fix(app): render mixed HTML headings without literal tags

Keep a matched heading together before splitting its image and text contents. Splitting first stranded the opening heading tag in a text slice without its closing tag.

packages/app/e2e/browser/add-project-flow.spec.ts

@@ -223,6 +223,7 @@ test.describe("Add Project command-center flow", () => {
 
     await page.keyboard.press("Enter");
     await expectAddProjectPage(page, "directory-search");
+    await expect(addProjectFlowInput(page)).toBeFocused();
     await page.keyboard.type(projectPickerFixture.fuzzyQuery);
     await expect(addProjectFlow(page)).toContainText(projectPickerFixture.projectName, {
       timeout: 30_000,

packages/app/e2e/browser/creation-old-daemon.spec.ts

@@ -116,6 +116,7 @@ for (const version of ["0.2.5", "0.7.2", "0.8.0"]) {
       );
       expect(workspaces).toHaveLength(1);
       gate.release();
+      await gate.waitForCreated();
       await expect.poll(async () => (await client.fetchAgents()).entries.length).toBe(1);
       const first = (await client.fetchAgents()).entries[0]!.agent;
       await client.waitForFinish(first.id, 20_000);
@@ -128,6 +129,7 @@ for (const version of ["0.2.5", "0.7.2", "0.8.0"]) {
       const secondPrompt = "Create another agent: emit 1 coalesced agent stream updates";
       await fillComposerDraft(page, secondPrompt);
       await pressSubmitBeforeTheNextRender(page, "Send message");
+      await gate.waitForCreated();
       await expect.poll(async () => (await client.fetchAgents()).entries.length).toBe(2);
       const second = (await client.fetchAgents()).entries.find(
         ({ agent }) => agent.id !== first.id,
@@ -206,21 +208,40 @@ for (const version of ["0.2.5", "0.7.2", "0.8.0"]) {
 async function holdLegacyAgentCreation(page: Page, port: number) {
   const readers = await loadSessionMessageReaders();
   const arrived = Promise.withResolvers<void>();
+  let created = Promise.withResolvers<void>();
+  let createRequestId: string | undefined;
   let release = () => {};
   let holding = true;
   await page.routeWebSocket(new RegExp(`:${port}/ws`), (browser) => {
     const server = browser.connectToServer();
     browser.onMessage((frame) => {
-      if (holding && readers.client(frame)?.type === "create_agent_request") {
+      const message = readers.client(frame);
+      if (message?.type === "create_agent_request") createRequestId = message.requestId;
+      if (holding && message?.type === "create_agent_request") {
         holding = false;
         release = () => server.send(frame);
         arrived.resolve();
       } else server.send(frame);
     });
-    server.onMessage((frame) => browser.send(frame));
+    server.onMessage((frame) => {
+      const message = readers.server(frame);
+      if (
+        message?.type === "status" &&
+        message.payload.status === "agent_created" &&
+        message.payload.requestId === createRequestId
+      ) {
+        created.resolve();
+      }
+      browser.send(frame);
+    });
   });
   return {
     waitForRequest: () => arrived.promise,
+    async waitForCreated() {
+      // Agent-list membership includes initialization, before the initial prompt starts.
+      await created.promise;
+      created = Promise.withResolvers<void>();
+    },
     release() {
       const send = release;
       release = () => {};

packages/app/e2e/browser/custom-model-removal.spec.ts

@@ -0,0 +1,29 @@
+import { test } from "../support/fixtures";
+import {
+  addCustomModel,
+  expectCustomModelRetained,
+  openCustomModels,
+  removeCustomModel,
+} from "../support/helpers/custom-models";
+
+const longModelId = "custom-model-with-a-long-name-".repeat(6);
+const shortModelId = "custom-short";
+
+for (const width of [1200, 390]) {
+  test(`removes a long custom model at ${width}px without removing another model`, async ({
+    page,
+  }) => {
+    await page.setViewportSize({ width: 1200, height: 1000 });
+    await openCustomModels(page);
+    await addCustomModel(page, shortModelId);
+    await addCustomModel(page, longModelId);
+
+    await test.step("remove the long model at the target width", async () => {
+      await page.setViewportSize({ width, height: 1000 });
+      await removeCustomModel(page, longModelId);
+      await expectCustomModelRetained(page, shortModelId);
+    });
+
+    await removeCustomModel(page, shortModelId);
+  });
+}

packages/app/e2e/browser/question-prompt-pagination.spec.ts

@@ -7,6 +7,7 @@ import {
   expectQuestionDismissEnabled,
   expectQuestionHidden,
   expectQuestionNavigationEnabled,
+  expectQuestionOptionPreview,
   expectQuestionOptionSelected,
   expectQuestionPrimaryActionDisabled,
   expectQuestionPrimaryActionEnabled,
@@ -61,6 +62,10 @@ test.describe("Question prompt pagination", () => {
       await expectQuestionOptionSelected(page, "App");
 
       await openQuestion(page, { index: 2, total: TOTAL_QUESTIONS });
+      await expectQuestionOptionPreview(page, {
+        option: "Behind feature flag",
+        preview: 'flags.enabled("new-surface")',
+      });
       await chooseQuestionOption(page, "Behind feature flag");
       await expectCurrentQuestion(page, {
         index: 3,

packages/app/e2e/mobile/agent-device/native-question-option-preview-preconditions.md

@@ -0,0 +1,7 @@
+# Native question option preview
+
+`native-question-option-preview.android.ad` checks that every line of a long option preview is reachable on Android. Before replay, open a mock agent prompted with `emit synthetic questions` so its question card shows the first question, on a phone-sized emulator (validated on a 1080×1920 API 35 AVD). The flow opens the `rollout` question, drags slowly up from inside the "Behind feature flag" preview, and asserts the preview's last line is visible.
+
+```sh
+agent-device replay packages/app/e2e/mobile/agent-device/native-question-option-preview.android.ad --platform android --serial emulator-5554
+```

packages/app/e2e/mobile/agent-device/native-question-option-preview.android.ad

@@ -0,0 +1,10 @@
+context platform=android timeout=60000 retries=0
+env APP_ID=sh.paseo.debug
+
+open "${APP_ID}"
+wait "label=\"rollout\"" 20000
+press "label=\"rollout\""
+wait "id=\"question-form-option-preview\"" 10000
+gesture pan 570 1120 0 -440 600
+is visible "text=\"// LAST PREVIEW LINE\""
+close

packages/app/e2e/support/helpers/custom-models.ts

@@ -0,0 +1,37 @@
+import { expect, type Page } from "@playwright/test";
+import { gotoAppShell, openSettings } from "./app";
+import { openSettingsHostSection } from "./settings";
+import { getServerId } from "./server-id";
+
+export async function openCustomModels(page: Page): Promise<void> {
+  await gotoAppShell(page);
+  await openSettings(page);
+  await openSettingsHostSection(page, getServerId(), "providers");
+  await page.getByRole("button", { name: "Claude provider details", exact: true }).click();
+  await expect(page.getByRole("textbox", { name: "Search models" })).toBeVisible();
+}
+
+export async function addCustomModel(page: Page, id: string): Promise<void> {
+  await page.getByRole("button", { name: "Add model", exact: true }).click();
+  await page.getByPlaceholder("e.g. openai/gpt-5").fill(id);
+  await page
+    .getByTestId("add-custom-model-sheet")
+    .getByRole("button", { name: "Add", exact: true })
+    .click();
+  await expect(page.getByRole("button", { name: `Remove ${id}`, exact: true })).toHaveCount(1);
+}
+
+export async function removeCustomModel(page: Page, id: string): Promise<void> {
+  await page.getByRole("textbox", { name: "Search models" }).fill(id);
+  const remove = page.getByRole("button", { name: `Remove ${id}`, exact: true });
+  await expect(remove).toBeInViewport({ ratio: 1 });
+  await remove.click();
+  await expect(remove).toHaveCount(0);
+}
+
+export async function expectCustomModelRetained(page: Page, id: string): Promise<void> {
+  await page.getByRole("textbox", { name: "Search models" }).fill(id);
+  await expect(page.getByRole("button", { name: `Remove ${id}`, exact: true })).toBeInViewport({
+    ratio: 1,
+  });
+}

packages/app/e2e/support/helpers/questions.ts

@@ -43,6 +43,15 @@ export async function expectQuestionOptionSelected(page: Page, option: string):
   await expect(questionOption(page, option)).toHaveAttribute("aria-checked", "true");
 }
 
