diff --git a/src/core/lib/iomgr/endpoint.h b/src/core/lib/iomgr/endpoint.h
index 3877ceb1e26..f9808bbda18 100644
--- a/src/core/lib/iomgr/endpoint.h
+++ b/src/core/lib/iomgr/endpoint.h
@@ -82,7 +82,7 @@ char *grpc_endpoint_get_peer(grpc_endpoint *ep);
 void grpc_endpoint_write(grpc_exec_ctx *exec_ctx, grpc_endpoint *ep,
                          gpr_slice_buffer *slices, grpc_closure *cb);
 
-/* Causes any pending read/write callbacks to run immediately with
+/* Causes any pending and future read/write callbacks to run immediately with
    success==0 */
 void grpc_endpoint_shutdown(grpc_exec_ctx *exec_ctx, grpc_endpoint *ep);
 void grpc_endpoint_destroy(grpc_exec_ctx *exec_ctx, grpc_endpoint *ep);
diff --git a/src/core/lib/iomgr/ev_poll_and_epoll_posix.c b/src/core/lib/iomgr/ev_poll_and_epoll_posix.c
index 943c404f917..ef8bbd62772 100644
--- a/src/core/lib/iomgr/ev_poll_and_epoll_posix.c
+++ b/src/core/lib/iomgr/ev_poll_and_epoll_posix.c
@@ -515,7 +515,9 @@ static void fd_unref(grpc_fd *fd) { unref_by(fd, 2); }
 
 static void notify_on_locked(grpc_exec_ctx *exec_ctx, grpc_fd *fd,
                              grpc_closure **st, grpc_closure *closure) {
-  if (*st == CLOSURE_NOT_READY) {
+  if (fd->shutdown) {
+    grpc_exec_ctx_enqueue(exec_ctx, closure, false, NULL);
+  } else if (*st == CLOSURE_NOT_READY) {
     /* not ready ==> switch to a waiting state by setting the closure */
     *st = closure;
   } else if (*st == CLOSURE_READY) {
@@ -557,13 +559,24 @@ static void set_read_notifier_pollset_locked(
 
 static void fd_shutdown(grpc_exec_ctx *exec_ctx, grpc_fd *fd) {
   gpr_mu_lock(&fd->mu);
-  GPR_ASSERT(!fd->shutdown);
-  fd->shutdown = 1;
-  set_ready_locked(exec_ctx, fd, &fd->read_closure);
-  set_ready_locked(exec_ctx, fd, &fd->write_closure);
+  /* only shutdown once */
+  if (!fd->shutdown) {
+    fd->shutdown = 1;
+    /* signal read/write closed to OS so that future operations fail */
+    shutdown(fd->fd, SHUT_RDWR);
+    set_ready_locked(exec_ctx, fd, &fd->read_closure);
+    set_ready_locked(exec_ctx, fd, &fd->write_closure);
+  }
   gpr_mu_unlock(&fd->mu);
 }
 
+static bool fd_is_shutdown(grpc_fd *fd) {
+  gpr_mu_lock(&fd->mu);
+  bool r = fd->shutdown;
+  gpr_mu_unlock(&fd->mu);
+  return r;
+}
+
 static void fd_notify_on_read(grpc_exec_ctx *exec_ctx, grpc_fd *fd,
                               grpc_closure *closure) {
   gpr_mu_lock(&fd->mu);
@@ -1938,6 +1951,7 @@ static const grpc_event_engine_vtable vtable = {
     .fd_wrapped_fd = fd_wrapped_fd,
     .fd_orphan = fd_orphan,
     .fd_shutdown = fd_shutdown,
+    .fd_is_shutdown = fd_is_shutdown,
     .fd_notify_on_read = fd_notify_on_read,
     .fd_notify_on_write = fd_notify_on_write,
     .fd_get_read_notifier_pollset = fd_get_read_notifier_pollset,
diff --git a/src/core/lib/iomgr/ev_poll_posix.c b/src/core/lib/iomgr/ev_poll_posix.c
index 0167999dada..63130328693 100644
--- a/src/core/lib/iomgr/ev_poll_posix.c
+++ b/src/core/lib/iomgr/ev_poll_posix.c
@@ -421,7 +421,9 @@ static void fd_unref(grpc_fd *fd) { unref_by(fd, 2); }
 
