,7 +623,6 @@ function ChatAgentContent({
     },
     (a, b) => a === b || JSON.stringify(a) === JSON.stringify(b),
   );
-  const pendingByDraftId = useCreateFlowStore((state) => state.pendingByDraftId);
   const isInitializingFromMap = useSessionStore((state) =>
     agentId ? (state.sessions[serverId]?.initializingAgents?.get(agentId) ?? false) : false,
   );
@@ -645,6 +637,9 @@ function ChatAgentContent({
   const agentHistorySyncGeneration = useSessionStore((state) =>
     agentId ? (state.sessions[serverId]?.agentHistorySyncGeneration?.get(agentId) ?? -1) : -1,
   );
+  const hasActiveCreateHandoff = useCreateFlowStore((state) =>
+    findActiveCreateHandoff({ pendingByDraftId: state.pendingByDraftId, serverId, agentId }),
+  );
   const hasSession = useSessionStore((state) => Boolean(state.sessions[serverId]));
   const { ensureAgentIsInitialized } = useAgentInitialization({
     serverId,
@@ -654,11 +649,6 @@ function ChatAgentContent({
     kind: "idle",
   });
 
-  const pendingCreate = useMemo(
-    () => findPendingCreateForPanel({ pendingByDraftId, serverId, agentId }),
-    [agentId, pendingByDraftId, serverId],
-  );
-  const isPendingCreateForPanel = Boolean(pendingCreate);
   const hasHydratedHistoryBefore = hasAppliedAuthoritativeHistory;
 
   const attentionController = useAgentAttentionClear({
@@ -768,43 +758,36 @@ function ChatAgentContent({
     return agentHistorySyncGeneration < historySyncGeneration;
   }, [agentHistorySyncGeneration, agentId, historySyncGeneration]);
 
-  const shouldUseOptimisticStream = isPendingCreateForPanel;
-  const authoritativeStatus = agentState.status;
-  const isAuthoritativeBootstrapping =
-    authoritativeStatus === "initializing" || authoritativeStatus === "idle";
-  const showPendingCreateSubmitLoading =
-    isPendingCreateForPanel && (!authoritativeStatus || isAuthoritativeBootstrapping);
-  const canFinalizePendingCreate = Boolean(authoritativeStatus) && !isAuthoritativeBootstrapping;
-
   const agent = useMemo<AgentScreenAgent | null>(
     () => buildChatAgentFromState(agentState, projectPlacement),
     [agentState, projectPlacement],
   );
-
-  const placeholderAgent: AgentScreenAgent | null = useMemo(() => {
-    if (!shouldUseOptimisticStream || !agentId) {
-      return null;
+  const continuity = useMemo<AgentScreenContinuity>(() => {
+    if (!hasActiveCreateHandoff || !agentId) {
+      return { kind: "none" };
     }
     return {
-      serverId,
-      id: agentId,
-      status: "running",
-      cwd: ".",
-      projectPlacement: null,
+      kind: "optimistic-create",
+      agent: {
+        serverId,
+        id: agentId,
+        status: "running",
+        cwd: agent?.cwd ?? ".",
+        projectPlacement: agent?.projectPlacement ?? null,
+      },
     };
-  }, [agentId, serverId, shouldUseOptimisticStream]);
+  }, [agent, agentId, hasActiveCreateHandoff, serverId]);
 
   const viewState = useAgentScreenStateMachine({
     routeKey: `${serverId}:${agentId ?? ""}`,
     input: {
       agent: agent ?? null,
-      placeholderAgent,
       missingAgentState,
       isConnected,
       isArchivingCurrentAgent,
       isHistorySyncing,
       needsAuthoritativeSync,
-      shouldUseOptimisticStream,
+      continuity,
       hasHydratedHistoryBefore,
     },
   });
@@ -872,7 +855,7 @@ function ChatAgentContent({
     if (!agentId) {
       return;
     }
-    if (agentState.id || shouldUseOptimisticStream) {
+    if (agentState.id) {
       if (missingAgentState.kind !== "idle") {
         setMissingAgentState({ kind: "idle" });
       }
@@ -936,7 +919,6 @@ function ChatAgentContent({
     isConnected,
     missingAgentState.kind,
     serverId,
-    shouldUseOptimisticStream,
   ]);
 