+export async function expectQuestionOptionPreview(
+  page: Page,
+  input: { option: string; preview: string },
+): Promise<void> {
+  await expect(
+    questionOption(page, input.option).getByTestId("question-form-option-preview"),
+  ).toContainText(input.preview);
+}
+
 export async function openQuestion(
   page: Page,
   input: { index: number; total: number },

packages/app/src/components/markdown/html-ish.test.ts

@@ -3,6 +3,71 @@ import { describe, expect, it } from "vitest";
 import { normalizeHtmlishMarkdown, splitHtmlishMarkdown } from "./html-ish";
 
 describe("splitHtmlishMarkdown", () => {
+  it("renders heading text beside a linked picture without literal heading tags", () => {
+    const source =
+      '<h2><a href="https://example.com/r"><picture><source srcset="https://example.com/d.svg"><img alt="Retrigger" src="https://example.com/l.svg"></picture></a>Confidence Score: 5/5</h2>';
+
+    expect(splitHtmlishMarkdown(source)).toEqual([
+      {
+        kind: "inlineImage",
+        alt: "Retrigger",
+        src: "https://example.com/l.svg",
+        href: "https://example.com/r",
+        flowsWithText: true,
+      },
+      { kind: "markdown", text: "Confidence Score: 5/5" },
+    ]);
+  });
+
+  it.each(["h1", "h2", "h3", "h4", "h5", "h6"])(
+    "keeps a mixed %s heading together after preceding markdown",
+    (heading) => {
+      const source = `Intro\n\n<${heading}><img alt="Icon" src="https://example.com/icon.svg">Caption</${heading}>\n\nOutro`;
+
+      expect(splitHtmlishMarkdown(source)).toEqual([
+        { kind: "markdown", text: "Intro\n\n" },
+        {
+          kind: "inlineImage",
+          alt: "Icon",
+          src: "https://example.com/icon.svg",
+          flowsWithText: true,
+        },
+        { kind: "markdown", text: "Caption\n\nOutro" },
+      ]);
+    },
+  );
+
+  it("preserves formatted text before and after images in a details heading", () => {
+    const source =
+      '<details><summary>More</summary><h2><strong>Before</strong><img alt="Icon" src="https://example.com/icon.svg"><em>After</em></h2></details>';
+
+    expect(splitHtmlishMarkdown(source)).toEqual([
+      {
+        kind: "details",
+        summary: "More",
+        body: "**Before***After*",
+        bodyParts: [
+          { kind: "markdown", text: "**Before**" },
+          { kind: "inlineImage", alt: "Icon", src: "https://example.com/icon.svg" },
+          { kind: "markdown", text: "*After*" },
+        ],
+      },
+    ]);
+  });
+
+  it("keeps mixed HTML headings literal in code examples", () => {
+    const heading = '<h2><img src="https://example.com/icon.svg">Caption</h2>';
+    const source = `Use \`${heading}\`\n\n\`\`\`html\n${heading}\n\`\`\``;
+
+    expect(splitHtmlishMarkdown(source)).toEqual([{ kind: "markdown", text: source }]);
+  });
+
+  it("preserves unknown wrappers around text-only headings", () => {
+    expect(splitHtmlishMarkdown("<section><h2>Heading</h2></section>")).toEqual([
+      { kind: "markdown", text: "<section>Heading</section>" },
+    ]);
+  });
+
   const inlineImageBody = [
     '<a href="#"><img alt="Priority" src="https://example.com/assets/priority.svg?v=9" align="top"></a> Spoofed browser User-Agent allows access control bypass',
     "",

packages/app/src/components/markdown/html-ish.ts

@@ -125,9 +125,20 @@ function splitHtmlishTokens(tokens: HtmlToken[]): MarkdownDisplayPart[] {
       continue;
     }
 
-    const nextDetailsIndex = findNextOpenTag(tokens, cursor + 1, "details");
-    const nextInlineImageIndex = findNextInlineImageIndex(tokens, cursor + 1);
-    const end = Math.min(nextDetailsIndex ?? tokens.length, nextInlineImageIndex ?? tokens.length);
+    if (isHeadingTag(token)) {
+      const closeIndex = findMixedHeadingClose(tokens, cursor);
+      if (closeIndex !== null) {
+        // Headings render as their contents. Split those contents together so an
+        // embedded image cannot strand the opening heading tag in a text slice.
+        for (const part of splitHtmlishTokens(tokens.slice(cursor + 1, closeIndex))) {
+          appendDisplayPart(parts, part);
+        }
+        cursor = closeIndex + 1;
+        continue;
+      }
+    }
+
+    const end = findNextDisplayPartIndex(tokens, cursor + 1) ?? tokens.length;
     appendMarkdownPart(parts, renderInlineTokens(tokens.slice(cursor, end)));
     cursor = end;
   }
@@ -259,15 +270,44 @@ function flowsWithFollowingText(tokens: HtmlToken[], start: number, end: number)
   return false;
 }
 
-function findNextInlineImageIndex(tokens: HtmlToken[], start: number): number | null {
+function findNextDisplayPartIndex(tokens: HtmlToken[], start: number): number | null {
   for (let index = start; index < tokens.length; index += 1) {
-    if (parseInlineImageAt(tokens, index)) {
+    if (
+      isOpenTag(tokens[index], "details") ||
+      findMixedHeadingClose(tokens, index) !== null ||
+      parseInlineImageAt(tokens, index)
+    ) {
       return index;
     }
   }
   return null;
 }
 
+function findMixedHeadingClose(tokens: HtmlToken[], start: number): number | null {
+  const token = tokens[start];
+  if (!isHeadingTag(token)) {
+    return null;
+  }
+  const closeIndex = findMatchingClose(tokens, start, token.name);
+  if (closeIndex === null) {
+    return null;
+  }
+  for (let index = start + 1; index < closeIndex; index += 1) {
+    if (parseInlineImageAt(tokens, index)) {
+      return closeIndex;
+    }
+  }
+  return null;
+}
+
+function appendDisplayPart(parts: MarkdownDisplayPart[], part: MarkdownDisplayPart): void {
+  if (part.kind === "markdown") {
+    appendMarkdownPart(parts, part.text);
+  } else {
+    parts.push(part);
+  }
+}
+
 function appendMarkdownPart(parts: MarkdownDisplayPart[], text: string): void {
   if (!text) {
     return;

