diff --git a/network/transports.go b/network/transports.go
index d96eda117..c97d0052e 100644
--- a/network/transports.go
+++ b/network/transports.go
@@ -55,6 +55,9 @@ var backOffTemplate = wait.Backoff{
 	Steps:    15,
 }
 
+// ErrTimeoutDialing when the timeout is reached after set amount of time.
+var ErrTimeoutDialing = errors.New("timed out dialing")
+
 // DialWithBackOff executes `net.Dialer.DialContext()` with exponentially increasing
 // dial timeouts. In addition it sleeps with random jitter between tries.
 var DialWithBackOff = NewBackoffDialer(backOffTemplate)
@@ -110,7 +113,7 @@ func dialBackOffHelper(ctx context.Context, network, address string, bo wait.Bac
 		return c, nil
 	}
 	elapsed := time.Since(start)
-	return nil, fmt.Errorf("timed out dialing after %.2fs", elapsed.Seconds())
+	return nil, fmt.Errorf("%w after %.2fs", ErrTimeoutDialing, elapsed.Seconds())
 }
 
 func newHTTPTransport(disableKeepAlives, disableCompression bool, maxIdle, maxIdlePerHost int) http.RoundTripper {
diff --git a/network/transports_test.go b/network/transports_test.go
index 7691e1628..4aeff2f08 100644
--- a/network/transports_test.go
+++ b/network/transports_test.go
@@ -20,18 +20,19 @@ import (
 	"context"
 	"crypto/tls"
 	"crypto/x509"
+	"errors"
+	"fmt"
+	"io"
 	"net"
 	"net/http"
 	"net/http/httptest"
 	"strings"
+	"syscall"
 	"testing"
+	"time"
 
 	"k8s.io/apimachinery/pkg/util/sets"
-)
-
-const (
-	timeoutErr           = "timed out dialing"
-	connectionRefusedErr = "connection refused"
+	"k8s.io/apimachinery/pkg/util/wait"
 )
 
 func TestHTTPRoundTripper(t *testing.T) {
@@ -76,67 +77,187 @@ func TestHTTPRoundTripper(t *testing.T) {
 	}
 }
 
-func TestDialWithBackoff(t *testing.T) {
-	// Make the test short.
-	bo := backOffTemplate
-	bo.Steps = 2
+func TestDialWithBackoffConnectionRefused(t *testing.T) {
+	testDialWithBackoffConnectionRefused(nil, t)
+}
 
-	// Nobody's listening on a random port. Usually.
-	c, err := dialBackOffHelper(context.Background(), "tcp4", "127.0.0.1:41482", bo, nil)
-	verifyFailedConnection(t, c, err, connectionRefusedErr)
+func TestDialWithBackoffTimeout(t *testing.T) {
+	testDialWithBackoffTimeout(nil, t)
+}
 
-	// Timeout. Use special testing IP address.
-	c, err = dialBackOffHelper(context.Background(), "tcp4", "198.18.0.254:8888", bo, nil)
-	verifyFailedConnection(t, c, err, timeoutErr)
+func TestDialWithBackoffSuccess(t *testing.T) {
+	testDialWithBackoffSuccess(nil, t)
+}
 
-	s := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {}))
+func TestDialTLSWithBackoffConnectionRefused(t *testing.T) {
+	testDialWithBackoffConnectionRefused(exampleTlsConf(), t)
+}
+
+func TestDialTLSWithBackoffTimeout(t *testing.T) {
+	testDialWithBackoffTimeout(exampleTlsConf(), t)
+}
+
+func TestDialTLSWithBackoffSuccess(t *testing.T) {
+	testDialWithBackoffSuccess(exampleTlsConf(), t)
+}
+
+func testDialWithBackoffConnectionRefused(tlsConf *tls.Config, t testingT) {
+	ctx := context.TODO()
+	port := findUnusedPortOrFail(t)
+	addr := fmt.Sprintf("127.0.0.1:%d", port)
+	dialer := newDialer(ctx, tlsConf)
+	c, err := dialer(addr)
+	closeOrFail(t, c)
+	if !errors.Is(err, syscall.ECONNREFUSED) {
+		t.Fatalf("Unexpected error: %+v", err)
+	}
+}
+
+func testDialWithBackoffTimeout(tlsConf *tls.Config, t testingT) {
+	ctx := context.TODO()
+	closer, addr, err := listenOne()
+	if err != nil {
+		t.Fatal("Unable to create listener:", err)
+	}
+	defer closer()
+	c1, err := net.Dial("tcp4", addr.String())
+	if err != nil {
+		t.Fatalf("Unable to connect to server on %s: %s", addr, err)
+	}
+	defer closeOrFail(t, c1)
+
+	// Since the backlog is full, the next request must time out.
+	dialer := newDialer(ctx, tlsConf)
+	c, err := dialer(addr.String())
+	if err == nil {
+		closeOrFail(t, c)
+		t.Fatal("Unexpected success dialing")
+	}
+	if !errors.Is(err, ErrTimeoutDialing) {
+		t.Fatalf("Unexpected error: %+v", err)
+	}
+}
+
+func testDialWithBackoffSuccess(tlsConf *tls.Config, t testingT) {
+	//goland:noinspection HttpUrlsUsage
+	const (
+		prefixHTTP  = "http://"
+		prefixHTTPS = "https://"
+	)
+	ctx := context.TODO()
+	var s *httptest.Server
+	servFn := httptest.NewServer
+	if tlsConf != nil {
+		servFn = httptest.NewTLSServer
+	}
+	s = servFn(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {}))
 	defer s.Close()
+	prefix := prefixHTTP
+	if tlsConf != nil {
+		prefix = prefixHTTPS
+		rootCAs := x509.NewCertPool()
+		rootCAs.AddCert(s.Certificate())
+		tlsConf.RootCAs = rootCAs
+	}
+	addr := strings.TrimPrefix(s.URL, prefix)
 
