diff --git a/app/src/main/java/org/linphone/activities/main/chat/data/ChatMessageContentData.kt b/app/src/main/java/org/linphone/activities/main/chat/data/ChatMessageContentData.kt
index 62e0f3636..81c13342f 100644
--- a/app/src/main/java/org/linphone/activities/main/chat/data/ChatMessageContentData.kt
+++ b/app/src/main/java/org/linphone/activities/main/chat/data/ChatMessageContentData.kt
@@ -44,7 +44,6 @@ import org.linphone.utils.ImageUtils
 class ChatMessageContentData(
     private val chatMessage: ChatMessage,
     private val contentIndex: Int,
-
 ) {
     var listener: OnContentClickedListener? = null
 
@@ -144,13 +143,7 @@ class ChatMessageContentData(
     fun destroy() {
         scope.cancel()
 
-        val path = filePath.value.orEmpty()
-        if (path.isNotEmpty() && isFileEncrypted) {
-            Log.i("[Content] Deleting file used for preview: $path")
-            FileUtils.deleteFile(path)
-            filePath.value = ""
-        }
-
+        deletePlainFilePath()
         chatMessage.removeListener(chatMessageListener)
 
         if (this::voiceRecordingPlayer.isInitialized) {
@@ -180,9 +173,22 @@ class ChatMessageContentData(
         listener?.onContentClicked(getContent())
     }
 
+    private fun deletePlainFilePath() {
+        val path = filePath.value.orEmpty()
+        if (path.isNotEmpty() && isFileEncrypted) {
+            Log.i("[Content] Deleting file used for preview: $path")
+            FileUtils.deleteFile(path)
+            filePath.value = ""
+        }
+    }
+
     private fun updateContent() {
+        Log.i("[Content] Updating content")
+        deletePlainFilePath()
+
         val content = getContent()
         isFileEncrypted = content.isFileEncrypted
+        Log.i("[Content] Is content encrypted ? $isFileEncrypted")
 
         filePath.value = ""
         fileName.value = if (content.name.isNullOrEmpty() && !content.filePath.isNullOrEmpty()) {
@@ -198,7 +204,7 @@ class ChatMessageContentData(
         downloadLabel.value = spannable
 
         if (content.isFile || (content.isFileTransfer && chatMessage.isOutgoing)) {
-            Log.i("[Content] Is content encrypted ? $isFileEncrypted")
+            Log.i("[Content] Content is encrypted, requesting plain file path")
             val path = if (isFileEncrypted) content.plainFilePath else content.filePath ?: ""
             downloadable.value = content.filePath.orEmpty().isEmpty()
 
@@ -320,8 +326,7 @@ class ChatMessageContentData(
         }
         voiceRecordingPlayer.addListener(playerListener)
 
-        val content = getContent()
-        val path = if (content.isFileEncrypted) content.plainFilePath else content.filePath ?: ""
+        val path = filePath.value
         voiceRecordingPlayer.open(path.orEmpty())
         voiceRecordDuration.value = voiceRecordingPlayer.duration
         formattedDuration.value = SimpleDateFormat("mm:ss", Locale.getDefault()).format(voiceRecordingPlayer.duration) // is already in milliseconds
diff --git a/app/src/main/java/org/linphone/activities/main/chat/fragments/DetailChatRoomFragment.kt b/app/src/main/java/org/linphone/activities/main/chat/fragments/DetailChatRoomFragment.kt
index 088128776..472b05ec4 100644
--- a/app/src/main/java/org/linphone/activities/main/chat/fragments/DetailChatRoomFragment.kt
+++ b/app/src/main/java/org/linphone/activities/main/chat/fragments/DetailChatRoomFragment.kt
@@ -901,11 +901,13 @@ class DetailChatRoomFragment : MasterFragment<ChatRoomDetailFragmentBinding, Cha
             {
                 dialog.dismiss()
                 lifecycleScope.launch {
+                    Log.w("[Chat Room] Content is encrypted, requesting plain file path")
                     val plainFilePath = content.plainFilePath
                     Log.i("[Cht Room] Making a copy of [$plainFilePath] to the cache directory before exporting it")
                     val cacheCopyPath = FileUtils.copyFileToCache(plainFilePath)
                     if (cacheCopyPath != null) {
                         Log.i("[Cht Room] Cache copy has been made: $cacheCopyPath")
+                        FileUtils.deleteFile(plainFilePath)
                         if (!FileUtils.openFileInThirdPartyApp(requireActivity(), cacheCopyPath)) {
                             showDialogToSuggestOpeningFileAsText()
                         }
diff --git a/app/src/main/java/org/linphone/activities/main/chat/viewmodels/ChatMessageSendingViewModel.kt b/app/src/main/java/org/linphone/activities/main/chat/viewmodels/ChatMessageSendingViewModel.kt
index 30917cae6..d334cb9f2 100644
--- a/app/src/main/java/org/linphone/activities/main/chat/viewmodels/ChatMessageSendingViewModel.kt
+++ b/app/src/main/java/org/linphone/activities/main/chat/viewmodels/ChatMessageSendingViewModel.kt
@@ -127,6 +127,7 @@ class ChatMessageSendingViewModel(private val chatRoom: ChatRoom) : ViewModel()
 
