diff --git a/apps/server/src/preview/ServerBrowser.ts b/apps/server/src/preview/ServerBrowser.ts
index ad9e20ef11b3c..6537576c89a73 100644
--- a/apps/server/src/preview/ServerBrowser.ts
+++ b/apps/server/src/preview/ServerBrowser.ts
@@ -2626,7 +2626,11 @@ const make = Effect.gen(function* () {
         return loadError ? { ...snapshot, url: loadError.url, loadError } : snapshot;
       }
       case "click": {
-        const clickInput = input as PreviewAutomationClickInput;
+        // Time spent queued behind other work on this tab counts against the broker's deadline.
+        const clickInput = {
+          ...(input as PreviewAutomationClickInput),
+          timeoutMs: Math.max(1, Math.floor(deadlineMs - performance.now())),
+        };
         await recordAction(tab, "click", () =>
           ServerBrowserPage.click(tab.page, clickInput, pointerFor(tab)),
         );
diff --git a/apps/server/src/preview/ServerBrowserPage.test.ts b/apps/server/src/preview/ServerBrowserPage.test.ts
index 74da1e3825716..550943312c2f1 100644
--- a/apps/server/src/preview/ServerBrowserPage.test.ts
+++ b/apps/server/src/preview/ServerBrowserPage.test.ts
@@ -173,10 +173,22 @@ describe("server browser element refs", () => {
     const hidden = await failure("button");
     expect(hidden.tag).toBe("PreviewAutomationTimeoutError");
     expect(hidden.message).toBe(
-      'The click may have happened; check the page before retrying. "button" still matches an element after the timeout.',
+      'The click may have happened; check the page before retrying. "button" still matches an element after the timeout. Playwright last saw: element is not visible.',
     );
   });
 
+  it("gives a late target only the click's remaining time, not a fresh timeout", async () => {
+    await page.setContent(`<script>
+      setTimeout(() => document.body.insertAdjacentHTML("beforeend",
+        '<button id="save" disabled onclick="document.body.dataset.clicked = 1">Save</button>'), 1000);
+      setTimeout(() => document.querySelector("#save").disabled = false, 2500);
+    </script>`);
+    await expect(
+      ServerBrowserPage.click(page, { selector: "#save", timeoutMs: 2_000 }),
+    ).rejects.toThrow();
+    expect(await page.locator("body").getAttribute("data-clicked")).toBeNull();
+  });
+
   it("does not retarget a removed ref to a replacement node", async () => {
     await page.setContent("<button onclick=\"this.textContent='clicked'\">original</button>");
     const locator = buttonLocator((await takeSnapshot()).accessibilityTree, "original");
diff --git a/apps/server/src/preview/ServerBrowserPage.ts b/apps/server/src/preview/ServerBrowserPage.ts
index 20df4457643eb..3354554f1dd90 100644
--- a/apps/server/src/preview/ServerBrowserPage.ts
+++ b/apps/server/src/preview/ServerBrowserPage.ts
@@ -22,6 +22,7 @@ import { constVoid } from "effect/Function";
 import * as Schema from "effect/Schema";
 import type { CDPSession, ConsoleMessage, Frame, Locator, Page } from "playwright-core";
 import * as NodeCrypto from "node:crypto";
+import * as NodeUtil from "node:util";
 import { BrowserControlInterrupted } from "./SessionControl.ts";
 
 const isBrowserControlInterrupted = Schema.is(BrowserControlInterrupted);
@@ -62,7 +63,7 @@ export const toOperationError = (
   if (cause instanceof Error && cause.name === "TimeoutError") {
     return new ServerBrowserOperationError({
       tag: "PreviewAutomationTimeoutError",
-      message: firstLine,
+      message: withActionabilityReason(firstLine, cause),
       detail: timeoutMs === undefined ? undefined : { timeoutMs },
     });
   }
@@ -84,6 +85,17 @@ export const toOperationError = (
   });
 };
 
