diff --git a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/ConversationActivityV2.kt b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/ConversationActivityV2.kt
index 0b8f893cb..3c30b19d4 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/ConversationActivityV2.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/ConversationActivityV2.kt
@@ -1754,6 +1754,13 @@ class ConversationActivityV2 : PassphraseRequiredActionBarActivity(), InputBarDe
         endActionMode()
     }
 
+    override fun resyncMessage(messages: Set<MessageRecord>) {
+        messages.iterator().forEach { messageRecord ->
+            ResendMessageUtilities.resend(this, messageRecord, viewModel.blindedPublicKey, isResync = true)
+        }
+        endActionMode()
+    }
+
     override fun resendMessage(messages: Set<MessageRecord>) {
         messages.iterator().forEach { messageRecord ->
             ResendMessageUtilities.resend(this, messageRecord, viewModel.blindedPublicKey)
@@ -1914,6 +1921,7 @@ class ConversationActivityV2 : PassphraseRequiredActionBarActivity(), InputBarDe
             val selectedItems = setOf(message)
             when (action) {
                 ConversationReactionOverlay.Action.REPLY -> reply(selectedItems)
+                ConversationReactionOverlay.Action.RESYNC -> resyncMessage(selectedItems)
                 ConversationReactionOverlay.Action.RESEND -> resendMessage(selectedItems)
                 ConversationReactionOverlay.Action.DOWNLOAD -> saveAttachment(selectedItems)
                 ConversationReactionOverlay.Action.COPY_MESSAGE -> copyMessages(selectedItems)
diff --git a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/ConversationReactionOverlay.java b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/ConversationReactionOverlay.java
index 1d81325e0..8f1fb6a0e 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/ConversationReactionOverlay.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/ConversationReactionOverlay.java
@@ -700,6 +700,10 @@ public final class ConversationReactionOverlay extends FrameLayout {
     if (message.isFailed()) {
       items.add(new ActionItem(R.attr.menu_reply_icon, getContext().getResources().getString(R.string.conversation_context__menu_resend_message), () -> handleActionItemClicked(Action.RESEND)));
     }
+    // Resync
+    if (message.isSyncFailed()) {
+      items.add(new ActionItem(R.attr.menu_reply_icon, getContext().getResources().getString(R.string.conversation_context__menu_resync_message), () -> handleActionItemClicked(Action.RESYNC)));
+    }
     // Save media
     if (message.isMms() && ((MediaMmsMessageRecord)message).containsMediaSlide()) {
       items.add(new ActionItem(R.attr.menu_save_icon, getContext().getResources().getString(R.string.conversation_context_image__save_attachment), () -> handleActionItemClicked(Action.DOWNLOAD),
@@ -885,6 +889,7 @@ public final class ConversationReactionOverlay extends FrameLayout {
   public enum Action {
     REPLY,
     RESEND,
+    RESYNC,
     DOWNLOAD,
     COPY_MESSAGE,
     COPY_SESSION_ID,
diff --git a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/menus/ConversationActionModeCallback.kt b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/menus/ConversationActionModeCallback.kt
index d475a6444..f86920f90 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/menus/ConversationActionModeCallback.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/menus/ConversationActionModeCallback.kt
@@ -70,6 +70,8 @@ class ConversationActionModeCallback(private val adapter: ConversationAdapter, p
         menu.findItem(R.id.menu_message_details).isVisible = (selectedItems.size == 1 && firstMessage.isOutgoing)
         // Resend
         menu.findItem(R.id.menu_context_resend).isVisible = (selectedItems.size == 1 && firstMessage.isFailed)
+        // Resync
+        menu.findItem(R.id.menu_context_resync).isVisible = (selectedItems.size == 1 && firstMessage.isSyncFailed)
         // Save media
         menu.findItem(R.id.menu_context_save_attachment).isVisible = (selectedItems.size == 1
             && firstMessage.isMms && (firstMessage as MediaMmsMessageRecord).containsMediaSlide())
@@ -90,6 +92,7 @@ class ConversationActionModeCallback(private val adapter: ConversationAdapter, p
             R.id.menu_context_ban_and_delete_all -> delegate?.banAndDeleteAll(selectedItems)
             R.id.menu_context_copy -> delegate?.copyMessages(selectedItems)
             R.id.menu_context_copy_public_key -> delegate?.copySessionID(selectedItems)
+            R.id.menu_context_resync -> delegate?.resyncMessage(selectedItems)
             R.id.menu_context_resend -> delegate?.resendMessage(selectedItems)
             R.id.menu_message_details -> delegate?.showMessageDetail(selectedItems)
             R.id.menu_context_save_attachment -> delegate?.saveAttachment(selectedItems)
@@ -113,6 +116,7 @@ interface ConversationActionModeCallbackDelegate {
     fun banAndDeleteAll(messages: Set<MessageRecord>)
     fun copyMessages(messages: Set<MessageRecord>)
     fun copySessionID(messages: Set<MessageRecord>)
+    fun resyncMessage(messages: Set<MessageRecord>)
     fun resendMessage(messages: Set<MessageRecord>)
     fun showMessageDetail(messages: Set<MessageRecord>)
     fun saveAttachment(messages: Set<MessageRecord>)
diff --git a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/messages/VisibleMessageView.kt b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/messages/VisibleMessageView.kt
index 2c04bcfce..ce6019e4c 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/messages/VisibleMessageView.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/messages/VisibleMessageView.kt
@@ -292,39 +292,46 @@ class VisibleMessageView : LinearLayout {
                                  @StringRes val messageText: Int?,
                                  val contentDescription: String?)
 
