diff --git a/internal/cli/doctor.go b/internal/cli/doctor.go
index 50876bd2c..bcbdfd238 100644
--- a/internal/cli/doctor.go
+++ b/internal/cli/doctor.go
@@ -2,6 +2,8 @@ package cli
 
 import (
 	"context"
+	"crypto/tls"
+	"crypto/x509"
 	"errors"
 	"fmt"
 	"maps"
@@ -66,6 +68,16 @@ var (
 	tplEFrontingDomain = template.Must(
 		template.New("").Parse("  ❌ {{ .address }}: {{ .error }}\n"),
 	)
+
+	tplOFrontingTLS = template.Must(
+		template.New("").Parse("  ✅ TLS certificate for {{ .host }} is valid\n"),
+	)
+	tplEFrontingTLS = template.Must(
+		template.New("").Parse("  ❌ TLS certificate for {{ .host }} is invalid: {{ .error }}\n"),
+	)
+	tplSFrontingTLS = template.Must(
+		template.New("").Parse("  ⏭ TLS certificate check skipped: proxy-protocol is enabled (the listener expects a PROXY header that mtg doctor does not send yet)\n"),
+	)
 )
 
 type Doctor struct {
@@ -339,13 +351,19 @@ func (d *Doctor) checkNetworkAddresses(ntw mtglib.Network, dc int, addresses []s
 }
 
 func (d *Doctor) checkFrontingDomain(ntw mtglib.Network) bool {
-	host := d.conf.Secret.Host
+	// SNI must always be the secret host: that is what domain fronting puts on
+	// the wire and what the certificate is issued for. The TCP target may be a
+	// different address when domain-fronting.host overrides it (in the
+	// sni-router setup it is an internal name like "web").
+	sniHost := d.conf.Secret.Host
+
+	dialHost := sniHost
 	if override := d.conf.GetDomainFrontingHost(); override != "" {
-		host = override
+		dialHost = override
 	}
 
 	port := d.conf.GetDomainFrontingPort(mtglib.DefaultDomainFrontingPort)
-	address := net.JoinHostPort(host, strconv.Itoa(int(port)))
+	address := net.JoinHostPort(dialHost, strconv.Itoa(int(port)))
 
 	ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
 	defer cancel()
@@ -367,9 +385,71 @@ func (d *Doctor) checkFrontingDomain(ntw mtglib.Network) bool {
 		"address": address,
 	})
 
+	// With proxy-protocol enabled the fronting listener expects a PROXY header
+	// before the TLS ClientHello, so a bare TLS handshake would hang or be
+	// rejected and report a misleading failure. mtg doctor does not emit that
+	// header yet, so skip the certificate probe rather than print a false
+	// negative. See issue #518.
+	if d.conf.GetDomainFrontingProxyProtocol(false) {
+		tplSFrontingTLS.Execute(os.Stdout, nil) //nolint: errcheck
+		return true
+	}
+
+	// A default crypto/tls client handshake against the fronting endpoint with
+	// ServerName = secret host validates the whole certificate in one shot:
+	// chain against the system roots, leaf SAN against the secret host, and
+	// validity period. An expired / untrusted / wrong-host certificate all
+	// surface as descriptive x509 errors.
+	if err := probeFrontingTLS(ctx, dialer, address, sniHost, nil); err != nil {
+		tplEFrontingTLS.Execute(os.Stdout, map[string]any{ //nolint: errcheck
+			"host":  sniHost,
+			"error": err,
+		})
+		return false
+	}
+
+	tplOFrontingTLS.Execute(os.Stdout, map[string]any{ //nolint: errcheck
+		"host": sniHost,
+	})
+
 	return true
 }
 