packages/app/src/components/provider-diagnostic-sheet.tsx

@@ -95,11 +95,11 @@ function CustomModelRow({
 
   return (
     <View style={sheetStyles.modelRow}>
-      <Text style={sheetStyles.modelTitle} numberOfLines={1}>
+      <Text style={[sheetStyles.modelTitle, sheetStyles.customModelText]} numberOfLines={1}>
         {model.label}
       </Text>
       <Text
-        style={sheetStyles.monoHint}
+        style={[sheetStyles.monoHint, sheetStyles.customModelText]}
         numberOfLines={1}
         selectable
         dataSet={CODE_SURFACE_DATASET}
@@ -762,6 +762,7 @@ const sheetStyles = StyleSheet.create((theme) => ({
   iconButton: {
     width: 28,
     height: 28,
+    flexShrink: 0,
     borderRadius: theme.borderRadius.full,
     alignItems: "center",
     justifyContent: "center",
@@ -807,6 +808,10 @@ const sheetStyles = StyleSheet.create((theme) => ({
     fontSize: theme.fontSize.base,
     flexShrink: 0,
   },
+  customModelText: {
+    flexShrink: 1,
+    minWidth: 0,
+  },
   modelRowFiller: {
     flex: 1,
   },

packages/app/src/components/question-form-card-core.test.ts

@@ -147,4 +147,29 @@ describe("question form card core", () => {
       Response: "custom",
     });
   });
+
+  test("keeps option previews so options can be compared", () => {
+    const questions = parseQuestionFormQuestions({
+      questions: [
+        {
+          question: "Which layout?",
+          header: "Layout",
+          options: [
+            {
+              label: "Tabs",
+              description: "One tab per section",
+              preview: "<Tabs>\n  <Tab />\n</Tabs>",
+            },
+            { label: "Single page" },
+          ],
+          multiSelect: false,
+        },
+      ],
+    });
+
+    expect(questions?.[0]?.options).toEqual([
+      { label: "Tabs", description: "One tab per section", preview: "<Tabs>\n  <Tab />\n</Tabs>" },
+      { label: "Single page", description: undefined, preview: undefined },
+    ]);
+  });
 });

packages/app/src/components/question-form-card-core.ts

@@ -1,6 +1,7 @@
 export interface QuestionOption {
   label: string;
   description?: string;
+  preview?: string;
 }
 
 export interface QuestionFormQuestion {
@@ -46,6 +47,7 @@ export function parseQuestionFormQuestions(input: unknown): QuestionFormQuestion
       options.push({
         label: o.label,
         description: typeof o.description === "string" ? o.description : undefined,
+        preview: readOptionalString(o, "preview"),
       });
     }
     questions.push({

packages/app/src/components/question-form-card.tsx

@@ -10,6 +10,7 @@ import type { AgentPermissionResponse } from "@getpaseo/protocol/agent-types";
 import { isWeb } from "@/constants/platform";
 import { EditingTextInput as TextInput } from "@/components/ui/text-input";
 import type { EditingTextInputHandle } from "@/components/ui/text-input/types";
+import { ScrollableCodeSurface } from "@/components/ui/scrollable-code-surface";
 import {
   areQuestionsAnswered,
   buildQuestionFormAnswers,
@@ -29,6 +30,9 @@ interface QuestionFormCardProps {
 }
 
 const IS_WEB = isWeb;
+// Native previews are uncapped: inside the option's Pressable, Android never hands a
+// drag to the preview's nested scroll, so lines past a cap would be unreachable.
+const OPTION_PREVIEW_MAX_HEIGHT = IS_WEB ? 240 : undefined;
 
 function getQuestionInputPlaceholder({
   question,
@@ -133,6 +137,20 @@ function QuestionOptionRow({
           {option.description ? (
             <Text style={optionDescriptionStyle}>{option.description}</Text>
           ) : null}
+          {option.preview ? (
+            // Shown for every option at once so they can be compared before picking.
+            // Long lines wrap, as in Claude Code, since most previews are prose.
+            <ScrollableCodeSurface
+              tone="surface0"
+              maxHeight={OPTION_PREVIEW_MAX_HEIGHT}
+              horizontal={false}
+              selectable={false}
+              textStyle={styles.optionPreviewText}
+              testID="question-form-option-preview"
+            >
+              {option.preview}
+            </ScrollableCodeSurface>
+          ) : null}
         </View>
       </View>
     </Pressable>
@@ -704,6 +722,10 @@ const styles = StyleSheet.create((theme) => ({
     fontSize: theme.fontSize.base,
     lineHeight: 20,
   },
+  optionPreviewText: {
+    lineHeight: 20,
+    ...(isWeb ? { whiteSpace: "pre-wrap", overflowWrap: "break-word" } : null),
+  },
   selectionControl: {
     width: 18,
     height: 18,

packages/client/src/daemon-client-relay-e2ee-transport.ts

@@ -1,3 +1,4 @@
+import { MAX_RELAY_WEBSOCKET_MESSAGE_BYTES } from "@getpaseo/protocol/websocket-message-limit";
 import {
   createClientChannel,
   type EncryptedChannel,
@@ -8,7 +9,11 @@ import type {
   DaemonTransportFactory,
   TransportLogger,
 } from "./daemon-client-transport-types.js";
-import { extractRelayMessage, normalizeTransportPayload } from "./daemon-client-transport-utils.js";
+import {
+  extractRelayMessage,
+  normalizeTransportPayload,
+  messageTooLargeError,
+} from "./daemon-client-transport-utils.js";
 
 type OpenHandler = () => void;
 type CloseHandler = (event?: unknown) => void;
@@ -137,7 +142,13 @@ export function createEncryptedTransport(
       if (!channel) {
         throw new Error("Encrypted channel not ready");
       }
-      void channel.send(normalizeTransportPayload(data)).catch((error) => {
+      const payload = normalizeTransportPayload(data);
+      // Reject synchronously so the requesting operation fails without closing the transport.
+      const wireBytes = channel.outboundWireByteLength(payload);
+      if (wireBytes > MAX_RELAY_WEBSOCKET_MESSAGE_BYTES) {
+        throw messageTooLargeError(wireBytes, MAX_RELAY_WEBSOCKET_MESSAGE_BYTES);
+      }
+      void channel.send(payload).catch((error) => {
         emitError(error);
       });
     },

packages/client/src/daemon-client-transport-utils.ts

@@ -133,3 +133,10 @@ export function encodeUtf8String(value: string): Uint8Array {
   }
   return out;
 }
+
+export function messageTooLargeError(size: number, limit: number): Error {
+  const toMiB = (bytes: number) => (bytes / (1024 * 1024)).toFixed(1);
+  return new Error(
+    `Message is too large to send (${toMiB(size)} MiB). The limit is ${toMiB(limit)} MiB, so send fewer or smaller attachments.`,
+  );
+}

packages/client/src/daemon-client.test.ts

@@ -7527,3 +7527,29 @@ test.each([false, true])(
     await send;
   },
 );
+
+test("measures an outbound message in UTF-8 bytes against the daemon's message limit", async () => {
+  const mock = createMockTransport();
+  const client = new DaemonClient({
+    url: "ws://test",
+    clientId: "message_limit_unit_test",
+    transportFactory: () => mock.transport,
+    reconnect: { enabled: false },
+  });
+  clients.push(client);
+  const connectPromise = client.connect();
+  mock.triggerOpen();
+  await connectPromise;
+  const mib = 1024 * 1024;
+
+  // "é" is one UTF-16 unit but two UTF-8 bytes, so this text is ~98 MiB on the wire.
+  void client.sendMessage("agent-1", "é".repeat(49 * mib)).catch(() => undefined);
+  expect(mock.sent).toHaveLength(1);
+
+  // ~60M characters is under the 100 MiB limit; ~120 MiB of UTF-8 is over it.
+  await expect(client.sendMessage("agent-1", "é".repeat(60 * mib))).rejects.toThrow(
+    "Message is too large to send (120.0 MiB). The limit is 100.0 MiB",
+  );
+  expect(mock.sent).toHaveLength(1);
+  expect(client.getConnectionState().status).toBe("connected");
+});

packages/client/src/daemon-client.ts

@@ -1,3 +1,4 @@
+import { messageTooLargeError } from "./daemon-client-transport-utils.js";
 import { legacyUsageIcon } from "./legacy-usage-icons.js";
 import { subscribeTimeline, type TimelineMessage } from "./timeline-subscription/index.js";
 import { ProviderSnapshotUpdates } from "./provider-snapshots/index.js";
@@ -13,6 +14,7 @@ import type { z } from "zod";
 import type { SessionEventSubscription } from "@getpaseo/protocol/messages";
 import type { ClientCapability } from "@getpaseo/protocol/client-capabilities";
 import type { AgentAttentionNotificationPayload } from "@getpaseo/protocol/agent-attention-notification";
+import { MAX_WEBSOCKET_MESSAGE_BYTES } from "@getpaseo/protocol/websocket-message-limit";
 import {
   AgentCreateFailedStatusPayloadSchema,
   AgentCreatedStatusPayloadSchema,
@@ -1132,6 +1134,19 @@ function getTransportFrameSize(frame: string | Uint8Array | ArrayBuffer): number
   return frame.byteLength;
 }
 
