diff --git a/prpl/attachments.c b/prpl/attachments.c
index 0621cbc..fd61c3d 100644
--- a/prpl/attachments.c
+++ b/prpl/attachments.c
@@ -544,13 +544,10 @@ struct chime_im {
 	ChimeContact *peer;
 };
 
-static void chime_send_init(PurpleXfer *xfer)
+static void init_upload(PurpleXfer *xfer, struct purple_chime *pc, ChimeObject *obj)
 {
 	purple_debug_info("chime", "Starting to handle upload of file '%s'\n", xfer->local_filename);
 
-	struct purple_chime *pc = purple_connection_get_protocol_data(xfer->account->gc);
-	struct chime_im *im = g_hash_table_lookup(pc->ims_by_email, xfer->who);
-
 	g_return_if_fail(CHIME_IS_CONNECTION(pc->cxn));
 	ChimeConnectionPrivate *priv = CHIME_CONNECTION_GET_PRIVATE(pc->cxn);
 
@@ -566,7 +563,7 @@ static void chime_send_init(PurpleXfer *xfer)
 	}
 	AttachmentUpload *data = g_new0(AttachmentUpload, 1);
 	data->conn = pc->cxn;
-	data->obj = im->m.obj;
+	data->obj = obj;
 	data->content = file_contents;
 	data->content_length = length;
 	get_mime_type(xfer->local_filename, &data->content_type);
@@ -578,6 +575,25 @@ static void chime_send_init(PurpleXfer *xfer)
 	request_upload_url(pc->cxn, priv->messaging_url, xfer);
 }
 
+static void chime_send_init(PurpleXfer *xfer)
+{
+	purple_debug_info("chime", "Starting to handle upload of file '%s'\n", xfer->local_filename);
+
+	struct purple_chime *pc = purple_connection_get_protocol_data(xfer->account->gc);
+	struct chime_im *im = g_hash_table_lookup(pc->ims_by_email, xfer->who);
+
+	init_upload(xfer, pc, im->m.obj);
+}
+
+static void chime_send_init_chat(PurpleXfer *xfer)
+{
+	purple_debug_info("chime", "Starting to handle upload of file '%s'\n", xfer->local_filename);
+	ChimeObject *obj = (ChimeObject*)xfer->data;
+	struct purple_chime *pc = purple_connection_get_protocol_data(xfer->account->gc);
+
+	init_upload(xfer, pc, obj);
+}
+
 static void chime_send_start(PurpleXfer *xfer)
 {
 	purple_debug_info("chime", "chime_send_start\n");
@@ -615,3 +631,24 @@ void chime_send_file(PurpleConnection *gc, const char *who, const char *filename
 		purple_xfer_request(xfer);
 	}
 }
+
+void chime_send_file_chat(PurpleConnection *gc, ChimeObject *obj, const char *who, const char *filename)
+{
+	purple_debug_info("chime", "chime_send_file_chat(who=%s, file=%s\n", who, filename);
+
+	PurpleXfer *xfer;
+	xfer = purple_xfer_new(gc->account, PURPLE_XFER_SEND, who);
+	if (xfer) {
+		purple_xfer_set_init_fnc(xfer, chime_send_init_chat);
+		purple_xfer_set_start_fnc(xfer, chime_send_start);
+		purple_xfer_set_cancel_send_fnc(xfer, chime_send_cancel);
+	}
+
+	xfer->data = obj;
+
+	if (filename) {
+		purple_xfer_request_accepted(xfer, filename);
+	} else {
+		purple_xfer_request(xfer);
+	}
+}
diff --git a/prpl/chat.c b/prpl/chat.c
index 250ed87..17fc13a 100644
--- a/prpl/chat.c
+++ b/prpl/chat.c
@@ -1250,6 +1250,36 @@ static void leave_room(PurpleBuddy *buddy, gpointer _chat)
 	chime_connection_remove_room_member_async(cxn, room, me, NULL, leave_room_cb, chat);
 }
 
+static void send_file(PurpleBuddy *buddy, gpointer *_pchat)
+{
+	purple_debug_info("chime", "send_file\n");
+	PurpleChat *pchat = (PurpleChat*)_pchat;
+	purple_debug_info("chime", "room\n");
+	if (!pchat->components)
+		return;
+
+	const gchar *roomid = g_hash_table_lookup(pchat->components, (char *)"RoomId");
+	if (!roomid)
+		return;
+
+	purple_debug_info("chime", "Chat menu for %s\n", roomid);
+
+	PurpleConnection *conn = pchat->account->gc;
+	if (!conn)
+		return;
+
+	struct purple_chime *pc = purple_connection_get_protocol_data(conn);
+	ChimeRoom *room = chime_connection_room_by_id(pc->cxn, roomid);
+	if (!room)
+		return;
+
+	struct chime_chat *chat = g_hash_table_lookup(pc->chats_by_room, room);
+	if (!chat)
+		return;
+	purple_debug_info("chime", "Has chat\n");
+	chime_send_file_chat(conn, chat->m.obj, roomid, NULL);
+}
+
 GList *chime_purple_chat_menu(PurpleChat *pchat)
 {
 
@@ -1276,6 +1306,10 @@ GList *chime_purple_chat_menu(PurpleChat *pchat)
 		return NULL;
 
 	GList *items = NULL;
+	items = g_list_append(items,
+			      purple_menu_action_new(_("Send file"),
+						     PURPLE_CALLBACK(send_file), pchat, NULL));
+
 	if (chat->call) {
 		items = g_list_append(items,
 				      purple_menu_action_new(_("Show participants"),
diff --git a/prpl/chime.h b/prpl/chime.h
index e86e8ed..eadd188 100644
--- a/prpl/chime.h
+++ b/prpl/chime.h
@@ -173,5 +173,6 @@ ChimeAttachment *extract_attachment(JsonNode *record);
 
 void download_attachment(ChimeConnection *cxn, ChimeAttachment *att, AttachmentContext *ctx);
 void chime_send_file(PurpleConnection *gc, const char *who, const char *filename);
+void chime_send_file_chat(PurpleConnection *gc, ChimeObject *obj, const char *who, const char *filename);
 
 #endif /* __CHIME_H__ */