 static void notify_on_locked(grpc_exec_ctx *exec_ctx, grpc_fd *fd,
                              grpc_closure **st, grpc_closure *closure) {
-  if (*st == CLOSURE_NOT_READY) {
+  if (fd->shutdown) {
+    grpc_exec_ctx_enqueue(exec_ctx, closure, false, NULL);
+  } else if (*st == CLOSURE_NOT_READY) {
     /* not ready ==> switch to a waiting state by setting the closure */
     *st = closure;
   } else if (*st == CLOSURE_READY) {
@@ -463,13 +465,24 @@ static void set_read_notifier_pollset_locked(
 
 static void fd_shutdown(grpc_exec_ctx *exec_ctx, grpc_fd *fd) {
   gpr_mu_lock(&fd->mu);
-  GPR_ASSERT(!fd->shutdown);
-  fd->shutdown = 1;
-  set_ready_locked(exec_ctx, fd, &fd->read_closure);
-  set_ready_locked(exec_ctx, fd, &fd->write_closure);
+  /* only shutdown once */
+  if (!fd->shutdown) {
+    fd->shutdown = 1;
+    /* signal read/write closed to OS so that future operations fail */
+    shutdown(fd->fd, SHUT_RDWR);
+    set_ready_locked(exec_ctx, fd, &fd->read_closure);
+    set_ready_locked(exec_ctx, fd, &fd->write_closure);
+  }
   gpr_mu_unlock(&fd->mu);
 }
 
+static bool fd_is_shutdown(grpc_fd *fd) {
+  gpr_mu_lock(&fd->mu);
+  bool r = fd->shutdown;
+  gpr_mu_unlock(&fd->mu);
+  return r;
+}
+
 static void fd_notify_on_read(grpc_exec_ctx *exec_ctx, grpc_fd *fd,
                               grpc_closure *closure) {
   gpr_mu_lock(&fd->mu);
@@ -1172,6 +1185,7 @@ static const grpc_event_engine_vtable vtable = {
     .fd_wrapped_fd = fd_wrapped_fd,
     .fd_orphan = fd_orphan,
     .fd_shutdown = fd_shutdown,
+    .fd_is_shutdown = fd_is_shutdown,
     .fd_notify_on_read = fd_notify_on_read,
     .fd_notify_on_write = fd_notify_on_write,
     .fd_get_read_notifier_pollset = fd_get_read_notifier_pollset,
diff --git a/src/core/lib/iomgr/ev_posix.c b/src/core/lib/iomgr/ev_posix.c
index 6477b05dcd8..a17ee17945a 100644
--- a/src/core/lib/iomgr/ev_posix.c
+++ b/src/core/lib/iomgr/ev_posix.c
@@ -153,6 +153,10 @@ void grpc_fd_shutdown(grpc_exec_ctx *exec_ctx, grpc_fd *fd) {
   g_event_engine->fd_shutdown(exec_ctx, fd);
 }
 
+bool grpc_fd_is_shutdown(grpc_fd *fd) {
+  return g_event_engine->fd_is_shutdown(fd);
+}
+
 void grpc_fd_notify_on_read(grpc_exec_ctx *exec_ctx, grpc_fd *fd,
                             grpc_closure *closure) {
   g_event_engine->fd_notify_on_read(exec_ctx, fd, closure);
diff --git a/src/core/lib/iomgr/ev_posix.h b/src/core/lib/iomgr/ev_posix.h
index 344bf63438a..53457aa9d53 100644
--- a/src/core/lib/iomgr/ev_posix.h
+++ b/src/core/lib/iomgr/ev_posix.h
@@ -55,6 +55,7 @@ typedef struct grpc_event_engine_vtable {
                             grpc_closure *closure);
   void (*fd_notify_on_write)(grpc_exec_ctx *exec_ctx, grpc_fd *fd,
                              grpc_closure *closure);
+  bool (*fd_is_shutdown)(grpc_fd *fd);
   grpc_pollset *(*fd_get_read_notifier_pollset)(grpc_exec_ctx *exec_ctx,
                                                 grpc_fd *fd);
 