-    private fun getMessageStatusImage(message: MessageRecord): MessageStatusInfo {
-        return when {
-            !message.isOutgoing -> MessageStatusInfo(null,
-                null,
-                null,
-                null)
-            message.isFailed ->
-                MessageStatusInfo(
-                    R.drawable.ic_delivery_status_failed,
-                    resources.getColor(R.color.destructive, context.theme),
-                    R.string.delivery_status_failed,
-                    null
-                )
-            message.isPending ->
-                MessageStatusInfo(
-                    R.drawable.ic_delivery_status_sending,
-                    context.getColorFromAttr(R.attr.message_status_color), R.string.delivery_status_sending,
-                    context.getString(R.string.AccessibilityId_message_sent_status_pending)
-                )
-            message.isRead ->
-                MessageStatusInfo(
-                    R.drawable.ic_delivery_status_read,
-                    context.getColorFromAttr(R.attr.message_status_color), R.string.delivery_status_read,
-                    null
-                )
-            else ->
-                MessageStatusInfo(
-                    R.drawable.ic_delivery_status_sent,
-                    context.getColorFromAttr(R.attr.message_status_color),
-                    R.string.delivery_status_sent,
-                    context.getString(R.string.AccessibilityId_message_sent_status_tick)
-                )
-        }
+    private fun getMessageStatusImage(message: MessageRecord): MessageStatusInfo = when {
+        message.isFailed ->
+            MessageStatusInfo(
+                R.drawable.ic_delivery_status_failed,
+                resources.getColor(R.color.destructive, context.theme),
+                R.string.delivery_status_failed,
+                null
+            )
+        message.isSyncFailed ->
+            MessageStatusInfo(
+                R.drawable.ic_delivery_status_failed,
+                context.getColor(R.color.accent_orange),
+                R.string.delivery_status_sync_failed,
+                null
+            )
+        message.isPending ->
+            MessageStatusInfo(
+                R.drawable.ic_delivery_status_sending,
+                context.getColorFromAttr(R.attr.message_status_color), R.string.delivery_status_sending,
+                context.getString(R.string.AccessibilityId_message_sent_status_pending)
+            )
+        message.isResyncing ->
+            MessageStatusInfo(
+                R.drawable.ic_delivery_status_sending,
+                context.getColor(R.color.accent_orange), R.string.delivery_status_syncing,
+                context.getString(R.string.AccessibilityId_message_sent_status_syncing)
+            )
+        message.isRead ->
+            MessageStatusInfo(
+                R.drawable.ic_delivery_status_read,
+                context.getColorFromAttr(R.attr.message_status_color), R.string.delivery_status_read,
+                null
+            )
+        else ->
+            MessageStatusInfo(
+                R.drawable.ic_delivery_status_sent,
+                context.getColorFromAttr(R.attr.message_status_color),
+                R.string.delivery_status_sent,
+                context.getString(R.string.AccessibilityId_message_sent_status_tick)
+            )
     }
 
     private fun updateExpirationTimer(message: MessageRecord) {
diff --git a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/utilities/ResendMessageUtilities.kt b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/utilities/ResendMessageUtilities.kt
index 80f4cc0bf..e01a75b30 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/utilities/ResendMessageUtilities.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/utilities/ResendMessageUtilities.kt
@@ -2,6 +2,7 @@ package org.thoughtcrime.securesms.conversation.v2.utilities
 
