diff --git a/CHANGES.md b/CHANGES.md
index a3b37761..d657337b 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -14,6 +14,7 @@ Bugfix:
  - Fix text diff linebreak display (#441)
  - Date change message repeats for each redaction until a normal message (#358)
  - Slide-in reply icon is distorted (#423)
+ - Regression / e2e replies not encrypted
 
 Translations:
  -
diff --git a/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/session/room/relation/DefaultRelationService.kt b/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/session/room/relation/DefaultRelationService.kt
index addad44b..9640cd4e 100644
--- a/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/session/room/relation/DefaultRelationService.kt
+++ b/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/session/room/relation/DefaultRelationService.kt
@@ -136,7 +136,7 @@ internal class DefaultRelationService @AssistedInject constructor(@Assisted priv
                 }
         if (cryptoService.isRoomEncrypted(roomId)) {
             val encryptWork = createEncryptEventWork(event, listOf("m.relates_to"))
-            val workRequest = createSendEventWork(event)
+            val workRequest = createSendEventWork(event, false)
             TimelineSendEventWorkCommon.postSequentialWorks(context, roomId, encryptWork, workRequest)
             return CancelableWork(context, encryptWork.id)
 
@@ -162,7 +162,7 @@ internal class DefaultRelationService @AssistedInject constructor(@Assisted priv
                 }
         if (cryptoService.isRoomEncrypted(roomId)) {
             val encryptWork = createEncryptEventWork(event, listOf("m.relates_to"))
-            val workRequest = createSendEventWork(event)
+            val workRequest = createSendEventWork(event, false)
             TimelineSendEventWorkCommon.postSequentialWorks(context, roomId, encryptWork, workRequest)
             return CancelableWork(context, encryptWork.id)
 
@@ -189,7 +189,7 @@ internal class DefaultRelationService @AssistedInject constructor(@Assisted priv
 
         if (cryptoService.isRoomEncrypted(roomId)) {
             val encryptWork = createEncryptEventWork(event, listOf("m.relates_to"))
-            val workRequest = createSendEventWork(event)
+            val workRequest = createSendEventWork(event, false)
             TimelineSendEventWorkCommon.postSequentialWorks(context, roomId, encryptWork, workRequest)
             return CancelableWork(context, encryptWork.id)
 
@@ -208,10 +208,10 @@ internal class DefaultRelationService @AssistedInject constructor(@Assisted priv
         return TimelineSendEventWorkCommon.createWork<EncryptEventWorker>(sendWorkData, true)
     }
 
-    private fun createSendEventWork(event: Event): OneTimeWorkRequest {
+    private fun createSendEventWork(event: Event, startChain: Boolean = true): OneTimeWorkRequest {
         val sendContentWorkerParams = SendEventWorker.Params(credentials.userId, roomId, event)
         val sendWorkData = WorkerParamsFactory.toData(sendContentWorkerParams)
-        return TimelineSendEventWorkCommon.createWork<SendEventWorker>(sendWorkData, true)
+        return TimelineSendEventWorkCommon.createWork<SendEventWorker>(sendWorkData, startChain)
     }
 
     override fun getEventSummaryLive(eventId: String): LiveData<EventAnnotationsSummary> {