diff --git a/pkg/proxy/endpoints.go b/pkg/proxy/endpoints.go
index 945237dd1cee..dea19375fe59 100644
--- a/pkg/proxy/endpoints.go
+++ b/pkg/proxy/endpoints.go
@@ -121,7 +121,9 @@ func (info *BaseEndpointInfo) Port() (int, error) {
 
 // Equal is part of proxy.Endpoint interface.
 func (info *BaseEndpointInfo) Equal(other Endpoint) bool {
-	return info.String() == other.String() && info.GetIsLocal() == other.GetIsLocal()
+	return info.String() == other.String() &&
+		info.GetIsLocal() == other.GetIsLocal() &&
+		info.IsReady() == other.IsReady()
 }
 
 // GetNodeName returns the NodeName for this endpoint.
@@ -536,13 +538,22 @@ func (em EndpointsMap) getLocalReadyEndpointIPs() map[types.NamespacedName]sets.
 // detectStaleConnections modifies <staleEndpoints> and <staleServices> with detected stale connections. <staleServiceNames>
 // is used to store stale udp service in order to clear udp conntrack later.
 func detectStaleConnections(oldEndpointsMap, newEndpointsMap EndpointsMap, staleEndpoints *[]ServiceEndpoint, staleServiceNames *[]ServicePortName) {
+	// Detect stale endpoints: an endpoint can have stale conntrack entries if it was receiving traffic
+	// and then goes unready or changes its IP address.
 	for svcPortName, epList := range oldEndpointsMap {
 		if svcPortName.Protocol != v1.ProtocolUDP {
 			continue
 		}
 
 		for _, ep := range epList {
+			// if the old endpoint wasn't ready is not possible to have stale entries
+			// since there was no traffic sent to it.
+			if !ep.IsReady() {
+				continue
+			}
 			stale := true
+			// Check if the endpoint has changed, including if it went from ready to not ready.
+			// If it did change stale entries for the old endpoint has to be cleared.
 			for i := range newEndpointsMap[svcPortName] {
 				if newEndpointsMap[svcPortName][i].Equal(ep) {
 					stale = false
@@ -556,13 +567,29 @@ func detectStaleConnections(oldEndpointsMap, newEndpointsMap EndpointsMap, stale
 		}
 	}
 
+	// Detect stale services
+	// For udp service, if its backend changes from 0 to non-0 ready endpoints.
+	// There may exist a conntrack entry that could blackhole traffic to the service.
 	for svcPortName, epList := range newEndpointsMap {
 		if svcPortName.Protocol != v1.ProtocolUDP {
 			continue
 		}
 
-		// For udp service, if its backend changes from 0 to non-0. There may exist a conntrack entry that could blackhole traffic to the service.
-		if len(epList) > 0 && len(oldEndpointsMap[svcPortName]) == 0 {
+		epReady := 0
+		for _, ep := range epList {
+			if ep.IsReady() {
+				epReady++
+			}
+		}
+
+		oldEpReady := 0
+		for _, ep := range oldEndpointsMap[svcPortName] {
+			if ep.IsReady() {
+				oldEpReady++
+			}
+		}
+
+		if epReady > 0 && oldEpReady == 0 {
 			*staleServiceNames = append(*staleServiceNames, svcPortName)
 		}
 	}
diff --git a/pkg/proxy/iptables/proxier.go b/pkg/proxy/iptables/proxier.go
index 15323340c8ec..1cc563652c43 100644
--- a/pkg/proxy/iptables/proxier.go
+++ b/pkg/proxy/iptables/proxier.go
@@ -164,7 +164,8 @@ func (e *endpointsInfo) Equal(other proxy.Endpoint) bool {
 	return e.Endpoint == o.Endpoint &&
 		e.IsLocal == o.IsLocal &&
 		e.protocol == o.protocol &&
-		e.chainName == o.chainName
+		e.chainName == o.chainName &&
+		e.Ready == o.Ready
 }
 
 // Returns the endpoint chain name for a given endpointsInfo.
diff --git a/pkg/proxy/iptables/proxier_test.go b/pkg/proxy/iptables/proxier_test.go
index 66eb9bcf92d3..4bfaef22827f 100644
--- a/pkg/proxy/iptables/proxier_test.go
+++ b/pkg/proxy/iptables/proxier_test.go
@@ -3898,6 +3898,32 @@ func TestProxierDeleteNodePortStaleUDP(t *testing.T) {
 			eps.AddressType = discovery.AddressTypeIPv4
 			eps.Endpoints = []discovery.Endpoint{{
 				Addresses: []string{epIP},
+				Conditions: discovery.EndpointConditions{
+					Ready: utilpointer.Bool(false),
+				},
+			}}
+			eps.Ports = []discovery.EndpointPort{{
+				Name:     utilpointer.StringPtr(svcPortName.Port),
+				Port:     utilpointer.Int32(int32(svcPort)),
+				Protocol: &udpProtocol,
+			}}
+		}),
+	)
+
+	fp.syncProxyRules()
+
+	if fexec.CommandCalls != 0 {
+		t.Fatalf("Updated UDP service with not ready endpoints must not clear UDP entries")
+	}
+
+	populateEndpointSlices(fp,
+		makeTestEndpointSlice(svcPortName.Namespace, svcPortName.Name, 1, func(eps *discovery.EndpointSlice) {
+			eps.AddressType = discovery.AddressTypeIPv4
+			eps.Endpoints = []discovery.Endpoint{{
+				Addresses: []string{epIP},
+				Conditions: discovery.EndpointConditions{
+					Ready: utilpointer.Bool(true),
+				},
 			}}
 			eps.Ports = []discovery.EndpointPort{{
 				Name:     utilpointer.StringPtr(svcPortName.Port),
diff --git a/test/e2e/network/conntrack.go b/test/e2e/network/conntrack.go
index 3fd25bbf8c0c..ee45c50a5e63 100644
--- a/test/e2e/network/conntrack.go
+++ b/test/e2e/network/conntrack.go
@@ -279,6 +279,79 @@ var _ = common.SIGDescribe("Conntrack", func() {
 		}
 	})
 
