diff --git a/apps/desktop/package.json b/apps/desktop/package.json
index ab4e1ed382dab..1b3bb0e32bb9c 100644
--- a/apps/desktop/package.json
+++ b/apps/desktop/package.json
@@ -37,6 +37,7 @@
     "acorn": "8.16.0",
     "cross-env": "^10.1.0",
     "electron-builder": "26.16.1",
+    "jsdom": "^30.0.1",
     "tailwindcss": "^4.0.0",
     "vite-plus": "catalog:"
   },
diff --git a/apps/desktop/src/preview/PickPreload.test.ts b/apps/desktop/src/preview/PickPreload.test.ts
new file mode 100644
index 0000000000000..8a080183b3830
--- /dev/null
+++ b/apps/desktop/src/preview/PickPreload.test.ts
@@ -0,0 +1,64 @@
+import { expect, it, vi } from "vite-plus/test";
+
+import { START_PICK_CHANNEL } from "./GuestProtocol.ts";
+import "./PickPreload.ts";
+
+const ipcListeners = vi.hoisted(() => new Map<string, Array<(...args: unknown[]) => void>>());
+
+vi.mock("electron", () => ({
+  ipcRenderer: {
+    on: (channel: string, listener: (...args: unknown[]) => void) => {
+      ipcListeners.set(channel, [...(ipcListeners.get(channel) ?? []), listener]);
+    },
+    off: () => {},
+    send: () => {},
+    invoke: async () => undefined,
+  },
+}));
+
+vi.mock("react-grab/primitives", () => ({ getElementContext: async () => null }));
+
+const startAnnotation = (): ShadowRoot => {
+  vi.stubGlobal(
+    "ResizeObserver",
+    class {
+      observe() {}
+      disconnect() {}
+    },
+  );
+  using attachShadow = vi.spyOn(Element.prototype, "attachShadow");
+  for (const listener of ipcListeners.get(START_PICK_CHANNEL) ?? []) listener({}, undefined, false);
+  const shadowRoot = attachShadow.mock.results[0]?.value;
+  if (!(shadowRoot instanceof ShadowRoot)) throw new Error("annotation overlay did not start");
+  return shadowRoot;
+};
+
+it("switches tools from the keyboard after a toolbar button is clicked", () => {
+  const shadowRoot = startAnnotation();
+  const region = Array.from(shadowRoot.querySelectorAll("button")).find(
+    (button) => button.textContent === "Region",
+  );
+  if (!region) throw new Error("Region toolbar button not found");
+
+  region.focus();
+  region.click();
+  expect(document.documentElement.getAttribute("data-t3code-annotation-tool")).toBe("marquee");
+
+  region.dispatchEvent(new KeyboardEvent("keydown", { key: "v", bubbles: true, composed: true }));
+
+  expect(
+    document.documentElement.getAttribute("data-t3code-annotation-tool"),
+    "V should switch to Select while focus is on a toolbar button",
+  ).toBe("select");
+});
+
+it("keeps the tool while typing a tool key in the comment", () => {
+  const shadowRoot = startAnnotation();
+  const comment = shadowRoot.querySelector("textarea");
+  if (!comment) throw new Error("comment textarea not found");
+
+  comment.focus();
+  comment.dispatchEvent(new KeyboardEvent("keydown", { key: "r", bubbles: true, composed: true }));
+
+  expect(document.documentElement.getAttribute("data-t3code-annotation-tool")).toBe("select");
+});
diff --git a/apps/desktop/src/preview/PickPreload.ts b/apps/desktop/src/preview/PickPreload.ts
index dcb16b851dc23..95aa3066f0952 100644
--- a/apps/desktop/src/preview/PickPreload.ts
+++ b/apps/desktop/src/preview/PickPreload.ts
@@ -1652,13 +1652,13 @@ function startAnnotation(
         return;
       }
     }
-    if (isAnnotationNode(event.target as Element) && event.key !== "Escape") return;
     if (event.key === "Escape") {
       event.preventDefault();
       event.stopPropagation();
       teardown(true);
       return;
     }
+    if (shadowRoot.activeElement?.matches("input, textarea, select")) return;
     if (event.key === "v") tool = "select";
     else if (event.key === "r") tool = "marquee";
     else if (event.key === "d") tool = "draw";
diff --git a/apps/desktop/vite.config.ts b/apps/desktop/vite.config.ts
index ba37576815097..4bb1e4541dd94 100644
--- a/apps/desktop/vite.config.ts
+++ b/apps/desktop/vite.config.ts
@@ -5,6 +5,7 @@ import { isDesktopRuntimeExternalDependency } from "../../scripts/lib/desktop-ex
 import { loadRepoEnv } from "../../scripts/lib/public-config.ts";
 
 const repoEnv = loadRepoEnv();
+const domTests = ["src/preview/PickPreload.test.ts"];
 
 // Install only bundle externals; the server bundle already carries its dependency tree.
 const isMainProcessExternal = (id: string) =>
@@ -151,13 +152,32 @@ export default defineConfig({
     },
   ],
   test: {
-    include: [...defaultInclude, "../../native/kde-snap-shot/src/*.test.ts"],
     // The Windows lane runs workspace suites concurrently; filesystem-heavy
     // desktop integration tests can exceed Vitest's 5 second default there.
     testTimeout: 15_000,
-    setupFiles: [
-      "../../packages/shared/src/testing/longTempDir.ts",
-      "../../packages/shared/src/testing/providerEnv.ts",
+    projects: [
+      {
+        extends: true,
+        test: {
+          name: "unit",
+          include: [...defaultInclude, "../../native/kde-snap-shot/src/*.test.ts"],
+          exclude: ["**/node_modules/**", ...domTests],
+          setupFiles: [
+            "../../packages/shared/src/testing/longTempDir.ts",
+            "../../packages/shared/src/testing/providerEnv.ts",
+          ],
+        },
+      },
+      {
+        extends: true,
+        test: {
+          name: "dom",
+          include: domTests,
+          // Guest preloads run in the page; these tests drive them against a DOM.
+          environment: "jsdom",
+          setupFiles: ["../../packages/shared/src/testing/providerEnv.ts"],
+        },
+      },
     ],
   },
 });
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index e7265664f0a44..928618460b79c 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -489,6 +489,9 @@ importers:
       electron-builder:
         specifier: 26.16.1
         version: 26.16.1(electron-builder-squirrel-windows@26.16.1)(supports-color@8.1.1)
+      jsdom:
+        specifier: ^30.0.1
+        version: 30.1.0(@noble/hashes@1.8.0)
       tailwindcss:
         specifier: 4.3.3
         version: 4.3.3