@@ -116,7 +117,10 @@ int grpc_fd_wrapped_fd(grpc_fd *fd);
 void grpc_fd_orphan(grpc_exec_ctx *exec_ctx, grpc_fd *fd, grpc_closure *on_done,
                     int *release_fd, const char *reason);
 
-/* Cause any current callbacks to error out with GRPC_CALLBACK_CANCELLED. */
+/* Has grpc_fd_shutdown been called on an fd? */
+bool grpc_fd_is_shutdown(grpc_fd *fd);
+
+/* Cause any current and future callbacks to fail. */
 void grpc_fd_shutdown(grpc_exec_ctx *exec_ctx, grpc_fd *fd);
 
 /* Register read interest, causing read_cb to be called once when fd becomes
diff --git a/src/core/lib/iomgr/tcp_posix.c b/src/core/lib/iomgr/tcp_posix.c
index e2869224f1f..1bfc190f7aa 100644
--- a/src/core/lib/iomgr/tcp_posix.c
+++ b/src/core/lib/iomgr/tcp_posix.c
@@ -408,7 +408,7 @@ static void tcp_write(grpc_exec_ctx *exec_ctx, grpc_endpoint *ep,
 
   if (buf->length == 0) {
     GPR_TIMER_END("tcp_write", 0);
-    grpc_exec_ctx_enqueue(exec_ctx, cb, true, NULL);
+    grpc_exec_ctx_enqueue(exec_ctx, cb, !grpc_fd_is_shutdown(tcp->em_fd), NULL);
     return;
   }
   tcp->outgoing_buffer = buf;
diff --git a/test/core/iomgr/endpoint_tests.c b/test/core/iomgr/endpoint_tests.c
index 6d15ecf141d..0f26c0edfdd 100644
--- a/test/core/iomgr/endpoint_tests.c
+++ b/test/core/iomgr/endpoint_tests.c
@@ -222,7 +222,7 @@ static void read_and_write_test(grpc_endpoint_test_config config,
      even when bytes_written is unsigned. */
   state.bytes_written -= state.current_write_size;
   read_and_write_test_write_handler(&exec_ctx, &state, 1);
-  grpc_exec_ctx_finish(&exec_ctx);
+  grpc_exec_ctx_flush(&exec_ctx);
 
   grpc_endpoint_read(&exec_ctx, state.read_ep, &state.incoming,
                      &state.done_read);
@@ -233,7 +233,7 @@ static void read_and_write_test(grpc_endpoint_test_config config,
     gpr_log(GPR_DEBUG, "shutdown write");
     grpc_endpoint_shutdown(&exec_ctx, state.write_ep);
   }
-  grpc_exec_ctx_finish(&exec_ctx);
+  grpc_exec_ctx_flush(&exec_ctx);
 
   gpr_mu_lock(g_mu);
   while (!state.read_done || !state.write_done) {
@@ -243,7 +243,7 @@ static void read_and_write_test(grpc_endpoint_test_config config,
                       gpr_now(GPR_CLOCK_MONOTONIC), deadline);
   }
   gpr_mu_unlock(g_mu);
-  grpc_exec_ctx_finish(&exec_ctx);
+  grpc_exec_ctx_flush(&exec_ctx);
 
   end_test(config);
   gpr_slice_buffer_destroy(&state.outgoing);
@@ -253,11 +253,64 @@ static void read_and_write_test(grpc_endpoint_test_config config,
   grpc_exec_ctx_finish(&exec_ctx);
 }
 
