diff --git a/apps/extension/package.json b/apps/extension/package.json
index fdccc1ea..d08c8729 100644
--- a/apps/extension/package.json
+++ b/apps/extension/package.json
@@ -9,7 +9,7 @@
     "dev": "vite --config vite.config.ts",
     "lint:firefox": "web-ext lint --source-dir dist-firefox --output text",
     "package:firefox": "bun run build:firefox && bun run lint:firefox && web-ext build --source-dir dist-firefox --artifacts-dir web-ext-artifacts --overwrite-dest",
-    "test": "bun test manifest.test.mjs context-menus.test.mjs image-clip.test.mjs tweet-clip.test.mjs selection-clip.test.mjs github-repo.test.mjs xhs-clip.test.mjs zhihu-clip.test.mjs reddit-clip.test.mjs"
+    "test": "bun test manifest.test.mjs context-menus.test.mjs popup.test.mjs image-clip.test.mjs tweet-clip.test.mjs selection-clip.test.mjs github-repo.test.mjs xhs-clip.test.mjs zhihu-clip.test.mjs reddit-clip.test.mjs"
   },
   "dependencies": {
     "@mixmark-io/domino": "2.2.0",
diff --git a/apps/extension/popup.html b/apps/extension/popup.html
index 7ca7b430..dec45ea2 100644
--- a/apps/extension/popup.html
+++ b/apps/extension/popup.html
@@ -23,7 +23,7 @@
           <span class="platform-tag">GitHub</span>
         </div>
       </div>
-      <button id="save" class="save-button" type="button">
+      <button id="save" class="save-button" type="button" disabled>
         <svg aria-hidden="true" viewBox="0 0 24 24" width="18" height="18">
           <path d="M5 4.75A1.75 1.75 0 0 1 6.75 3h8.836c.464 0 .91.184 1.238.513l1.663 1.663c.329.328.513.774.513 1.238v12.836A1.75 1.75 0 0 1 17.25 21H6.75A1.75 1.75 0 0 1 5 19.25V4.75Z" />
           <path d="M8 3v5h7V3M8 21v-7h8v7" />
diff --git a/apps/extension/popup.test.mjs b/apps/extension/popup.test.mjs
new file mode 100644
index 00000000..4a73ba3a
--- /dev/null
+++ b/apps/extension/popup.test.mjs
@@ -0,0 +1,64 @@
+import { expect, test } from "bun:test";
+
+test("requests instance permission during the popup click user action", async () => {
+  const previousChrome = globalThis.chrome;
+  const previousDocument = globalThis.document;
+  const listeners = new Map();
+  const saveButton = {
+    disabled: false,
+    addEventListener: (event, listener) => listeners.set(`save:${event}`, listener),
+  };
+  const settingsButton = { addEventListener: () => {} };
+  const status = { textContent: "", dataset: {} };
+  let finishLoadingSettings;
+  let insideClick = false;
+  let permissionRequests = 0;
+  let captures = 0;
+
+  globalThis.document = {
+    documentElement: { lang: "", dir: "" },
+    querySelectorAll: () => [],
+    querySelector: (selector) => ({ "#save": saveButton, "#settings": settingsButton, "#status": status })[selector],
+  };
+  globalThis.chrome = {
+    i18n: { getMessage: (key) => key, getUILanguage: () => "en" },
+    storage: { local: { get: () => new Promise((resolve) => { finishLoadingSettings = resolve; }) } },
+    permissions: {
+      request: ({ origins }) => {
+        expect(insideClick).toBe(true);
+        expect(origins).toEqual(["https://example.com/*"]);
+        permissionRequests += 1;
+        return Promise.resolve(true);
+      },
+    },
+    runtime: {
+      sendMessage: async (message) => {
+        expect(message).toEqual({ type: "captureCurrentPage" });
+        captures += 1;
+        return { ok: true };
+      },
+    },
+  };
+
+  try {
+    await import("./src/popup.ts");
+    expect(saveButton.disabled).toBe(true);
+
+    finishLoadingSettings({ instanceUrl: "https://example.com", token: "token", notebookId: "" });
+    await new Promise((resolve) => setTimeout(resolve, 0));
+    expect(saveButton.disabled).toBe(false);
+
+    insideClick = true;
+    const click = listeners.get("save:click")();
+    insideClick = false;
+    await click;
+
+    expect(permissionRequests).toBe(1);
+    expect(captures).toBe(1);
+    expect(status.textContent).toBe("savedToEdgeEver");
+    expect(saveButton.disabled).toBe(false);
+  } finally {
+    globalThis.chrome = previousChrome;
+    globalThis.document = previousDocument;
+  }
+});
diff --git a/apps/extension/src/popup.ts b/apps/extension/src/popup.ts
index 4dab6858..dfc27881 100644
--- a/apps/extension/src/popup.ts
+++ b/apps/extension/src/popup.ts
@@ -1,5 +1,5 @@
 import "./styles.css";
-import { getSettings, requestInstancePermission } from "./extension";
+import { getSettings, requestInstancePermission, type ExtensionSettings } from "./extension";
 import { localizeDocument, t } from "./i18n";
 
 localizeDocument();
@@ -7,6 +7,7 @@ localizeDocument();
 const saveButton = document.querySelector<HTMLButtonElement>("#save");
 const settingsButton = document.querySelector<HTMLButtonElement>("#settings");
 const status = document.querySelector<HTMLParagraphElement>("#status");
+let settings: ExtensionSettings | null = null;
 
 const setStatus = (message: string, kind: "normal" | "error" | "success" = "normal") => {
   if (status) {
@@ -15,12 +16,20 @@ const setStatus = (message: string, kind: "normal" | "error" | "success" = "norm
   }
 };
 
+if (saveButton) saveButton.disabled = true;
+void getSettings().then((loadedSettings) => {
+  settings = loadedSettings;
+  if (saveButton) saveButton.disabled = false;
+}).catch((error: unknown) => {
+  setStatus(error instanceof Error ? error.message : t("saveFailed"), "error");
+});
+
 saveButton?.addEventListener("click", async () => {
+  if (!settings) return;
   saveButton.disabled = true;
   setStatus(t("readingAndSaving"));
 
   try {
-    const settings = await getSettings();
     if (!settings.instanceUrl || !settings.token) {
       throw new Error(t("completePluginConfiguration"));
     }