diff --git a/app/src/main/java/com/nextcloud/talk/adapters/messages/IncomingPreviewMessageViewHolder.java b/app/src/main/java/com/nextcloud/talk/adapters/messages/IncomingPreviewMessageViewHolder.java
index 06e7084af..85d4626d8 100644
--- a/app/src/main/java/com/nextcloud/talk/adapters/messages/IncomingPreviewMessageViewHolder.java
+++ b/app/src/main/java/com/nextcloud/talk/adapters/messages/IncomingPreviewMessageViewHolder.java
@@ -57,6 +57,7 @@ public class IncomingPreviewMessageViewHolder extends PreviewMessageViewHolder {
         super.onBind(message);
         if(!message.isVoiceMessage()
             && !Objects.equals(message.getMessage(), "{file}")
+            && message.getEnableCaption()
         ) {
             Spanned processedMessageText = null;
             binding.incomingPreviewMessageBubble.setBackgroundResource(R.drawable.shape_grouped_incoming_message);
diff --git a/app/src/main/java/com/nextcloud/talk/adapters/messages/OutcomingPreviewMessageViewHolder.java b/app/src/main/java/com/nextcloud/talk/adapters/messages/OutcomingPreviewMessageViewHolder.java
index 618d757b2..1ab4291c0 100644
--- a/app/src/main/java/com/nextcloud/talk/adapters/messages/OutcomingPreviewMessageViewHolder.java
+++ b/app/src/main/java/com/nextcloud/talk/adapters/messages/OutcomingPreviewMessageViewHolder.java
@@ -56,6 +56,7 @@ public class OutcomingPreviewMessageViewHolder extends PreviewMessageViewHolder
         super.onBind(message);
         if(!message.isVoiceMessage()
             && !Objects.equals(message.getMessage(), "{file}")
+            && message.getEnableCaption()
         ) {
             Spanned processedMessageText = null;
             binding.outgoingPreviewMessageBubble.setBackgroundResource(R.drawable.shape_grouped_outcoming_message);
diff --git a/app/src/main/java/com/nextcloud/talk/chat/ChatActivity.kt b/app/src/main/java/com/nextcloud/talk/chat/ChatActivity.kt
index 3ace986ef..eddb0b9b9 100644
--- a/app/src/main/java/com/nextcloud/talk/chat/ChatActivity.kt
+++ b/app/src/main/java/com/nextcloud/talk/chat/ChatActivity.kt
@@ -246,6 +246,8 @@ import kotlinx.coroutines.launch
 import kotlinx.coroutines.withContext
 import org.greenrobot.eventbus.Subscribe
 import org.greenrobot.eventbus.ThreadMode
+import org.json.JSONException
+import org.json.JSONObject
 import retrofit2.HttpException
 import retrofit2.Response
 import java.io.File
@@ -2673,16 +2675,25 @@ class ChatActivity :
     }
 
     private fun uploadFiles(files: MutableList<String>, caption: String = "") {
-        for (i in 0 until files.size) {
-            if (i == files.size - 1) {
-                uploadFile(files[i], false, caption)
-            } else {
-                uploadFile(files[i], false)
-            }
+        val captionJsonObject = if (caption != "") {
+            JSONObject(
+                mapOf(
+                    "caption" to mapOf(
+                        "groupID" to SystemClock.elapsedRealtime(),
+                        "captionText" to "\"$caption\""
+                    ).toString()
+                )
+            )
+        } else {
+            null
+        }
+
+        for (file in files) {
+            uploadFile(file, false, captionJsonObject)
         }
     }
 
-    private fun uploadFile(fileUri: String, isVoiceMessage: Boolean, caption: String = "") {
+    private fun uploadFile(fileUri: String, isVoiceMessage: Boolean, metaDataJSONObject: JSONObject? = null) {
         var metaData = ""
 
         if (!participantPermissions.hasChatPermission()) {
@@ -2694,8 +2705,9 @@ class ChatActivity :
             metaData = VOICE_MESSAGE_META_DATA
         }
 
-        if (caption != "") {
-            metaData = "{\"caption\":\"$caption\"}"
+        metaDataJSONObject?.let {
+            metaData = metaDataJSONObject.toString()
+            Log.d("Julius", "MetaData: $metaData")
         }
 
         try {
@@ -3256,6 +3268,14 @@ class ChatActivity :
 