   const animatedContentStyle = useMemo(
@@ -966,9 +948,6 @@ function ChatAgentContent({
       isArchivingCurrentAgent={isArchivingCurrentAgent}
       agentState={agentState}
       effectiveAgent={effectiveAgent}
-      pendingCreate={pendingCreate}
-      shouldUseOptimisticStream={shouldUseOptimisticStream}
-      canFinalizePendingCreate={canFinalizePendingCreate}
       routeBottomAnchorRequest={routeBottomAnchorRequest}
       hasAppliedAuthoritativeHistory={hasAppliedAuthoritativeHistory}
       panelToast={panelToast}
@@ -978,7 +957,6 @@ function ChatAgentContent({
       handleAddImagesCallback={handleAddImagesCallback}
       handleComposerHeightChange={handleComposerHeightChange}
       handleMessageSent={handleMessageSent}
-      showPendingCreateSubmitLoading={showPendingCreateSubmitLoading}
       showHistorySyncOverlay={showHistorySyncOverlay}
       cwd={agentCwd}
       attentionController={attentionController}
@@ -994,9 +972,6 @@ function ChatAgentReadyContent({
   isArchivingCurrentAgent,
   agentState,
   effectiveAgent,
-  pendingCreate,
-  shouldUseOptimisticStream,
-  canFinalizePendingCreate,
   routeBottomAnchorRequest,
   hasAppliedAuthoritativeHistory,
   panelToast,
@@ -1006,7 +981,6 @@ function ChatAgentReadyContent({
   handleAddImagesCallback,
   handleComposerHeightChange,
   handleMessageSent,
-  showPendingCreateSubmitLoading,
   showHistorySyncOverlay,
   cwd,
   attentionController,
@@ -1018,9 +992,6 @@ function ChatAgentReadyContent({
   isArchivingCurrentAgent: boolean;
   agentState: ChatAgentSelectedState;
   effectiveAgent: AgentScreenAgent;
-  pendingCreate: PendingCreateAttempt | null;
-  shouldUseOptimisticStream: boolean;
-  canFinalizePendingCreate: boolean;
   routeBottomAnchorRequest: RouteBottomAnchorRequest;
   hasAppliedAuthoritativeHistory: boolean;
   panelToast: ReturnType<typeof useToastHost>;
@@ -1030,7 +1001,6 @@ function ChatAgentReadyContent({
   handleAddImagesCallback: (addImages: (images: ImageAttachment[]) => void) => void;
   handleComposerHeightChange: (height: number) => void;
   handleMessageSent: () => void;
-  showPendingCreateSubmitLoading: boolean;
   showHistorySyncOverlay: boolean;
   cwd: string;
   attentionController: ReturnType<typeof useAgentAttentionClear>;
@@ -1055,9 +1025,6 @@ function ChatAgentReadyContent({
                   serverId={serverId}
                   agentId={agentId}
                   agent={effectiveAgent}
-                  pendingCreate={pendingCreate}
-                  shouldUseOptimisticStream={shouldUseOptimisticStream}
-                  canFinalizePendingCreate={canFinalizePendingCreate}
                   routeBottomAnchorRequest={routeBottomAnchorRequest}
                   hasAppliedAuthoritativeHistory={hasAppliedAuthoritativeHistory}
                   toast={panelToast.api}
@@ -1073,7 +1040,7 @@ function ChatAgentReadyContent({
               isArchivingCurrentAgent={isArchivingCurrentAgent}
               archivedAt={agentState.archivedAt}
               cwd={cwd}
-              isSubmitLoading={showPendingCreateSubmitLoading}
+              isSubmitLoading={false}
               agentInputDraft={agentInputDraft}
               onAttentionInputFocus={attentionController.clearOnInputFocus}
               onAttentionPromptSend={attentionController.clearOnPromptSend}
@@ -1113,9 +1080,6 @@ function AgentStreamSection({
   serverId,
   agentId,
   agent,
-  pendingCreate,
-  shouldUseOptimisticStream,
-  canFinalizePendingCreate,
   routeBottomAnchorRequest,
   hasAppliedAuthoritativeHistory,
   toast,
@@ -1125,9 +1089,6 @@ function AgentStreamSection({
   serverId: string;
   agentId?: string;
   agent: AgentScreenAgent;
-  pendingCreate: PendingCreateAttempt | null;
-  shouldUseOptimisticStream: boolean;
-  canFinalizePendingCreate: boolean;
   routeBottomAnchorRequest: RouteBottomAnchorRequest;
   hasAppliedAuthoritativeHistory: boolean;
   toast: ReturnType<typeof useToastHost>["api"];
@@ -1163,98 +1124,6 @@ function AgentStreamSection({
     }
     return new Map(pendingPermissionList.map((permission) => [permission.key, permission]));
   }, [pendingPermissionList]);
-  const setAgentStreamTail = useSessionStore((state) => state.setAgentStreamTail);
-  const markPendingCreateLifecycle = useCreateFlowStore((state) => state.markLifecycle);
-  const clearPendingCreate = useCreateFlowStore((state) => state.clear);
-
-  const optimisticStreamItems = useMemo<StreamItem[]>(() => {
-    if (!shouldUseOptimisticStream || !pendingCreate) {
-      return EMPTY_STREAM_ITEMS;
-    }
-    return [
-      {
-        kind: "user_message",
-        id: pendingCreate.clientMessageId,
-        text: pendingCreate.text,
-        timestamp: new Date(pendingCreate.timestamp),
-        optimistic: true,
-        ...(pendingCreate.images && pendingCreate.images.length > 0
-          ? { images: pendingCreate.images }
-          : {}),
-        ...(pendingCreate.attachments && pendingCreate.attachments.length > 0
-          ? { attachments: pendingCreate.attachments }
-          : {}),
-      },
-    ];
-  }, [pendingCreate, shouldUseOptimisticStream]);
-
-  const mergedStreamItems = useMemo<StreamItem[]>(() => {
-    if (optimisticStreamItems.length === 0) {
-      return streamItems;
-    }
-    const optimistic = optimisticStreamItems[0];
-    if (!optimistic) {
-      return streamItems;
-    }
-    const alreadyHasOptimistic = streamItems.some(
-      (item) => item.kind === "user_message" && item.id === optimistic.id,
-    );
-    return alreadyHasOptimistic ? streamItems : [...optimisticStreamItems, ...streamItems];
-  }, [optimisticStreamItems, streamItems]);
-
-  useEffect(() => {
-    if (!shouldUseOptimisticStream || !pendingCreate) {
-      return;
-    }
-    const hasUserMessage = streamItems.some(
-      (item) => item.kind === "user_message" && item.id === pendingCreate.clientMessageId,
-    );
-    if (!hasUserMessage || !canFinalizePendingCreate) {
-      return;
-    }
-
-    const pendingImages = pendingCreate.images;
-    const pendingAttachments = pendingCreate.attachments;
-    const hasPendingImages = Boolean(pendingImages && pendingImages.length > 0);
-    const hasPendingAttachments = Boolean(pendingAttachments && pendingAttachments.length > 0);
-    if (agentId && (hasPendingImages || hasPendingAttachments)) {
-      setAgentStreamTail(serverId, (previous) => {
-        const current = previous.get(agentId);
-        if (!current) {
-          return previous;
-        }
-
-        const merged = mergePendingCreateImages({
-          streamItems: current,
-          clientMessageId: pendingCreate.clientMessageId,
-          images: pendingImages,
-          attachments: pendingAttachments,
-        });
-        if (merged === current) {
-          return previous;
-        }
-
-        const next = new Map(previous);
-        next.set(agentId, merged);
-        return next;
-      });
-    }
-    markPendingCreateLifecycle({
-      draftId: pendingCreate.draftId,
-      lifecycle: "sent",
-    });
-    clearPendingCreate({ draftId: pendingCreate.draftId });
-  }, [
-    agentId,
-    canFinalizePendingCreate,
-    clearPendingCreate,
-    markPendingCreateLifecycle,
-    pendingCreate,
-    serverId,
-    setAgentStreamTail,
-    shouldUseOptimisticStream,
-    streamItems,
-  ]);
 
