diff --git a/apps/web/src/components/ChatView.logic.test.ts b/apps/web/src/components/ChatView.logic.test.ts
index 0f48fa1b9f06..9e6b96b21018 100644
--- a/apps/web/src/components/ChatView.logic.test.ts
+++ b/apps/web/src/components/ChatView.logic.test.ts
@@ -628,6 +628,30 @@ describe("hasServerAcknowledgedLocalDispatch", () => {
     ).toBe(true);
   });
 
+  it("holds a first send while the thread shell still reports a preparing run", () => {
+    // The draft had no run. The server thread's shell shows the new run before
+    // the detail projection behind `phase` loads.
+    const localDispatch = createLocalDispatchSnapshot(makeThread());
+    const preparingRun = {
+      ...completedTurn,
+      status: "preparing" as const,
+      startedAt: null,
+      completedAt: null,
+    };
+
+    expect(
+      hasServerAcknowledgedLocalDispatch({
+        localDispatch,
+        phase: "disconnected",
+        latestRun: preparingRun,
+        runtime: { ...readySession, status: "preparing", activeRunId: preparingRun.runId },
+        hasPendingApproval: false,
+        hasPendingUserInput: false,
+        threadError: null,
+      }),
+    ).toBe(false);
+  });
+
   it("waits for the matching running turn before acknowledging", () => {
     const localDispatch = createLocalDispatchSnapshot(
       makeThread({ latestRun: completedTurn, runtime: readySession }),
diff --git a/apps/web/src/components/ChatView.logic.ts b/apps/web/src/components/ChatView.logic.ts
index 255a4f7e8cd3..3323a8f3e0b9 100644
--- a/apps/web/src/components/ChatView.logic.ts
+++ b/apps/web/src/components/ChatView.logic.ts
@@ -57,7 +57,7 @@ import { stripInlineContextReferences } from "~/lib/composerContextReferences";
 import type { DraftThreadEnvMode } from "../composerDraftStore";
 import { collapseExpandedComposerCursor, type ComposerSubmissionIntent } from "../composer-logic";
 import type { ReviewCommentContext } from "../reviewCommentContext";
-import type { TimelineEntry } from "../session-logic";
+import { derivePhase, type TimelineEntry } from "../session-logic";
 import type { PreviewMiniPlayerSource } from "../previewMiniPlayerStore";
 import type { DesktopPreviewOverlay } from "../previewStateStore";
 import type { RightPanelSurface } from "../rightPanelStore";
@@ -1248,7 +1248,10 @@ export function hasServerAcknowledgedLocalDispatch(input: {
   if (input.hasPendingApproval || input.hasPendingUserInput || Boolean(input.threadError)) {
     return true;
   }
-  if (input.phase === "connecting") {
+  // The thread shell can report a preparing or starting run before the detail
+  // projection behind `phase` loads, so either source still connecting holds
+  // the send.
+  if (input.phase === "connecting" || derivePhase(input.runtime ?? null) === "connecting") {
     return false;
   }
 
diff --git a/apps/web/src/components/ChatView.tsx b/apps/web/src/components/ChatView.tsx
index b5a96518892c..e2037c2a0645 100644
--- a/apps/web/src/components/ChatView.tsx
+++ b/apps/web/src/components/ChatView.tsx
@@ -6396,6 +6396,9 @@ export default function ChatView(props: ChatViewProps) {
     optimisticUserMessages,
   ]);
 
+  // Keyed on the thread, not the draft: a draft's promotion to its server
+  // route keeps this instance and drops `draftId`, and the send it is still
+  // dispatching must survive that swap.
   useEffect(() => {
     setOptimisticUserMessages((existing) => {
       for (const message of existing) {
@@ -6405,7 +6408,7 @@ export default function ChatView(props: ChatViewProps) {
     });
     resetLocalDispatch();
     setExpandedImage(null);
-  }, [draftId, resetLocalDispatch, threadId]);
+  }, [resetLocalDispatch, threadId]);
 
   const closeExpandedImage = useCallback(() => {
     setExpandedImage(null);
diff --git a/apps/web/src/components/chat/MessagesTimeline.logic.test.ts b/apps/web/src/components/chat/MessagesTimeline.logic.test.ts
index e7c0afa479d6..7c2fb5bd8893 100644
--- a/apps/web/src/components/chat/MessagesTimeline.logic.test.ts
+++ b/apps/web/src/components/chat/MessagesTimeline.logic.test.ts
@@ -4625,6 +4625,22 @@ it("keeps the working header in place across worktree setup handoff", () => {
   expect(handoffRows.map((row) => row.kind)).toEqual(["message", "working", "worktree-setup"]);
   expect(handoffRows[2]).toMatchObject({ kind: "worktree-setup", embedded: false });
 
