diff --git a/pkg/proxy/healthcheck/proxier_health.go b/pkg/proxy/healthcheck/proxier_health.go
index ca3a9acd6d7..77ea1542d52 100644
--- a/pkg/proxy/healthcheck/proxier_health.go
+++ b/pkg/proxy/healthcheck/proxier_health.go
@@ -44,6 +44,7 @@ type ProxierHealthUpdater interface {
 }
 
 var _ ProxierHealthUpdater = &proxierHealthServer{}
+var zeroTime = time.Time{}
 
 // proxierHealthServer returns 200 "OK" by default. It verifies that the delay between
 // QueuedUpdate() calls and Updated() calls never exceeds healthTimeout.
@@ -57,8 +58,8 @@ type proxierHealthServer struct {
 	recorder      events.EventRecorder
 	nodeRef       *v1.ObjectReference
 
-	lastUpdated atomic.Value
-	lastQueued  atomic.Value
+	lastUpdated         atomic.Value
+	oldestPendingQueued atomic.Value
 }
 
 // NewProxierHealthServer returns a proxier health http server.
@@ -80,12 +81,14 @@ func newProxierHealthServer(listener listener, httpServerFactory httpServerFacto
 
 // Updated updates the lastUpdated timestamp.
 func (hs *proxierHealthServer) Updated() {
+	hs.oldestPendingQueued.Store(zeroTime)
 	hs.lastUpdated.Store(hs.clock.Now())
 }
 
 // QueuedUpdate updates the lastQueued timestamp.
 func (hs *proxierHealthServer) QueuedUpdate() {
-	hs.lastQueued.Store(hs.clock.Now())
+	// Set oldestPendingQueued only if it's currently zero
+	hs.oldestPendingQueued.CompareAndSwap(zeroTime, hs.clock.Now())
 }
 
 // Run starts the healthz HTTP server and blocks until it exits.
@@ -117,9 +120,9 @@ type healthzHandler struct {
 }
 
 func (h healthzHandler) ServeHTTP(resp http.ResponseWriter, req *http.Request) {
-	var lastQueued, lastUpdated time.Time
-	if val := h.hs.lastQueued.Load(); val != nil {
-		lastQueued = val.(time.Time)
+	var oldestPendingQueued, lastUpdated time.Time
+	if val := h.hs.oldestPendingQueued.Load(); val != nil {
+		oldestPendingQueued = val.(time.Time)
 	}
 	if val := h.hs.lastUpdated.Load(); val != nil {
 		lastUpdated = val.(time.Time)
@@ -128,15 +131,11 @@ func (h healthzHandler) ServeHTTP(resp http.ResponseWriter, req *http.Request) {
 
 	healthy := false
 	switch {
-	case lastUpdated.IsZero():
+	case oldestPendingQueued.IsZero():
 		// The proxy is healthy while it's starting up
-		// TODO: this makes it useless as a readinessProbe. Consider changing
-		// to only become healthy after the proxy is fully synced.
+		// or the proxy is fully synced.
 		healthy = true
-	case lastUpdated.After(lastQueued):
-		// We've processed all updates
-		healthy = true
-	case currentTime.Sub(lastQueued) < h.hs.healthTimeout:
+	case currentTime.Sub(oldestPendingQueued) < h.hs.healthTimeout:
 		// There's an unprocessed update queued, but it's not late yet
 		healthy = true
 	}
@@ -147,14 +146,12 @@ func (h healthzHandler) ServeHTTP(resp http.ResponseWriter, req *http.Request) {
 		resp.WriteHeader(http.StatusServiceUnavailable)
 	} else {
 		resp.WriteHeader(http.StatusOK)
-
 		// In older releases, the returned "lastUpdated" time indicated the last
 		// time the proxier sync loop ran, even if nothing had changed. To
 		// preserve compatibility, we use the same semantics: the returned
 		// lastUpdated value is "recent" if the server is healthy. The kube-proxy
 		// metrics provide more detailed information.
 		lastUpdated = currentTime
-
 	}
 	fmt.Fprintf(resp, `{"lastUpdated": %q,"currentTime": %q}`, lastUpdated, currentTime)
 }