diff --git a/src/app/features/room/RoomInput.tsx b/src/app/features/room/RoomInput.tsx
index 27126a3624..ed8b3ae4ca 100644
--- a/src/app/features/room/RoomInput.tsx
+++ b/src/app/features/room/RoomInput.tsx
@@ -274,6 +274,7 @@ export const getReplyContent = (
 
 const log = createLogger('RoomInput');
 const debugLog = createDebugLogger('RoomInput');
+const ENCRYPTION_PREPARATION_INTERVAL_MS = 60_000;
 interface ReplyEventContent {
   'm.relates_to'?: IEventRelation;
 }
@@ -497,9 +498,17 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
     const handlePaste = useFilePasteHandler(handleFiles);
     const dropZoneVisible = useFileDropZone(fileDropContainerRef, handleFiles);
     const [hasText, setHasText] = useState(false);
+    const lastEncryptionPreparationAt = useRef(0);
     const handleEditorChange = useCallback(() => {
       setHasText(!isEmptyEditor(editor));
-    }, [editor]);
+      if (!room.hasEncryptionStateEvent()) return;
+
+      const now = Date.now();
+      if (now - lastEncryptionPreparationAt.current < ENCRYPTION_PREPARATION_INTERVAL_MS) return;
+
+      lastEncryptionPreparationAt.current = now;
+      mx.getCrypto()?.prepareToEncrypt(room);
+    }, [editor, mx, room]);
     const hasContent = hasText || selectedFiles.length > 0;
 
     const isComposing = useComposingCheck();
diff --git a/src/app/features/room/message/EncryptedContent.tsx b/src/app/features/room/message/EncryptedContent.tsx
index 2ac498318f..99261956d5 100644
--- a/src/app/features/room/message/EncryptedContent.tsx
+++ b/src/app/features/room/message/EncryptedContent.tsx
@@ -5,8 +5,11 @@ import { useEffect, useState } from 'react';
 
 import { useMatrixClient } from '$hooks/useMatrixClient';
 import { scheduleDecrypt } from '$utils/decryptScheduler';
+import { createDebugLogger } from '$utils/debugLogger';
 import * as Sentry from '@sentry/react';
 
+const debugLog = createDebugLogger('EncryptedContent');
+
 type EncryptedContentProps = {
   mEvent: MatrixEvent;
   children: () => ReactNode;
@@ -39,6 +42,12 @@ export function EncryptedContent({ mEvent, children }: EncryptedContentProps) {
     toggleEncrypted(mEvent.getType() === (EventType.RoomMessageEncrypted as string));
     const handleDecrypted: MatrixEventHandlerMap[MatrixEventEvent.Decrypted] = (event) => {
       if (event.isDecryptionFailure()) {
+        debugLog.error('error', 'Failed to decrypt room event', {
+          eventId: event.getId(),
+          roomId: event.getRoomId(),
+          sender: event.getSender(),
+          reason: event.decryptionFailureReason ?? 'UNKNOWN_ERROR',
+        });
         Sentry.metrics.count('sable.decryption.failure', 1, {
           attributes: { reason: event.decryptionFailureReason ?? 'UNKNOWN_ERROR' },
         });