diff --git a/commet/lib/ui/molecules/timeline_events/timeline_event_menu.dart b/commet/lib/ui/molecules/timeline_events/timeline_event_menu.dart
index 3934b7bf3..298b6074c 100644
--- a/commet/lib/ui/molecules/timeline_events/timeline_event_menu.dart
+++ b/commet/lib/ui/molecules/timeline_events/timeline_event_menu.dart
@@ -7,9 +7,11 @@ import 'package:commet/client/components/photo_album_room/photo_album_room_compo
 import 'package:commet/client/components/pinned_messages/pinned_messages_component.dart';
 import 'package:commet/client/components/push_notification/notification_content.dart';
 import 'package:commet/client/components/push_notification/notification_manager.dart';
+import 'package:commet/client/matrix/timeline_events/matrix_timeline_event.dart';
 import 'package:commet/client/timeline.dart';
 import 'package:commet/client/timeline_events/timeline_event.dart';
 import 'package:commet/client/timeline_events/timeline_event_emote.dart';
+import 'package:commet/client/timeline_events/timeline_event_encrypted.dart';
 import 'package:commet/client/timeline_events/timeline_event_message.dart';
 import 'package:commet/client/timeline_events/timeline_event_sticker.dart';
 import 'package:commet/main.dart';
@@ -19,6 +21,7 @@ import 'package:commet/ui/navigation/adaptive_dialog.dart';
 import 'package:commet/utils/autofill_utils.dart';
 import 'package:commet/utils/common_strings.dart';
 import 'package:commet/utils/download_utils.dart';
+import 'package:commet/utils/error_utils.dart';
 import 'package:commet/utils/event_bus.dart';
 import 'package:flutter/material.dart';
 import 'package:flutter/services.dart';
@@ -202,6 +205,18 @@ class TimelineEventMenu {
     }
 
     primaryActions = [
+      if (event is TimelineEventEncrypted)
+        TimelineEventMenuEntry(
+          name: "Retry Decrypt",
+          icon: Icons.lock_open,
+          action: (context) {
+            var mx = (event as MatrixTimelineEvent).event;
+
+            ErrorUtils.tryRun(context, () async {
+              await mx.requestKey();
+            });
+          },
+        ),
       if (canRetrySend)
         TimelineEventMenuEntry(
           name: promptRetryEventSend,
diff --git a/commet/lib/ui/pages/settings/categories/account/security/matrix/cross_signing/cross_signing_page.dart b/commet/lib/ui/pages/settings/categories/account/security/matrix/cross_signing/cross_signing_page.dart
index a0edf4b17..e42146928 100644
--- a/commet/lib/ui/pages/settings/categories/account/security/matrix/cross_signing/cross_signing_page.dart
+++ b/commet/lib/ui/pages/settings/categories/account/security/matrix/cross_signing/cross_signing_page.dart
@@ -45,8 +45,8 @@ class MatrixCrossSigningPageState extends State<MatrixCrossSigningPage> {
       onSetNewSsss: (passphrase) {
         bootstrapper?.newSsss(passphrase);
       },
-      onAskSetupCrossSigning: () {
-        bootstrapper?.askSetupCrossSigning(
+      onAskSetupCrossSigning: () async {
+        await bootstrapper?.askSetupCrossSigning(
           setupMasterKey: true,
           setupSelfSigningKey: true,
           setupUserSigningKey: true,
@@ -70,11 +70,12 @@ class MatrixCrossSigningPageState extends State<MatrixCrossSigningPage> {
       },
       openExistingSsss: (key) async {
         await bootstrapper?.newSsssKey!.unlock(keyOrPassphrase: key);
-        await bootstrapper?.client.encryption!.crossSigning
-            .selfSign(keyOrPassphrase: key);
         await bootstrapper?.openExistingSsss();
-        await bootstrapper?.askSetupCrossSigning(setupMasterKey: true);
-        bootstrapper?.wipeOnlineKeyBackup(false);
+
+        if (bootstrapper!.encryption.crossSigning.enabled) {
+          await bootstrapper?.client.encryption!.crossSigning
+              .selfSign(keyOrPassphrase: key);
+        }
       },
       wipeCrossSigning: (wipe) {
         bootstrapper?.wipeCrossSigning(wipe);
diff --git a/commet/lib/ui/pages/settings/categories/account/security/matrix/cross_signing/cross_signing_view.dart b/commet/lib/ui/pages/settings/categories/account/security/matrix/cross_signing/cross_signing_view.dart
index 5d208871a..2b2693b21 100644
--- a/commet/lib/ui/pages/settings/categories/account/security/matrix/cross_signing/cross_signing_view.dart
+++ b/commet/lib/ui/pages/settings/categories/account/security/matrix/cross_signing/cross_signing_view.dart
@@ -1,5 +1,7 @@
+import 'package:commet/main.dart';
 import 'package:commet/ui/atoms/code_block.dart';
 import 'package:commet/utils/common_strings.dart';
+import 'package:commet/utils/error_utils.dart';
 import 'package:commet/utils/text_utils.dart';
 import 'package:flutter/material.dart' as m;
 import 'package:flutter/services.dart' as services;
@@ -24,7 +26,7 @@ class MatrixCrossSigningView extends StatefulWidget {
   final BootstrapState state;
 
