diff --git a/apps/web/src/app-effects.js b/apps/web/src/app-effects.js
index 345fd3a6b..ca02349df 100644
--- a/apps/web/src/app-effects.js
+++ b/apps/web/src/app-effects.js
@@ -45,11 +45,8 @@ import { isTesting } from "./utils/platform";
 import { updateStatus, removeStatus, getStatus } from "./hooks/use-status";
 import { showToast } from "./utils/toast";
 import { interruptedOnboarding } from "./components/dialogs/onboarding-dialog";
-import { WebExtensionRelay } from "./utils/web-extension-relay";
 import { hashNavigate } from "./navigation";
 
-const relay = new WebExtensionRelay();
-
 export default function AppEffects({ setShow }) {
   const refreshNavItems = useStore((store) => store.refreshNavItems);
   const updateLastSynced = useStore((store) => store.updateLastSynced);
@@ -103,7 +100,6 @@ export default function AppEffects({ setShow }) {
         await showOnboardingDialog(interruptedOnboarding());
         await showFeatureDialog("highlights");
         await scheduleBackups();
-        relay.connect();
       })();
 
       return () => {
diff --git a/apps/web/src/app.js b/apps/web/src/app.js
index 4a5a06913..23b0b1c94 100644
--- a/apps/web/src/app.js
+++ b/apps/web/src/app.js
@@ -35,6 +35,9 @@ import StatusBar from "./components/status-bar";
 import { EditorLoader } from "./components/loaders/editor-loader";
 import { FlexScrollContainer } from "./components/scroll-container";
 import CachedRouter from "./components/cached-router";
+import { WebExtensionRelay } from "./utils/web-extension-relay";
+
+new WebExtensionRelay();
 
 const GlobalMenuWrapper = React.lazy(() =>
   import("./components/global-menu-wrapper")
diff --git a/apps/web/src/utils/web-extension-relay.ts b/apps/web/src/utils/web-extension-relay.ts
index f572aacf0..ed8e808a0 100644
--- a/apps/web/src/utils/web-extension-relay.ts
+++ b/apps/web/src/utils/web-extension-relay.ts
@@ -19,22 +19,10 @@ along with this program.  If not, see <http://www.gnu.org/licenses/>.
 
 import { expose, Remote, wrap } from "comlink";
 import { updateStatus } from "../hooks/use-status";
-import { db } from "../common/db";
 import {
   Gateway,
-  ItemReference,
-  NotebookReference,
-  Server,
-  Clip,
   WEB_EXTENSION_CHANNEL_EVENTS
 } from "@notesnook/web-clipper/dist/common/bridge";
-import { isUserPremium } from "../hooks/use-is-user-premium";
-import { store as themestore } from "../stores/theme-store";
-import { store as appstore } from "../stores/app-store";
-import { formatDate } from "@notesnook/core/utils/date";
-import { h } from "./html";
-import { sanitizeFilename } from "./filename";
-import { attachFile } from "../components/editor/picker";
 
 export class WebExtensionRelay {
   private gateway?: Remote<Gateway>;
@@ -52,6 +40,8 @@ export class WebExtensionRelay {
 
