diff --git a/src/matrix/Session.js b/src/matrix/Session.js
index 7d821b14..f8ac2f40 100644
--- a/src/matrix/Session.js
+++ b/src/matrix/Session.js
@@ -28,6 +28,7 @@ import {MEGOLM_ALGORITHM} from "./e2ee/common.js";
 import {RoomEncryption} from "./e2ee/RoomEncryption.js";
 import {DeviceTracker} from "./e2ee/DeviceTracker.js";
 import {LockMap} from "../utils/LockMap.js";
+import {groupBy} from "../utils/groupBy.js";
 
 const PICKLE_KEY = "DEFAULT_KEY";
 
@@ -212,9 +213,20 @@ export class Session {
             await txn.complete();
         }
 
+        const opsTxn = await this._storage.readWriteTxn([
+            this._storage.storeNames.operations
+        ]);
+        const operations = await opsTxn.operations.getAll();
+        const operationsByScope = groupBy(operations, o => o.scope);
+
         this._sendScheduler.start();
         for (const [, room] of this._rooms) {
-            room.start();
+            let roomOperationsByType;
+            const roomOperations = operationsByScope.get(room.id);
+            if (roomOperations) {
+                roomOperationsByType = groupBy(roomOperations, r => r.type);
+            }
+            room.start(roomOperationsByType);
         }
     }
 
diff --git a/src/matrix/room/Room.js b/src/matrix/room/Room.js
index dea9545d..f4b69229 100644
--- a/src/matrix/room/Room.js
+++ b/src/matrix/room/Room.js
@@ -259,14 +259,17 @@ export class Room extends EventEmitter {
     }
 
     /** @package */
-    async start() {
+    async start(pendingOperations) {
         if (this._roomEncryption) {
             try {
-                // if we got interrupted last time sending keys to newly joined members
-                await this._roomEncryption.shareRoomKeyToPendingMembers(this._hsApi);
+                const roomKeyShares = pendingOperations?.get("share_room_key");
+                if (roomKeyShares) {
+                    // if we got interrupted last time sending keys to newly joined members
+                    await this._roomEncryption.flushPendingRoomKeyShares(this._hsApi, roomKeyShares);
+                }
             } catch (err) {
                 // we should not throw here
-                console.error(`could not send out pending room keys for room ${this.id}`, err.stack);
+                console.error(`could not send out (all) pending room keys for room ${this.id}`, err.stack);
             }
         }
         this._sendQueue.resumeSending();