diff --git a/konnectivity-https-proxy/cmd.go b/konnectivity-https-proxy/cmd.go
index dbdb6248529..cb0f1633207 100644
--- a/konnectivity-https-proxy/cmd.go
+++ b/konnectivity-https-proxy/cmd.go
@@ -1,6 +1,7 @@
 package konnectivityhttpsproxy
 
 import (
+	"context"
 	"crypto/tls"
 	"encoding/base64"
 	"fmt"
@@ -151,7 +152,6 @@ func NewStartCommand() *cobra.Command {
 				l.V(4).Info("Should proxy", "url", u)
 				return u, nil
 			},
-			Dial:        konnectivityDialer.Dial,
 			DialContext: konnectivityDialer.DialContext,
 		}
 		if httpsProxyURL != "" {
@@ -175,12 +175,13 @@ func NewStartCommand() *cobra.Command {
 }
 
 type dialFunc func(network, addr string) (net.Conn, error)
+type dialContextFunc func(ctx context.Context, network, addr string) (net.Conn, error)
 type dialRequestFunc func(req *http.Request, network, addr string) (net.Conn, error)
 
-func dialDirectFunc(httpProxy *goproxy.ProxyHttpServer) dialFunc {
-	// NOTE: the function signature is determined by the goproxy library, it requires the deprecated version
-	// nolint:staticcheck
-	return httpProxy.Tr.Dial
+func dialDirectFunc(httpProxy *goproxy.ProxyHttpServer) dialContextFunc {
+	return func(ctx context.Context, network, addr string) (net.Conn, error) {
+		return httpProxy.Tr.DialContext(ctx, network, addr)
+	}
 }
 
 func dialThroughProxyFunc(httpProxy *goproxy.ProxyHttpServer, proxyURL string, proxyURLUser *url.Userinfo) dialFunc {
@@ -219,14 +220,14 @@ func addBasicAuthHeader(proxyUser *url.Userinfo) func(req *http.Request) {
 	}
 }
 
-func connectDialFunc(shouldDialDirect func(*url.URL) (bool, error), dialDirectly dialFunc, dialThroughProxy dialFunc) dialRequestFunc {
+func connectDialFunc(shouldDialDirect func(*url.URL) (bool, error), dialDirectly dialContextFunc, dialThroughProxy dialFunc) dialRequestFunc {
 	return func(req *http.Request, network, addr string) (net.Conn, error) {
 		shouldDialDirectly, err := shouldDialDirect(req.URL)
 		if err != nil {
 			return nil, err
 		}
 		if shouldDialDirectly {
-			return dialDirectly(network, addr)
+			return dialDirectly(req.Context(), network, addr)
 		}
 		return dialThroughProxy(network, addr)
 	}
diff --git a/konnectivity-https-proxy/cmd_test.go b/konnectivity-https-proxy/cmd_test.go
index 9f1c8f6c696..103affc8a01 100644
--- a/konnectivity-https-proxy/cmd_test.go
+++ b/konnectivity-https-proxy/cmd_test.go
@@ -1,8 +1,11 @@
 package konnectivityhttpsproxy
 
 import (
+	"context"
 	"encoding/base64"
+	"errors"
 	"fmt"
+	"net"
 	"net/http"
 	"net/url"
 	"strings"
@@ -10,6 +13,7 @@ import (
 
 	. "github.com/onsi/gomega"
 
+	"github.com/elazarl/goproxy"
 	"golang.org/x/net/http/httpproxy"
 )
 