   return (
     <AgentStreamView
@@ -1262,7 +1131,7 @@ function AgentStreamSection({
       agentId={agent.id}
       serverId={serverId}
       agent={agent}
-      streamItems={shouldUseOptimisticStream ? mergedStreamItems : streamItems}
+      streamItems={streamItems}
       pendingPermissions={pendingPermissions}
       routeBottomAnchorRequest={routeBottomAnchorRequest}
       isAuthoritativeHistoryReady={hasAppliedAuthoritativeHistory}
diff --git a/packages/app/src/panels/draft-panel.tsx b/packages/app/src/panels/draft-panel.tsx
index 7b666190c..adc8813ca 100644
--- a/packages/app/src/panels/draft-panel.tsx
+++ b/packages/app/src/panels/draft-panel.tsx
@@ -33,12 +33,12 @@ function DraftPanel() {
   const handleCreated = useCallback(
     (agentSnapshot: Parameters<typeof normalizeAgentSnapshot>[0]) => {
       const normalized = normalizeAgentSnapshot(agentSnapshot, serverId);
-      retargetCurrentTab({ kind: "agent", agentId: agentSnapshot.id });
       useSessionStore.getState().setAgents(serverId, (prev) => {
         const next = new Map(prev);
         next.set(agentSnapshot.id, normalized);
         return next;
       });
+      retargetCurrentTab({ kind: "agent", agentId: agentSnapshot.id });
     },
     [retargetCurrentTab, serverId],
   );
diff --git a/packages/app/src/screens/workspace/workspace-pane-content.test.tsx b/packages/app/src/screens/workspace/workspace-pane-content.test.tsx
index d700da58c..fa353542f 100644
--- a/packages/app/src/screens/workspace/workspace-pane-content.test.tsx
+++ b/packages/app/src/screens/workspace/workspace-pane-content.test.tsx
@@ -48,14 +48,14 @@ function ProbePanel() {
   return null;
 }
 
-const tab: WorkspaceTabDescriptor = {
+const agentTab: WorkspaceTabDescriptor = {
   key: "agent_agent-a",
   tabId: "agent_agent-a",
   kind: "agent",
   target: { kind: "agent", agentId: "agent-a" },
 };
 
-function buildContent() {
+function buildContent(tab: WorkspaceTabDescriptor = agentTab) {
   return buildWorkspacePaneContentModel({
     tab,
     normalizedServerId: "server-a",
@@ -120,4 +120,43 @@ describe("WorkspacePaneContent", () => {
       focusPane: expect.any(Function),
     });
   });
+
+  it("keeps pane content mounted when a draft tab is retargeted in place", () => {
+    container = document.createElement("div");
+    document.body.appendChild(container);
+    root = createRoot(container);
+
+    const draftContent = buildContent({
+      key: "draft-a",
+      tabId: "draft-a",
+      kind: "draft",
+      target: { kind: "draft", draftId: "draft-a" },
+    });
+    const agentContent = buildContent({
+      key: "draft-a",
+      tabId: "draft-a",
+      kind: "agent",
+      target: { kind: "agent", agentId: "agent-a" },
+    });
+
+    act(() => {
+      root?.render(
+        <WorkspacePaneContent content={draftContent} isPaneFocused isWorkspaceFocused={true} />,
+      );
+    });
+    act(() => {
+      root?.render(
+        <WorkspacePaneContent content={agentContent} isPaneFocused isWorkspaceFocused={true} />,
+      );
+    });
+
+    expect(mountCount).toHaveBeenCalledTimes(1);
+    expect(unmountCount).not.toHaveBeenCalled();
+    expect(snapshots).toHaveLength(2);
+    expect(snapshots[1]?.paneContextValue.tabId).toBe("draft-a");
+    expect(snapshots[1]?.paneContextValue.target).toEqual({
+      kind: "agent",
+      agentId: "agent-a",
+    });
+  });
 });
diff --git a/packages/app/src/screens/workspace/workspace-pane-content.tsx b/packages/app/src/screens/workspace/workspace-pane-content.tsx
index 27fe2ba6c..3987980fd 100644
--- a/packages/app/src/screens/workspace/workspace-pane-content.tsx
+++ b/packages/app/src/screens/workspace/workspace-pane-content.tsx
@@ -42,7 +42,7 @@ export function buildWorkspacePaneContentModel({
   const registration = getPanelRegistration(tab.kind);
   invariant(registration, `No panel registration for kind: ${tab.kind}`);
   return {
-    key: `${normalizedServerId}:${normalizedWorkspaceId}:${tab.tabId}:${tab.kind}`,
+    key: `${normalizedServerId}:${normalizedWorkspaceId}:${tab.tabId}`,
     Component: registration.component,
     paneContextValue: {
       serverId: normalizedServerId,
diff --git a/packages/app/src/screens/workspace/workspace-screen.tsx b/packages/app/src/screens/workspace/workspace-screen.tsx
index d11229f8f..4c2088da5 100644
--- a/packages/app/src/screens/workspace/workspace-screen.tsx
+++ b/packages/app/src/screens/workspace/workspace-screen.tsx
@@ -1746,9 +1746,6 @@ function WorkspaceScreenContent({
   const unpinWorkspaceAgent = useWorkspaceLayoutStore((state) => state.unpinAgent);
   const hideWorkspaceAgent = useWorkspaceLayoutStore((state) => state.hideAgent);
   const retargetWorkspaceTab = useWorkspaceLayoutStore((state) => state.retargetTab);
-  const convertWorkspaceDraftToAgent = useWorkspaceLayoutStore(
-    (state) => state.convertDraftToAgent,
-  );
   const reconcileWorkspaceTabs = useWorkspaceLayoutStore((state) => state.reconcileTabs);
   const splitWorkspacePane = useWorkspaceLayoutStore((state) => state.splitPane);
   const splitWorkspacePaneEmpty = useWorkspaceLayoutStore((state) => state.splitPaneEmpty);
@@ -2842,10 +2839,6 @@ function WorkspaceScreenContent({
           if (!persistenceKey) {
             return;
           }
-          if (input.tab.kind === "draft" && target.kind === "agent") {
-            convertWorkspaceDraftToAgent(persistenceKey, input.tab.tabId, target.agentId);
-            return;
-          }
           retargetWorkspaceTab(persistenceKey, input.tab.tabId, target);
         },
         onOpenWorkspaceFile: (request: WorkspaceFileOpenRequest) => {
@@ -2875,7 +2868,6 @@ function WorkspaceScreenContent({
       openImportSheet,
       openWorkspaceChildTabFocused,
       persistenceKey,
-      convertWorkspaceDraftToAgent,
       retargetWorkspaceTab,
     ],
   );
diff --git a/packages/app/src/stores/create-flow-store.test.ts b/packages/app/src/stores/create-flow-store.test.ts
index 78f0d6ec4..17844e4bd 100644
--- a/packages/app/src/stores/create-flow-store.test.ts
+++ b/packages/app/src/stores/create-flow-store.test.ts
@@ -71,4 +71,21 @@ describe("create-flow-store", () => {
     useCreateFlowStore.getState().clear({ draftId: "draft-1" });
     expect(useCreateFlowStore.getState().pendingByDraftId["draft-1"]).toBeUndefined();
   });
+
+  it("clears pending handoff state by agent", () => {
+    useCreateFlowStore.getState().setPending({
+      draftId: "draft-1",
+      serverId: "server-1",
+      agentId: null,
+      clientMessageId: "msg-1",
+      text: "hello",
+      timestamp: Date.now(),
+    });
+    useCreateFlowStore.getState().updateAgentId({ draftId: "draft-1", agentId: "agent-1" });
+    useCreateFlowStore.getState().markLifecycle({ draftId: "draft-1", lifecycle: "sent" });
+
+    useCreateFlowStore.getState().clearByAgent({ serverId: "server-1", agentId: "agent-1" });
+
+    expect(useCreateFlowStore.getState().pendingByDraftId["draft-1"]).toBeUndefined();
+  });
 });
diff --git a/packages/app/src/stores/create-flow-store.ts b/packages/app/src/stores/create-flow-store.ts
index 84cad6e49..fd6af5311 100644
--- a/packages/app/src/stores/create-flow-store.ts
+++ b/packages/app/src/stores/create-flow-store.ts
@@ -4,7 +4,7 @@ import type { AgentAttachment } from "@server/shared/messages";
 
