diff --git a/event.c b/event.c
index f13cdcf1..df104554 100644
--- a/event.c
+++ b/event.c
@@ -1258,12 +1258,12 @@ event_persist_closure(struct event_base *base, struct event *ev)
 		 * ev_io_timeout after the last time it was _scheduled_ for,
 		 * not ev_io_timeout after _now_.  If it fired for another
 		 * reason, though, the timeout ought to start ticking _now_. */
-		struct timeval run_at;
+		struct timeval run_at, relative_to, delay, now;
+		ev_uint32_t usec_mask = 0;
 		EVUTIL_ASSERT(is_same_common_timeout(&ev->ev_timeout,
 			&ev->ev_io_timeout));
+		gettime(base, &now);
 		if (is_common_timeout(&ev->ev_timeout, base)) {
-			ev_uint32_t usec_mask;
-			struct timeval delay, relative_to;
 			delay = ev->ev_io_timeout;
 			usec_mask = delay.tv_usec & ~MICROSECONDS_MASK;
 			delay.tv_usec &= MICROSECONDS_MASK;
@@ -1271,20 +1271,26 @@ event_persist_closure(struct event_base *base, struct event *ev)
 				relative_to = ev->ev_timeout;
 				relative_to.tv_usec &= MICROSECONDS_MASK;
 			} else {
-				gettime(base, &relative_to);
+				relative_to = now;
 			}
-			evutil_timeradd(&relative_to, &delay, &run_at);
-			run_at.tv_usec |= usec_mask;
 		} else {
-			struct timeval relative_to;
+			delay = ev->ev_io_timeout;
 			if (ev->ev_res & EV_TIMEOUT) {
 				relative_to = ev->ev_timeout;
 			} else {
-				gettime(base, &relative_to);
+				relative_to = now;
 			}
-			evutil_timeradd(&ev->ev_io_timeout, &relative_to,
-			    &run_at);
 		}
+		evutil_timeradd(&relative_to, &delay, &run_at);
+		if (evutil_timercmp(&run_at, &now, <)) {
+			/* Looks like we missed at least one invocation due to
+			 * a clock jump, not running the event loop for a
+			 * while, really slow callbacks, or
+			 * something. Reschedule relative to now.
+			 */
+			evutil_timeradd(&now, &delay, &run_at);
+		}
+		run_at.tv_usec |= usec_mask;
 		event_add_internal(ev, &run_at, 1);
 	}
 	EVBASE_RELEASE_LOCK(base, th_base_lock);
diff --git a/test/regress.c b/test/regress.c
index 2d48583d..3d97d0b2 100644
--- a/test/regress.c
+++ b/test/regress.c
@@ -627,6 +627,27 @@ test_persistent_timeout(void)
 	event_del(&ev);
 }
 
+static void
+test_persistent_timeout_jump(void *ptr)
+{
+	struct basic_test_data *data = ptr;
+	struct event ev;
+	int count = 0;
+	struct timeval msec100 = { 0, 100 * 1000 };
+	struct timeval msec50 = { 0, 50 * 1000 };
+
+	event_assign(&ev, data->base, -1, EV_PERSIST, periodic_timeout_cb, &count);
+	event_add(&ev, &msec100);
+	/* Wait for a bit */
+	sleep(1);
+	event_base_loopexit(data->base, &msec50);
+	event_base_dispatch(data->base);
+	tt_int_op(count, ==, 1);
+
+end:
+	event_del(&ev);
+}
+
 struct persist_active_timeout_called {
 	int n;
 	short events[16];
@@ -2338,8 +2359,8 @@ struct testcase_t main_testcases[] = {
 	BASIC(bad_assign, TT_FORK|TT_NEED_BASE|TT_NO_LOGS),
 	BASIC(bad_reentrant, TT_FORK|TT_NEED_BASE|TT_NO_LOGS),
 
-	/* These are still using the old API */
 	LEGACY(persistent_timeout, TT_FORK|TT_NEED_BASE),
+	{ "persistent_timeout_jump", test_persistent_timeout_jump, TT_FORK|TT_NEED_BASE, &basic_setup, NULL },
 	{ "persistent_active_timeout", test_persistent_active_timeout,
 	  TT_FORK|TT_NEED_BASE, &basic_setup, NULL },
 	LEGACY(priorities, TT_FORK|TT_NEED_BASE),