 import android.content.Context
 import org.session.libsession.messaging.MessagingModuleConfiguration
+import org.session.libsession.messaging.messages.Destination
 import org.session.libsession.messaging.messages.visible.LinkPreview
 import org.session.libsession.messaging.messages.visible.OpenGroupInvitation
 import org.session.libsession.messaging.messages.visible.Quote
@@ -15,7 +16,7 @@ import org.thoughtcrime.securesms.database.model.MmsMessageRecord
 
 object ResendMessageUtilities {
 
-    fun resend(context: Context, messageRecord: MessageRecord, userBlindedKey: String?) {
+    fun resend(context: Context, messageRecord: MessageRecord, userBlindedKey: String?, isResync: Boolean = false) {
         val recipient: Recipient = messageRecord.recipient
         val message = VisibleMessage()
         message.id = messageRecord.getId()
@@ -55,8 +56,13 @@ object ResendMessageUtilities {
         val sentTimestamp = message.sentTimestamp
         val sender = MessagingModuleConfiguration.shared.storage.getUserPublicKey()
         if (sentTimestamp != null && sender != null) {
-            MessagingModuleConfiguration.shared.storage.markAsSending(sentTimestamp, sender)
+            if (isResync) {
+                MessagingModuleConfiguration.shared.storage.markAsResyncing(sentTimestamp, sender)
+                MessageSender.send(message, Destination.from(recipient.address), isSyncMessage = true)
+            } else {
+                MessagingModuleConfiguration.shared.storage.markAsSending(sentTimestamp, sender)
+                MessageSender.send(message, recipient.address)
+            }
         }
-        MessageSender.send(message, recipient.address)
     }
 }
\ No newline at end of file
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/MessagingDatabase.java b/app/src/main/java/org/thoughtcrime/securesms/database/MessagingDatabase.java
index d3ba31747..edc6bc1a6 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/MessagingDatabase.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/MessagingDatabase.java
@@ -37,6 +37,13 @@ public abstract class MessagingDatabase extends Database implements MmsSmsColumn
   public abstract void markExpireStarted(long messageId, long startTime);
 
   public abstract void markAsSent(long messageId, boolean secure);
+
+  public abstract void markAsSyncing(long id);
+
+  public abstract void markAsResyncing(long id);
+
+  public abstract void markAsSyncFailed(long id);
+
   public abstract void markUnidentified(long messageId, boolean unidentified);
 
   public abstract void markAsDeleted(long messageId, boolean read, boolean hasMention);
@@ -199,7 +206,6 @@ public abstract class MessagingDatabase extends Database implements MmsSmsColumn
     contentValues.put(THREAD_ID, newThreadId);
     db.update(getTableName(), contentValues, where, args);
   }
-
   public static class SyncMessageId {
 
     private final Address address;
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/MmsDatabase.kt b/app/src/main/java/org/thoughtcrime/securesms/database/MmsDatabase.kt
index 3a4b35ad1..9e854698f 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/MmsDatabase.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/MmsDatabase.kt
@@ -276,6 +276,16 @@ class MmsDatabase(context: Context, databaseHelper: SQLCipherOpenHelper) : Messa
         notifyConversationListeners(threadId)
     }
 
+    override fun markAsSyncing(messageId: Long) {
+        markAs(messageId, MmsSmsColumns.Types.BASE_SYNCING_TYPE)
+    }
+    override fun markAsResyncing(messageId: Long) {
+        markAs(messageId, MmsSmsColumns.Types.BASE_RESYNCING_TYPE)
+    }
+    override fun markAsSyncFailed(messageId: Long) {
+        markAs(messageId, MmsSmsColumns.Types.BASE_SYNC_FAILED_TYPE)
+    }
+
     fun markAsSending(messageId: Long) {
         markAs(messageId, MmsSmsColumns.Types.BASE_SENDING_TYPE)
     }
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/MmsSmsColumns.java b/app/src/main/java/org/thoughtcrime/securesms/database/MmsSmsColumns.java
index f3110a5c7..1e1cc5089 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/MmsSmsColumns.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/MmsSmsColumns.java
@@ -47,8 +47,13 @@ public interface MmsSmsColumns {
     protected static final long BASE_PENDING_INSECURE_SMS_FALLBACK = 26;
     public    static final long BASE_DRAFT_TYPE                    = 27;
     protected static final long BASE_DELETED_TYPE                  = 28;
+    protected static final long BASE_SYNCING_TYPE                  = 29;
+    protected static final long BASE_RESYNCING_TYPE                = 30;
+    protected static final long BASE_SYNC_FAILED_TYPE              = 31;
 