 export type CreateFlowLifecycleState = "active" | "abandoned" | "sent";
 
-interface PendingCreateAttempt {
+export interface PendingCreateAttempt {
   draftId: string;
   serverId: string;
   agentId: string | null;
@@ -23,6 +23,7 @@ interface CreateFlowState {
   markLifecycle: (input: { draftId: string; lifecycle: CreateFlowLifecycleState }) => void;
   rekeyDraft: (input: { fromDraftId: string; toDraftId: string }) => void;
   clear: (input: { draftId: string }) => void;
+  clearByAgent: (input: { serverId: string; agentId: string }) => void;
   clearAll: () => void;
 }
 
@@ -89,5 +90,17 @@ export const useCreateFlowStore = create<CreateFlowState>((set) => ({
       const { [draftId]: _removed, ...rest } = state.pendingByDraftId;
       return { pendingByDraftId: rest };
     }),
+  clearByAgent: ({ serverId, agentId }) =>
+    set((state) => {
+      const next = Object.fromEntries(
+        Object.entries(state.pendingByDraftId).filter(
+          ([, pending]) => pending.serverId !== serverId || pending.agentId !== agentId,
+        ),
+      );
+      if (Object.keys(next).length === Object.keys(state.pendingByDraftId).length) {
+        return state;
+      }
+      return { pendingByDraftId: next };
+    }),
   clearAll: () => set({ pendingByDraftId: {} }),
 }));
diff --git a/packages/app/src/stores/session-store.ts b/packages/app/src/stores/session-store.ts
index 3f5f3ec95..61044035e 100644
--- a/packages/app/src/stores/session-store.ts
+++ b/packages/app/src/stores/session-store.ts
@@ -3,7 +3,12 @@ import { create } from "zustand";
 import { subscribeWithSelector } from "zustand/middleware";
 import type { DaemonClient } from "@server/client/daemon-client";
 import type { AgentDirectoryEntry } from "@/types/agent-directory";
-import type { StreamItem } from "@/types/stream";
+import {
+  appendOptimisticUserMessageToStream,
+  type OptimisticUserMessagePlacement,
+  type StreamItem,
+  type UserMessageItem,
+} from "@/types/stream";
 import type { PendingPermission } from "@/types/shared";
 import type { ComposerAttachment } from "@/attachments/types";
 import type { AgentLifecycleStatus } from "@server/shared/agent-lifecycle";
@@ -351,6 +356,15 @@ interface SessionStoreActions {
     agentId: string,
     state: { tail?: StreamItem[]; head?: StreamItem[] },
   ) => void;
+  appendOptimisticUserMessageToAgentStream: (
+    serverId: string,
+    agentId: string,
+    message: UserMessageItem,
+    options: {
+      placement: OptimisticUserMessagePlacement;
+      skipIfUserMessageExists?: boolean;
+    },
+  ) => boolean;
   clearAgentStreamHead: (serverId: string, agentId: string) => void;
   setAgentTimelineCursor: (
     serverId: string,
@@ -836,6 +850,50 @@ export const useSessionStore = create<SessionStore>()(
         });
       },
 
+      appendOptimisticUserMessageToAgentStream: (serverId, agentId, message, options) => {
+        let didAppend = false;
+        set((prev) => {
+          const session = prev.sessions[serverId];
+          if (!session) {
+            return prev;
+          }
+
+          const currentTail = session.agentStreamTail.get(agentId) ?? [];
+          const currentHead = session.agentStreamHead.get(agentId) ?? [];
+          const result = appendOptimisticUserMessageToStream({
+            tail: currentTail,
+            head: currentHead,
+            message,
+            placement: options.placement,
+            skipIfUserMessageExists: options.skipIfUserMessageExists,
+          });
+          if (!result.changedTail && !result.changedHead) {
+            return prev;
+          }
+
+          const nextTail = result.changedTail
+            ? new Map(session.agentStreamTail).set(agentId, result.tail)
+            : session.agentStreamTail;
+          const nextHead = result.changedHead
+            ? new Map(session.agentStreamHead).set(agentId, result.head)
+            : session.agentStreamHead;
+          didAppend = true;
+
+          return {
+            ...prev,
+            sessions: {
+              ...prev.sessions,
+              [serverId]: {
+                ...session,
+                agentStreamTail: nextTail,
+                agentStreamHead: nextHead,
+              },
+            },
+          };
+        });
+        return didAppend;
+      },
+
       clearAgentStreamHead: (serverId, agentId) => {
         set((prev) => {
           const session = prev.sessions[serverId];
diff --git a/packages/app/src/timeline/session-stream-reducers.test.ts b/packages/app/src/timeline/session-stream-reducers.test.ts
index 13bdec08e..496ac6c96 100644
--- a/packages/app/src/timeline/session-stream-reducers.test.ts
+++ b/packages/app/src/timeline/session-stream-reducers.test.ts
@@ -1,6 +1,11 @@
 import { describe, expect, it } from "vitest";
 import type { AgentStreamEventPayload } from "@server/shared/messages";
-import { hydrateStreamState, type AgentToolCallItem, type StreamItem } from "@/types/stream";
+import {
+  buildOptimisticUserMessage,
+  hydrateStreamState,
+  type AgentToolCallItem,
+  type StreamItem,
+} from "@/types/stream";
 import {
   createAgentStreamReducerQueue,
   processTimelineResponse,
@@ -103,6 +108,17 @@ function makeAssistantItem(text: string, id = `assistant-${text.length}`): Strea
   };
 }
 