                             processCallStartedMessages(chatMessageList)
 
+                            val lastTen = adapter?.items?.take(ADAPTER_FILTER_LIMIT)
+                            val prunedList = mutableListOf<ChatMessage>()
+                            for (item in lastTen!!) {
+                                if (item.item is ChatMessage) prunedList.add(item.item as ChatMessage)
+                            }
+                            prunedList.addAll(chatMessageList)
+                            processFileCaptions(prunedList)
+
                             updateReadStatusOfAllMessages(newXChatLastCommonRead)
                             adapter?.notifyDataSetChanged()
 
@@ -3316,6 +3336,28 @@ class ChatActivity :
         }
     }
 
+    @SuppressLint("NotifyDataSetChanged", "NestedBlockDepth")
+    private fun processFileCaptions(chatMessageList: List<ChatMessage>) {
+        val captionMap = mutableMapOf<Long, ChatMessage>()
+        for (message in chatMessageList.reversed()) {
+            if (message.hasFileAttachment()) {
+                try {
+                    val obj = JSONObject(message.message!!)
+                    val groupID = obj.getLong("groupID")
+                    val caption = obj.getString("captionText")
+                    message.message = caption
+                    if (captionMap.contains(groupID)) {
+                        captionMap[groupID]!!.enableCaption = false
+                    }
+                    captionMap[groupID] = message
+                    captionMap[groupID]!!.enableCaption = true
+                } catch (e: JSONException) {
+                    Log.w(TAG, "File caption not in JSON form: $e")
+                }
+            }
+        }
+    }
+
     private fun setupFieldsForPullChatMessages(
         lookIntoFuture: Boolean,
         xChatLastCommonRead: Int?,
@@ -4608,5 +4650,6 @@ class ChatActivity :
         private const val MILISEC_15: Long = 15
         private const val LINEBREAK = "\n"
         private const val CURSOR_KEY = "_cursor"
+        private const val ADAPTER_FILTER_LIMIT = 3
     }
 }
diff --git a/app/src/main/java/com/nextcloud/talk/models/json/chat/ChatMessage.kt b/app/src/main/java/com/nextcloud/talk/models/json/chat/ChatMessage.kt
index c9d70038a..187ccaf96 100644
--- a/app/src/main/java/com/nextcloud/talk/models/json/chat/ChatMessage.kt
+++ b/app/src/main/java/com/nextcloud/talk/models/json/chat/ChatMessage.kt
@@ -147,7 +147,9 @@ data class ChatMessage(
 
     var hiddenByCollapse: Boolean = false,
 
-    var openWhenDownloaded: Boolean = true
+    var openWhenDownloaded: Boolean = true,
+
+    var enableCaption: Boolean = false
 
 ) : Parcelable, MessageContentType, MessageContentType.Image {
 
diff --git a/app/src/main/java/com/nextcloud/talk/utils/message/MessageUtils.kt b/app/src/main/java/com/nextcloud/talk/utils/message/MessageUtils.kt
index 786d9f7f4..37a289345 100644
--- a/app/src/main/java/com/nextcloud/talk/utils/message/MessageUtils.kt
+++ b/app/src/main/java/com/nextcloud/talk/utils/message/MessageUtils.kt
@@ -38,6 +38,9 @@ import io.noties.markwon.core.MarkwonTheme
 import io.noties.markwon.ext.strikethrough.StrikethroughPlugin
 import io.noties.markwon.ext.tasklist.TaskListDrawable
 import io.noties.markwon.ext.tasklist.TaskListPlugin
+import org.json.JSONArray
+import org.json.JSONException
+import org.json.JSONObject
 
 class MessageUtils(val context: Context) {
     fun enrichChatReplyMessageText(
@@ -171,7 +174,20 @@ class MessageUtils(val context: Context) {
         return markwon.toMarkdown(markdown)
     }
 
+    @Suppress("SwallowedException")
     companion object {
+        fun isJSONValid(test: String): Boolean {
+            try {
+                JSONObject(test)
+            } catch (ex: JSONException) {
+                try {
+                    JSONArray(test)
+                } catch (ex1: JSONException) {
+                    return false
+                }
+            }
+            return true
+        }
         private const val TAG = "MessageUtils"
         const val MAX_REPLY_LENGTH = 250
     }