diff --git a/src/browser/chrome-extension-background-utils.test.ts b/src/browser/chrome-extension-background-utils.test.ts
index 7f383398d8e..0a0ba76ac28 100644
--- a/src/browser/chrome-extension-background-utils.test.ts
+++ b/src/browser/chrome-extension-background-utils.test.ts
@@ -1,9 +1,18 @@
+import { createRequire } from "node:module";
 import { describe, expect, it } from "vitest";
-import {
-  buildRelayWsUrl,
-  isRetryableReconnectError,
-  reconnectDelayMs,
-} from "../../assets/chrome-extension/background-utils.js";
+
+type BackgroundUtilsModule = {
+  buildRelayWsUrl: (port: number, gatewayToken: string) => string;
+  isRetryableReconnectError: (err: unknown) => boolean;
+  reconnectDelayMs: (
+    attempt: number,
+    opts?: { baseMs?: number; maxMs?: number; jitterMs?: number; random?: () => number },
+  ) => number;
+};
+
+const require = createRequire(import.meta.url);
+const { buildRelayWsUrl, isRetryableReconnectError, reconnectDelayMs } =
+  require("../../assets/chrome-extension/background-utils.js") as BackgroundUtilsModule;
 
 describe("chrome extension background utils", () => {
   it("builds websocket url with encoded gateway token", () => {
diff --git a/src/commands/doctor.migrates-routing-allowfrom-channels-whatsapp-allowfrom.test.ts b/src/commands/doctor.migrates-routing-allowfrom-channels-whatsapp-allowfrom.test.ts
index 872a48d3dfc..95fe4be23f4 100644
--- a/src/commands/doctor.migrates-routing-allowfrom-channels-whatsapp-allowfrom.test.ts
+++ b/src/commands/doctor.migrates-routing-allowfrom-channels-whatsapp-allowfrom.test.ts
@@ -16,7 +16,7 @@ import {
 } from "./doctor.e2e-harness.js";
 import "./doctor.fast-path-mocks.js";
 
-const DOCTOR_MIGRATION_TIMEOUT_MS = 20_000;
+const DOCTOR_MIGRATION_TIMEOUT_MS = process.platform === "win32" ? 60_000 : 45_000;
 const { doctorCommand } = await import("./doctor.js");
 
 describe("doctor command", () => {
diff --git a/src/commands/doctor.migrates-slack-discord-dm-policy-aliases.test.ts b/src/commands/doctor.migrates-slack-discord-dm-policy-aliases.test.ts
index 5dcec07fd23..adfecc03d29 100644
--- a/src/commands/doctor.migrates-slack-discord-dm-policy-aliases.test.ts
+++ b/src/commands/doctor.migrates-slack-discord-dm-policy-aliases.test.ts
@@ -1,7 +1,7 @@
 import { describe, expect, it, vi } from "vitest";
 import { readConfigFileSnapshot, writeConfigFile } from "./doctor.e2e-harness.js";
 
-const DOCTOR_MIGRATION_TIMEOUT_MS = 20_000;
+const DOCTOR_MIGRATION_TIMEOUT_MS = process.platform === "win32" ? 60_000 : 45_000;
 const { doctorCommand } = await import("./doctor.js");
 
 describe("doctor command", () => {
diff --git a/src/commands/sandbox-explain.test.ts b/src/commands/sandbox-explain.test.ts
index 573ac8b9b79..6774c86b72c 100644
--- a/src/commands/sandbox-explain.test.ts
+++ b/src/commands/sandbox-explain.test.ts
@@ -1,5 +1,7 @@
 import { describe, expect, it, vi } from "vitest";
 
+const SANDBOX_EXPLAIN_TEST_TIMEOUT_MS = process.platform === "win32" ? 45_000 : 30_000;
+
 let mockCfg: unknown = {};
 
 vi.mock("../config/config.js", async (importOriginal) => {
@@ -13,7 +15,7 @@ vi.mock("../config/config.js", async (importOriginal) => {
 const { sandboxExplainCommand } = await import("./sandbox-explain.js");
 
 describe("sandbox explain command", () => {
-  it("prints JSON shape + fix-it keys", async () => {
+  it("prints JSON shape + fix-it keys", { timeout: SANDBOX_EXPLAIN_TEST_TIMEOUT_MS }, async () => {
     mockCfg = {
       agents: {
         defaults: {
@@ -42,5 +44,5 @@ describe("sandbox explain command", () => {
     expect(Array.isArray(parsed.fixIt)).toBe(true);
     expect(parsed.fixIt).toContain("agents.defaults.sandbox.mode=off");
     expect(parsed.fixIt).toContain("tools.sandbox.tools.deny");
-  }, 15_000);
+  });
 });
diff --git a/src/telegram/bot.media.downloads-media-file-path-no-file-download.test.ts b/src/telegram/bot.media.downloads-media-file-path-no-file-download.test.ts
index 07e3e4ecc03..c43c3f1746c 100644
--- a/src/telegram/bot.media.downloads-media-file-path-no-file-download.test.ts
+++ b/src/telegram/bot.media.downloads-media-file-path-no-file-download.test.ts
@@ -12,6 +12,7 @@ const TELEGRAM_TEST_TIMINGS = {
   mediaGroupFlushMs: 20,
   textFragmentGapMs: 30,
 } as const;
+const TELEGRAM_BOT_IMPORT_TIMEOUT_MS = process.platform === "win32" ? 180_000 : 150_000;
 let createTelegramBot: typeof import("./bot.js").createTelegramBot;
 let replySpy: ReturnType<typeof vi.fn>;
 
@@ -98,7 +99,7 @@ beforeAll(async () => {
   ({ createTelegramBot } = await import("./bot.js"));
   const replyModule = await import("../auto-reply/reply.js");
   replySpy = (replyModule as unknown as { __replySpy: ReturnType<typeof vi.fn> }).__replySpy;
-});
+}, TELEGRAM_BOT_IMPORT_TIMEOUT_MS);
 
 vi.mock("./sticker-cache.js", () => ({
   cacheSticker: (...args: unknown[]) => cacheStickerSpy(...args),