diff --git a/sys/net/if_tuntap.c b/sys/net/if_tuntap.c
--- a/sys/net/if_tuntap.c
+++ b/sys/net/if_tuntap.c
@@ -623,19 +623,33 @@
 	CURVNET_RESTORE();
 }
 
-static void
-tun_destroy(struct tuntap_softc *tp)
+static int
+tun_destroy(struct tuntap_softc *tp, bool may_intr)
 {
+	int error;
 
 	TUN_LOCK(tp);
 	tp->tun_flags |= TUN_DYING;
-	if (tp->tun_busy != 0)
-		cv_wait_unlock(&tp->tun_cv, &tp->tun_mtx);
-	else
-		TUN_UNLOCK(tp);
+	error = 0;
+	while (tp->tun_busy != 0) {
+		if (may_intr)
+			error = cv_wait_sig(&tp->tun_cv, &tp->tun_mtx);
+		else
+			cv_wait(&tp->tun_cv, &tp->tun_mtx);
+		if (error != 0) {
+			tp->tun_flags &= ~TUN_DYING;
+			TUN_UNLOCK(tp);
+			return (error);
+		}
+	}
+	TUN_UNLOCK(tp);
 
 	CURVNET_SET(TUN2IFP(tp)->if_vnet);
 
+	mtx_lock(&tunmtx);
+	TAILQ_REMOVE(&tunhead, tp, tun_list);
+	mtx_unlock(&tunmtx);
+
 	/* destroy_dev will take care of any alias. */
 	destroy_dev(tp->tun_dev);
 	seldrain(&tp->tun_rsel);
@@ -656,6 +670,8 @@
 	cv_destroy(&tp->tun_cv);
 	free(tp, M_TUN);
 	CURVNET_RESTORE();
+
+	return (0);
 }
 
 static int
@@ -663,12 +679,7 @@
 {
 	struct tuntap_softc *tp = ifp->if_softc;
 
-	mtx_lock(&tunmtx);
-	TAILQ_REMOVE(&tunhead, tp, tun_list);
-	mtx_unlock(&tunmtx);
-	tun_destroy(tp);
-
-	return (0);
+	return (tun_destroy(tp, true));
 }
 
 static void
@@ -723,9 +734,9 @@
 
 	mtx_lock(&tunmtx);
 	while ((tp = TAILQ_FIRST(&tunhead)) != NULL) {
-		TAILQ_REMOVE(&tunhead, tp, tun_list);
 		mtx_unlock(&tunmtx);
-		tun_destroy(tp);
+		/* tun_destroy() will remove it from the tailq. */
+		tun_destroy(tp, false);
 		mtx_lock(&tunmtx);
 	}
 	mtx_unlock(&tunmtx);