+function assertTransportFrameFits(frame: string | Uint8Array | ArrayBuffer): void {
+  if (typeof frame !== "string") {
+    if (frame.byteLength > MAX_WEBSOCKET_MESSAGE_BYTES)
+      throw messageTooLargeError(frame.byteLength, MAX_WEBSOCKET_MESSAGE_BYTES);
+    return;
+  }
+  // UTF-8 needs at most three bytes per UTF-16 unit, so only a string near the limit is measured.
+  if (frame.length * 3 <= MAX_WEBSOCKET_MESSAGE_BYTES) return;
+  const size = new TextEncoder().encode(frame).byteLength;
+  if (size > MAX_WEBSOCKET_MESSAGE_BYTES)
+    throw messageTooLargeError(size, MAX_WEBSOCKET_MESSAGE_BYTES);
+}
+
 function describeInboundTransportFrame(
   frame: unknown,
   rawBytes: Uint8Array | null,
@@ -1767,6 +1782,8 @@ export class DaemonClient {
     if (!this.transport) {
       throw new DaemonConnectionError("Transport not connected");
     }
+    // The daemon closes the connection on an oversized message, and creations resubmit on reconnect.
+    assertTransportFrameFits(frame);
     const isOpen = this.beginTraceSection("paseo.ws.frame.outbound", {
       kind: typeof frame === "string" ? "text" : "binary",
       size: String(getTransportFrameSize(frame)),

packages/protocol/src/websocket-message-limit.ts

@@ -0,0 +1,5 @@
+/** Largest WebSocket message the daemon accepts. A bigger one closes the connection with 1009. */
+export const MAX_WEBSOCKET_MESSAGE_BYTES = 100 * 1024 * 1024;
+
+/** Largest encrypted frame the relay accepts. */
+export const MAX_RELAY_WEBSOCKET_MESSAGE_BYTES = 32 * 1024 * 1024;

packages/server/package.json

@@ -89,7 +89,7 @@
     "speech:transcribe:local": "tsx scripts/transcribe-local-wav.ts",
     "test": "npm run test:unit && npm run test:integration",
     "test:unit": "vitest run --fileParallelism --exclude \"**/*.e2e.test.ts\"",
-    "test:integration": "vitest run --maxWorkers=1 src/server/daemon-e2e/filesystem.e2e.test.ts src/server/daemon-e2e/file-download.e2e.test.ts src/server/daemon-e2e/cli-logs-follow.e2e.test.ts src/server/creation/creation.e2e.test.ts src/server/daemon-e2e/terminal-workspace-sdk.e2e.test.ts src/server/daemon-e2e/models.e2e.test.ts src/server/daemon-e2e/live-preferences.e2e.test.ts src/server/agent/model-catalog.e2e.test.ts src/server/plugins/plugin-paseo-api.e2e.test.ts && vitest run --maxWorkers=1 src/server/daemon-e2e/git-operations.e2e.test.ts -t \"merges into\" && vitest run --maxWorkers=1 src/server/session.create-agent-worktree-autoarchive.e2e.test.ts -t \"creates a worktree and auto-archives both\" && vitest run --maxWorkers=1 src/server/agent/providers/opencode-bridge.local.e2e.test.ts -t \"versioned runtime\"",
+    "test:integration": "vitest run --maxWorkers=1 src/server/daemon-e2e/filesystem.e2e.test.ts src/server/daemon-e2e/file-download.e2e.test.ts src/server/daemon-e2e/cli-logs-follow.e2e.test.ts src/server/creation/creation.e2e.test.ts src/server/daemon-e2e/terminal-workspace-sdk.e2e.test.ts src/server/daemon-e2e/models.e2e.test.ts src/server/daemon-e2e/live-preferences.e2e.test.ts src/server/daemon-e2e/oversized-message.e2e.test.ts src/server/agent/model-catalog.e2e.test.ts src/server/plugins/plugin-paseo-api.e2e.test.ts && vitest run --maxWorkers=1 src/server/daemon-e2e/git-operations.e2e.test.ts -t \"merges into\" && vitest run --maxWorkers=1 src/server/session.create-agent-worktree-autoarchive.e2e.test.ts -t \"creates a worktree and auto-archives both\" && vitest run --maxWorkers=1 src/server/agent/providers/opencode-bridge.local.e2e.test.ts -t \"versioned runtime\" && vitest run --maxWorkers=1 src/server/daemon-e2e/relay-transport.e2e.test.ts -t \"oversized attachments\"",
     "test:hub-cli-contract": "vitest run --maxWorkers=1 src/server/hub/hub-cli-contract.test.ts",
     "test:integration:all": "npm run test:e2e",
     "test:integration:real": "vitest run real.e2e.test.ts",

packages/server/src/server/agent/providers/mock-load-test-agent.ts

@@ -232,6 +232,7 @@ type SteeringReplayShape = "claude" | "codex";
 interface MockQuestionOption {
   label: string;
   description?: string;
+  preview?: string;
 }
 
 interface MockQuestionPromptQuestion {
@@ -271,6 +272,16 @@ function parseSettledAssistantImageMarkdown(prompt: AgentPromptInput): string |
   return match?.[1] ?? null;
 }
 
+const ROLLOUT_FLAG_PREVIEW = [
+  "Ship it dark behind the new-surface flag, then turn it on for internal users before everyone else.",
+  "",
+  'if (flags.enabled("new-surface")) {',
+  "  render(<NewSurface />);",
+  "}",
+  ...Array.from({ length: 40 }, (_, i) => `// rollout step ${i + 1}`),
+  "// LAST PREVIEW LINE",
+].join("\n");
+
 function parseMockQuestionPrompt(prompt: AgentPromptInput): MockQuestionPromptRequest | null {
   const text = promptToText(prompt);
   if (!/emit\s+(?:a\s+)?synthetic\s+questions?/i.test(text)) {
@@ -309,7 +320,10 @@ function parseMockQuestionPrompt(prompt: AgentPromptInput): MockQuestionPromptRe
       {
         question: "Which rollout should we use?",
         header: "rollout",
-        options: [{ label: "Immediately" }, { label: "Behind feature flag" }],
+        options: [
+          { label: "Immediately" },
+          { label: "Behind feature flag", preview: ROLLOUT_FLAG_PREVIEW },
+        ],
         multiSelect: false,
       },
       {