     protected static final long[] OUTGOING_MESSAGE_TYPES = {BASE_OUTBOX_TYPE, BASE_SENT_TYPE,
+                                                            BASE_SYNCING_TYPE, BASE_RESYNCING_TYPE,
+                                                            BASE_SYNC_FAILED_TYPE,
                                                             BASE_SENDING_TYPE, BASE_SENT_FAILED_TYPE,
                                                             BASE_PENDING_SECURE_SMS_FALLBACK,
                                                             BASE_PENDING_INSECURE_SMS_FALLBACK,
@@ -109,6 +114,18 @@ public interface MmsSmsColumns {
       return (type & BASE_TYPE_MASK) == BASE_DRAFT_TYPE;
     }
 
+    public static boolean isResyncingType(long type) {
+      return (type & BASE_TYPE_MASK) == BASE_RESYNCING_TYPE;
+    }
+
+    public static boolean isSyncingType(long type) {
+      return (type & BASE_TYPE_MASK) == BASE_SYNCING_TYPE;
+    }
+
+    public static boolean isSyncFailedMessageType(long type) {
+      return (type & BASE_TYPE_MASK) == BASE_SYNC_FAILED_TYPE;
+    }
+
     public static boolean isFailedMessageType(long type) {
       return (type & BASE_TYPE_MASK) == BASE_SENT_FAILED_TYPE;
     }
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/SmsDatabase.java b/app/src/main/java/org/thoughtcrime/securesms/database/SmsDatabase.java
index 0d61b2679..42a00ccbb 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/SmsDatabase.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/SmsDatabase.java
@@ -202,6 +202,21 @@ public class SmsDatabase extends MessagingDatabase {
     updateTypeBitmask(id, Types.BASE_TYPE_MASK, Types.BASE_SENDING_TYPE);
   }
 
+  @Override
+  public void markAsSyncing(long id) {
+    updateTypeBitmask(id, Types.BASE_TYPE_MASK, Types.BASE_SYNCING_TYPE);
+  }
+
+  @Override
+  public void markAsResyncing(long id) {
+    updateTypeBitmask(id, Types.BASE_TYPE_MASK, Types.BASE_RESYNCING_TYPE);
+  }
+
+  @Override
+  public void markAsSyncFailed(long id) {
+    updateTypeBitmask(id, Types.BASE_TYPE_MASK, Types.BASE_SYNC_FAILED_TYPE);
+  }
+
   @Override
   public void markUnidentified(long id, boolean unidentified) {
     ContentValues contentValues = new ContentValues(1);
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/Storage.kt b/app/src/main/java/org/thoughtcrime/securesms/database/Storage.kt
index 076fa57af..33896803b 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/Storage.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/Storage.kt
@@ -377,6 +377,22 @@ class Storage(context: Context, helper: SQLCipherOpenHelper) : Database(context,
         }
     }
 
+    override fun markAsSyncing(timestamp: Long, author: String) {
+        DatabaseComponent.get(context).mmsSmsDatabase()
+            .getMessageFor(timestamp, author)
+            ?.run { getMmsDatabaseElseSms(isMms).markAsSyncing(id) }
+    }
+
+    private fun getMmsDatabaseElseSms(isMms: Boolean) =
+        if (isMms) DatabaseComponent.get(context).mmsDatabase()
+        else DatabaseComponent.get(context).smsDatabase()
+
+    override fun markAsResyncing(timestamp: Long, author: String) {
+        DatabaseComponent.get(context).mmsSmsDatabase()
+            .getMessageFor(timestamp, author)
+            ?.run { getMmsDatabaseElseSms(isMms).markAsResyncing(id) }
+    }
+
     override fun markAsSending(timestamp: Long, author: String) {
         val database = DatabaseComponent.get(context).mmsSmsDatabase()
         val messageRecord = database.getMessageFor(timestamp, author) ?: return
@@ -402,7 +418,7 @@ class Storage(context: Context, helper: SQLCipherOpenHelper) : Database(context,
         }
     }
 