+static void inc_on_failure(grpc_exec_ctx *exec_ctx, void *arg, bool success) {
+  *(int *)arg += (success == false);
+}
+
+static void wait_for_fail_count(grpc_exec_ctx *exec_ctx, int *fail_count,
+                                int want_fail_count) {
+  grpc_exec_ctx_flush(exec_ctx);
+  for (int i = 0; i < 5 && *fail_count < want_fail_count; i++) {
+    grpc_pollset_worker *worker = NULL;
+    gpr_timespec now = gpr_now(GPR_CLOCK_REALTIME);
+    gpr_timespec deadline =
+        gpr_time_add(now, gpr_time_from_seconds(1, GPR_TIMESPAN));
+    gpr_mu_lock(g_mu);
+    grpc_pollset_work(exec_ctx, g_pollset, &worker, now, deadline);
+    gpr_mu_unlock(g_mu);
+    grpc_exec_ctx_flush(exec_ctx);
+  }
+  GPR_ASSERT(*fail_count == want_fail_count);
+}
+
+static void multiple_shutdown_test(grpc_endpoint_test_config config) {
+  grpc_endpoint_test_fixture f =
+      begin_test(config, "multiple_shutdown_test", 128);
+  int fail_count = 0;
+
+  gpr_slice_buffer slice_buffer;
+  gpr_slice_buffer_init(&slice_buffer);
+
+  grpc_exec_ctx exec_ctx = GRPC_EXEC_CTX_INIT;
+  grpc_endpoint_add_to_pollset(&exec_ctx, f.client_ep, g_pollset);
+  grpc_endpoint_read(&exec_ctx, f.client_ep, &slice_buffer,
+                     grpc_closure_create(inc_on_failure, &fail_count));
+  wait_for_fail_count(&exec_ctx, &fail_count, 0);
+  grpc_endpoint_shutdown(&exec_ctx, f.client_ep);
+  wait_for_fail_count(&exec_ctx, &fail_count, 1);
+  grpc_endpoint_read(&exec_ctx, f.client_ep, &slice_buffer,
+                     grpc_closure_create(inc_on_failure, &fail_count));
+  wait_for_fail_count(&exec_ctx, &fail_count, 2);
+  gpr_slice_buffer_add(&slice_buffer, gpr_slice_from_copied_string("a"));
+  grpc_endpoint_write(&exec_ctx, f.client_ep, &slice_buffer,
+                      grpc_closure_create(inc_on_failure, &fail_count));
+  wait_for_fail_count(&exec_ctx, &fail_count, 3);
+  grpc_endpoint_shutdown(&exec_ctx, f.client_ep);
+  wait_for_fail_count(&exec_ctx, &fail_count, 3);
+
+  gpr_slice_buffer_destroy(&slice_buffer);
+
+  grpc_endpoint_destroy(&exec_ctx, f.client_ep);
+  grpc_endpoint_destroy(&exec_ctx, f.server_ep);
+  grpc_exec_ctx_finish(&exec_ctx);
+}
+
 void grpc_endpoint_tests(grpc_endpoint_test_config config,
                          grpc_pollset *pollset, gpr_mu *mu) {
   size_t i;
   g_pollset = pollset;
   g_mu = mu;
+  multiple_shutdown_test(config);
   read_and_write_test(config, 10000000, 100000, 8192, 0);
   read_and_write_test(config, 1000000, 100000, 1, 0);
   read_and_write_test(config, 100000000, 100000, 1, 1);
@@ -265,4 +318,5 @@ void grpc_endpoint_tests(grpc_endpoint_test_config config,
     read_and_write_test(config, 40320, i, i, 0);
   }
   g_pollset = NULL;
+  g_mu = NULL;
 }
diff --git a/test/core/iomgr/tcp_posix_test.c b/test/core/iomgr/tcp_posix_test.c
index 19ba258303e..1112e8a3aa5 100644
--- a/test/core/iomgr/tcp_posix_test.c
+++ b/test/core/iomgr/tcp_posix_test.c
@@ -517,8 +517,8 @@ int main(int argc, char **argv) {
   grpc_init();
   g_pollset = gpr_malloc(grpc_pollset_size());
   grpc_pollset_init(g_pollset, &g_mu);
-  run_tests();
   grpc_endpoint_tests(configs[0], g_pollset, g_mu);
+  run_tests();
   grpc_closure_init(&destroyed, destroy_pollset, g_pollset);
   grpc_pollset_shutdown(&exec_ctx, g_pollset, &destroyed);
   grpc_exec_ctx_finish(&exec_ctx);