diff --git a/lib/encryption/key_manager.dart b/lib/encryption/key_manager.dart
index a17944ed..a8038cf7 100644
--- a/lib/encryption/key_manager.dart
+++ b/lib/encryption/key_manager.dart
@@ -271,7 +271,7 @@ class KeyManager {
   /// devices have been changed. Returns false if the session has not been cleared because
   /// it wasn't necessary. Otherwise returns true.
   Future<bool> clearOrUseOutboundGroupSession(String roomId,
-      {bool wipe = false}) async {
+      {bool wipe = false, bool use = true}) async {
     final room = client.getRoomById(roomId);
     final sess = getOutboundGroupSession(roomId);
     if (room == null || sess == null) {
@@ -334,8 +334,13 @@ class KeyManager {
             break;
           }
           // and now add all the new devices!
-          final oldDeviceIds = Set.from(sess.devices[userId].keys);
-          final newDeviceIds = Set.from(newDeviceKeyIds[userId].keys);
+          final oldDeviceIds = Set.from(sess.devices[userId].entries
+              .where((e) => !e.value)
+              .map((e) => e.key));
+          final newDeviceIds = Set.from(newDeviceKeyIds[userId]
+              .entries
+              .where((e) => !e.value)
+              .map((e) => e.key));
           final newDevices = newDeviceIds.difference(oldDeviceIds);
           if (newDeviceIds.isNotEmpty) {
             devicesToReceive.addAll(newDeviceKeys.where(
@@ -345,6 +350,9 @@ class KeyManager {
       }
 
       if (!wipe) {
+        if (!use) {
+          return false;
+        }
         // okay, we use the outbound group session!
         sess.sentMessages++;
         sess.devices = newDeviceKeyIds;
@@ -355,7 +363,7 @@ class KeyManager {
           'session_key': sess.outboundGroupSession.session_key(),
         };
         try {
-          devicesToReceive.removeWhere((k) => k.blocked);
+          devicesToReceive.removeWhere((k) => !k.encryptToDevice);
           if (devicesToReceive.isNotEmpty) {
             // update allowedAtIndex
             for (final device in devicesToReceive) {
@@ -394,6 +402,7 @@ class KeyManager {
     return true;
   }
 
+  /// Store an outbound group session in the database
   Future<void> storeOutboundGroupSession(
       String roomId, OutboundGroupSession sess) async {
     if (sess == null) {
@@ -411,6 +420,7 @@ class KeyManager {
   final Map<String, Future<OutboundGroupSession>>
       _pendingNewOutboundGroupSessions = {};
 
+  /// Creates an outbound group session for a given room id
   Future<OutboundGroupSession> createOutboundGroupSession(String roomId) async {
     if (_pendingNewOutboundGroupSessions.containsKey(roomId)) {
       return _pendingNewOutboundGroupSessions[roomId];
@@ -421,6 +431,18 @@ class KeyManager {
     return _pendingNewOutboundGroupSessions.remove(roomId);
   }
 
+  /// Prepares an outbound group session for a given room ID. That is, load it from
+  /// the database, cycle it if needed and create it if absent.
+  Future<void> prepareOutboundGroupSession(String roomId) async {
+    if (getOutboundGroupSession(roomId) == null) {
+      await loadOutboundGroupSession(roomId);
+    }
+    await clearOrUseOutboundGroupSession(roomId, use: false);
+    if (getOutboundGroupSession(roomId) == null) {
+      await createOutboundGroupSession(roomId);
+    }
+  }
+
   Future<OutboundGroupSession> _createOutboundGroupSession(
       String roomId) async {
     await clearOrUseOutboundGroupSession(roomId, wipe: true);
@@ -477,10 +499,12 @@ class KeyManager {
     return sess;
   }
 
+  /// Get an outbound group session for a room id
   OutboundGroupSession getOutboundGroupSession(String roomId) {
     return _outboundGroupSessions[roomId];
   }
 
+  /// Load an outbound group session from database
   Future<void> loadOutboundGroupSession(String roomId) async {
     if (_loadedOutboundGroupSessions.contains(roomId) ||
         _outboundGroupSessions.containsKey(roomId) ||
diff --git a/lib/src/client.dart b/lib/src/client.dart
index dd601fb6..06f710af 100644
--- a/lib/src/client.dart
+++ b/lib/src/client.dart
@@ -22,6 +22,7 @@ import 'dart:core';
 import 'dart:typed_data';
 
 import 'package:http/http.dart' as http;
+import 'package:pedantic/pedantic.dart';
 
 import '../encryption.dart';
 import '../famedlysdk.dart';
@@ -542,6 +543,22 @@ class Client extends MatrixApi {
     return mxc;
   }
 
+  /// Sends a typing notification and initiates a megolm session, if needed
+  @override
+  Future<void> sendTypingNotification(
+    String userId,
+    String roomId,
+    bool typing, {
+    int timeout,
+  }) async {
+    await super
+        .sendTypingNotification(userId, roomId, typing, timeout: timeout);
+    final room = getRoomById(roomId);
+    if (typing && room != null && encryptionEnabled && room.encrypted) {
+      unawaited(encryption.keyManager.prepareOutboundGroupSession(roomId));
+    }
+  }
+
   /// Uploads a new user avatar for this user.
   Future<void> setAvatar(MatrixFile file) async {
     final uploadResp = await upload(file.bytes, file.name);
diff --git a/test/encryption/key_manager_test.dart b/test/encryption/key_manager_test.dart
index 3de5fe89..4d51c2d5 100644
--- a/test/encryption/key_manager_test.dart
+++ b/test/encryption/key_manager_test.dart
@@ -133,6 +133,26 @@ void main() {
       client.userDeviceKeys['@alice:example.com'].deviceKeys['JLAFKJWSCS']
           .blocked = false;
 
+      // lazy-create if it would rotate
+      sess =
+          await client.encryption.keyManager.createOutboundGroupSession(roomId);
+      final oldSessKey = sess.outboundGroupSession.session_key();
+      client.userDeviceKeys['@alice:example.com'].deviceKeys['JLAFKJWSCS']
+          .blocked = true;
+      await client.encryption.keyManager.prepareOutboundGroupSession(roomId);
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          true);
+      expect(
+          client.encryption.keyManager
+                  .getOutboundGroupSession(roomId)
+                  .outboundGroupSession
+                  .session_key() !=
+              oldSessKey,
+          true);
+      client.userDeviceKeys['@alice:example.com'].deviceKeys['JLAFKJWSCS']
+          .blocked = false;
+
       // rotate if too far in the past
       sess =
           await client.encryption.keyManager.createOutboundGroupSession(roomId);