packages/server/src/server/daemon-e2e/oversized-message.e2e.test.ts

@@ -0,0 +1,58 @@
+import { describe, test, expect, beforeEach, afterEach } from "vitest";
+import { mkdtempSync, rmSync } from "fs";
+import { tmpdir } from "os";
+import path from "path";
+import { createDaemonTestContext, type DaemonTestContext } from "../test-utils/index.js";
+
+let ctx: DaemonTestContext;
+let cwd: string;
+
+beforeEach(async () => {
+  ctx = await createDaemonTestContext();
+  cwd = mkdtempSync(path.join(tmpdir(), "daemon-e2e-"));
+});
+
+afterEach(async () => {
+  await ctx.cleanup();
+  rmSync(cwd, { recursive: true, force: true });
+}, 60000);
+
+describe("a message larger than the daemon accepts", () => {
+  const oversizedImage = { data: "A".repeat(101 * 1024 * 1024), mimeType: "image/png" };
+
+  test("fails the creation and keeps the connection up", async () => {
+    const statuses: string[] = [];
+    const unsubscribe = ctx.client.subscribeConnectionStatus((state) => {
+      statuses.push(state.status);
+    });
+
+    await expect(
+      ctx.client.createAgent({
+        provider: "claude",
+        cwd,
+        title: "Oversized first message",
+        initialPrompt: "Describe these screens.",
+        images: [oversizedImage],
+      }),
+    ).rejects.toThrow(/too large/);
+    unsubscribe();
+
+    expect(statuses).toEqual(["connected"]);
+    expect((await ctx.client.fetchAgents()).entries).toEqual([]);
+  }, 30000);
+
+  test("fails the send and keeps the connection up", async () => {
+    const agent = await ctx.client.createAgent({ provider: "claude", cwd, title: "Agent" });
+    const statuses: string[] = [];
+    const unsubscribe = ctx.client.subscribeConnectionStatus((state) => {
+      statuses.push(state.status);
+    });
+
+    await expect(
+      ctx.client.sendMessage(agent.id, "Describe these screens.", { images: [oversizedImage] }),
+    ).rejects.toThrow(/too large/);
+    unsubscribe();
+
+    expect(statuses).toEqual(["connected"]);
+  }, 30000);
+});

packages/server/src/server/daemon-e2e/relay-transport.e2e.test.ts

@@ -1,4 +1,6 @@
 import { describe, expect, test } from "vitest";
+import { withTimeout } from "../../utils/promise-timeout.js";
+import { DaemonClient } from "../test-utils/daemon-client.js";
 import { WebSocket } from "ws";
 import pino from "pino";
 import { Writable } from "node:stream";
@@ -202,12 +204,20 @@ async function waitForCapturedLog(
     if (options.useLocalRelay) {
       relayArgs.push("--var", "PASEO_RELAY_UPSTREAM:");
     }
-    relayProcess = spawn("npx", relayArgs, {
-      cwd: relayDir,
-      env: { ...process.env },
-      stdio: ["ignore", "pipe", "pipe"],
-      detached: false,
-    });
+    relayProcess = spawn(
+      process.execPath,
+      [
+        "--experimental-vm-modules",
+        path.resolve(relayDir, "../../node_modules/wrangler/wrangler-dist/cli.js"),
+        ...relayArgs.slice(1),
+      ],
+      {
+        cwd: relayDir,
+        env: { ...process.env },
+        stdio: ["ignore", "pipe", "pipe"],
+        detached: false,
+      },
+    );
 
     relayProcess.stdout?.on("data", (data: Buffer) => {
       const lines = data
@@ -241,6 +251,73 @@ async function waitForCapturedLog(
     relayProcess = null;
   };
 
+  test("oversized attachments fail without disconnecting or resubmitting over the relay", async () => {
+    await startRelay({ useLocalRelay: true });
+    const daemon = await createTestPaseoDaemon({
+      relayEnabled: true,
+      relayEndpoint: `127.0.0.1:${relayPort}`,
+      relayUseTls: false,
+      relayPublicUseTls: false,
+    });
+    let client: DaemonClient | null = null;
+    try {
+      const offerUrl = await getPairingOfferUrl({
+        paseoHome: daemon.paseoHome,
+        relayEnabled: true,
+        relayEndpoint: daemon.config.relayEndpoint,
+      });
+      const { serverId, daemonPublicKeyB64 } = decodeOfferFromFragmentUrl(offerUrl);
+      client = new DaemonClient({
+        url: buildRelayWebSocketUrl({
+          endpoint: `127.0.0.1:${relayPort}`,
+          useTls: false,
+          serverId,
+          role: "client",
+        }),
+        e2ee: { enabled: true, daemonPublicKeyB64 },
+        reconnect: { baseDelayMs: 100, maxDelayMs: 100 },
+      });
+      await client.connect();
+      const statuses: string[] = [];
+      client.subscribeConnectionStatus((state) => statuses.push(state.status));
+      for (const imageMiB of [30, 61]) {
+        // Attachments are base64 in the JSON, then E2EE base64 expands the frame again.
+        const images = [
+          { data: "A".repeat(4 * Math.ceil((imageMiB * 1024 * 1024) / 3)), mimeType: "image/png" },
+        ];
+        await expect(
+          withTimeout(
+            client.createWorkspace({
+              source: { kind: "directory", path: daemon.staticDir },
+              agent: {
+                provider: "claude",
+                cwd: daemon.staticDir,
+                initialPrompt: "Describe these screens.",
+                images,
+              },
+            }),
+            10000,
+            "Workspace creation did not settle",
+          ),
+        ).rejects.toThrow(/too large.*32\.0 MiB/);
+        expect((await client.fetchAgents()).entries).toEqual([]);
+      }
+      const agent = await client.createAgent({ provider: "claude", cwd: daemon.staticDir });
+      await expect(
+        client.sendMessage(agent.id, "Describe these screens.", {
+          images: [{ data: "A".repeat(40 * 1024 * 1024), mimeType: "image/png" }],
+        }),
+      ).rejects.toThrow(/too large.*32\.0 MiB/);
+      await client.sendMessage(agent.id, "A small follow-up still works.");
+      expect((await client.fetchAgents()).entries).toHaveLength(1);
+      expect(statuses).toEqual(["connected"]);
+    } finally {
+      await client?.close();
+      await daemon.close();
+      await stopRelay();
+    }
+  }, 60000);
+
   test("daemon connects to relay and client ping/pong works through relay", async () => {
     process.env.PASEO_PRIMARY_LAN_IP = "192.168.1.12";
 

packages/server/src/server/hub/relationship-controller.test.ts

@@ -773,8 +773,12 @@ describe("Hub relationship", () => {
     const second = await relationship.ownedCreateResult("second-create");
 
     expect(relationship.relationshipFile()?.relationship.daemonId).toBe(daemonId);
-    expect(first).toMatchObject({ payload: { success: true, executionId: "first-execution" } });
-    expect(second).toMatchObject({ payload: { success: true, executionId: "second-execution" } });
+    expect(first).toMatchObject({
+      payload: { success: true, executionId: "first-execution", error: null },
+    });
+    expect(second).toMatchObject({
+      payload: { success: true, executionId: "second-execution", error: null },
+    });
     expect(await relationship.durableOwnedAgentIds()).toHaveLength(2);
   });
 

packages/server/src/server/websocket-server.ts

@@ -33,6 +33,7 @@ import {
 } from "./messages.js";
 import { asUint8Array, decodeBinaryFrame } from "@getpaseo/protocol/binary-frames/index";
 import type { TerminalActivity } from "@getpaseo/protocol/terminal-activity";
+import { MAX_WEBSOCKET_MESSAGE_BYTES } from "@getpaseo/protocol/websocket-message-limit";
 import type { HostnamesConfig } from "./hostnames.js";
 import { isHostnameAllowed } from "./hostnames.js";
 import {
@@ -822,6 +823,7 @@ export class VoiceAssistantWebSocketServer {
     const wss = new WebSocketServer({
       server,
       path: "/ws",
+      maxPayload: MAX_WEBSOCKET_MESSAGE_BYTES,
       handleProtocols: (protocols) => selectWebSocketProtocol(protocols, password),
       verifyClient: ({ req }, callback) => {
         this.verifyWsUpgrade(

packages/server/src/server/workspace-service-port-registry.test.ts

@@ -33,7 +33,7 @@ describe("ensureWorkspaceServicePortPlan", () => {
     expect(allocatedServices).toEqual(["api", "web", "worker"]);
   });
 
