diff --git a/src/application/main-window.vala b/src/application/main-window.vala
index 63e0cc4..499f30e 100644
--- a/src/application/main-window.vala
+++ b/src/application/main-window.vala
@@ -69,7 +69,7 @@ public class MainWindow : Adw.ApplicationWindow
         }
 
         try {   
-            Repository.get_instance().send_message(selected_conversation, body);
+            Repository.get_instance().send_message(selected_conversation, body, attachment_guids.to_array());
         } catch (Error e) {
             GLib.warning("Failed to send message: %s", e.message);
         }
diff --git a/src/service/interface/dbusservice.vala b/src/service/interface/dbusservice.vala
index 1a6d95c..f352da2 100644
--- a/src/service/interface/dbusservice.vala
+++ b/src/service/interface/dbusservice.vala
@@ -48,7 +48,7 @@ namespace DBusService {
 		public abstract GLib.HashTable<string, GLib.Variant>[] get_messages(string conversation_id, string last_message_id) throws DBusError, IOError;
 
 		[DBus (name = "SendMessage")]
-		public abstract string send_message(string conversation_id, string text) throws DBusError, IOError;
+		public abstract string send_message(string conversation_id, string text, string[] attachment_guids) throws DBusError, IOError;
 
 		[DBus (name = "MessagesUpdated")]
 		public signal void messages_updated(string conversation_id);
diff --git a/src/service/interface/xml/net.buzzert.kordophonecd.Server.xml b/src/service/interface/xml/net.buzzert.kordophonecd.Server.xml
index bdc0fb2..8e93ca5 100644
--- a/src/service/interface/xml/net.buzzert.kordophonecd.Server.xml
+++ b/src/service/interface/xml/net.buzzert.kordophonecd.Server.xml
@@ -81,10 +81,20 @@
         <method name="SendMessage">
             <arg type="s" name="conversation_id" direction="in"/>
             <arg type="s" name="text" direction="in"/>
+            <arg type="as" name="attachment_guids" direction="in"/>
+
             <arg type="s" name="outgoing_message_id" direction="out"/>
 
             <annotation name="org.freedesktop.DBus.DocString"
-                        value="Sends a message to the server. Returns the outgoing message ID."/>
+                        value="Sends a message to the server. Returns the outgoing message ID.
+                        Arguments:
+                        - conversation_id: The ID of the conversation to send the message to.
+                        - text: The text of the message to send.
+                        - attachment_guids: The GUIDs of the attachments to send.
+
+                        Returns:
+                        - outgoing_message_id: The ID of the outgoing message.
+                        "/>
         </method>
 
         <signal name="MessagesUpdated">
diff --git a/src/service/repository.vala b/src/service/repository.vala
index 8753f6b..f89f757 100644
--- a/src/service/repository.vala
+++ b/src/service/repository.vala
@@ -82,12 +82,12 @@ public class Repository : DBusServiceProxy {
         return returned_messages;
     }
 
-    public string send_message(string conversation_guid, string message) throws DBusServiceProxyError, GLib.Error {
+    public string send_message(string conversation_guid, string message, string[] attachment_guids) throws DBusServiceProxyError, GLib.Error {
         if (dbus_repository == null) {
             throw new DBusServiceProxyError.NOT_CONNECTED("Repository not connected");
         }
 
-        return dbus_repository.send_message(conversation_guid, message);
+        return dbus_repository.send_message(conversation_guid, message, attachment_guids);
     }
 
     public void sync_conversation(string conversation_guid) throws DBusServiceProxyError, GLib.Error {
diff --git a/src/transcript/transcript-container-view.vala b/src/transcript/transcript-container-view.vala
index 9b26d06..4da4f65 100644
--- a/src/transcript/transcript-container-view.vala
+++ b/src/transcript/transcript-container-view.vala
@@ -34,6 +34,12 @@ class TranscriptContainerView : Adw.Bin
         }
     }
 
+    private bool can_send {
+        get {
+            return (message_entry.text.length > 0 || completed_attachments.size > 0) && pending_uploads.size == 0;
+        }
+    }
+
     public TranscriptContainerView () {
         container = new Gtk.Box (Gtk.Orientation.VERTICAL, 0);
         set_child (container);
@@ -183,11 +189,11 @@ class TranscriptContainerView : Adw.Bin
     }
 
     private void update_send_button_sensitivity() {
-        send_button.set_sensitive(message_entry.text.length > 0 && pending_uploads.size == 0);
+        send_button.set_sensitive(can_send);
     }
 
     private void on_request_send() {
-        if (message_entry.text.length > 0 && pending_uploads.size == 0) {
+        if (can_send) {
             on_send(this);
 
             // Clear the message entry