Index: sys/dev/iscsi/iscsi.c
===================================================================
--- sys/dev/iscsi/iscsi.c
+++ sys/dev/iscsi/iscsi.c
@@ -473,12 +473,7 @@
 		    STAILQ_EMPTY(&is->is_postponed))
 			cv_wait(&is->is_maintenance_cv, &is->is_lock);
 
-		if (is->is_reconnecting) {
-			ISCSI_SESSION_UNLOCK(is);
-			iscsi_maintenance_thread_reconnect(is);
-			continue;
-		}
-
+		/* Terminate supersedes reconnect. */
 		if (is->is_terminating) {
 			ISCSI_SESSION_UNLOCK(is);
 			iscsi_maintenance_thread_terminate(is);
@@ -486,6 +481,12 @@
 			return;
 		}
 
+		if (is->is_reconnecting) {
+			ISCSI_SESSION_UNLOCK(is);
+			iscsi_maintenance_thread_reconnect(is);
+			continue;
+		}
+
 		iscsi_session_send_postponed(is);
 		ISCSI_SESSION_UNLOCK(is);
 	}
@@ -2322,23 +2323,16 @@
 {
 	struct iscsi_session *is;
 
+	ISCSI_DEBUG("removing all sessions due to shutdown");
+
 	/*
 	 * Trying to reconnect during system shutdown would lead to hang.
 	 */
 	fail_on_disconnection = 1;
 
-	/*
-	 * If we have any sessions waiting for reconnection, request
-	 * maintenance thread to fail them immediately instead of waiting
-	 * for reconnect timeout.
-	 */
 	sx_slock(&sc->sc_lock);
-	TAILQ_FOREACH(is, &sc->sc_sessions, is_next) {
-		ISCSI_SESSION_LOCK(is);
-		if (is->is_waiting_for_iscsid)
-			iscsi_session_reconnect(is);
-		ISCSI_SESSION_UNLOCK(is);
-	}
+	TAILQ_FOREACH(is, &sc->sc_sessions, is_next)
+		iscsi_session_terminate(is);
 	sx_sunlock(&sc->sc_lock);
 }
 
@@ -2364,8 +2358,14 @@
 	}
 	sc->sc_cdev->si_drv1 = sc;
 
-	sc->sc_shutdown_eh = EVENTHANDLER_REGISTER(shutdown_pre_sync,
-	    iscsi_shutdown, sc, SHUTDOWN_PRI_DEFAULT-1);
+	/*
+	 * Note that this needs to get run after filesystem shutdown and before
+	 * CAM shutdown otherwise when rebooting with an iSCSI session that is
+	 * disconnected but has outstanding requests, dashutdown() will hang on
+	 * cam_periph_runccb().
+	 */
+	sc->sc_shutdown_eh = EVENTHANDLER_REGISTER(shutdown_post_sync,
+	    iscsi_shutdown, sc, SHUTDOWN_PRI_DEFAULT - 1);
 
 	return (0);
 }
@@ -2382,7 +2382,7 @@
 	}
 
 	if (sc->sc_shutdown_eh != NULL)
-		EVENTHANDLER_DEREGISTER(shutdown_pre_sync, sc->sc_shutdown_eh);
+		EVENTHANDLER_DEREGISTER(shutdown_post_sync, sc->sc_shutdown_eh);
 
 	sx_slock(&sc->sc_lock);
 	TAILQ_FOREACH_SAFE(is, &sc->sc_sessions, is_next, tmp)