diff --git a/keyserver/src/session/cookies.js b/keyserver/src/session/cookies.js
--- a/keyserver/src/session/cookies.js
+++ b/keyserver/src/session/cookies.js
@@ -823,6 +823,26 @@
   );
 }
 
+async function isCookieMissingOlmNotificationsSession(
+  viewer: Viewer,
+): Promise<boolean> {
+  if (
+    !viewer.platformDetails ||
+    viewer.platformDetails.platform !== 'ios' ||
+    !viewer.platformDetails.codeVersion ||
+    viewer.platformDetails.codeVersion < 1000
+  ) {
+    return false;
+  }
+  const query = SQL`
+    SELECT * 
+    FROM olm_sessions
+    WHERE cookie_id = ${viewer.cookieID} AND is_content = FALSE;
+  `;
+  const [queryResult] = await dbQuery(query);
+  return queryResult.length === 0;
+}
+
 async function setCookiePlatform(
   viewer: Viewer,
   platform: Platform,
@@ -874,4 +894,5 @@
   isCookieMissingSignedIdentityKeysBlob,
   setCookiePlatform,
   setCookiePlatformDetails,
+  isCookieMissingOlmNotificationsSession,
 };
diff --git a/keyserver/src/socket/socket.js b/keyserver/src/socket/socket.js
--- a/keyserver/src/socket/socket.js
+++ b/keyserver/src/socket/socket.js
@@ -80,6 +80,7 @@
   extendCookieLifespan,
   createNewAnonymousCookie,
   isCookieMissingSignedIdentityKeysBlob,
+  isCookieMissingOlmNotificationsSession,
 } from '../session/cookies.js';
 import { Viewer } from '../session/viewer.js';
 import { commitSessionUpdate } from '../updaters/session-updaters.js';
@@ -479,6 +480,9 @@
     const isCookieMissingSignedIdentityKeysBlobPromise =
       isCookieMissingSignedIdentityKeysBlob(viewer.cookieID);
 
+    const isCookieMissingOlmNotificationsSessionPromise =
+      isCookieMissingOlmNotificationsSession(viewer);
+
     if (!sessionInitializationResult.sessionContinued) {
       const [threadsResult, entriesResult, currentUserInfo, knownUserInfos] =
         await Promise.all([
@@ -555,8 +559,11 @@
       });
     }
 
-    const signedIdentityKeysBlobMissing =
-      await isCookieMissingSignedIdentityKeysBlobPromise;
+    const [signedIdentityKeysBlobMissing, olmNotificationsSessionMissing] =
+      await Promise.all([
+        isCookieMissingSignedIdentityKeysBlobPromise,
+        isCookieMissingOlmNotificationsSessionPromise,
+      ]);
 
     if (signedIdentityKeysBlobMissing) {
       serverRequests.push({
@@ -564,6 +571,12 @@
       });
     }
 
+    if (olmNotificationsSessionMissing) {
+      serverRequests.push({
+        type: serverRequestTypes.INITIAL_NOTIFICATIONS_ENCRYPTED_MESSAGE,
+      });
+    }
+
     if (serverRequests.length > 0 || clientResponses.length > 0) {
       // We send this message first since the STATE_SYNC triggers the client's
       // connection status to shift to "connected", and we want to make sure the