-	c, err = DialWithBackOff(context.Background(), "tcp4", strings.TrimPrefix(s.URL, "http://"))
+	dialer := newDialer(ctx, tlsConf)
+	c, err := dialer(addr)
 	if err != nil {
 		t.Fatal("Dial error =", err)
 	}
-	c.Close()
+	closeOrFail(t, c)
 }
 
-func TestDialTLSWithBackoff(t *testing.T) {
-	// Make the test short.
-	bo := backOffTemplate
-	bo.Steps = 2
-
-	tlsConf := &tls.Config{
+func exampleTlsConf() *tls.Config {
+	return &tls.Config{
 		InsecureSkipVerify: false,
 		ServerName:         "example.com",
 		MinVersion:         tls.VersionTLS12,
 	}
+}
 
-	// Nobody's listening on a random port. Usually.
-	c, err := dialBackOffHelper(context.Background(), "tcp4", "127.0.0.1:41482", bo, tlsConf)
-	verifyFailedConnection(t, c, err, connectionRefusedErr)
+func newDialer(ctx context.Context, tlsConf *tls.Config) func(addr string) (net.Conn, error) {
+	// Make the test short.
+	bo := wait.Backoff{
+		Duration: time.Millisecond,
+		Factor:   1.4,
+		Jitter:   0.1, // At most 10% jitter.
+		Steps:    1,
+	}
 
-	// Timeout. Use special testing IP address.
-	c, err = dialBackOffHelper(context.Background(), "tcp4", "198.18.0.254:8888", bo, tlsConf)
-	verifyFailedConnection(t, c, err, timeoutErr)
+	dialFn := func(addr string) (net.Conn, error) {
+		return NewBackoffDialer(bo)(ctx, "tcp4", addr)
+	}
+	if tlsConf != nil {
+		dialFn = func(addr string) (net.Conn, error) {
+			bo.Duration = 10 * time.Millisecond
+			bo.Steps = 3
+			return NewTLSBackoffDialer(bo)(ctx, "tcp4", addr, tlsConf)
+		}
+	}
+	return dialFn
+}
 
-	s := httptest.NewTLSServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {}))
-	defer s.Close()
+func closeOrFail(t testingT, con io.Closer) {
+	if con == nil {
+		return
+	}
+	if err := con.Close(); err != nil {
+		t.Fatal(err)
+	}
+}
 
-	rootCAs := x509.NewCertPool()
-	rootCAs.AddCert(s.Certificate())
-	tlsConf.RootCAs = rootCAs
-
-	c, err = DialTLSWithBackOff(context.Background(), "tcp4", strings.TrimPrefix(s.URL, "https://"), tlsConf)
+func findUnusedPortOrFail(t testingT) int {
+	l, err := net.Listen("tcp", "localhost:0")
 	if err != nil {
-		t.Fatal("Dial error =", err)
+		t.Fatal(err)
 	}
-	c.Close()
+	defer closeOrFail(t, l)
+	return l.Addr().(*net.TCPAddr).Port
 }
 
-func verifyFailedConnection(t *testing.T, c net.Conn, err error, prefix string) {
-	if err == nil {
-		c.Close()
-		t.Error("Unexpected success dialing")
-	} else if !strings.Contains(err.Error(), prefix) {
-		t.Errorf("Error = %v, want: %s(...)", err, prefix)
-	}
+var errTest = errors.New("testing")
+
+func newTestErr(msg string, err error) error {
+	return fmt.Errorf("%w: %s: %v", errTest, msg, err)
+}
+
+// listenOne creates a socket with backlog of one, and use that socket, so
+// any other connection will guarantee to timeout.
+//
+// Golang doesn't allow us to set the backlog argument on syscall.Listen from
+// net.ListenTCP, so we need to get directly into syscall land.
+func listenOne() (func(), *net.TCPAddr, error) {
+	fd, err := syscall.Socket(syscall.AF_INET, syscall.SOCK_STREAM, 0)
+	if err != nil {
+		return nil, nil, newTestErr("Couldn't get socket", err)
+	}
+	sa := &syscall.SockaddrInet4{
+		Port: 0,
+		Addr: [4]byte{127, 0, 0, 1},
+	}
+	if err = syscall.Bind(fd, sa); err != nil {
+		return nil, nil, newTestErr("Unable to bind", err)
+	}
+	if err = syscall.Listen(fd, 0); err != nil {
+		return nil, nil, newTestErr("Unable to Listen", err)
+	}
+	closer := func() { _ = syscall.Close(fd) }
+	listenaddr, err := syscall.Getsockname(fd)
+	if err != nil {
+		closer()
+		return nil, nil, newTestErr("Could not get sockname", err)
+	}
+	sa = listenaddr.(*syscall.SockaddrInet4)
+	addr := &net.TCPAddr{
+		IP:   sa.Addr[:],
+		Port: sa.Port,
+	}
+	return closer, addr, nil
+}
+
+type testingT interface {
+	Fatal(args ...interface{})
+	Fatalf(format string, args ...interface{})
 }