2 files changed, 43 insertions, 3 deletions

diff --git a/libemail-engine/e-mail-session-utils.c b/libemail-engine/e-mail-session-utils.c
index 524b09d771..cd5dd50c52 100644
--- a/libemail-engine/e-mail-session-utils.c
+++ b/libemail-engine/e-mail-session-utils.c
@@ -542,6 +542,26 @@ mail_session_send_to_thread (GSimpleAsyncResult *simple,
 
 	status = camel_service_get_connection_status (context->transport);
 	if (status != CAMEL_SERVICE_CONNECTED) {
+		EMailSession *session;
+		ESourceRegistry *registry;
+		ESource *source;
+
+		/* Make sure user will be asked for a password, in case he/she cancelled it */
+		session = E_MAIL_SESSION (camel_service_ref_session (context->transport));
+		registry = e_mail_session_get_registry (session);
+		source = e_source_registry_ref_source (registry, camel_service_get_uid (context->transport));
+		g_object_unref (session);
+
+		if (source) {
+			e_source_allow_auth_prompt_sync (source, cancellable, &error);
+			g_object_unref (source);
+
+			if (error) {
+				g_simple_async_result_take_error (simple, error);
+				return;
+			}
+		}
+
 		did_connect = TRUE;
 
 		camel_service_connect_sync (
diff --git a/libemail-engine/mail-ops.c b/libemail-engine/mail-ops.c
index 81ed9a32e6..67fc5a9742 100644
--- a/libemail-engine/mail-ops.c
+++ b/libemail-engine/mail-ops.c
@@ -645,10 +645,30 @@ mail_send_message (struct _send_queue_msg *m,
 			/* silently ignore */
 			goto exit;
 		}
+		if (camel_service_get_connection_status (service) != CAMEL_SERVICE_CONNECTED) {
+			EMailSession *session;
+			ESourceRegistry *registry;
+			ESource *source;
+
+			/* Make sure user will be asked for a password, in case he/she cancelled it */
+			session = E_MAIL_SESSION (camel_service_ref_session (service));
+			registry = e_mail_session_get_registry (session);
+			source = e_source_registry_ref_source (registry, camel_service_get_uid (service));
+			g_object_unref (session);
+
+			if (source) {
+				gboolean success;
 
-		if (!camel_service_connect_sync (
-			service, cancellable, error))
-			goto exit;
+				success = e_source_allow_auth_prompt_sync (source, cancellable, error);
+				g_object_unref (source);
+
+				if (!success)
+					goto exit;
+			}
+
+			if (!camel_service_connect_sync (service, cancellable, error))
+				goto exit;
+		}
 
 		/* expand, or remove empty, group addresses */
 		em_utils_expand_groups (CAMEL_INTERNET_ADDRESS (recipients));