   async connect(): Promise<boolean> {
     if (this.gateway) return true;
+    const { WebExtensionServer } = await import("./web-extension-server");
+
     const channel = new MessageChannel();
     channel.port1.start();
     channel.port2.start();
@@ -76,96 +66,3 @@ export class WebExtensionRelay {
     return true;
   }
 }
-
-class WebExtensionServer implements Server {
-  async login() {
-    const user = await db.user?.getUser();
-    if (!user) return null;
-    const { theme, accent } = themestore.get();
-    return { email: user.email, pro: isUserPremium(user), accent, theme };
-  }
-
-  async getNotes(): Promise<ItemReference[] | undefined> {
-    await db.notes?.init();
-
-    return db.notes?.all
-      .filter((n) => !n.locked)
-      .map((note) => ({ id: note.id, title: note.title }));
-  }
-
-  async getNotebooks(): Promise<NotebookReference[] | undefined> {
-    return db.notebooks?.all.map((nb) => ({
-      id: nb.id,
-      title: nb.title,
-      topics: nb.topics.map((topic: ItemReference) => ({
-        id: topic.id,
-        title: topic.title
-      }))
-    }));
-  }
-
-  async getTags(): Promise<ItemReference[] | undefined> {
-    return db.tags?.all.map((tag) => ({
-      id: tag.id,
-      title: tag.title
-    }));
-  }
-
-  async saveClip(clip: Clip) {
-    let clipContent = "";
-
-    if (clip.mode === "simplified" || clip.mode === "screenshot") {
-      clipContent += clip.data;
-    } else {
-      const clippedFile = new File(
-        [new TextEncoder().encode(clip.data).buffer],
-        `${sanitizeFilename(clip.title)}.clip`,
-        {
-          type: "application/vnd.notesnook.web-clip"
-        }
-      );
-
-      const attachment = await attachFile(clippedFile);
-      if (!attachment) return;
-
-      clipContent += h("iframe", [], {
-        "data-hash": attachment.hash,
-        "data-mime": attachment.type,
-        src: clip.url,
-        title: clip.pageTitle || clip.title,
-        width: clip.width ? `${clip.width}` : undefined,
-        height: clip.height ? `${clip.height}` : undefined,
-        class: "web-clip"
-      }).outerHTML;
-    }
-
-    const note =
-      (clip.note?.id && db.notes?.note(clip.note?.id)) ||
-      db.notes?.note(await db.notes?.add({ title: clip.title }));
-    let content = (await note?.content()) || "";
-    content += clipContent;
-    content += h("div", [
-      h("hr"),
-      h("p", ["Clipped from ", h("a", [clip.title], { href: clip.url })]),
-      h("p", [`Date clipped: ${formatDate(Date.now())}`])
-    ]).innerHTML;
-
-    await db.notes?.add({
-      id: note?.id,
-      content: { type: "tiptap", data: content }
-    });
-
-    if (clip.notebook && note) {
-      await db.notes?.addToNotebook(
-        { id: clip.notebook.id, topic: clip.notebook.topic.id },
-        note.id
-      );
-    }
-    if (clip.tags && note) {
-      for (const tag of clip.tags) {
-        await db.tags?.add(tag, note.id);
-      }
-    }
-    await appstore.refresh();
-  }
-}
diff --git a/apps/web/src/utils/web-extension-server.ts b/apps/web/src/utils/web-extension-server.ts
new file mode 100644
index 000000000..960b64496
--- /dev/null
+++ b/apps/web/src/utils/web-extension-server.ts
@@ -0,0 +1,126 @@
+/*
+This file is part of the Notesnook project (https://notesnook.com/)
+
+Copyright (C) 2023 Streetwriters (Private) Limited
+
+This program is free software: you can redistribute it and/or modify
+it under the terms of the GNU General Public License as published by
+the Free Software Foundation, either version 3 of the License, or
+(at your option) any later version.
+
+This program is distributed in the hope that it will be useful,
+but WITHOUT ANY WARRANTY; without even the implied warranty of
+MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+GNU General Public License for more details.
+
+You should have received a copy of the GNU General Public License
+along with this program.  If not, see <http://www.gnu.org/licenses/>.
+*/
+
+import { db } from "../common/db";
+import {