+function makeOptimisticUserMessage(
+  text: string,
+  id = `optimistic-${text.length}`,
+): Extract<StreamItem, { kind: "user_message" }> {
+  return buildOptimisticUserMessage({
+    id,
+    text,
+    timestamp: new Date(1000),
+  });
+}
+
 function getAssistantTexts(items: StreamItem[]): string[] {
   return items
     .filter((item): item is Extract<StreamItem, { kind: "assistant_message" }> => {
@@ -275,6 +291,76 @@ describe("processTimelineResponse", () => {
     expect(assistant?.timestamp.toISOString()).toBe("2025-01-01T12:00:04.000Z");
   });
 
+  it("reconciles an optimistic user message during tail replacement", () => {
+    const image = {
+      id: "optimistic-image",
+      mimeType: "image/png",
+      storageType: "web-indexeddb" as const,
+      storageKey: "optimistic-image",
+      createdAt: 1000,
+    };
+    const attachment = {
+      type: "text" as const,
+      mimeType: "text/plain" as const,
+      text: "attached context",
+      title: "context.txt",
+    };
+    const optimistic = buildOptimisticUserMessage({
+      id: "optimistic-create-user",
+      text: "Analyze this",
+      timestamp: new Date(1000),
+      images: [image],
+      attachments: [attachment],
+    });
+
+    const result = processTimelineResponse({
+      ...baseTimelineInput,
+      currentTail: [optimistic],
+      payload: {
+        ...baseTimelineInput.payload,
+        reset: true,
+        startCursor: { seq: 1 },
+        endCursor: { seq: 1 },
+        entries: [
+          {
+            ...makeTimelineEntry(1, "Analyze this", "user_message"),
+            item: {
+              type: "user_message",
+              text: "Analyze this",
+              messageId: "canonical-create-user",
+            },
+          },
+        ],
+      },
+    });
+
+    const userMessages = result.tail.filter((item) => item.kind === "user_message");
+    expect(userMessages).toHaveLength(1);
+    expect(userMessages[0]).toMatchObject({
+      id: "canonical-create-user",
+      text: "Analyze this",
+      images: [image],
+      attachments: [attachment],
+    });
+    expect(userMessages[0]?.optimistic).toBeUndefined();
+  });
+
+  it("keeps an unmatched optimistic user message during tail replacement", () => {
+    const optimistic = makeOptimisticUserMessage("still sending", "optimistic-unmatched");
+
+    const result = processTimelineResponse({
+      ...baseTimelineInput,
+      currentTail: [optimistic],
+      payload: {
+        ...baseTimelineInput.payload,
+        reset: true,
+        entries: [],
+      },
+    });
+
+    expect(result.tail).toEqual([optimistic]);
+  });
+
   it("sets cursor to null when reset=true but no cursors in payload", () => {
     const existingTail: StreamItem[] = [
       {
@@ -363,6 +449,40 @@ describe("processTimelineResponse", () => {
     expect(result.error).toBe(null);
   });
 
+  it("reconciles an optimistic user message during an after-page response", () => {
+    const existingCursor: TimelineCursor = {
+      epoch: "epoch-1",
+      startSeq: 1,
+      endSeq: 1,
+    };
+    const optimistic = makeOptimisticUserMessage("sent while catching up", "optimistic-after");
+
+    const result = processTimelineResponse({
+      ...baseTimelineInput,
+      currentTail: [optimistic],
+      currentCursor: existingCursor,
+      payload: {
+        ...baseTimelineInput.payload,
+        epoch: "epoch-1",
+        entries: [
+          {
+            ...makeTimelineEntry(2, "sent while catching up", "user_message"),
+            item: {
+              type: "user_message",
+              text: "sent while catching up",
+              messageId: "canonical-after",
+            },
+          },
+        ],
+      },
+    });
+
+    const userMessages = result.tail.filter((item) => item.kind === "user_message");
+    expect(userMessages).toHaveLength(1);
+    expect(userMessages[0]?.id).toBe("canonical-after");
+    expect(userMessages[0]?.optimistic).toBeUndefined();
+  });
+
   it("keeps an active assistant head live when an incremental fetch accepts same-turn assistant text", () => {
     const existingCursor: TimelineCursor = {
       epoch: "epoch-1",
@@ -483,6 +603,43 @@ describe("processTimelineResponse", () => {
     });
   });
 
+  it("does not reconcile an active optimistic user message from a before-page response", () => {
+    const optimistic = makeOptimisticUserMessage("active prompt", "optimistic-active");
+    const existingCursor: TimelineCursor = {
+      epoch: "epoch-1",
+      startSeq: 3,
+      endSeq: 5,
+    };
+
+    const result = processTimelineResponse({
+      ...baseTimelineInput,
+      currentTail: [optimistic],
+      currentCursor: existingCursor,
+      payload: {
+        ...baseTimelineInput.payload,
+        direction: "before",
+        epoch: "epoch-1",
+        startCursor: { seq: 1 },
+        endCursor: { seq: 2 },
+        entries: [
+          {
+            ...makeTimelineEntry(1, "older prompt", "user_message"),
+            item: {
+              type: "user_message",
+              text: "older prompt",
+              messageId: "canonical-before",
+            },
+          },
+        ],
+      },
+    });
+
+    const userMessages = result.tail.filter((item) => item.kind === "user_message");
+    expect(userMessages).toHaveLength(2);
+    expect(userMessages.map((item) => item.id)).toEqual(["canonical-before", "optimistic-active"]);
+    expect(userMessages[1]?.optimistic).toBe(true);
+  });
+
   it("leaves the cursor alone when a before page makes no progress", () => {
     const currentTail: StreamItem[] = [
       {
diff --git a/packages/app/src/timeline/session-stream-reducers.ts b/packages/app/src/timeline/session-stream-reducers.ts
index e8a0ee738..0f1c07f38 100644
--- a/packages/app/src/timeline/session-stream-reducers.ts
+++ b/packages/app/src/timeline/session-stream-reducers.ts
@@ -2,7 +2,7 @@ import type { AgentStreamEventPayload } from "@server/shared/messages";
 import type { AgentLifecycleStatus } from "@server/shared/agent-lifecycle";
 import type { Agent } from "@/stores/session-store";
 import { useSessionStore } from "@/stores/session-store";
-import type { StreamItem } from "@/types/stream";
+import type { StreamItem, UserMessageItem } from "@/types/stream";
 import {
   applyStreamEvent,
   hydrateStreamState,
@@ -240,15 +240,22 @@ function applyTimelineReplacePath(args: {
   timelineUnits: TimelineUnit[];
   payload: ProcessTimelineResponseInput["payload"];
   bootstrapPolicy: ReturnType<typeof deriveBootstrapTailTimelinePolicy>;
+  currentTail: StreamItem[];
   currentHead: StreamItem[];
   toHydratedEvents: (
     units: TimelineUnit[],
   ) => Array<{ event: AgentStreamEventPayload; timestamp: Date }>;
 }): TimelinePathResult {
-  const { timelineUnits, payload, bootstrapPolicy, currentHead, toHydratedEvents } = args;
+  const { timelineUnits, payload, bootstrapPolicy, currentTail, currentHead, toHydratedEvents } =
+    args;
   const hydratedTail = hydrateStreamState(toHydratedEvents(timelineUnits), { source: "canonical" });
+  const reconciledTail = reconcileOptimisticUsersAfterReplace({
+    canonicalTail: hydratedTail,
+    previousTail: currentTail,
+    previousHead: currentHead,
+  });
   const { tail, head } = preserveReplacePathAssistantHead({
-    tail: hydratedTail,
+    tail: reconciledTail,
     currentHead,
   });
   const cursor: TimelineCursor | null =
@@ -266,6 +273,93 @@ function applyTimelineReplacePath(args: {
   return { tail, head, cursor, cursorChanged: true, sideEffects };
 }
 
