diff --git a/Riot/Modules/Room/MXKRoomViewController.h b/Riot/Modules/Room/MXKRoomViewController.h
index 45ad325b5..6cdaab93a 100644
--- a/Riot/Modules/Room/MXKRoomViewController.h
+++ b/Riot/Modules/Room/MXKRoomViewController.h
@@ -444,4 +444,10 @@ typedef NS_ENUM(NSUInteger, MXKRoomViewControllerJoinRoomResult) {
  */
 - (void)handleTypingNotification:(BOOL)typing;
 
+
+/**
+ Share encryption keys in this room.
+ */
+- (void)shareEncryptionKeys;
+
 @end
diff --git a/Riot/Modules/Room/RoomViewController.m b/Riot/Modules/Room/RoomViewController.m
index ce081145f..966a76e45 100644
--- a/Riot/Modules/Room/RoomViewController.m
+++ b/Riot/Modules/Room/RoomViewController.m
@@ -4564,6 +4564,15 @@ const NSTimeInterval kResizeComposerAnimationDuration = .05;
     [self.userSuggestionCoordinator processTextMessage:toolbarView.textMessage];
 }
 
+- (void)roomInputToolbarViewDidOpenActionMenu:(MXKRoomInputToolbarView*)toolbarView
+{
+    // Consider opening the action menu as beginning to type and share encryption keys if requested.
+    if ([MXKAppSettings standardAppSettings].outboundGroupSessionKeyPreSharingStrategy == MXKKeyPreSharingWhenTyping)
+    {
+        [self shareEncryptionKeys];
+    }
+}
+
 #pragma mark - MXKRoomMemberDetailsViewControllerDelegate
 
 - (void)roomMemberDetailsViewController:(MXKRoomMemberDetailsViewController *)roomMemberDetailsViewController startChatWithMemberId:(NSString *)matrixId completion:(void (^)(void))completion
diff --git a/Riot/Modules/Room/Views/InputToolbar/RoomInputToolbarView.h b/Riot/Modules/Room/Views/InputToolbar/RoomInputToolbarView.h
index 282687128..e3feed12e 100644
--- a/Riot/Modules/Room/Views/InputToolbar/RoomInputToolbarView.h
+++ b/Riot/Modules/Room/Views/InputToolbar/RoomInputToolbarView.h
@@ -47,6 +47,13 @@ typedef enum : NSUInteger
  */
 - (void)roomInputToolbarViewDidChangeTextMessage:(MXKRoomInputToolbarView*)toolbarView;
 
+/**
+ Inform the delegate that the action menu was opened.
+ 
+ @param toolbarView the room input toolbar view
+ */
+- (void)roomInputToolbarViewDidOpenActionMenu:(MXKRoomInputToolbarView*)toolbarView;
+
 @end
 
 /**
diff --git a/Riot/Modules/Room/Views/InputToolbar/RoomInputToolbarView.m b/Riot/Modules/Room/Views/InputToolbar/RoomInputToolbarView.m
index cffe8fe1b..2ce98c82c 100644
--- a/Riot/Modules/Room/Views/InputToolbar/RoomInputToolbarView.m
+++ b/Riot/Modules/Room/Views/InputToolbar/RoomInputToolbarView.m
@@ -429,6 +429,7 @@ static const NSTimeInterval kActionMenuComposerHeightAnimationDuration = .3;
         if (_actionMenuOpened) {
             self.actionsBar.hidden = NO;
             [self.actionsBar animateWithShowIn:_actionMenuOpened completion:nil];
+            [self.delegate roomInputToolbarViewDidOpenActionMenu:self];
         }
         else
         {
diff --git a/changelog.d/5564.bugfix b/changelog.d/5564.bugfix
new file mode 100644
index 000000000..b9c450d48
--- /dev/null
+++ b/changelog.d/5564.bugfix
@@ -0,0 +1 @@
+Fix for images sometimes being sent unencrypted inside an encrypted room.
\ No newline at end of file