-    override fun setErrorMessage(timestamp: Long, author: String, error: Exception) {
+    override fun markAsSentFailed(timestamp: Long, author: String, error: Exception) {
         val database = DatabaseComponent.get(context).mmsSmsDatabase()
         val messageRecord = database.getMessageFor(timestamp, author) ?: return
         if (messageRecord.isMms) {
@@ -425,6 +441,26 @@ class Storage(context: Context, helper: SQLCipherOpenHelper) : Database(context,
         }
     }
 
+    override fun markAsSyncFailed(timestamp: Long, author: String, error: Exception) {
+        val database = DatabaseComponent.get(context).mmsSmsDatabase()
+        val messageRecord = database.getMessageFor(timestamp, author) ?: return
+
+        database.getMessageFor(timestamp, author)
+            ?.run { getMmsDatabaseElseSms(isMms).markAsSyncFailed(id) }
+
+        if (error.localizedMessage != null) {
+            val message: String
+            if (error is OnionRequestAPI.HTTPRequestFailedAtDestinationException && error.statusCode == 429) {
+                message = "429: Rate limited."
+            } else {
+                message = error.localizedMessage!!
+            }
+            DatabaseComponent.get(context).lokiMessageDatabase().setErrorMessage(messageRecord.getId(), message)
+        } else {
+            DatabaseComponent.get(context).lokiMessageDatabase().setErrorMessage(messageRecord.getId(), error.javaClass.simpleName)
+        }
+    }
+
     override fun clearErrorMessage(messageID: Long) {
         val db = DatabaseComponent.get(context).lokiMessageDatabase()
         db.clearErrorMessage(messageID)
@@ -983,5 +1019,4 @@ class Storage(context: Context, helper: SQLCipherOpenHelper) : Database(context,
         val recipientDb = DatabaseComponent.get(context).recipientDatabase()
         return recipientDb.blockedContacts
     }
-
 }
\ No newline at end of file
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/model/DisplayRecord.java b/app/src/main/java/org/thoughtcrime/securesms/database/model/DisplayRecord.java
index ef0f4b54f..39fba182a 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/model/DisplayRecord.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/model/DisplayRecord.java
@@ -80,6 +80,18 @@ public abstract class DisplayRecord {
     return !isFailed() && !isPending();
   }
 
+  public boolean isSyncing() {
+    return MmsSmsColumns.Types.isSyncingType(type);
+  }
+
+  public boolean isResyncing() {
+    return MmsSmsColumns.Types.isResyncingType(type);
+  }
+
+  public boolean isSyncFailed() {
+    return MmsSmsColumns.Types.isSyncFailedMessageType(type);
+  }
+
   public boolean isFailed() {
     return MmsSmsColumns.Types.isFailedMessageType(type)
       || MmsSmsColumns.Types.isPendingSecureSmsFallbackType(type)
diff --git a/app/src/main/res/menu/menu_conversation_item_action.xml b/app/src/main/res/menu/menu_conversation_item_action.xml
index 8e2093922..ea8168561 100644
--- a/app/src/main/res/menu/menu_conversation_item_action.xml
+++ b/app/src/main/res/menu/menu_conversation_item_action.xml
@@ -32,6 +32,11 @@
         android:icon="?menu_copy_icon"
         app:showAsAction="always" />
 