+// probeFrontingTLS dials dialAddress over TCP and performs a TLS handshake
+// presenting sniHost as the SNI / ServerName. Verification is left at the
+// crypto/tls default (InsecureSkipVerify=false), so the handshake fails with a
+// descriptive x509 error if the certificate chain is untrusted, the leaf SAN
+// does not cover sniHost, or the certificate is expired/not-yet-valid.
+//
+// rootCAs overrides the trust anchors; it is nil in production (system roots)
+// and is only set by tests that need a self-signed anchor.
+func probeFrontingTLS(
+	ctx context.Context,
+	dialer *net.Dialer,
+	dialAddress string,
+	sniHost string,
+	rootCAs *x509.CertPool,
+) error {
+	conn, err := dialer.DialContext(ctx, "tcp", dialAddress)
+	if err != nil {
+		return fmt.Errorf("cannot dial %s: %w", dialAddress, err)
+	}
+	defer conn.Close() //nolint: errcheck
+
+	if deadline, ok := ctx.Deadline(); ok {
+		conn.SetDeadline(deadline) //nolint: errcheck
+	}
+
+	tlsConn := tls.Client(conn, &tls.Config{
+		ServerName: sniHost,
+		RootCAs:    rootCAs,
+		MinVersion: tls.VersionTLS12,
+	})
+	defer tlsConn.Close() //nolint: errcheck
+
+	return tlsConn.HandshakeContext(ctx)
+}
+
 func (d *Doctor) checkSecretHost(resolver *net.Resolver, ntw mtglib.Network) bool {
 	res := runSNICheck(context.Background(), resolver, d.conf, ntw)
 
