diff --git a/src/engine/api/geary-client-service.vala b/src/engine/api/geary-client-service.vala
index 0fbb76ce..2ff1204a 100644
--- a/src/engine/api/geary-client-service.vala
+++ b/src/engine/api/geary-client-service.vala
@@ -400,6 +400,8 @@ public abstract class Geary.ClientService : BaseObject, Logging.Source {
         this.last_error = error;
         this.current_status = CONNECTION_FAILED;
         connection_error(error);
+        // Network error, so try to connect again
+        on_connectivity_change();
     }
 
     /**
diff --git a/src/engine/imap/api/imap-client-service.vala b/src/engine/imap/api/imap-client-service.vala
index c956850b..12258515 100644
--- a/src/engine/imap/api/imap-client-service.vala
+++ b/src/engine/imap/api/imap-client-service.vala
@@ -546,6 +546,12 @@ public class Geary.Imap.ClientService : Geary.ClientService {
                 session,
                 (obj, res) => { this.remove_session_async.end(res); }
             );
+            if (session.disconnected == ClientSession.DisconnectReason.REMOTE_ERROR) {
+                Geary.ErrorContext context = new Geary.ErrorContext(
+                    new GLib.IOError.NOT_CONNECTED("Session disconnected, remote error")
+                );
+                notify_connection_failed(context);
+            }
         }
     }
 
diff --git a/src/engine/util/util-connectivity-manager.vala b/src/engine/util/util-connectivity-manager.vala
index ac5bf66c..14216bba 100644
--- a/src/engine/util/util-connectivity-manager.vala
+++ b/src/engine/util/util-connectivity-manager.vala
@@ -189,8 +189,9 @@ public class Geary.ConnectivityManager : BaseObject {
         // localhost.  (This is a Linux program, after all...)
         debug("Network changed: %s",
               some_available ? "some available" : "none available");
+
+        cancel_check();
         if (some_available) {
-            cancel_check();
             this.delayed_check.start_ms(CHECK_SOON);
         } else {
             // None available, so definitely not reachable.