diff --git a/rest/request.go b/rest/request.go
index fe048ec4..96fb19ce 100644
--- a/rest/request.go
+++ b/rest/request.go
@@ -669,7 +669,7 @@ func (r *Request) Watch(ctx context.Context) (watch.Interface, error) {
 	if err != nil {
 		// The watch stream mechanism handles many common partial data errors, so closed
 		// connections can be retried in many cases.
-		if net.IsProbableEOF(err) {
+		if net.IsProbableEOF(err) || net.IsTimeout(err) {
 			return watch.NewEmptyWatch(), nil
 		}
 		return nil, err
diff --git a/tools/cache/reflector.go b/tools/cache/reflector.go
index 7c581ced..8dfc4169 100644
--- a/tools/cache/reflector.go
+++ b/tools/cache/reflector.go
@@ -396,6 +396,8 @@ func (r *Reflector) ListAndWatch(stopCh <-chan struct{}) error {
 			AllowWatchBookmarks: true,
 		}
 
+		// start the clock before sending the request, since some proxies won't flush headers until after the first watch event is sent
+		start := r.clock.Now()
 		w, err := r.listerWatcher.Watch(options)
 		if err != nil {
 			// If this is "connection refused" error, it means that most likely apiserver is not responsive.
@@ -409,7 +411,7 @@ func (r *Reflector) ListAndWatch(stopCh <-chan struct{}) error {
 			return err
 		}
 
-		if err := r.watchHandler(w, &resourceVersion, resyncerrc, stopCh); err != nil {
+		if err := r.watchHandler(start, w, &resourceVersion, resyncerrc, stopCh); err != nil {
 			if err != errorStopRequested {
 				switch {
 				case isExpiredError(err):
@@ -436,8 +438,7 @@ func (r *Reflector) syncWith(items []runtime.Object, resourceVersion string) err
 }
 
 // watchHandler watches w and keeps *resourceVersion up to date.
-func (r *Reflector) watchHandler(w watch.Interface, resourceVersion *string, errc chan error, stopCh <-chan struct{}) error {
-	start := r.clock.Now()
+func (r *Reflector) watchHandler(start time.Time, w watch.Interface, resourceVersion *string, errc chan error, stopCh <-chan struct{}) error {
 	eventCount := 0
 
 	// Stopping the watcher should be idempotent and if we return from this function there's no way
diff --git a/tools/cache/reflector_test.go b/tools/cache/reflector_test.go
index 59b66256..3e2fcc19 100644
--- a/tools/cache/reflector_test.go
+++ b/tools/cache/reflector_test.go
@@ -136,7 +136,7 @@ func TestReflectorWatchHandlerError(t *testing.T) {
 		fw.Stop()
 	}()
 	var resumeRV string
-	err := g.watchHandler(fw, &resumeRV, nevererrc, wait.NeverStop)
+	err := g.watchHandler(time.Now(), fw, &resumeRV, nevererrc, wait.NeverStop)
 	if err == nil {
 		t.Errorf("unexpected non-error")
 	}
@@ -156,7 +156,7 @@ func TestReflectorWatchHandler(t *testing.T) {
 		fw.Stop()
 	}()
 	var resumeRV string
-	err := g.watchHandler(fw, &resumeRV, nevererrc, wait.NeverStop)
+	err := g.watchHandler(time.Now(), fw, &resumeRV, nevererrc, wait.NeverStop)
 	if err != nil {
 		t.Errorf("unexpected error %v", err)
 	}
@@ -205,7 +205,7 @@ func TestReflectorStopWatch(t *testing.T) {
 	var resumeRV string
 	stopWatch := make(chan struct{}, 1)
 	stopWatch <- struct{}{}
-	err := g.watchHandler(fw, &resumeRV, nevererrc, stopWatch)
+	err := g.watchHandler(time.Now(), fw, &resumeRV, nevererrc, stopWatch)
 	if err != errorStopRequested {
 		t.Errorf("expected stop error, got %q", err)
 	}
diff --git a/tools/watch/retrywatcher.go b/tools/watch/retrywatcher.go
index 47ae9df4..edf28d16 100644
--- a/tools/watch/retrywatcher.go
+++ b/tools/watch/retrywatcher.go
@@ -120,7 +120,7 @@ func (rw *RetryWatcher) doReceive() (bool, time.Duration) {
 
 	default:
 		msg := "Watch failed: %v"
-		if net.IsProbableEOF(err) {
+		if net.IsProbableEOF(err) || net.IsTimeout(err) {
 			klog.V(5).Infof(msg, err)
 			// Retry
 			return false, 0