diff --git a/pkg/crypto/missing_san.go b/pkg/crypto/missing_san.go
new file mode 100644
index 0000000000..bf17008a7f
--- /dev/null
+++ b/pkg/crypto/missing_san.go
@@ -0,0 +1,40 @@
+package crypto
+
+import (
+	"crypto/x509"
+	"errors"
+	"strings"
+)
+
+// CertHasSAN returns true if the given certificate includes a SAN field, else false.
+func CertHasSAN(c *x509.Certificate) bool {
+	if c == nil {
+		return false
+	}
+
+	sanOID := []int{2, 5, 29, 17}
+
+	for i := range c.Extensions {
+		if c.Extensions[i].Id.Equal(sanOID) {
+			return true
+		}
+	}
+	return false
+}
+
+// IsHostnameError returns true if the error indicates a host name error about legacy CN fields
+// else false as a result of `x509.Certificate#VerifyHostname`.
+//
+// For Golang <1.17: If GODEBUG=x509ignoreCN=0 is set this will always return false.
+// In this case, use `crypto.CertHasSAN` to assert validity of the certificate directly.
+//
+// See https://github.com/golang/go/blob/go1.16.12/src/crypto/x509/verify.go#L119
+func IsHostnameError(err error) bool {
+	if err != nil &&
+		errors.As(err, &x509.HostnameError{}) &&
+		strings.Contains(err.Error(), "x509: certificate relies on legacy Common Name field") {
+		return true
+	}
+
+	return false
+}
diff --git a/pkg/crypto/missing_san_test.go b/pkg/crypto/missing_san_test.go
new file mode 100644
index 0000000000..b816b03d93
--- /dev/null
+++ b/pkg/crypto/missing_san_test.go
@@ -0,0 +1,104 @@
+package crypto
+
+import (
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/asn1"
+	"errors"
+	"math/big"
+	"testing"
+)
+
+func TestCertHasSAN(t *testing.T) {
+	for _, tc := range []struct {
+		name           string
+		cert           *x509.Certificate
+		expectedHasSAN bool
+	}{
+		{
+			name:           "nil cert",
+			expectedHasSAN: false,
+		},
+		{
+			name: "sole identifier",
+			cert: &x509.Certificate{
+				Extensions: []pkix.Extension{
+					{Id: asn1.ObjectIdentifier{2, 5, 29, 17}},
+				},
+			},
+			expectedHasSAN: true,
+		},
+		{
+			name: "last identifier",
+			cert: &x509.Certificate{
+				Extensions: []pkix.Extension{
+					{Id: asn1.ObjectIdentifier{1}},
+					{Id: asn1.ObjectIdentifier{2, 5, 29, 17}},
+				},
+			},
+			expectedHasSAN: true,
+		},
+		{
+			name: "first identifier",
+			cert: &x509.Certificate{
+				Extensions: []pkix.Extension{
+					{Id: asn1.ObjectIdentifier{2, 5, 29, 17}},
+					{Id: asn1.ObjectIdentifier{1}},
+				},
+			},
+			expectedHasSAN: true,
+		},
+		{
+			name: "no identifier",
+			cert: &x509.Certificate{
+				Extensions: []pkix.Extension{
+					{Id: asn1.ObjectIdentifier{1}},
+					{Id: asn1.ObjectIdentifier{2}},
+				},
+			},
+			expectedHasSAN: false,
+		},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			if got := CertHasSAN(tc.cert); got != tc.expectedHasSAN {
+				t.Errorf("expected result %t, got %t", tc.expectedHasSAN, got)
+			}
+		})
+	}
+}
+
+func TestIsHostnameError(t *testing.T) {
+	for _, tc := range []struct {
+		name     string
+		err      error
+		expected bool
+	}{
+		{
+			name: "invalid hostname error",
+			err: x509.HostnameError{
+				Certificate: &x509.Certificate{
+					Subject:      pkix.Name{CommonName: "foo.bar"},
+					SerialNumber: big.NewInt(1),
+				},
+				Host: "foo.bar",
+			},
+			expected: true,
+		},
+		{
+			name:     "other error",
+			err:      errors.New("boom"),
+			expected: false,
+		},
+		{
+			name:     "nil error",
+			err:      nil,
+			expected: false,
+		},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			if got := IsHostnameError(tc.err); got != tc.expected {
+				t.Errorf("expected %t, got %t", tc.expected, got)
+			}
+		})
+	}
+}
diff --git a/pkg/transport/missing_san_roundtripper.go b/pkg/transport/missing_san_roundtripper.go
new file mode 100644
index 0000000000..8e6fad4010
--- /dev/null
+++ b/pkg/transport/missing_san_roundtripper.go
@@ -0,0 +1,43 @@
+package transport
+
+import (
+	"net/http"
+
+	"github.com/openshift/library-go/pkg/crypto"
+)
+
+type roundTripperFunc func(req *http.Request) (*http.Response, error)
+
+func (rt roundTripperFunc) RoundTrip(r *http.Request) (*http.Response, error) {
+	return rt(r)
+}
+
+type counter interface {
+	Inc()
+}
+
+// NewMissingSANRoundTripper returns a round tripper that increases the given counter
+// if the wrapped roundtripper returns an error indicating usage of legacy CN fields
+// or if the wrapped roundtripper response leaf certificate includes no SAN field.