+function collectOptimisticUserMessages(items: StreamItem[]): Array<{
+  ordinal: number;
+  item: UserMessageItem;
+}> {
+  const optimistic: Array<{ ordinal: number; item: UserMessageItem }> = [];
+  let ordinal = 0;
+  for (const item of items) {
+    if (item.kind !== "user_message") {
+      continue;
+    }
+    if (item.optimistic) {
+      optimistic.push({ ordinal, item });
+    }
+    ordinal += 1;
+  }
+  return optimistic;
+}
+
+function mergeCanonicalUserWithOptimistic(
+  canonical: UserMessageItem,
+  optimistic: UserMessageItem,
+): UserMessageItem {
+  const shouldPreserveImages =
+    (!canonical.images || canonical.images.length === 0) &&
+    Boolean(optimistic.images && optimistic.images.length > 0);
+  const shouldPreserveAttachments =
+    (!canonical.attachments || canonical.attachments.length === 0) &&
+    Boolean(optimistic.attachments && optimistic.attachments.length > 0);
+  return {
+    ...canonical,
+    ...(shouldPreserveImages ? { images: optimistic.images } : {}),
+    ...(shouldPreserveAttachments ? { attachments: optimistic.attachments } : {}),
+  };
+}
+
+function reconcileOptimisticUsersAfterReplace(params: {
+  canonicalTail: StreamItem[];
+  previousTail: StreamItem[];
+  previousHead: StreamItem[];
+}): StreamItem[] {
+  const optimisticUsers = collectOptimisticUserMessages([
+    ...params.previousTail,
+    ...params.previousHead,
+  ]);
+  if (optimisticUsers.length === 0) {
+    return params.canonicalTail;
+  }
+
+  const canonicalUserIndexes: number[] = [];
+  params.canonicalTail.forEach((item, index) => {
+    if (item.kind === "user_message") {
+      canonicalUserIndexes.push(index);
+    }
+  });
+
+  let changed = false;
+  const nextTail = [...params.canonicalTail];
+  let searchFromOrdinal = 0;
+  const unmatched: UserMessageItem[] = [];
+
+  for (const optimistic of optimisticUsers) {
+    const canonicalOrdinal = canonicalUserIndexes.findIndex(
+      (_index, ordinal) => ordinal >= Math.max(optimistic.ordinal, searchFromOrdinal),
+    );
+    if (canonicalOrdinal < 0) {
+      unmatched.push(optimistic.item);
+      continue;
+    }
+
+    const canonicalIndex = canonicalUserIndexes[canonicalOrdinal];
+    const canonicalItem = canonicalIndex !== undefined ? nextTail[canonicalIndex] : undefined;
+    if (!canonicalItem || canonicalItem.kind !== "user_message") {
+      unmatched.push(optimistic.item);
+      continue;
+    }
+    nextTail[canonicalIndex] = mergeCanonicalUserWithOptimistic(canonicalItem, optimistic.item);
+    searchFromOrdinal = canonicalOrdinal + 1;
+    changed = true;
+  }
+
+  if (unmatched.length === 0) {
+    return changed ? nextTail : params.canonicalTail;
+  }
+
+  return [...nextTail, ...unmatched];
+}
+
 interface IncrementalAcceptResult {
   acceptedUnits: TimelineUnit[];
   cursor: TimelineCursor | undefined;
@@ -531,6 +625,7 @@ export function processTimelineResponse(
         timelineUnits,
         payload,
         bootstrapPolicy,
+        currentTail,
         currentHead,
         toHydratedEvents,
       })
diff --git a/packages/app/src/types/stream.test.ts b/packages/app/src/types/stream.test.ts
index 65d9e2881..abd7b2512 100644
--- a/packages/app/src/types/stream.test.ts
+++ b/packages/app/src/types/stream.test.ts
@@ -4,6 +4,8 @@ import { describe, expect, it } from "vitest";
 
 import {
   applyStreamEvent,
+  appendOptimisticUserMessageToStream,
+  buildOptimisticUserMessage,
   clearOptimisticUserMessages,
   hydrateStreamState,
   mergeToolCallDetail,
@@ -1030,6 +1032,102 @@ describe("turn lifecycle events", () => {
     assert.strictEqual(userMessage.optimistic, undefined);
   });
 