+    <item
+        android:title="@string/conversation_context__menu_resync_message"
+        android:id="@+id/menu_context_resync"
+        app:showAsAction="never" />
+
     <item
         android:title="@string/conversation_context__menu_resend_message"
         android:id="@+id/menu_context_resend"
diff --git a/app/src/main/res/values/strings.xml b/app/src/main/res/values/strings.xml
index 76f859a84..1609f7e2a 100644
--- a/app/src/main/res/values/strings.xml
+++ b/app/src/main/res/values/strings.xml
@@ -112,6 +112,7 @@
     <!-- Conversation View-->
     <string name="AccessibilityId_message_sent_status_tick">Message sent status: Sent</string>
     <string name="AccessibilityId_message_sent_status_pending">Message sent status pending</string>
+    <string name="AccessibilityId_message_sent_status_syncing">Message sent status syncing</string>
     <string name="AccessibilityId_message_request_config_message">Message request has been accepted</string>
     <string name="AccessibilityId_message_body">Message Body</string>
     <string name="AccessibilityId_voice_message">Voice message</string>
@@ -627,6 +628,7 @@
     <string name="conversation_context__menu_delete_message">Delete message</string>
     <string name="conversation_context__menu_ban_user">Ban user</string>
     <string name="conversation_context__menu_ban_and_delete_all">Ban and delete all</string>
+    <string name="conversation_context__menu_resync_message">Resync message</string>
     <string name="conversation_context__menu_resend_message">Resend message</string>
     <string name="conversation_context__menu_reply">Reply</string>
     <string name="conversation_context__menu_reply_to_message">Reply to message</string>
@@ -1007,9 +1009,11 @@
     <string name="new_conversation_dialog_close_button_content_description">Close Dialog</string>
     <string name="ErrorNotifier_migration">Database Upgrade Failed</string>
     <string name="ErrorNotifier_migration_downgrade">Please contact support to report the error.</string>
+    <string name="delivery_status_syncing">Syncing</string>
     <string name="delivery_status_sending">Sending</string>
     <string name="delivery_status_read">Read</string>
     <string name="delivery_status_sent">Sent</string>
+    <string name="delivery_status_sync_failed">Failed to sync</string>
     <string name="delivery_status_failed">Failed to send</string>
     <string name="giphy_permission_title">Search GIFs?</string>
     <string name="giphy_permission_message">Session will connect to Giphy to provide search results. You will not have full metadata protection when sending GIFs.</string>
diff --git a/libsession/src/main/java/org/session/libsession/database/StorageProtocol.kt b/libsession/src/main/java/org/session/libsession/database/StorageProtocol.kt
index d75e209d1..48d15a18a 100644
--- a/libsession/src/main/java/org/session/libsession/database/StorageProtocol.kt
+++ b/libsession/src/main/java/org/session/libsession/database/StorageProtocol.kt
@@ -106,10 +106,13 @@ interface StorageProtocol {
     fun getAttachmentsForMessage(messageID: Long): List<DatabaseAttachment>
     fun getMessageIdInDatabase(timestamp: Long, author: String): Long? // TODO: This is a weird name
     fun updateSentTimestamp(messageID: Long, isMms: Boolean, openGroupSentTimestamp: Long, threadId: Long)
+    fun markAsResyncing(timestamp: Long, author: String)
+    fun markAsSyncing(timestamp: Long, author: String)
     fun markAsSending(timestamp: Long, author: String)
     fun markAsSent(timestamp: Long, author: String)
     fun markUnidentified(timestamp: Long, author: String)
-    fun setErrorMessage(timestamp: Long, author: String, error: Exception)
+    fun markAsSyncFailed(timestamp: Long, author: String, error: Exception)
+    fun markAsSentFailed(timestamp: Long, author: String, error: Exception)
     fun clearErrorMessage(messageID: Long)
     fun setMessageServerHash(messageID: Long, serverHash: String)
 
diff --git a/libsession/src/main/java/org/session/libsession/messaging/messages/Destination.kt b/libsession/src/main/java/org/session/libsession/messaging/messages/Destination.kt
index 3abf0ed3e..f30c1b916 100644
--- a/libsession/src/main/java/org/session/libsession/messaging/messages/Destination.kt
+++ b/libsession/src/main/java/org/session/libsession/messaging/messages/Destination.kt
@@ -7,13 +7,13 @@ import org.session.libsignal.utilities.toHexString
 
 sealed class Destination {
 
-    class Contact(var publicKey: String) : Destination() {
+    data class Contact(var publicKey: String) : Destination() {
         internal constructor(): this("")
     }
-    class ClosedGroup(var groupPublicKey: String) : Destination() {
+    data class ClosedGroup(var groupPublicKey: String) : Destination() {
         internal constructor(): this("")
     }
-    class LegacyOpenGroup(var roomToken: String, var server: String) : Destination() {
+    data class LegacyOpenGroup(var roomToken: String, var server: String) : Destination() {
         internal constructor(): this("", "")
     }
 
diff --git a/libsession/src/main/java/org/session/libsession/messaging/messages/visible/VisibleMessage.kt b/libsession/src/main/java/org/session/libsession/messaging/messages/visible/VisibleMessage.kt
index e66147da1..705fc7ce4 100644
--- a/libsession/src/main/java/org/session/libsession/messaging/messages/visible/VisibleMessage.kt
+++ b/libsession/src/main/java/org/session/libsession/messaging/messages/visible/VisibleMessage.kt
@@ -11,20 +11,22 @@ import org.session.libsignal.protos.SignalServiceProtos
 import org.session.libsignal.utilities.Log
 import org.session.libsession.messaging.sending_receiving.attachments.Attachment as SignalAttachment
 