+  ItemReference,
+  NotebookReference,
+  Server,
+  Clip
+} from "@notesnook/web-clipper/dist/common/bridge";
+import { isUserPremium } from "../hooks/use-is-user-premium";
+import { store as themestore } from "../stores/theme-store";
+import { store as appstore } from "../stores/app-store";
+import { formatDate } from "@notesnook/core/utils/date";
+import { h } from "./html";
+import { sanitizeFilename } from "./filename";
+import { attachFile } from "../components/editor/picker";
+
+export class WebExtensionServer implements Server {
+  async login() {
+    const user = await db.user?.getUser();
+    const { theme, accent } = themestore.get();
+    if (!user) return { pro: false, theme, accent };
+    return { email: user.email, pro: isUserPremium(user), theme, accent };
+  }
+
+  async getNotes(): Promise<ItemReference[] | undefined> {
+    await db.notes?.init();
+
+    return db.notes?.all
+      .filter((n) => !n.locked)
+      .map((note) => ({ id: note.id, title: note.title }));
+  }
+
+  async getNotebooks(): Promise<NotebookReference[] | undefined> {
+    return db.notebooks?.all.map((nb) => ({
+      id: nb.id,
+      title: nb.title,
+      topics: nb.topics.map((topic: ItemReference) => ({
+        id: topic.id,
+        title: topic.title
+      }))
+    }));
+  }
+
+  async getTags(): Promise<ItemReference[] | undefined> {
+    return db.tags?.all.map((tag) => ({
+      id: tag.id,
+      title: tag.title
+    }));
+  }
+
+  async saveClip(clip: Clip) {
+    let clipContent = "";
+
+    if (clip.mode === "simplified" || clip.mode === "screenshot") {
+      clipContent += clip.data;
+    } else {
+      const clippedFile = new File(
+        [new TextEncoder().encode(clip.data).buffer],
+        `${sanitizeFilename(clip.title)}.clip`,
+        {
+          type: "application/vnd.notesnook.web-clip"
+        }
+      );
+
+      const attachment = await attachFile(clippedFile);
+      if (!attachment) return;
+
+      clipContent += h("iframe", [], {
+        "data-hash": attachment.hash,
+        "data-mime": attachment.type,
+        src: clip.url,
+        title: clip.pageTitle || clip.title,
+        width: clip.width ? `${clip.width}` : undefined,
+        height: clip.height ? `${clip.height}` : undefined,
+        class: "web-clip"
+      }).outerHTML;
+    }
+
+    const note =
+      (clip.note?.id && db.notes?.note(clip.note?.id)) ||
+      db.notes?.note(await db.notes?.add({ title: clip.title }));
+    let content = (await note?.content()) || "";
+    content += clipContent;
+    content += h("div", [
+      h("hr"),
+      h("p", ["Clipped from ", h("a", [clip.title], { href: clip.url })]),
+      h("p", [`Date clipped: ${formatDate(Date.now())}`])
+    ]).innerHTML;
+
+    await db.notes?.add({
+      id: note?.id,
+      content: { type: "tiptap", data: content }
+    });
+
+    if (clip.notebook && note) {
+      await db.notes?.addToNotebook(
+        { id: clip.notebook.id, topic: clip.notebook.topic.id },
+        note.id
+      );
+    }
+    if (clip.tags && note) {
+      for (const tag of clip.tags) {
+        await db.tags?.add(tag, note.id);
+      }
+    }
+    await appstore.refresh();
+  }
+}
diff --git a/extensions/web-clipper/src/api.ts b/extensions/web-clipper/src/api.ts
index 245f2af64..ea6a16b1d 100644
--- a/extensions/web-clipper/src/api.ts
+++ b/extensions/web-clipper/src/api.ts
@@ -16,7 +16,7 @@ GNU General Public License for more details.
 You should have received a copy of the GNU General Public License
 along with this program.  If not, see <http://www.gnu.org/licenses/>.
 */
-import { browser, Runtime } from "webextension-polyfill-ts";
+import { browser, Runtime, Tabs } from "webextension-polyfill-ts";
 import { Remote, wrap } from "comlink";
 import { createEndpoint } from "./utils/comlink-extension";
 import { Server } from "./common/bridge";
@@ -28,14 +28,32 @@ let api: Remote<Server> | undefined;
 export async function connectApi(openNew = false, onDisconnect?: () => void) {
   if (api) return api;
 