+  // A clean finish before the turn is live keeps that same layout, so the card
+  // does not jump above the header in the gap before the run starts.
+  const settledRows = deriveMessagesTimelineRows({
+    timelineEntries: [userEntry],
+    isWorking: true,
+    activeTurnStartedAt: "2026-01-01T00:00:00Z",
+    turnDiffSummaries: [],
+    supportsConversationRollback: false,
+    worktreeSetup: {
+      ...snapshot,
+      phase: "done",
+      stages: [stage("setup-script", "done"), stage("agent", "done")],
+    },
+  });
+  expect(settledRows.map((row) => row.kind)).toEqual(["message", "working", "worktree-setup"]);
+
   // A script that already finished has nothing left to show once the turn is live.
   const finishedRows = deriveMessagesTimelineRows({
     timelineEntries: [userEntry],
diff --git a/apps/web/src/components/chat/MessagesTimeline.logic.ts b/apps/web/src/components/chat/MessagesTimeline.logic.ts
index b035839c4ae4..88da32d28fc3 100644
--- a/apps/web/src/components/chat/MessagesTimeline.logic.ts
+++ b/apps/web/src/components/chat/MessagesTimeline.logic.ts
@@ -1673,7 +1673,11 @@ export function deriveMessagesTimelineRows(input: {
     input.worktreeSetup !== undefined &&
     worktreeSetupAgentStarted(input.worktreeSetup) &&
     input.latestRun?.startedAt != null;
-  const setupRunning = !setupHandedOff && input.worktreeSetup?.phase === "running";
+  // A finished setup keeps the slot until the turn is live, so the card does
+  // not jump above the working header in the gap before the run starts.
+  const setupOwnsWorkingSlot =
+    !setupHandedOff &&
+    (input.worktreeSetup?.phase === "running" || input.worktreeSetup?.phase === "done");
   if (input.worktreeSetup && (!setupHandedOff || input.worktreeSetup.phase !== "running")) {
     const setupRow = {
       kind: "worktree-setup",
@@ -1688,7 +1692,9 @@ export function deriveMessagesTimelineRows(input: {
     // While the setup runs, the working header leads the card in the same
     // slot it keeps once the agent's own turn takes over. The main pass may
     // already have placed that header (a bootstrap counts as working).
-    const workingRowIndex = setupRunning ? nextRows.findIndex((row) => row.kind === "working") : -1;
+    const workingRowIndex = setupOwnsWorkingSlot
+      ? nextRows.findIndex((row) => row.kind === "working")
+      : -1;
     if (workingRowIndex >= 0) {
       nextRows.splice(workingRowIndex + 1, 0, setupRow);
     } else {
@@ -1696,7 +1702,7 @@ export function deriveMessagesTimelineRows(input: {
       nextRows.splice(
         insertAt,
         0,
-        ...(setupRunning
+        ...(setupOwnsWorkingSlot
           ? [
               {
                 kind: "working",
@@ -1710,15 +1716,15 @@ export function deriveMessagesTimelineRows(input: {
     }
   }
 
-  // A running setup owns the working slot above its card and shows no
-  // activity row of its own; every other state gets the usual tail.
+  // A setup that owns the working slot sits under it and shows no activity
+  // row of its own; every other state gets the usual tail.
   const hasWorkingRow = nextRows.some((row) => row.kind === "working");
   if (input.isWorking && !hasWorkingRow && activeTurnHeaderIndex === timelineEntries.length) {
     appendWorkingRow();
   }
   if (
     input.isWorking &&
-    !setupRunning &&
+    !setupOwnsWorkingSlot &&
     !hasActiveCompaction &&
     (!hasActivityRow || latestToolFailed)
   ) {
diff --git a/apps/web/src/components/chat/WorktreeSetupCard.tsx b/apps/web/src/components/chat/WorktreeSetupCard.tsx
index ae625c6a0d6f..0d0a0bc1b415 100644
--- a/apps/web/src/components/chat/WorktreeSetupCard.tsx
+++ b/apps/web/src/components/chat/WorktreeSetupCard.tsx
@@ -356,17 +356,20 @@ export function WorktreeSetupCard({
   const setupStage = snapshot.stages.find((stage) => stage.id === "setup-script");
   const showTerminal = onOpenTerminal && setupStage && setupStage.status !== "pending";
   const collapsed = embedded && !running;
-  // While running, the timeline's working row above the card carries the
-  // "Setting up worktree…" label (and keeps that slot when the agent takes
-  // over). The card only brings its own header for a settled outcome that
-  // has no working row to sit under.
-  const showHeader = !embedded && !running;
+  // While running, and after a clean finish until the agent's turn is live,
+  // the timeline's working row above the card carries the label (and keeps
+  // that slot when the agent takes over). The card only brings its own
+  // header for a failed or cancelled setup that has no working row above it.
+  const showHeader = !embedded && !running && snapshot.phase !== "done";
   // The tail box is part of the script row's footprint while the script runs
   // (and after it failed, so the last lines explain the failure). It mounts
-  // as soon as the script is running, empty lines and all, so the card takes
-  // its final height once instead of growing with each output line.
+  // with the first output line at its full fixed height, so the card grows
+  // once instead of with each line. A script that ends before printing
+  // anything never flashes an empty box.
   const showTail =
-    setupStage !== undefined && (setupStage.status === "running" || setupStage.status === "failed");
+    setupStage !== undefined &&
+    (setupStage.status === "failed" ||
+      (setupStage.status === "running" && setupStage.tail.length > 0));
 
   return (
     <section aria-label="Worktree setup" data-worktree-setup-phase={snapshot.phase}>