-class VisibleMessage : Message()  {
-    /** In the case of a sync message, the public key of the person the message was targeted at.
-     *
-     * **Note:** `nil` if this isn't a sync message.
-     */
-    var syncTarget: String? = null
-    var text: String? = null
-    val attachmentIDs: MutableList<Long> = mutableListOf()
-    var quote: Quote? = null
-    var linkPreview: LinkPreview? = null
-    var profile: Profile? = null
-    var openGroupInvitation: OpenGroupInvitation? = null
-    var reaction: Reaction? = null
+/**
+ * @param syncTarget In the case of a sync message, the public key of the person the message was targeted at.
+ *
+ * **Note:** `nil` if this isn't a sync message.
+ */
+class VisibleMessage(
+    var syncTarget: String? = null,
+    var text: String? = null,
+    val attachmentIDs: MutableList<Long> = mutableListOf(),
+    var quote: Quote? = null,
+    var linkPreview: LinkPreview? = null,
+    var profile: Profile? = null,
+    var openGroupInvitation: OpenGroupInvitation? = null,
+    var reaction: Reaction? = null,
     var hasMention: Boolean = false
+) : Message()  {
 
     override val isSelfSendValid: Boolean = true
 
diff --git a/libsession/src/main/java/org/session/libsession/messaging/sending_receiving/MessageSender.kt b/libsession/src/main/java/org/session/libsession/messaging/sending_receiving/MessageSender.kt
index eb0d15739..fa0a49a64 100644
--- a/libsession/src/main/java/org/session/libsession/messaging/sending_receiving/MessageSender.kt
+++ b/libsession/src/main/java/org/session/libsession/messaging/sending_receiving/MessageSender.kt
@@ -61,11 +61,11 @@ object MessageSender {
     }
 
     // Convenience
-    fun send(message: Message, destination: Destination): Promise<Unit, Exception> {
+    fun send(message: Message, destination: Destination, isSyncMessage: Boolean = false): Promise<Unit, Exception> {
         return if (destination is Destination.LegacyOpenGroup || destination is Destination.OpenGroup || destination is Destination.OpenGroupInbox) {
             sendToOpenGroupDestination(destination, message)
         } else {
-            sendToSnodeDestination(destination, message)
+            sendToSnodeDestination(destination, message, isSyncMessage)
         }
     }
 
@@ -86,7 +86,7 @@ object MessageSender {
         val isSelfSend = (message.recipient == userPublicKey)
         // Set the failure handler (need it here already for precondition failure handling)
         fun handleFailure(error: Exception) {
-            handleFailedMessageSend(message, error)
+            handleFailedMessageSend(message, error, isSyncMessage)
             if (destination is Destination.Contact && message is VisibleMessage && !isSelfSend) {
                 SnodeModule.shared.broadcaster.broadcast("messageFailed", message.sentTimestamp!!)
             }
@@ -374,16 +374,23 @@ object MessageSender {
         // • the destination was a contact
         // • we didn't sync it already
         if (destination is Destination.Contact && !isSyncMessage) {
-            if (message is VisibleMessage) { message.syncTarget = destination.publicKey }
-            if (message is ExpirationTimerUpdate) { message.syncTarget = destination.publicKey }
+            if (message is VisibleMessage) message.syncTarget = destination.publicKey
+            if (message is ExpirationTimerUpdate) message.syncTarget = destination.publicKey
+
+            storage.markAsSyncing(message.sentTimestamp!!, userPublicKey)
             sendToSnodeDestination(Destination.Contact(userPublicKey), message, true)
         }
     }
 
-    fun handleFailedMessageSend(message: Message, error: Exception) {
+    fun handleFailedMessageSend(message: Message, error: Exception, isSyncMessage: Boolean = false) {
         val storage = MessagingModuleConfiguration.shared.storage
         val userPublicKey = storage.getUserPublicKey()!!
-        storage.setErrorMessage(message.sentTimestamp!!, message.sender?:userPublicKey, error)
+
+        val timestamp = message.sentTimestamp!!
+        val author = message.sender ?: userPublicKey
+
+        if (isSyncMessage) storage.markAsSyncFailed(timestamp, author, error)
+        else storage.markAsSentFailed(timestamp, author, error)
     }
 
     // Convenience