diff --git a/.changeset/playwright-extension-dry-run-1-58.md b/.changeset/playwright-extension-dry-run-1-58.md
new file mode 100644
index 00000000000..4ea983116b9
--- /dev/null
+++ b/.changeset/playwright-extension-dry-run-1-58.md
@@ -0,0 +1,5 @@
+---
+"@trigger.dev/build": patch
+---
+
+The `playwright` build extension now works with Playwright 1.58 and later. 1.58 changed the `playwright install --dry-run` output, which made deploy image builds fail while downloading the browsers.
diff --git a/packages/build/src/extensions/playwright.test.ts b/packages/build/src/extensions/playwright.test.ts
new file mode 100644
index 00000000000..73716883e76
--- /dev/null
+++ b/packages/build/src/extensions/playwright.test.ts
@@ -0,0 +1,39 @@
+import { describe, expect, it } from "vitest";
+import { dryRunHeaderPattern } from "./playwright.js";
+
+// Real `playwright install --dry-run` headers, before and after the 1.58 format change.
+const HEADERS = {
+  "1.57": {
+    chromium: "browser: chromium version 143.0.7499.4",
+    "chromium-headless-shell": "browser: chromium-headless-shell version 143.0.7499.4",
+    firefox: "browser: firefox version 144.0.2",
+    webkit: "browser: webkit version 26.0",
+  },
+  "1.62": {
+    chromium: "Chrome for Testing 151.0.7922.34 (playwright chromium v1234)",
+    "chromium-headless-shell":
+      "Chrome Headless Shell 151.0.7922.34 (playwright chromium-headless-shell v1234)",
+    firefox: "Firefox 153.0 (playwright firefox v1538)",
+    webkit: "WebKit 26.5 (playwright webkit v2336)",
+  },
+} as const;
+
+const browsers = Object.keys(HEADERS["1.57"]) as Array<keyof (typeof HEADERS)["1.57"]>;
+
+describe("playwright extension dry-run header pattern", () => {
+  it.each(browsers)("selects the %s block in both output formats", (browser) => {
+    const pattern = new RegExp(dryRunHeaderPattern(browser));
+
+    expect(pattern.test(HEADERS["1.57"][browser])).toBe(true);
+    expect(pattern.test(HEADERS["1.62"][browser])).toBe(true);
+  });
+
+  it.each(browsers)("does not select another browser's block for %s", (browser) => {
+    const pattern = new RegExp(dryRunHeaderPattern(browser));
+
+    for (const other of browsers.filter((b) => b !== browser)) {
+      expect(pattern.test(HEADERS["1.57"][other])).toBe(false);
+      expect(pattern.test(HEADERS["1.62"][other])).toBe(false);
+    }
+  });
+});
diff --git a/packages/build/src/extensions/playwright.ts b/packages/build/src/extensions/playwright.ts
index 0931a4855c7..8a390fcd8d5 100644
--- a/packages/build/src/extensions/playwright.ts
+++ b/packages/build/src/extensions/playwright.ts
@@ -196,6 +196,19 @@ export function playwright(options: PlaywrightExtensionOptions = {}) {
   return new PlaywrightExtension(options);
 }
 
+/**
+ * Extended regex selecting a browser's block header in `playwright install --dry-run` output.
+ *
+ * Playwright < 1.58 prints `browser: <name> version <v>`; 1.58+ prints
+ * `<Product> <v> (playwright <name> v<build>)`. The trailing space / `v` keep
+ * `chromium` from matching the `chromium-headless-shell` block.
+ *
+ * @internal
+ */
+export function dryRunHeaderPattern(browser: string): string {
+  return `browser: ${browser} |\\(playwright ${browser} v`;
+}
+
 /**
  * Background:
  *
@@ -317,7 +330,9 @@ class PlaywrightExtension implements BuildExtension {
 
     Array.from(browsersToInstall).forEach((browser) => {
       instructions.push(
-        `RUN grep -A5 -m1 "browser: ${browser}" /tmp/browser-info.txt > /tmp/${browser}-info.txt`,
+        // Only the two lines after the header (install location, download url)
+        // are read, so the window stops there.
+        `RUN grep -A2 -m1 -E "${dryRunHeaderPattern(browser)}" /tmp/browser-info.txt > /tmp/${browser}-info.txt`,
 
         `RUN INSTALL_DIR=$(grep "Install location:" /tmp/${browser}-info.txt | cut -d':' -f2- | xargs) && \
           DIR_NAME=$(basename "$INSTALL_DIR") && \