+  it("replaces an optimistic image user message with the next canonical server user message", () => {
+    const optimisticTimestamp = new Date("2025-01-01T15:03:10Z");
+    const image = {
+      id: "image-canonical",
+      mimeType: "image/png",
+      storageType: "web-indexeddb" as const,
+      storageKey: "image-canonical",
+      createdAt: optimisticTimestamp.getTime(),
+    };
+    const attachment = {
+      type: "text" as const,
+      mimeType: "text/plain" as const,
+      text: "context",
+      title: "context.txt",
+    };
+    const optimistic = buildOptimisticUserMessage({
+      id: "msg_optimistic_canonical",
+      text: "Analyze this",
+      timestamp: optimisticTimestamp,
+      images: [image],
+      attachments: [attachment],
+    });
+
+    const state = reduceStreamUpdate(
+      [optimistic],
+      {
+        type: "timeline",
+        provider: "claude",
+        item: {
+          type: "user_message",
+          text: "Analyze this",
+          messageId: "provider-owned-canonical",
+        },
+      },
+      new Date("2025-01-01T15:03:11Z"),
+      { source: "canonical" },
+    );
+
+    const userMessages = state.filter((item) => item.kind === "user_message");
+    assert.strictEqual(userMessages.length, 1);
+    const userMessage = userMessages[0];
+    invariant(userMessage?.kind === "user_message");
+    assert.strictEqual(userMessage.id, "provider-owned-canonical");
+    assert.strictEqual(userMessage.optimistic, undefined);
+    assert.deepStrictEqual(userMessage.images, [image]);
+    assert.deepStrictEqual(userMessage.attachments, [attachment]);
+  });
+
+  it("places optimistic user messages through one append helper", () => {
+    const optimistic = buildOptimisticUserMessage({
+      id: "msg_append_once",
+      text: "append once",
+      timestamp: new Date("2025-01-01T15:03:20Z"),
+    });
+    const headItem: StreamItem = {
+      kind: "assistant_message",
+      id: "assistant-head",
+      text: "streaming",
+      timestamp: new Date("2025-01-01T15:03:19Z"),
+    };
+
+    const first = appendOptimisticUserMessageToStream({
+      tail: [],
+      head: [headItem],
+      message: optimistic,
+      placement: "active-head",
+    });
+    const second = appendOptimisticUserMessageToStream({
+      tail: first.tail,
+      head: first.head,
+      message: optimistic,
+      placement: "active-head",
+    });
+    const skipped = appendOptimisticUserMessageToStream({
+      tail: [
+        {
+          kind: "user_message",
+          id: "canonical-user",
+          text: "already canonical",
+          timestamp: new Date("2025-01-01T15:03:21Z"),
+        },
+      ],
+      head: [],
+      message: optimistic,
+      placement: "tail",
+      skipIfUserMessageExists: true,
+    });
+
+    assert.deepStrictEqual(first.tail, []);
+    assert.deepStrictEqual(first.head, [headItem, optimistic]);
+    assert.strictEqual(second.changedHead, false);
+    assert.strictEqual(second.head, first.head);
+    assert.strictEqual(skipped.changedTail, false);
+    assert.strictEqual(skipped.tail.length, 1);
+  });
+
   it("reconciles an optimistic user message that was pending in the streaming head", () => {
     const optimistic: StreamItem = {
       kind: "user_message",
diff --git a/packages/app/src/types/stream.ts b/packages/app/src/types/stream.ts
index 96edfdbaf..d6c0b36c9 100644
--- a/packages/app/src/types/stream.ts
+++ b/packages/app/src/types/stream.ts
@@ -64,6 +64,16 @@ export interface UserMessageItem {
   attachments?: AgentAttachment[];
 }
 
+export interface OptimisticUserMessageInput {
+  id: string;
+  text: string;
+  timestamp: Date;
+  images?: UserMessageImageAttachment[];
+  attachments?: AgentAttachment[];
+}
+
+export type OptimisticUserMessagePlacement = "tail" | "active-head";
+
 export interface AssistantMessageItem {
   kind: "assistant_message";
   id: string;
@@ -206,11 +216,61 @@ function buildUserMessageItem(input: {
   };
 }
 
+export function buildOptimisticUserMessage(input: OptimisticUserMessageInput): UserMessageItem {
+  return {
+    kind: "user_message",
+    id: input.id,
+    text: input.text,
+    timestamp: input.timestamp,
+    optimistic: true,
+    ...(input.images && input.images.length > 0 ? { images: input.images } : {}),
+    ...(input.attachments && input.attachments.length > 0
+      ? { attachments: input.attachments }
+      : {}),
+  };
+}
+
+function hasUserMessage(state: StreamItem[]): boolean {
+  return state.some((item) => item.kind === "user_message");
+}
+
+export function appendOptimisticUserMessageToStream(params: {
+  tail: StreamItem[];
+  head: StreamItem[];
+  message: UserMessageItem;
+  placement: OptimisticUserMessagePlacement;
+  skipIfUserMessageExists?: boolean;
+}): ApplyStreamEventResult {
+  const { tail, head, message, placement } = params;
+  if (
+    tail.some((item) => item.id === message.id) ||
+    head.some((item) => item.id === message.id) ||
+    (params.skipIfUserMessageExists && (hasUserMessage(tail) || hasUserMessage(head)))
+  ) {
+    return { tail, head, changedTail: false, changedHead: false };
+  }
+
+  if (placement === "active-head" && head.length > 0) {
+    return {
+      tail,
+      head: [...head, message],
+      changedTail: false,
+      changedHead: true,
+    };
+  }
+
+  return {
+    tail: [...tail, message],
+    head,
+    changedTail: true,
+    changedHead: false,
+  };
+}
+
 function appendUserMessage(
   state: StreamItem[],
   text: string,
   timestamp: Date,
-  source: StreamUpdateSource,
   messageId?: string,
 ): StreamItem[] {
   const { chunk, hasContent } = normalizeChunk(text);
@@ -220,10 +280,9 @@ function appendUserMessage(
 
   const chunkSeed = chunk.trim() || chunk;
   const entryId = messageId ?? createUniqueTimelineId(state, "user", chunkSeed, timestamp);
-  const optimisticIndex =
-    source === "live"
-      ? state.findIndex((entry) => entry.kind === "user_message" && entry.optimistic)
-      : -1;
+  const optimisticIndex = state.findIndex(
+    (entry) => entry.kind === "user_message" && entry.optimistic,
+  );
   const optimistic = optimisticIndex >= 0 ? (state[optimisticIndex] as UserMessageItem) : null;
 