-  it("returns the existing plan without calling the allocator on later calls", async () => {
+  it("extends the existing plan with newly declared services without reallocating peers", async () => {
     let allocationCount = 0;
 
     const firstPlan = await ensureWorkspaceServicePortPlan({
@@ -54,9 +54,11 @@ describe("ensureWorkspaceServicePortPlan", () => {
       },
     });
 
-    expect(Array.from(secondPlan.entries())).toEqual(Array.from(firstPlan.entries()));
-    expect(secondPlan.has("new-service")).toBe(false);
-    expect(allocationCount).toBe(2);
+    expect(Array.from(secondPlan.entries())).toEqual([
+      ...firstPlan.entries(),
+      ["new-service", 4300],
+    ]);
+    expect(allocationCount).toBe(3);
   });
 
   it("shares one first-plan build across concurrent callers", async () => {
@@ -101,6 +103,103 @@ describe("ensureWorkspaceServicePortPlan", () => {
     expect(allocationCount).toBe(2);
   });
 
+  it("extends a pending plan for a concurrent caller with another service", async () => {
+    const allocation = createDeferredPort();
+    const workspaceId = "registry-concurrent-extension-workspace";
+    const firstPlan = ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "backend-dev" }],
+      allocatePort: async () => allocation.promise,
+    });
+    let allocations = 0;
+    const secondPlan = ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "backend-dev" }, { scriptName: "web" }],
+      allocatePort: async () => {
+        allocations += 1;
+        return 6101;
+      },
+    });
+    allocation.resolve(6100);
+    expect(Array.from((await firstPlan).entries())).toEqual([["backend-dev", 6100]]);
+    expect(Array.from((await secondPlan).entries())).toEqual([
+      ["backend-dev", 6100],
+      ["web", 6101],
+    ]);
+    expect(allocations).toBe(1);
+    releaseWorkspaceServicePortPlan(workspaceId);
+  });
+
+  it("keeps the previous plan and reservations when an extension fails", async () => {
+    const workspaceId = "registry-failed-extension-workspace";
+    await ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "backend-dev" }],
+      allocatePort: async () => 6200,
+    });
+    let allocations = 0;
+    await expect(
+      ensureWorkspaceServicePortPlan({
+        workspaceId,
+        services: [{ scriptName: "backend-dev" }, { scriptName: "web" }, { scriptName: "worker" }],
+        allocatePort: async () => {
+          allocations += 1;
+          if (allocations === 1) return 6201;
+          throw new Error("Allocation failed");
+        },
+      }),
+    ).rejects.toThrow("Allocation failed");
+    const priorPlan = await ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "backend-dev" }],
+      allocatePort: async () => {
+        throw new Error("Existing port must survive");
+      },
+    });
+    expect(Array.from(priorPlan.entries())).toEqual([["backend-dev", 6200]]);
+    const otherWorkspace = "registry-failed-extension-other-workspace";
+    const reusedPlan = await ensureWorkspaceServicePortPlan({
+      workspaceId: otherWorkspace,
+      services: [{ scriptName: "web" }],
+      allocatePort: async ({ reservedPorts }) => {
+        expect(reservedPorts.has(6200)).toBe(true);
+        expect(reservedPorts.has(6201)).toBe(false);
+        return 6201;
+      },
+    });
+    expect(reusedPlan.get("web")).toBe(6201);
+    releaseWorkspaceServicePortPlan(workspaceId);
+    releaseWorkspaceServicePortPlan(otherWorkspace);
+  });
+
+  it("rejects a new explicit port that collides with an existing service", async () => {
+    const workspaceId = "registry-extension-explicit-collision-workspace";
+    await ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "backend-dev" }],
+      allocatePort: async () => 6300,
+    });
+    await expect(
+      ensureWorkspaceServicePortPlan({
+        workspaceId,
+        services: [{ scriptName: "backend-dev" }, { scriptName: "web", port: 6300 }],
+        allocatePort: async () => 6301,
+      }),
+    ).rejects.toThrow("Service 'web' has a duplicate port 6300");
+    const plan = await ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "backend-dev" }, { scriptName: "web", port: 6301 }],
+      allocatePort: async () => {
+        throw new Error("No allocation needed");
+      },
+    });
+    expect(Array.from(plan.entries())).toEqual([
+      ["backend-dev", 6300],
+      ["web", 6301],
+    ]);
+    releaseWorkspaceServicePortPlan(workspaceId);
+  });
+
   it("uses explicit configured ports without calling the allocator", async () => {
     let allocationCount = 0;
 
@@ -312,6 +411,123 @@ describe("refreshWorkspaceServicePort", () => {
     ]);
   });
 
+  it("preserves a concurrent service addition while refreshing a stopped service", async () => {
+    const workspaceId = "registry-refresh-and-extend-workspace";
+    await ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "backend-dev" }],
+      allocatePort: async () => 6400,
+    });
+    const allocation = createDeferredPort();
+    const refreshing = refreshWorkspaceServicePort({
+      workspaceId,
+      service: { scriptName: "backend-dev" },
+      allocatePort: async () => allocation.promise,
+    });
+    const extending = ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "backend-dev" }, { scriptName: "web", port: 6402 }],
+      allocatePort: async () => {
+        throw new Error("Explicit addition needs no allocation");
+      },
+    });
+    allocation.resolve(6401);
+    expect(await refreshing).toBe(6401);
+    await extending;
+    const plan = await ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [],
+      allocatePort: async () => {
+        throw new Error("No allocation needed");
+      },
+    });
+    expect(Array.from(plan.entries())).toEqual([
+      ["backend-dev", 6401],
+      ["web", 6402],
+    ]);
+    releaseWorkspaceServicePortPlan(workspaceId);
+  });
+
+  it.each(["reused port", "allocation failure"])(
+    "cancels a pending refresh and its waiter after workspace release (%s)",
+    async (outcome) => {
+      const workspaceId = "registry-cancelled-refresh-workspace";
+      await ensureWorkspaceServicePortPlan({
+        workspaceId,
+        services: [{ scriptName: "api" }],
+        allocatePort: async () => 6500,
+      });
+      const allocation = createDeferredPort();
+      const refreshing = refreshWorkspaceServicePort({
+        workspaceId,
+        service: { scriptName: "api" },
+        allocatePort: async () => {
+          const port = await allocation.promise;
+          if (outcome === "allocation failure") throw new Error("Allocation failed");
+          return port;
+        },
+      });
+      const waiting = refreshWorkspaceServicePort({
+        workspaceId,
+        service: { scriptName: "web", port: 6501 },
+        allocatePort: async () => 6501,
+      });
+      const assertions = Promise.all([
+        expect(refreshing).rejects.toThrow("Workspace service port plan was released"),
+        expect(waiting).rejects.toThrow("Workspace service port plan was released"),
+      ]);
+      releaseWorkspaceServicePortPlan(workspaceId);
+      allocation.resolve(6500);
+      await assertions;
+      const reusedPlan = await ensureWorkspaceServicePortPlan({
+        workspaceId: "registry-after-cancelled-refresh-workspace",
+        services: [{ scriptName: "api" }],
+        allocatePort: async () => 6500,
+      });
+      expect(reusedPlan.get("api")).toBe(6500);
+      releaseWorkspaceServicePortPlan("registry-after-cancelled-refresh-workspace");
+    },
+  );
+
+  it("lets a waiting service restart allocate after another service's restart fails", async () => {
+    const workspaceId = "registry-independent-refresh-failure-workspace";
+    await ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [{ scriptName: "api" }, { scriptName: "web" }],
+      allocatePort: createSequentialPortAllocator(6600),
+    });
+    const allocation = createDeferredPort();
+    const failedRefresh = refreshWorkspaceServicePort({
+      workspaceId,
+      service: { scriptName: "api" },
+      allocatePort: async () => {
+        await allocation.promise;
+        throw new Error("API port script failed");
+      },
+    });
+    const failedAssertion = expect(failedRefresh).rejects.toThrow("API port script failed");
+    const waitingRefresh = refreshWorkspaceServicePort({
+      workspaceId,
+      service: { scriptName: "web" },
+      allocatePort: async () => 6602,
+    });
+    allocation.resolve(0);
+    await failedAssertion;
+    expect(await waitingRefresh).toBe(6602);
+    const plan = await ensureWorkspaceServicePortPlan({
+      workspaceId,
+      services: [],
+      allocatePort: async () => {
+        throw new Error("No allocation needed");
+      },
+    });
+    expect(Array.from(plan.entries())).toEqual([
+      ["api", 6600],
+      ["web", 6602],
+    ]);
+    releaseWorkspaceServicePortPlan(workspaceId);
+  });
+
   it("uses an explicit configured port without calling the allocator", async () => {
     let allocationCount = 0;
 