+	// Regression test for #105657
+	// 1. Create an UDP Service
+	// 2. Client Pod sending traffic to the UDP service
+	// 3. Create an UDP server associated to the Service created in 1. with an init container that sleeps for some time
+	// The init container makes that the server pod is not ready, however, the endpoint slices are created, it is just
+	// that the Endpoint conditions Ready is false.
+	// If the kube-proxy conntrack logic doesn't check readiness, it will delete the conntrack entries for the UDP server
+	// when the endpoint slice has been created, however, the iptables rules will not installed until at least one
+	// endpoint is ready. If some traffic arrives to since kube-proxy clear the entries (see the endpoint slice) and
+	// installs the corresponding iptables rules (the endpoint is ready), a conntrack entry will be generated blackholing
+	// subsequent traffic.
+	ginkgo.It("should be able to preserve UDP traffic when initial unready endpoints get ready", func() {
+
+		// Create a ClusterIP service
+		udpJig := e2eservice.NewTestJig(cs, ns, serviceName)
+		ginkgo.By("creating a UDP service " + serviceName + " with type=ClusterIP in " + ns)
+		udpService, err := udpJig.CreateUDPService(func(svc *v1.Service) {
+			svc.Spec.Type = v1.ServiceTypeClusterIP
+			svc.Spec.Ports = []v1.ServicePort{
+				{Port: 80, Name: "udp", Protocol: v1.ProtocolUDP, TargetPort: intstr.FromInt(80)},
+			}
+		})
+		framework.ExpectNoError(err)
+
+		// Create a pod in one node to create the UDP traffic against the ClusterIP service every 5 seconds
+		ginkgo.By("creating a client pod for probing the service " + serviceName)
+		clientPod := e2epod.NewAgnhostPod(ns, podClient, nil, nil, nil)
+		nodeSelection := e2epod.NodeSelection{Name: clientNodeInfo.name}
+		e2epod.SetNodeSelection(&clientPod.Spec, nodeSelection)
+		cmd := fmt.Sprintf(`date; for i in $(seq 1 3000); do echo "$(date) Try: ${i}"; echo hostname | nc -u -w 5 -p %d %s %d; echo; done`, srcPort, udpService.Spec.ClusterIP, udpService.Spec.Ports[0].Port)
+		clientPod.Spec.Containers[0].Command = []string{"/bin/sh", "-c", cmd}
+		clientPod.Spec.Containers[0].Name = podClient
+		fr.PodClient().CreateSync(clientPod)
+
+		// Read the client pod logs
+		logs, err := e2epod.GetPodLogs(cs, ns, podClient, podClient)
+		framework.ExpectNoError(err)
+		framework.Logf("Pod client logs: %s", logs)
+
+		// Add a backend pod to the service in the other node
+		ginkgo.By("creating a backend pod " + podBackend1 + " for the service " + serviceName)
+		serverPod1 := e2epod.NewAgnhostPod(ns, podBackend1, nil, nil, nil, "netexec", fmt.Sprintf("--udp-port=%d", 80))
+		serverPod1.Labels = udpJig.Labels
+		nodeSelection = e2epod.NodeSelection{Name: serverNodeInfo.name}
+		// Add an init container to hold the pod to be ready for 15 seconds
+		serverPod1.Spec.InitContainers = []v1.Container{
+			{
+				Name:    "init",
+				Image:   imageutils.GetE2EImage(imageutils.BusyBox),
+				Command: []string{"/bin/sh", "-c", "echo Pausing start. && sleep 15"},
+			},
+		}
+		e2epod.SetNodeSelection(&serverPod1.Spec, nodeSelection)
+		fr.PodClient().CreateSync(serverPod1)
+
+		// wait until the endpoints are ready
+		validateEndpointsPortsOrFail(cs, ns, serviceName, portsByPodName{podBackend1: {80}})
+
+		// Note that the fact that Endpoints object already exists, does NOT mean
+		// that iptables (or whatever else is used) was already programmed.
+		// Additionally take into account that UDP conntract entries timeout is
+		// 30 seconds by default.
+		// Based on the above check if the pod receives the traffic.
+		ginkgo.By("checking client pod connected to the backend on Node IP " + serverNodeInfo.nodeIP)
+		if err := wait.PollImmediate(5*time.Second, time.Minute, logContainsFn(podBackend1, podClient)); err != nil {
+			logs, err = e2epod.GetPodLogs(cs, ns, podClient, podClient)
+			framework.ExpectNoError(err)
+			framework.Logf("Pod client logs: %s", logs)
+			framework.Failf("Failed to connect to backend pod")
+		}
+
+	})
+
 	// Regression test for #74839, where:
 	// Packets considered INVALID by conntrack are now dropped. In particular, this fixes
 	// a problem where spurious retransmits in a long-running TCP connection to a service