@@ -101,6 +105,133 @@ func TestShouldDialDirectFunc(t *testing.T) {
 	}
 }
 
+func TestDialDirectFunc(t *testing.T) {
+	dialErr := errors.New("dial failed")
+
+	tests := []struct {
+		name      string
+		dialCtx   func(ctx context.Context, network, addr string) (net.Conn, error)
+		addr      func(t *testing.T) string
+		expectErr error
+	}{
+		{
+			name:    "When dialing with a valid listener it should connect successfully",
+			dialCtx: (&net.Dialer{}).DialContext,
+			addr: func(t *testing.T) string {
+				listener, err := (&net.ListenConfig{}).Listen(t.Context(), "tcp", "127.0.0.1:0")
+				if err != nil {
+					t.Fatalf("failed to create listener: %v", err)
+				}
+				t.Cleanup(func() { listener.Close() })
+				return listener.Addr().String()
+			},
+		},
+		{
+			name: "When the transport DialContext fails it should return an error",
+			dialCtx: func(ctx context.Context, network, addr string) (net.Conn, error) {
+				return nil, dialErr
+			},
+			addr:      func(t *testing.T) string { return "127.0.0.1:1" },
+			expectErr: dialErr,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			g := NewGomegaWithT(t)
+
+			httpProxy := goproxy.NewProxyHttpServer()
+			httpProxy.Tr = &http.Transport{
+				DialContext: tc.dialCtx,
+			}
+
+			dialFn := dialDirectFunc(httpProxy)
+			conn, err := dialFn(t.Context(), "tcp", tc.addr(t))
+
+			if tc.expectErr != nil {
+				g.Expect(err).To(MatchError(tc.expectErr))
+				g.Expect(conn).To(BeNil())
+			} else {
+				g.Expect(err).NotTo(HaveOccurred())
+				g.Expect(conn).NotTo(BeNil())
+				conn.Close()
+			}
+		})
+	}
+}
+
+func TestConnectDialFunc(t *testing.T) {
+	lookupErr := errors.New("lookup failed")
+
+	tests := []struct {
+		name                string
+		shouldDialDirect    bool
+		shouldDialDirectErr error
+		expectDialDirect    bool
+		expectDialProxy     bool
+		expectErr           error
+	}{
+		{
+			name:             "When shouldDialDirect returns true it should dial directly with request context",
+			shouldDialDirect: true,
+			expectDialDirect: true,
+		},
+		{
+			name:            "When shouldDialDirect returns false it should dial through proxy",
+			expectDialProxy: true,
+		},
+		{
+			name:                "When shouldDialDirect returns an error it should propagate the error",
+			shouldDialDirectErr: lookupErr,
+			expectErr:           lookupErr,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			g := NewGomegaWithT(t)
+
+			type contextKey string
+			reqCtx := context.WithValue(t.Context(), contextKey("test"), "value")
+			req, err := http.NewRequestWithContext(reqCtx, http.MethodConnect, "https://example.com:443", nil)
+			g.Expect(err).NotTo(HaveOccurred())
+
+			directCalled := false
+			proxyCalled := false
+			var capturedCtx any
+
+			dialDirectly := func(ctx context.Context, network, addr string) (net.Conn, error) {
+				directCalled = true
+				capturedCtx = ctx
+				return nil, nil
+			}
+			dialThroughProxy := func(network, addr string) (net.Conn, error) {
+				proxyCalled = true
+				return nil, nil
+			}
+			shouldDialDirect := func(u *url.URL) (bool, error) {
+				return tc.shouldDialDirect, tc.shouldDialDirectErr
+			}
+
+			f := connectDialFunc(shouldDialDirect, dialDirectly, dialThroughProxy)
+			conn, err := f(req, "tcp", "example.com:443")
+
+			if tc.expectErr != nil {
+				g.Expect(err).To(MatchError(tc.expectErr))
+				g.Expect(conn).To(BeNil())
+			} else {
+				g.Expect(err).NotTo(HaveOccurred())
+			}
+			g.Expect(directCalled).To(Equal(tc.expectDialDirect))
+			g.Expect(proxyCalled).To(Equal(tc.expectDialProxy))
+			if tc.expectDialDirect {
+				g.Expect(capturedCtx).To(Equal(reqCtx))
+				g.Expect(capturedCtx.(context.Context).Value(contextKey("test"))).To(Equal("value"))
+			}
+		})
+	}
+}
+
 func TestAddBasicAuthHeader(t *testing.T) {
 	userInfo := url.UserPassword("user", "password")
 	tests := []struct {