-  const tab = await getTab(openNew);
-  if (!tab) return false;
+  const tabs = await findNotesnookTabs(openNew);
+  for (const tab of tabs) {
+    try {
+      const api = await Promise.race([
+        connectToTab(tab, onDisconnect),
+        timeout(5000)
+      ]);
+      if (!api) continue;
+      return api as Remote<Server>;
+    } catch (e) {
+      console.error(e);
+    }
+  }
 
-  return await new Promise<Remote<Server> | false>(function connect(resolve) {
+  return false;
+}
+
+function timeout(ms: number) {
+  return new Promise((resolve) => setTimeout(resolve, ms, false));
+}
+
+function connectToTab(tab: Tabs.Tab, onDisconnect?: () => void) {
+  return new Promise<Remote<Server> | false>(function connect(resolve) {
     if (!tab.id) return resolve(false);
 
     const port = browser.tabs.connect(tab.id);
-
     port.onDisconnect.addListener(() => {
       api = undefined;
       onDisconnect?.();
@@ -58,23 +76,26 @@ export async function connectApi(openNew = false, onDisconnect?: () => void) {
   });
 }
 
-async function getTab(openNew = false) {
+export async function findNotesnookTabs(openNew = false) {
   const tabs = await browser.tabs.query({
-    url: APP_URL_FILTER
+    url: APP_URL_FILTER,
+    discarded: false,
+    status: "complete"
   });
 
-  if (tabs.length) return tabs[0];
+  if (tabs.length) return tabs;
 
   if (openNew) {
-    const [tab] = await Promise.all([
-      browser.tabs.create({ url: APP_URL, active: false }),
-      new Promise((resolve) => {
-        browser.runtime.onMessage.addListener((message) => {
-          if (message.type === "start_connection") resolve(true);
-        });
+    const tab = await browser.tabs.create({ url: APP_URL, active: false });
+    await new Promise<void>((resolve) =>
+      browser.tabs.onUpdated.addListener(function onUpdated(id, info) {
+        if (id === tab.id && info.status === "complete") {
+          browser.tabs.onUpdated.removeListener(onUpdated);
+          resolve();
+        }
       })
-    ]);
-    return tab;
+    );
+    return [tab];
   }
-  return undefined;
+  return [];
 }
diff --git a/extensions/web-clipper/src/common/bridge.ts b/extensions/web-clipper/src/common/bridge.ts
index efae420aa..1ff0c5537 100644
--- a/extensions/web-clipper/src/common/bridge.ts
+++ b/extensions/web-clipper/src/common/bridge.ts
@@ -22,7 +22,7 @@ export type ClipArea = "full-page" | "visible" | "selection" | "article";
 export type ClipMode = "simplified" | "screenshot" | "complete";
 
 export type User = {
-  email: string;
+  email?: string;
   pro: boolean;
   accent: string;
   theme: "dark" | "light";
diff --git a/extensions/web-clipper/src/content-scripts/nn.ts b/extensions/web-clipper/src/content-scripts/nn.ts
index efe0232ac..822fbcc18 100644
--- a/extensions/web-clipper/src/content-scripts/nn.ts
+++ b/extensions/web-clipper/src/content-scripts/nn.ts
@@ -26,43 +26,38 @@ import {
   WEB_EXTENSION_CHANNEL_EVENTS
 } from "../common/bridge";
 
-let mainPort: MessagePort | undefined;
-
 browser.runtime.onConnect.addListener((port) => {
-  if (mainPort) {
-    const server: Remote<Server> = wrap<Server>(mainPort);
-    expose(
-      {
-        login: () => server.login(),
-        getNotes: () => server.getNotes(),
-        getNotebooks: () => server.getNotebooks(),
-        getTags: () => server.getTags(),
-        saveClip: (clip: Clip) => server.saveClip(clip)
-      },
-      createEndpoint(port)
-    );
-    port.postMessage({ success: true });
-  } else {
-    port.postMessage({ success: false });
-  }
-});
+  window.addEventListener("message", (ev) => {
+    const { type } = ev.data;
+    switch (type) {
+      case WEB_EXTENSION_CHANNEL_EVENTS.ON_CREATED:
+        if (ev.ports.length) {
+          const mainPort = ev.ports.at(0);
+          if (mainPort) {
+            expose(new BackgroundGateway(), mainPort);
+            const server: Remote<Server> = wrap<Server>(mainPort);
+            expose(
+              {
+                login: () => server.login(),
+                getNotes: () => server.getNotes(),
+                getNotebooks: () => server.getNotebooks(),
+                getTags: () => server.getTags(),
+                saveClip: (clip: Clip) => server.saveClip(clip)
+              },
+              createEndpoint(port)
+            );
+            port.postMessage({ success: true });
+          } else {
+            port.postMessage({ success: false });
+          }
+        }
+        break;
+    }
+  });
 
-window.addEventListener("message", (ev) => {
-  const { type } = ev.data;
-  switch (type) {
-    case WEB_EXTENSION_CHANNEL_EVENTS.ON_CREATED:
-      if (ev.ports.length) {
-        const [port] = ev.ports;
-        mainPort = port;
-        expose(new BackgroundGateway(), port);
-        browser.runtime.sendMessage(undefined, { type: "start_connection" });
-      }
-      break;
-  }
+  window.postMessage({ type: WEB_EXTENSION_CHANNEL_EVENTS.ON_READY }, "*");
 });
 
-window.postMessage({ type: WEB_EXTENSION_CHANNEL_EVENTS.ON_READY }, "*");
-
 class BackgroundGateway implements Gateway {
   connect() {
     return {