diff --git a/Makefile b/Makefile
index 6ef7823fcf..d4d038b9d6 100644
--- a/Makefile
+++ b/Makefile
@@ -16,7 +16,7 @@ else
 endif
 
 # Go version to use for builds
-GO_VERSION=1.20
+GO_VERSION=1.21
 
 # K8s version used for Makefile helpers
 K8S_VERSION=1.24.6
diff --git a/pkg/backend/vxlan/device_windows.go b/pkg/backend/vxlan/device_windows.go
index 332fca3a3f..08d6b29006 100644
--- a/pkg/backend/vxlan/device_windows.go
+++ b/pkg/backend/vxlan/device_windows.go
@@ -146,20 +146,9 @@ func ensureNetwork(expectedNetwork *hcn.HostComputeNetwork, expectedAddressPrefi
 			return nil, errors.Wrapf(lastErr, "timeout, failed to get management IP from HostComputeNetwork %s", networkName)
 		}
 
-		managementIP := getManagementIP(newNetwork)
-		// Wait for the interface with the management IP
-		log.Infof("Waiting to get net interface for HostComputeNetwork %s (%s)", networkName, managementIP)
-		managementIPv4, err := ip.ParseIP4(managementIP)
+		err = checkHostNetworkReady(newNetwork)
 		if err != nil {
-			return nil, errors.Wrapf(err, "Failed to parse management ip (%s)", managementIP)
-		}
-
-		waitErr = wait.Poll(2000*time.Millisecond, 20*time.Second, func() (done bool, err error) {
-			_, lastErr = ip.GetInterfaceByIP(managementIPv4.ToIP())
-			return lastErr == nil, nil
-		})
-		if waitErr == wait.ErrWaitTimeout {
-			return nil, errors.Wrapf(lastErr, "timeout, failed to get net interface for HostComputeNetwork %s (%s)", networkName, managementIP)
+			return nil, errors.Wrapf(err, "Interface bound to %s took too long to get ready. Please check your network host configuration", networkName)
 		}
 
 		log.Infof("Created HostComputeNetwork %s", networkName)
@@ -236,3 +225,28 @@ func addNetAdapterName(network *hcn.HostComputeNetwork, netAdapterName string) e
 
 	return nil
 }
+
+// checkHostNetworkReady waits for the host network to be ready: the main interface must be up and have an IP address
+func checkHostNetworkReady(network *hcn.HostComputeNetwork) error {
+	managementIP := getManagementIP(network)
+	// Wait for the interface with the management IP
+	log.Infof("Waiting to get net interface for HostComputeNetwork %s (%s)", network.Name, managementIP)
+	managementIPv4, err := ip.ParseIP4(managementIP)
+	if err != nil {
+		return errors.Wrapf(err, "Failed to parse management ip (%s)", managementIP)
+	}
+
+	waitErr := wait.Poll(3*time.Second, 25*time.Second, func() (done bool, err error) {
+		iface, lastErr := ip.GetInterfaceByIP(managementIPv4.ToIP())
+		if lastErr == nil {
+			log.V(2).Infof("Host interface: %s bound by %s ready", iface.Name, network.Name)
+			return true, nil
+		}
+		log.V(2).Infof("Host interface bound by %s not ready", network.Name)
+		return false, nil
+	})
+	if waitErr == wait.ErrWaitTimeout {
+		return errors.Wrapf(waitErr, "timeout, failed to get net interface for HostComputeNetwork %s (%s)", network.Name, managementIP)
+	}
+	return nil
+}
diff --git a/pkg/backend/vxlan/vxlan_windows.go b/pkg/backend/vxlan/vxlan_windows.go
index 763e6d9883..81cbdb5fe7 100644
--- a/pkg/backend/vxlan/vxlan_windows.go
+++ b/pkg/backend/vxlan/vxlan_windows.go
@@ -73,7 +73,7 @@ func newSubnetAttrs(publicIP net.IP, vnid uint16, mac net.HardwareAddr) (*lease.
 	}
 	data, err := json.Marshal(&leaseAttrs)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to marshal vxlanLeaseAttrs: %w", err)
 	}
 
 	return &lease.LeaseAttrs{
@@ -153,7 +153,7 @@ func (be *VXLANBackend) RegisterNetwork(ctx context.Context, wg *sync.WaitGroup,
 
 	dev, err := newVXLANDevice(&devAttrs)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to create VXLAN network: %w", err)
 	}
 	dev.directRouting = cfg.DirectRouting
 	dev.macPrefix = cfg.MacPrefix
@@ -165,7 +165,7 @@ func (be *VXLANBackend) RegisterNetwork(ctx context.Context, wg *sync.WaitGroup,
 
 	hcnNetwork, err := hcn.GetNetworkByName(cfg.Name)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to get HNS network: %w", err)
 	}
 
 	var newDrMac string
@@ -174,7 +174,7 @@ func (be *VXLANBackend) RegisterNetwork(ctx context.Context, wg *sync.WaitGroup,
 			policySettings := hcn.DrMacAddressNetworkPolicySetting{}
 			err = json.Unmarshal(policy.Settings, &policySettings)
 			if err != nil {
-				return nil, fmt.Errorf("Failed to unmarshal settings")
+				return nil, fmt.Errorf("failed to unmarshal settings")
 			}
 			newDrMac = policySettings.Address
 		}
@@ -182,7 +182,7 @@ func (be *VXLANBackend) RegisterNetwork(ctx context.Context, wg *sync.WaitGroup,
 
 	mac, err := net.ParseMAC(string(newDrMac))
 	if err != nil {
-		return nil, fmt.Errorf("Cannot parse DR MAC %v: %+v", newDrMac, err)
+		return nil, fmt.Errorf("cannot parse DR MAC %v: %+v", newDrMac, err)
 	}
 
 	subnetAttrs, err = newSubnetAttrs(be.extIface.ExtAddr, uint16(cfg.VNI), mac)
@@ -190,9 +190,15 @@ func (be *VXLANBackend) RegisterNetwork(ctx context.Context, wg *sync.WaitGroup,
 		return nil, err
 	}
 
+	// Before contacting the lease server (e.g. kube-api), we verify that the physical interface is ready
+	err = checkHostNetworkReady(hcnNetwork)
+	if err != nil {
+		return nil, fmt.Errorf("interface bound to %s took too long to get ready. Please check your network host configuration", hcnNetwork.Name)
+	}
+
 	lease, err = be.subnetMgr.AcquireLease(ctx, subnetAttrs)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to acquire lease: %w", err)
 	}
 	network.SubnetLease = lease
 	return network, nil
diff --git a/pkg/lease/lease.go b/pkg/lease/lease.go
index c7503eaf6f..f429525fbe 100644
--- a/pkg/lease/lease.go
+++ b/pkg/lease/lease.go
@@ -45,7 +45,7 @@ type LeaseAttrs struct {
 	BackendV6Data json.RawMessage `json:",omitempty"`
 }
 
-// Lease includes information about the lease 
+// Lease includes information about the lease
 type Lease struct {
 	EnableIPv4 bool
 	EnableIPv6 bool
@@ -67,7 +67,7 @@ type LeaseWatchResult struct {
 }
 
 type LeaseWatcher struct {
-	OwnLease *Lease //Lease with the subnet of the local node
+	OwnLease *Lease  //Lease with the subnet of the local node
 	Leases   []Lease //Leases with subnets from other nodes
 }