diff --git a/internal/cli/doctor_test.go b/internal/cli/doctor_test.go
new file mode 100644
index 000000000..129521a18
--- /dev/null
+++ b/internal/cli/doctor_test.go
@@ -0,0 +1,174 @@
+package cli
+
+import (
+	"context"
+	"crypto/ecdsa"
+	"crypto/elliptic"
+	"crypto/rand"
+	"crypto/tls"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"math/big"
+	"net"
+	"strings"
+	"testing"
+	"time"
+)
+
+// makeCert builds a self-signed leaf certificate valid for the supplied DNS
+// name (and IP, so dialing 127.0.0.1 still reaches the listener) plus a
+// matching tls.Config and an x509 pool that trusts it.
+func makeCert(t *testing.T, dnsName string, notAfter time.Time) (tls.Certificate, *x509.CertPool) {
+	t.Helper()
+
+	key, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
+	if err != nil {
+		t.Fatalf("generate key: %v", err)
+	}
+
+	tmpl := &x509.Certificate{
+		SerialNumber:          big.NewInt(1),
+		Subject:               pkix.Name{CommonName: dnsName},
+		NotBefore:             time.Now().Add(-time.Hour),
+		NotAfter:              notAfter,
+		KeyUsage:              x509.KeyUsageDigitalSignature | x509.KeyUsageCertSign,
+		ExtKeyUsage:           []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
+		BasicConstraintsValid: true,
+		IsCA:                  true,
+		DNSNames:              []string{dnsName},
+		IPAddresses:           []net.IP{net.IPv4(127, 0, 0, 1), net.IPv6loopback},
+	}
+
+	der, err := x509.CreateCertificate(rand.Reader, tmpl, tmpl, &key.PublicKey, key)
+	if err != nil {
+		t.Fatalf("create certificate: %v", err)
+	}
+
+	leaf, err := x509.ParseCertificate(der)
+	if err != nil {
+		t.Fatalf("parse certificate: %v", err)
+	}
+
+	pool := x509.NewCertPool()
+	pool.AddCert(leaf)
+
+	return tls.Certificate{Certificate: [][]byte{der}, PrivateKey: key, Leaf: leaf}, pool
+}
+
+// startTLSServer spins up a TLS listener that completes handshakes using cert
+// and returns its address. It is closed when the test finishes.
+func startTLSServer(t *testing.T, cert tls.Certificate) string {
+	t.Helper()
+
+	ln, err := tls.Listen("tcp", "127.0.0.1:0", &tls.Config{
+		Certificates: []tls.Certificate{cert},
+		MinVersion:   tls.VersionTLS12,
+	})
+	if err != nil {
+		t.Fatalf("listen: %v", err)
+	}
+
+	t.Cleanup(func() { _ = ln.Close() })
+
+	go func() {
+		for {
+			conn, err := ln.Accept()
+			if err != nil {
+				return
+			}
+
+			go func() {
+				// Drive the handshake so the client side completes, then drop.
+				if tc, ok := conn.(*tls.Conn); ok {
+					_ = tc.Handshake()
+				}
+				_ = conn.Close()
+			}()
+		}
+	}()
+
+	return ln.Addr().String()
+}
+
+func TestProbeFrontingTLS_ValidCert(t *testing.T) {
+	cert, pool := makeCert(t, "front.example.org", time.Now().Add(24*time.Hour))
+	addr := startTLSServer(t, cert)
+
+	ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+	defer cancel()
+
+	err := probeFrontingTLS(ctx, &net.Dialer{}, addr, "front.example.org", pool)
+	if err != nil {
+		t.Fatalf("expected success, got error: %v", err)
+	}
+}
+
+func TestProbeFrontingTLS_WrongHost(t *testing.T) {
+	// Cert is for front.example.org, but we verify against other.example.org.
+	cert, pool := makeCert(t, "front.example.org", time.Now().Add(24*time.Hour))
+	addr := startTLSServer(t, cert)
+
+	ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+	defer cancel()
+
+	err := probeFrontingTLS(ctx, &net.Dialer{}, addr, "other.example.org", pool)
+	if err == nil {
+		t.Fatal("expected SAN-mismatch failure, got success")
+	}
+	if !strings.Contains(err.Error(), "x509") {
+		t.Fatalf("expected x509 verification error, got: %v", err)
+	}
+}
+
+func TestProbeFrontingTLS_UntrustedCA(t *testing.T) {
+	// Server cert is self-signed; we hand the client an empty pool that does
+	// not trust it. Default verification must reject.
+	cert, _ := makeCert(t, "front.example.org", time.Now().Add(24*time.Hour))
+	addr := startTLSServer(t, cert)
+
+	ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+	defer cancel()
+
+	err := probeFrontingTLS(ctx, &net.Dialer{}, addr, "front.example.org", x509.NewCertPool())
+	if err == nil {
+		t.Fatal("expected untrusted-CA failure, got success")
+	}
+	if !strings.Contains(err.Error(), "x509") {
+		t.Fatalf("expected x509 verification error, got: %v", err)
+	}
+}
+
+func TestProbeFrontingTLS_ExpiredCert(t *testing.T) {
+	// Same trust anchor, but the cert is already expired.
+	cert, pool := makeCert(t, "front.example.org", time.Now().Add(-time.Hour))
+	addr := startTLSServer(t, cert)
+
+	ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+	defer cancel()
+
+	err := probeFrontingTLS(ctx, &net.Dialer{}, addr, "front.example.org", pool)
+	if err == nil {
+		t.Fatal("expected expiry failure, got success")
+	}
+	if !strings.Contains(err.Error(), "expired") {
+		t.Fatalf("expected expiry error, got: %v", err)
+	}
+}
+
+func TestProbeFrontingTLS_OverrideDialDifferentFromSNI(t *testing.T) {
+	// Domain-fronting override: dial one address (the listener bound to
+	// 127.0.0.1), but verify the cert against the secret host name. The cert
+	// is issued for the secret host, so verification must pass even though the
+	// dial target is a bare IP:port.
+	cert, pool := makeCert(t, "secret.example.org", time.Now().Add(24*time.Hour))
+	addr := startTLSServer(t, cert) // e.g. 127.0.0.1:NNNNN
+
+	ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+	defer cancel()
+
+	// dial-target (addr, an IP:port) != SNI (secret.example.org)
+	err := probeFrontingTLS(ctx, &net.Dialer{}, addr, "secret.example.org", pool)
+	if err != nil {
+		t.Fatalf("expected success when dialing override addr with secret-host SNI, got: %v", err)
+	}
+}