   final Function(String?)? onSetNewSsss;
-  final Function()? onAskSetupCrossSigning;
+  final Future<void> Function()? onAskSetupCrossSigning;
   final Function(bool)? onAskSetupOnlineBackup;
   final Function(bool)? useExistingKeys;
   final Function(bool)? wipeSsss;
@@ -47,6 +49,8 @@ class _MatrixCrossSigningViewState extends State<MatrixCrossSigningView> {
 
   String copyBackupCodeText = CommonStrings.promptCopy;
 
+  bool isActionLoading = false;
+
   String get promptWipeMatrixKeys => Intl.message("Wipe Keys",
       desc: "Text on the button to wipe matrix encryption keys",
       name: "promptWipeMatrixKeys");
@@ -222,7 +226,15 @@ class _MatrixCrossSigningViewState extends State<MatrixCrossSigningView> {
       constraints: const BoxConstraints(maxWidth: 500, maxHeight: 500),
       child: Padding(
         padding: const EdgeInsets.all(8.0),
-        child: showState(),
+        child: m.Column(
+          mainAxisSize: MainAxisSize.min,
+          crossAxisAlignment: CrossAxisAlignment.start,
+          children: [
+            showState(),
+            if (preferences.developerMode.value)
+              tiamat.Text.labelLow(widget.state.toString()),
+          ],
+        ),
       ),
     );
   }
@@ -295,8 +307,19 @@ class _MatrixCrossSigningViewState extends State<MatrixCrossSigningView> {
         ),
         tiamat.Button(
             text: CommonStrings.promptConfirm,
-            onTap: () {
-              widget.onAskSetupCrossSigning?.call();
+            isLoading: isActionLoading,
+            onTap: () async {
+              setState(() {
+                isActionLoading = true;
+              });
+
+              await ErrorUtils.tryRun(context, () async {
+                await widget.onAskSetupCrossSigning?.call();
+              });
+
+              setState(() {
+                isActionLoading = false;
+              });
             })
       ],
     );
@@ -326,8 +349,21 @@ class _MatrixCrossSigningViewState extends State<MatrixCrossSigningView> {
           ),
           tiamat.Button(
               text: CommonStrings.promptConfirm,
-              onTap: () {
-                widget.openExistingSsss?.call(keyInputController.text);
+              isLoading: isActionLoading,
+              onTap: () async {
+                setState(() {
+                  isActionLoading = true;
+                });
+
+                await Future.delayed(Duration(milliseconds: 300));
+
+                await ErrorUtils.tryRun(context, () async {
+                  await widget.openExistingSsss?.call(keyInputController.text);
+                });
+
+                setState(() {
+                  isActionLoading = false;
+                });
               })
         ],
       ),