diff --git a/src/core/ev.c b/src/core/ev.c
index 78fe96dd..50f1a34c 100644
--- a/src/core/ev.c
+++ b/src/core/ev.c
@@ -604,8 +604,31 @@ void janet_ev_init_common(void) {
 #endif
 }
 
+static void handle_timeout_worker(JanetTimeout to) {
+    if (!to.has_worker) return;
+#ifdef JANET_WINDOWS
+    QueueUserAPC(janet_timeout_stop, to.worker, 0);
+    WaitForSingleObject(to.worker, INFINITE);
+    CloseHandle(to.worker);
+#else
+#ifdef JANET_ANDROID
+    pthread_kill(to.worker, SIGUSR1);
+#else
+    int ret = pthread_cancel(to.worker);
+    janet_assert(!ret, "pthread_cancel");
+#endif
+    void *res = NULL;
+    janet_assert(!pthread_join(to.worker, &res), "pthread_join");
+#endif
+}
+
 /* Common deinit code */
 void janet_ev_deinit_common(void) {
+    JanetTimeout to;
+    while (peek_timeout(&to)) {
+        handle_timeout_worker(to);
+        pop_timeout(0);
+    }
     janet_q_deinit(&janet_vm.spawn);
     janet_free(janet_vm.tq);
     janet_table_deinit(&janet_vm.threaded_abstracts);
@@ -1434,6 +1457,7 @@ JanetFiber *janet_loop1(void) {
     JanetTimestamp now = ts_now();
     while (peek_timeout(&to) && to.when <= now) {
         pop_timeout(0);
+        handle_timeout_worker(to);
         if (to.curr_fiber != NULL) {
             if (janet_fiber_can_resume(to.curr_fiber)) {
                 janet_cancel(to.fiber, janet_cstringv("deadline expired"));
@@ -1495,27 +1519,14 @@ JanetFiber *janet_loop1(void) {
         while ((has_timeout = peek_timeout(&to))) {
             if (to.curr_fiber != NULL) {
                 if (!janet_fiber_can_resume(to.curr_fiber)) {
-                    if (to.has_worker) {
-#ifdef JANET_WINDOWS
-                        QueueUserAPC(janet_timeout_stop, to.worker, 0);
-                        WaitForSingleObject(to.worker, INFINITE);
-                        CloseHandle(to.worker);
-#else
-#ifdef JANET_ANDROID
-                        pthread_kill(to.worker, SIGUSR1);
-#else
-                        pthread_cancel(to.worker);
-#endif
-                        void *res;
-                        pthread_join(to.worker, &res);
-#endif
-                    }
-                    janet_table_remove(&janet_vm.active_tasks, janet_wrap_fiber(to.curr_fiber));
                     pop_timeout(0);
+                    janet_table_remove(&janet_vm.active_tasks, janet_wrap_fiber(to.curr_fiber));
+                    handle_timeout_worker(to);
                     continue;
                 }
             } else if (to.fiber->sched_id != to.sched_id) {
                 pop_timeout(0);
+                handle_timeout_worker(to);
                 continue;
             }
             break;
@@ -3170,6 +3181,7 @@ JANET_NO_RETURN void janet_sleep_await(double sec) {
     to.is_error = 0;
     to.sched_id = to.fiber->sched_id;
     to.curr_fiber = NULL;
+    to.has_worker = 0;
     add_timeout(to);
     janet_await();
 }
@@ -3227,7 +3239,6 @@ JANET_CORE_FN(cfun_ev_deadline,
             janet_free(tto);
             janet_panicf("%s", janet_strerror(err));
         }
-        janet_assert(!pthread_detach(worker), "pthread_detach");
 #endif
         to.has_worker = 1;
         to.worker = worker;
diff --git a/test/suite-ev.janet b/test/suite-ev.janet
index b2d294a6..9e0ed4d9 100644
--- a/test/suite-ev.janet
+++ b/test/suite-ev.janet
@@ -546,9 +546,33 @@
   (ev/sleep 0.15)
   (assert (not terminated-normally) "early termination failure 3"))
 
-(let [f (coro (forever :foo))]
-  (ev/deadline 0.01 nil f true)
-  (assert-error "deadline expired" (resume f)))
+# Deadline with interrupt
+(defmacro with-deadline2
+  ``
+  Create a fiber to execute `body`, schedule the event loop to cancel
+  the task (root fiber) associated with `body`'s fiber, and start
+  `body`'s fiber by resuming it.
+
+  The event loop will try to cancel the root fiber if `body`'s fiber
+  has not completed after at least `sec` seconds.
+
+  `sec` is a number that can have a fractional part.
+  ``
+  [sec & body]
+  (with-syms [f]
+    ~(let [,f (coro ,;body)]
+       (,ev/deadline ,sec nil ,f true)
+       (,resume ,f))))
+
+(repeat 10
+        (assert (= :done (with-deadline2 10
+                           (ev/sleep 0.01)
+                           :done)) "deadline with interrupt exits normally"))
+
+(repeat 10
+        (let [f (coro (forever :foo))]
+          (ev/deadline 0.01 nil f true)
+          (assert-error "deadline expired" (resume f))))
 
 # Use :err :stdout
 (def- subproc-code '(do (eprint "hi") (eflush) (print "there") (flush)))