packages/server/src/server/workspace-service-port-registry.ts

@@ -24,6 +24,24 @@ interface PendingWorkspaceServicePortPlanToken {
   isReleased: boolean;
 }
 
+class WorkspaceServicePortPlanReleasedError extends Error {
+  constructor(workspaceId: string) {
+    super(`Workspace service port plan was released while being created for '${workspaceId}'`);
+  }
+}
+
+async function waitForWorkspaceServicePortPlanUpdate(
+  pendingPlan: Promise<Map<string, number>>,
+): Promise<void> {
+  try {
+    await pendingPlan;
+  } catch (error) {
+    // Allocation failure belongs to the original request. A waiting request
+    // retries against the rolled-back plan; workspace archival cancels both.
+    if (error instanceof WorkspaceServicePortPlanReleasedError) throw error;
+  }
+}
+
 const workspaceServicePortPlans = new Map<string, Map<string, number>>();
 const pendingWorkspaceServicePortPlans = new Map<string, Promise<Map<string, number>>>();
 const pendingWorkspaceServicePortPlanTokens = new Map<
@@ -37,25 +55,19 @@ const MAX_DYNAMIC_PORT_ALLOCATION_ATTEMPTS = 10;
 export async function ensureWorkspaceServicePortPlan(
   options: EnsureWorkspaceServicePortPlanOptions,
 ): Promise<ReadonlyMap<string, number>> {
-  const existingPlan = workspaceServicePortPlans.get(options.workspaceId);
-  if (existingPlan) {
+  const pendingPlan = pendingWorkspaceServicePortPlans.get(options.workspaceId);
+  if (pendingPlan) {
+    await waitForWorkspaceServicePortPlanUpdate(pendingPlan);
+    return ensureWorkspaceServicePortPlan(options);
+  }
+
+  const existingPlan =
+    workspaceServicePortPlans.get(options.workspaceId) ?? new Map<string, number>();
+  if (options.services.every((service) => existingPlan.has(service.scriptName))) {
     return new Map(existingPlan);
   }
 
-  let pendingPlan = pendingWorkspaceServicePortPlans.get(options.workspaceId);
-  if (!pendingPlan) {
-    const token: PendingWorkspaceServicePortPlanToken = { isReleased: false };
-    pendingPlan = createPendingWorkspaceServicePortPlan({
-      workspaceId: options.workspaceId,
-      services: options.services,
-      allocatePort: options.allocatePort,
-      token,
-    });
-    pendingWorkspaceServicePortPlans.set(options.workspaceId, pendingPlan);
-    pendingWorkspaceServicePortPlanTokens.set(options.workspaceId, token);
-  }
-
-  return new Map(await pendingPlan);
+  return new Map(await startWorkspaceServicePortPlanUpdate({ ...options, existingPlan }));
 }
 
 export function requirePlannedWorkspaceServicePort(
@@ -82,27 +94,62 @@ export function releaseWorkspaceServicePortPlan(workspaceId: string): void {
   dynamicPortsByWorkspace.delete(workspaceId);
 }
 
-async function createPendingWorkspaceServicePortPlan(options: {
-  workspaceId: string;
-  services: readonly WorkspaceServicePortDeclaration[];
-  allocatePort: (request: WorkspaceServicePortAllocationRequest) => Promise<number>;
-  token: PendingWorkspaceServicePortPlanToken;
-}): Promise<Map<string, number>> {
+interface WorkspaceServicePortPlanUpdateOptions extends EnsureWorkspaceServicePortPlanOptions {
+  existingPlan: ReadonlyMap<string, number>;
+  refreshScriptName?: string;
+}
+
+function startWorkspaceServicePortPlanUpdate(
+  options: WorkspaceServicePortPlanUpdateOptions,
+): Promise<Map<string, number>> {
+  const token: PendingWorkspaceServicePortPlanToken = { isReleased: false };
+  const plan = createPendingWorkspaceServicePortPlan({ ...options, token });
+  pendingWorkspaceServicePortPlans.set(options.workspaceId, plan);
+  pendingWorkspaceServicePortPlanTokens.set(options.workspaceId, token);
+  return plan;
+}
+
+async function createPendingWorkspaceServicePortPlan(
+  options: WorkspaceServicePortPlanUpdateOptions & { token: PendingWorkspaceServicePortPlanToken },
+): Promise<Map<string, number>> {
+  const previousDynamicPorts = new Map(dynamicPortsByWorkspace.get(options.workspaceId));
+  const retainedPlan = new Map(options.existingPlan);
+  if (options.refreshScriptName !== undefined) retainedPlan.delete(options.refreshScriptName);
   try {
-    const plan = await buildWorkspaceServicePortPlan({
+    const updatedPlan = await buildWorkspaceServicePortPlan({
       workspaceId: options.workspaceId,
       services: options.services,
       allocatePort: options.allocatePort,
+      existingPlan: retainedPlan,
     });
+    const plan = new Map(options.existingPlan);
+    for (const [scriptName, port] of updatedPlan) plan.set(scriptName, port);
     if (options.token.isReleased) {
-      throw new Error(
-        `Workspace service port plan was released while being created for '${options.workspaceId}'`,
-      );
+      throw new WorkspaceServicePortPlanReleasedError(options.workspaceId);
+    }
+    for (const [scriptName, port] of previousDynamicPorts) {
+      if (plan.get(scriptName) !== port) {
+        releaseDynamicPort({ workspaceId: options.workspaceId, scriptName, port });
+      }
     }
     workspaceServicePortPlans.set(options.workspaceId, plan);
     return plan;
   } catch (error) {
-    releaseWorkspaceServicePortPlan(options.workspaceId);
+    const dynamicPorts = dynamicPortsByWorkspace.get(options.workspaceId);
+    if (dynamicPorts) {
+      for (const [scriptName, port] of dynamicPorts) {
+        if (options.token.isReleased || previousDynamicPorts.get(scriptName) !== port) {
+          releaseDynamicPort({ workspaceId: options.workspaceId, scriptName, port });
+        }
+      }
+    }
+    if (!options.token.isReleased) {
+      for (const [scriptName, port] of previousDynamicPorts) {
+        reserveDynamicPort({ workspaceId: options.workspaceId, scriptName, port });
+      }
+    }
+    if (options.token.isReleased)
+      throw new WorkspaceServicePortPlanReleasedError(options.workspaceId);
     throw error;
   } finally {
     pendingWorkspaceServicePortPlans.delete(options.workspaceId);
@@ -111,12 +158,16 @@ async function createPendingWorkspaceServicePortPlan(options: {
 }
 