   const nextItem = buildUserMessageItem({
@@ -688,9 +747,7 @@ function reduceTimelineEvent(
   const item = event.item;
   switch (item.type) {
     case "user_message":
-      return finalizeActiveThoughts(
-        appendUserMessage(state, item.text, timestamp, source, item.messageId),
-      );
+      return finalizeActiveThoughts(appendUserMessage(state, item.text, timestamp, item.messageId));
     case "assistant_message":
       return finalizeActiveThoughts(
         appendAssistantMessage(state, item.text, timestamp, source, item.messageId),
diff --git a/packages/app/src/utils/pending-create-images.test.ts b/packages/app/src/utils/pending-create-images.test.ts
deleted file mode 100644
index ba84c1da2..000000000
--- a/packages/app/src/utils/pending-create-images.test.ts
+++ /dev/null
@@ -1,154 +0,0 @@
-import { describe, expect, it } from "vitest";
-import type { StreamItem } from "@/types/stream";
-import { mergePendingCreateImages } from "./pending-create-images";
-import type { AgentAttachment } from "@server/shared/messages";
-
-function userMessage(params: {
-  id: string;
-  text: string;
-  images?: Array<{
-    id: string;
-    storageType: "native-file";
-    storageKey: string;
-    mimeType: string;
-    createdAt: number;
-  }>;
-  attachments?: AgentAttachment[];
-}): StreamItem {
-  return {
-    kind: "user_message",
-    id: params.id,
-    text: params.text,
-    timestamp: new Date("2026-01-01T00:00:00Z"),
-    ...(params.images ? { images: params.images } : {}),
-    ...(params.attachments ? { attachments: params.attachments } : {}),
-  };
-}
-
-function buildImage(id: string) {
-  return [
-    {
-      id,
-      storageType: "native-file" as const,
-      storageKey: `/tmp/${id}.jpg`,
-      mimeType: "image/jpeg",
-      createdAt: Date.now(),
-    },
-  ];
-}
-
-function buildReviewAttachment(): AgentAttachment {
-  return {
-    type: "review",
-    mimeType: "application/paseo-review",
-    cwd: "/repo",
-    mode: "base",
-    comments: [],
-  };
-}
-
-describe("mergePendingCreateImages", () => {
-  it("returns same reference when pending images are absent", () => {
-    const streamItems = [userMessage({ id: "msg-1", text: "hello" })];
-    const result = mergePendingCreateImages({
-      streamItems,
-      clientMessageId: "msg-1",
-      images: [],
-    });
-    expect(result).toBe(streamItems);
-  });
-
-  it("merges images by clientMessageId when matched message has none", () => {
-    const streamItems = [userMessage({ id: "msg-1", text: "hello" })];
-    const images = buildImage("image-1");
-    const result = mergePendingCreateImages({
-      streamItems,
-      clientMessageId: "msg-1",
-      images,
-    });
-
-    expect(result).not.toBe(streamItems);
-    const updated = result[0];
-    expect(updated?.kind).toBe("user_message");
-    if (updated?.kind !== "user_message") {
-      throw new Error("Expected user_message item");
-    }
-    expect(updated.images).toEqual(images);
-  });
-
-  it("merges attachments by clientMessageId when matched message has none", () => {
-    const streamItems = [userMessage({ id: "msg-1", text: "hello" })];
-    const attachments = [buildReviewAttachment()];
-    const result = mergePendingCreateImages({
-      streamItems,
-      clientMessageId: "msg-1",
-      attachments,
-    });
-
-    expect(result).not.toBe(streamItems);
-    const updated = result[0];
-    expect(updated?.kind).toBe("user_message");
-    if (updated?.kind !== "user_message") {
-      throw new Error("Expected user_message item");
-    }
-    expect(updated.attachments).toEqual(attachments);
-  });
-
-  it("does not merge when clientMessageId does not match", () => {
-    const streamItems = [userMessage({ id: "msg-1", text: "same text" })];
-    const images = buildImage("image-2");
-    const result = mergePendingCreateImages({
-      streamItems,
-      clientMessageId: "missing-id",
-      images,
-    });
-
-    expect(result).toBe(streamItems);
-  });
-
-  it("does not overwrite existing user message images", () => {
-    const existingImages = buildImage("existing");
-    const streamItems = [userMessage({ id: "msg-1", text: "hello", images: existingImages })];
-    const result = mergePendingCreateImages({
-      streamItems,
-      clientMessageId: "msg-1",
-      images: buildImage("new"),
-    });
-
-    expect(result).toBe(streamItems);
-    const unchanged = result[0];
-    expect(unchanged?.kind).toBe("user_message");
-    if (unchanged?.kind !== "user_message") {
-      throw new Error("Expected user_message item");
-    }
-    expect(unchanged.images).toEqual(existingImages);
-  });
-
-  it("does not overwrite existing user message attachments", () => {
-    const existingAttachments = [buildReviewAttachment()];
-    const streamItems = [
-      userMessage({ id: "msg-1", text: "hello", attachments: existingAttachments }),
-    ];
-    const result = mergePendingCreateImages({
-      streamItems,
-      clientMessageId: "msg-1",
-      attachments: [
-        {
-          type: "github_issue",
-          mimeType: "application/github-issue",
-          number: 7,
-          title: "Issue",
-          url: "https://github.com/getpaseo/paseo/issues/7",
-        },
-      ],
-    });
-
-    expect(result).toBe(streamItems);
-    const unchanged = result[0];
-    expect(unchanged?.kind).toBe("user_message");
-    if (unchanged?.kind !== "user_message") {
-      throw new Error("Expected user_message item");
-    }
-    expect(unchanged.attachments).toEqual(existingAttachments);
-  });
-});
diff --git a/packages/app/src/utils/pending-create-images.ts b/packages/app/src/utils/pending-create-images.ts
deleted file mode 100644
index ea700f754..000000000
--- a/packages/app/src/utils/pending-create-images.ts
+++ /dev/null
@@ -1,48 +0,0 @@
-import type { StreamItem, UserMessageImageAttachment } from "@/types/stream";
-import type { AgentAttachment } from "@server/shared/messages";
-
-interface MergePendingCreateImagesParams {
-  streamItems: StreamItem[];
-  clientMessageId: string;
-  images?: UserMessageImageAttachment[];
-  attachments?: AgentAttachment[];
-}
-
-export function mergePendingCreateImages({
-  streamItems,
-  clientMessageId,
-  images,
-  attachments,
-}: MergePendingCreateImagesParams): StreamItem[] {
-  const hasPendingImages = Boolean(images && images.length > 0);
-  const hasPendingAttachments = Boolean(attachments && attachments.length > 0);
-  if (!hasPendingImages && !hasPendingAttachments) {
-    return streamItems;
-  }
-
-  const targetIndex = streamItems.findIndex(
-    (item) => item.kind === "user_message" && item.id === clientMessageId,
-  );
-  if (targetIndex < 0) {
-    return streamItems;
-  }
-
-  const target = streamItems[targetIndex];
-  if (target.kind !== "user_message") {
-    return streamItems;
-  }
-  const shouldMergeImages = hasPendingImages && (!target.images || target.images.length === 0);
-  const shouldMergeAttachments =
-    hasPendingAttachments && (!target.attachments || target.attachments.length === 0);
-  if (!shouldMergeImages && !shouldMergeAttachments) {
-    return streamItems;
-  }
-
-  const next = [...streamItems];
-  next[targetIndex] = {
-    ...target,
-    ...(shouldMergeImages ? { images } : {}),
-    ...(shouldMergeAttachments ? { attachments } : {}),
-  };
-  return next;
-}