+//
+// The counter is compatible both with native Prometheus and k8s metrics types.
+func NewMissingSANRoundTripper(rt http.RoundTripper, c counter) http.RoundTripper {
+	return roundTripperFunc(func(req *http.Request) (resp *http.Response, err error) {
+		resp, err = rt.RoundTrip(req)
+		if crypto.IsHostnameError(err) {
+			c.Inc()
+			return
+		}
+
+		if resp == nil || resp.TLS == nil || len(resp.TLS.PeerCertificates) == 0 {
+			return
+		}
+
+		// The first element is the leaf certificate.
+		if !crypto.CertHasSAN(resp.TLS.PeerCertificates[0]) {
+			c.Inc()
+		}
+
+		return
+	})
+}
diff --git a/pkg/transport/missing_san_roundtripper_test.go b/pkg/transport/missing_san_roundtripper_test.go
new file mode 100644
index 0000000000..465324f151
--- /dev/null
+++ b/pkg/transport/missing_san_roundtripper_test.go
@@ -0,0 +1,128 @@
+package transport
+
+import (
+	"crypto/rand"
+	"crypto/rsa"
+	"crypto/tls"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"math/big"
+	"net/http"
+	"testing"
+)
+
+type mockCounter int
+
+func (c *mockCounter) Inc() {
+	*c = *c + 1
+}
+
+func TestMissingSANRoundTripper(t *testing.T) {
+	for _, tc := range []struct {
+		name string
+
+		resp    *http.Response
+		respErr error
+
+		expectedCounts int
+		expectedErr    string
+	}{
+		{
+			name: "non tls response",
+			resp: &http.Response{},
+		},
+		{
+			name: "valid cert",
+			resp: &http.Response{
+				TLS: &tls.ConnectionState{
+					PeerCertificates: []*x509.Certificate{
+						newCert(t, &x509.Certificate{
+							Subject:      pkix.Name{CommonName: "foo.bar"},
+							SerialNumber: big.NewInt(1),
+							DNSNames:     []string{"foo.bar"},
+						})},
+				},
+			},
+			expectedCounts: 0,
+		},
+		{
+			name: "go 1.16: legacy cert verification error",
+			respErr: x509.HostnameError{
+				Certificate: newCert(t, &x509.Certificate{
+					Subject:      pkix.Name{CommonName: "foo.bar"},
+					SerialNumber: big.NewInt(1),
+				}),
+				Host: "foo.bar",
+			},
+			expectedErr:    "x509: certificate relies on legacy Common Name field, use SANs or temporarily enable Common Name matching with GODEBUG=x509ignoreCN=0",
+			expectedCounts: 1,
+		},
+		{
+			name: "go 1.16: invalid cert",
+			resp: &http.Response{
+				TLS: &tls.ConnectionState{
+					PeerCertificates: []*x509.Certificate{
+						newCert(t, &x509.Certificate{
+							Subject:      pkix.Name{CommonName: "foo.bar"},
+							SerialNumber: big.NewInt(1),
+						})},
+				},
+			},
+			expectedCounts: 1,
+		},
+		{
+			name: "invalid hostname",
+			respErr: x509.HostnameError{
+				Certificate: newCert(t, &x509.Certificate{
+					Subject:      pkix.Name{CommonName: "foo.bar"},
+					SerialNumber: big.NewInt(1),
+				}),
+				Host: "some.host",
+			},
+			expectedErr:    "x509: certificate is not valid for any names, but wanted to match some.host",
+			expectedCounts: 0,
+		},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			rt := roundTripperFunc(func(_ *http.Request) (*http.Response, error) {
+				return tc.resp, tc.respErr
+			})
+
+			var (
+				cnt    mockCounter
+				gotErr string
+			)
+			_, err := NewMissingSANRoundTripper(rt, &cnt).RoundTrip(nil)
+			if err != nil {
+				gotErr = err.Error()
+			}
+
+			if tc.expectedErr != gotErr {
+				t.Errorf("expected error %q, got %q", tc.expectedErr, gotErr)
+			}
+
+			if tc.expectedCounts != int(cnt) {
+				t.Errorf("expected %v counts, got %v", tc.expectedCounts, int(cnt))
+			}
+		})
+	}
+}
+
+func newCert(t *testing.T, template *x509.Certificate) *x509.Certificate {
+	pk, err := rsa.GenerateKey(rand.Reader, 2048)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	certBytes, err := x509.CreateCertificate(rand.Reader, template, template, &pk.PublicKey, pk)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	certs, err := x509.ParseCertificates(certBytes)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	return certs[0]
+}