 async function buildWorkspaceServicePortPlan(options: {
+  existingPlan: ReadonlyMap<string, number>;
   workspaceId: string;
   services: readonly WorkspaceServicePortDeclaration[];
   allocatePort: (request: WorkspaceServicePortAllocationRequest) => Promise<number>;
 }): Promise<Map<string, number>> {
-  const explicitPortOwners = new Map<number, string>();
+  const explicitPortOwners = new Map<number, string>(
+    Array.from(options.existingPlan, ([scriptName, port]) => [port, scriptName]),
+  );
   for (const service of options.services) {
+    if (options.existingPlan.has(service.scriptName)) continue;
     if (service.port === undefined) continue;
     if (explicitPortOwners.has(service.port)) {
       throw new Error(`Service '${service.scriptName}' has a duplicate port ${service.port}`);
@@ -124,8 +175,9 @@ async function buildWorkspaceServicePortPlan(options: {
     explicitPortOwners.set(service.port, service.scriptName);
   }
 
-  const plan = new Map<string, number>();
+  const plan = new Map(options.existingPlan);
   for (const service of options.services) {
+    if (plan.has(service.scriptName)) continue;
     if (service.port !== undefined) {
       plan.set(service.scriptName, service.port);
       continue;
@@ -148,32 +200,20 @@ async function buildWorkspaceServicePortPlan(options: {
 export async function refreshWorkspaceServicePort(
   options: RefreshWorkspaceServicePortOptions,
 ): Promise<number> {
-  const plan = workspaceServicePortPlans.get(options.workspaceId) ?? new Map<string, number>();
+  const pendingPlan = pendingWorkspaceServicePortPlans.get(options.workspaceId);
+  if (pendingPlan) {
+    await waitForWorkspaceServicePortPlanUpdate(pendingPlan);
+    return refreshWorkspaceServicePort(options);
+  }
 
-  const reservedPorts = new Set(plan.values());
-  const previousPort = plan.get(options.service.scriptName);
-  if (previousPort !== undefined) {
-    reservedPorts.delete(previousPort);
-  }
-  const oldDynamicPort = dynamicPortsByWorkspace
-    .get(options.workspaceId)
-    ?.get(options.service.scriptName);
-  const port = await resolveServicePort({
-    service: options.service,
+  const plan = await startWorkspaceServicePortPlanUpdate({
     workspaceId: options.workspaceId,
+    services: [options.service],
     allocatePort: options.allocatePort,
-    reservedPorts,
+    existingPlan: workspaceServicePortPlans.get(options.workspaceId) ?? new Map<string, number>(),
+    refreshScriptName: options.service.scriptName,
   });
-  if (oldDynamicPort !== undefined && oldDynamicPort !== port) {
-    releaseDynamicPort({
-      workspaceId: options.workspaceId,
-      scriptName: options.service.scriptName,
-      port: oldDynamicPort,
-    });
-  }
-  plan.set(options.service.scriptName, port);
-  workspaceServicePortPlans.set(options.workspaceId, plan);
-  return port;
+  return requirePlannedWorkspaceServicePort(plan, options.service.scriptName);
 }
 
 async function resolveServicePort(options: {

packages/server/src/server/worktree-bootstrap.test.ts

@@ -837,6 +837,54 @@ describe("runAsyncWorktreeBootstrap", () => {
     });
   });
 
+  it("starts a service added to paseo.json without restarting the daemon", async () => {
+    const backend = {
+      type: "service" as const,
+      command: "uv run uvicorn app.main:app --reload --port $PASEO_PORT",
+    };
+    commitPaseoScripts({ "backend-dev": backend });
+
+    const serviceProxy = new ScriptRouteStore();
+    const runtimeStore = new WorkspaceScriptRuntimeStore();
+    const createTerminalCalls: CreateTerminalCall[] = [];
+    const terminalRecords: StubTerminalRecord[] = [];
+    const options = {
+      repoRoot: repoDir,
+      workspaceId: repoDir,
+      projectSlug: "repo",
+      branchName: "feature-added-service",
+      daemonPort: 6767,
+      serviceProxy,
+      runtimeStore,
+      terminalManager: createStubTerminalManager(createTerminalCalls, terminalRecords),
+    };
+    const backendResult = await spawnWorkspaceScript({ ...options, scriptName: "backend-dev" });
+
+    writeFileSync(
+      join(repoDir, "paseo.json"),
+      JSON.stringify({
+        scripts: {
+          "backend-dev": backend,
+          web: { type: "service", command: "pnpm run dev -- --port $PASEO_PORT" },
+        },
+      }),
+    );
+    const webResult = await spawnWorkspaceScript({ ...options, scriptName: "web" });
+
+    expect(webResult.port).toEqual(expect.any(Number));
+    expect(webResult.port).not.toBe(backendResult.port);
+    expect(terminalRecords[1]?.sentInputs).toEqual(["pnpm run dev -- --port $PASEO_PORT\r"]);
+    expect(createTerminalCalls[1]?.env?.PASEO_PORT).toBe(String(webResult.port));
+    expect(createTerminalCalls[1]?.env?.PASEO_SERVICE_BACKEND_DEV_PORT).toBe(
+      String(backendResult.port),
+    );
+    expect(serviceProxy.listRoutes()).toHaveLength(2);
+    expect(runtimeStore.get({ workspaceId: repoDir, scriptName: "backend-dev" })).toMatchObject({
+      lifecycle: "running",
+      terminalId: backendResult.terminalId,
+    });
+  });
+
   it("spawns services with public aliases and public service URLs", async () => {
     commitPaseoScripts(
       {

packages/server/src/utils/checkout-git.ts

@@ -1,3 +1,4 @@
+import { MAX_RELAY_WEBSOCKET_MESSAGE_BYTES } from "@getpaseo/protocol/websocket-message-limit";
 import { resolve, dirname, basename } from "path";
 import { existsSync, realpathSync } from "fs";
 import { open as openFile, readFile, stat as statFile } from "fs/promises";
@@ -2152,13 +2153,13 @@ export async function getCheckoutSnapshotFacts(
 
 const PER_FILE_DIFF_MAX_BYTES = 1024 * 1024; // 1MB
 const TOTAL_DIFF_MAX_BYTES = 2 * 1024 * 1024; // 2MB
-const RELAY_MAX_FRAME_BYTES = 32 * 1024 * 1024;
 const CHECKOUT_DIFF_FRAME_HEADROOM_BYTES = 1024 * 1024;
 // Temporary until diffs load lazily per file. The Paseo relay's 32 MiB frame limit is
 // binding: string frames are encrypted and base64-encoded. Reserve 1 MiB plaintext for
 // the surrounding WebSocket JSON envelope after inverting that exact wire expansion.
 export const CHECKOUT_DIFF_MAX_STRUCTURED_BYTES =
-  maxBase64EncryptedPlaintextByteLength(RELAY_MAX_FRAME_BYTES) - CHECKOUT_DIFF_FRAME_HEADROOM_BYTES;
+  maxBase64EncryptedPlaintextByteLength(MAX_RELAY_WEBSOCKET_MESSAGE_BYTES) -
+  CHECKOUT_DIFF_FRAME_HEADROOM_BYTES;
 
 interface StructuredDiffAccumulator {
   files: ParsedDiffFile[];