     override fun onCleared() {
         attachments.value.orEmpty().forEach(ChatMessageAttachmentData::destroy)
+        pendingChatMessageToReplyTo.value?.destroy()
 
         if (recorder.state != RecorderState.Closed) {
             recorder.close()
diff --git a/app/src/main/java/org/linphone/activities/main/files/viewmodels/FileViewerViewModel.kt b/app/src/main/java/org/linphone/activities/main/files/viewmodels/FileViewerViewModel.kt
index 8de31a6ce..45db338c4 100644
--- a/app/src/main/java/org/linphone/activities/main/files/viewmodels/FileViewerViewModel.kt
+++ b/app/src/main/java/org/linphone/activities/main/files/viewmodels/FileViewerViewModel.kt
@@ -29,7 +29,12 @@ open class FileViewerViewModel(val content: Content) : ViewModel() {
     private val deleteAfterUse: Boolean = content.isFileEncrypted
 
     init {
-        filePath = if (deleteAfterUse) content.plainFilePath else content.filePath.orEmpty()
+        filePath = if (deleteAfterUse) {
+            Log.i("[File Viewer] Content is encrypted, requesting plain file path")
+            content.plainFilePath
+        } else {
+            content.filePath.orEmpty()
+        }
     }
 
     override fun onCleared() {
diff --git a/app/src/main/java/org/linphone/compatibility/Api21Compatibility.kt b/app/src/main/java/org/linphone/compatibility/Api21Compatibility.kt
index 278bc66cc..9b3eaa38b 100644
--- a/app/src/main/java/org/linphone/compatibility/Api21Compatibility.kt
+++ b/app/src/main/java/org/linphone/compatibility/Api21Compatibility.kt
@@ -79,6 +79,7 @@ class Api21Compatibility {
 
             val plainFilePath = content.plainFilePath.orEmpty()
             val isVfsEncrypted = plainFilePath.isNotEmpty()
+            Log.w("[Media Store] Content is encrypted, requesting plain file path")
             val filePath = if (isVfsEncrypted) plainFilePath else content.filePath
             if (filePath == null) {
                 Log.e("[Media Store] Content doesn't have a file path!")
@@ -116,6 +117,7 @@ class Api21Compatibility {
 
             val plainFilePath = content.plainFilePath.orEmpty()
             val isVfsEncrypted = plainFilePath.isNotEmpty()
+            Log.w("[Media Store] Content is encrypted, requesting plain file path")
             val filePath = if (isVfsEncrypted) plainFilePath else content.filePath
             if (filePath == null) {
                 Log.e("[Media Store] Content doesn't have a file path!")
@@ -154,6 +156,7 @@ class Api21Compatibility {
 
             val plainFilePath = content.plainFilePath.orEmpty()
             val isVfsEncrypted = plainFilePath.isNotEmpty()
+            Log.w("[Media Store] Content is encrypted, requesting plain file path")
             val filePath = if (isVfsEncrypted) plainFilePath else content.filePath
             if (filePath == null) {
                 Log.e("[Media Store] Content doesn't have a file path!")
diff --git a/app/src/main/java/org/linphone/compatibility/Api29Compatibility.kt b/app/src/main/java/org/linphone/compatibility/Api29Compatibility.kt
index 0e587f6ef..9bb62eedc 100644
--- a/app/src/main/java/org/linphone/compatibility/Api29Compatibility.kt
+++ b/app/src/main/java/org/linphone/compatibility/Api29Compatibility.kt
@@ -101,6 +101,7 @@ class Api29Compatibility {
         suspend fun addImageToMediaStore(context: Context, content: Content): Boolean {
             val plainFilePath = content.plainFilePath.orEmpty()
             val isVfsEncrypted = plainFilePath.isNotEmpty()
+            Log.w("[Media Store] Content is encrypted, requesting plain file path")
             val filePath = if (isVfsEncrypted) plainFilePath else content.filePath
             if (filePath == null) {
                 Log.e("[Media Store] Content doesn't have a file path!")
@@ -136,6 +137,7 @@ class Api29Compatibility {
         suspend fun addVideoToMediaStore(context: Context, content: Content): Boolean {
             val plainFilePath = content.plainFilePath.orEmpty()
             val isVfsEncrypted = plainFilePath.isNotEmpty()
+            Log.w("[Media Store] Content is encrypted, requesting plain file path")
             val filePath = if (isVfsEncrypted) plainFilePath else content.filePath
             if (filePath == null) {
                 Log.e("[Media Store] Content doesn't have a file path!")
@@ -172,6 +174,7 @@ class Api29Compatibility {
         suspend fun addAudioToMediaStore(context: Context, content: Content): Boolean {
             val plainFilePath = content.plainFilePath.orEmpty()
             val isVfsEncrypted = plainFilePath.isNotEmpty()
+            Log.w("[Media Store] Content is encrypted, requesting plain file path")
             val filePath = if (isVfsEncrypted) plainFilePath else content.filePath
             if (filePath == null) {
                 Log.e("[Media Store] Content doesn't have a file path!")