+/** Playwright puts why an element was not actionable in its call log, below the first line. */
+const withActionabilityReason = (message: string, cause: Error) => {
+  // Playwright dims call-log lines with ANSI escapes when colour is on.
+  const reason = NodeUtil.stripVTControlCharacters(cause.message)
+    .split("\n")
+    .map((line) => line.trim())
+    .findLast((line) => line.startsWith("- element is "))
+    ?.slice(2);
+  return reason === undefined ? message : `${message} Playwright last saw: ${reason}.`;
+};
+
 const DEFAULT_TIMEOUT_MS = 15_000;
 const TARGET_COUNT_MS = 250;
 const MAX_TARGET_CHARS = 200;
@@ -168,11 +180,11 @@ const targetPoint = async (
   page: Page,
   locator: Locator | null,
   input: { readonly x?: number | undefined; readonly y?: number | undefined },
-  timeout: number,
+  timeout: () => number,
 ) => {
   if (locator === null) return { x: input.x ?? 0, y: input.y ?? 0 };
-  await scrollIntoView(locator, timeout);
-  const box = await locator.boundingBox({ timeout });
+  await scrollIntoView(locator, timeout());
+  const box = await locator.boundingBox({ timeout: timeout() });
   if (box) return { x: box.x + box.width / 2, y: box.y + box.height / 2 };
   const viewport = page.viewportSize();
   return { x: (viewport?.width ?? 0) / 2, y: (viewport?.height ?? 0) / 2 };
@@ -711,10 +723,12 @@ export const click = async (
   input: PreviewAutomationClickInput,
   pointer: PointerReporter = noPointer,
 ): Promise<{ readonly x: number; readonly y: number }> => {
-  const timeout = input.timeoutMs ?? DEFAULT_TIMEOUT_MS;
+  // One deadline across steps keeps the reply inside the broker's grace; Playwright reads 0 as none.
+  const deadline = Date.now() + (input.timeoutMs ?? DEFAULT_TIMEOUT_MS);
+  const remaining = () => Math.max(1, deadline - Date.now());
   const locator = targetLocator(page, input);
   try {
-    return await clickTarget(page, locator, input, timeout, pointer);
+    return await clickTarget(page, locator, input, remaining, pointer);
   } catch (cause) {
     throw locator === null ? cause : await namedTargetTimeout(locator, input, cause);
   }
@@ -750,10 +764,11 @@ const namedTargetTimeout = async (
       : matches === 0
         ? `The click may have happened and removed its target or navigated; check the page before retrying. No element matches ${target} after the timeout; take a fresh snapshot and use its locator.`
         : `The click may have happened; check the page before retrying. ${target} still matches an element after the timeout.`;
+  const message = withActionabilityReason(reason, cause);
   return new ServerBrowserOperationError({
     tag: "PreviewAutomationTimeoutError",
-    message: reason,
-    detail: { reason },
+    message,
+    detail: { reason: message },
     cause,
   });
 };
@@ -762,7 +777,7 @@ const clickTarget = async (
   page: Page,
   locator: Locator | null,
   input: PreviewAutomationClickInput,
-  timeout: number,
+  timeout: () => number,
   pointer: PointerReporter,
 ) => {
   const point = await targetPoint(page, locator, input, timeout);
@@ -771,7 +786,7 @@ const clickTarget = async (
   const clicked =
     locator === null
       ? page.mouse.click(point.x, point.y, options)
-      : locator.click({ ...options, timeout });
+      : locator.click({ ...options, timeout: timeout() });
   let onDialog = constVoid;
   const dialogOpened = new Promise<"dialog">((resolve) => {
     onDialog = () => resolve("dialog");
@@ -852,7 +867,7 @@ export const hover = async (
 ) => {
   const timeout = input.timeoutMs ?? DEFAULT_TIMEOUT_MS;
   const locator = targetLocator(page, input);
-  await pointer(await targetPoint(page, locator, input, timeout), "move");
+  await pointer(await targetPoint(page, locator, input, () => timeout), "move");
   if (locator === null) {
     await page.mouse.move(input.x ?? 0, input.y ?? 0);
     return;
@@ -903,7 +918,7 @@ export const drag = async (
   const timeout = input.timeoutMs ?? DEFAULT_TIMEOUT_MS;
   const source = targetLocator(page, { locator: input.source })!;
   const target = targetLocator(page, { locator: input.target })!;
-  await pointer(await targetPoint(page, source, {}, timeout), "move");
+  await pointer(await targetPoint(page, source, {}, () => timeout), "move");
   // Observe drag rejection immediately; an unhandled rejection during cursor movement exits the server.
   // Chromium delivers a single move before dragstart; steps give the page mousemoves during the drag.
   const dragFailure = source.dragTo(target, { timeout, steps: 5 }).then(