health, net/tlsdial: add healthcheck for self-signed cert

When we make a connection to a server, we previously would verify with
the system roots, and then fall back to verifying with our baked-in
Let's Encrypt root if the system root cert verification failed.

We now explicitly check for, and log a health error on, self-signed
certificates. Additionally, we now always verify against our baked-in
Let's Encrypt root certificate and log an error if that isn't
successful. We don't consider this a health failure, since if we ever
change our server certificate issuer in the future older non-updated
versions of Tailscale will no longer be healthy despite being able to
connect.

Updates #3198

Change-Id: I00be5ceb8afee544ee795e3c7a2815476abc4abf
Signed-off-by: Andrew Dunham <andrew@du.nham.ca>

cmd/derper/depaware.txt

@@ -34,6 +34,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         tailscale.com/derp/derphttp                                  from tailscale.com/cmd/derper
         tailscale.com/disco                                          from tailscale.com/derp
         tailscale.com/envknob                                        from tailscale.com/derp+
+        tailscale.com/health                                         from tailscale.com/net/tlsdial
         tailscale.com/hostinfo                                       from tailscale.com/net/interfaces+
         tailscale.com/ipn                                            from tailscale.com/client/tailscale
         tailscale.com/ipn/ipnstate                                   from tailscale.com/client/tailscale+
@@ -81,6 +82,8 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         tailscale.com/util/httpm                                     from tailscale.com/client/tailscale
         tailscale.com/util/lineread                                  from tailscale.com/hostinfo+
         tailscale.com/util/mak                                       from tailscale.com/syncs
+        tailscale.com/util/multierr                                  from tailscale.com/health
+        tailscale.com/util/set                                       from tailscale.com/health
         tailscale.com/util/singleflight                              from tailscale.com/net/dnscache
         tailscale.com/util/vizerror                                  from tailscale.com/tsweb
    W 💣 tailscale.com/util/winutil                                   from tailscale.com/hostinfo+

cmd/tailscale/depaware.txt

@@ -57,6 +57,7 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
         tailscale.com/derp/derphttp                                  from tailscale.com/net/netcheck
         tailscale.com/disco                                          from tailscale.com/derp
         tailscale.com/envknob                                        from tailscale.com/cmd/tailscale/cli+
+        tailscale.com/health                                         from tailscale.com/net/tlsdial
         tailscale.com/health/healthmsg                               from tailscale.com/cmd/tailscale/cli
         tailscale.com/hostinfo                                       from tailscale.com/net/interfaces+
         tailscale.com/ipn                                            from tailscale.com/cmd/tailscale/cli+
@@ -111,9 +112,10 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
         tailscale.com/util/httpm                                     from tailscale.com/client/tailscale
         tailscale.com/util/lineread                                  from tailscale.com/net/interfaces+
         tailscale.com/util/mak                                       from tailscale.com/net/netcheck+
-        tailscale.com/util/multierr                                  from tailscale.com/control/controlhttp
+        tailscale.com/util/multierr                                  from tailscale.com/control/controlhttp+
         tailscale.com/util/must                                      from tailscale.com/cmd/tailscale/cli
         tailscale.com/util/quarantine                                from tailscale.com/cmd/tailscale/cli
+        tailscale.com/util/set                                       from tailscale.com/health
         tailscale.com/util/singleflight                              from tailscale.com/net/dnscache
      💣 tailscale.com/util/winutil                                   from tailscale.com/hostinfo+
         tailscale.com/version                                        from tailscale.com/cmd/tailscale/cli+

health/health.go

@@ -48,6 +48,7 @@
 	controlHealth           []string
 	lastLoginErr            error
 	localLogConfigErr       error
+	tlsConnectionErrors     = map[string]error{} // map[ServerName]error
 )
 
 // Subsystem is the name of a subsystem whose health can be monitored.
@@ -209,6 +210,18 @@ func SetLocalLogConfigHealth(err error) {
 	localLogConfigErr = err
 }
 
+// SetTLSConnectionError sets the error state for connections to a specific
+// host. Setting the error to nil will clear any previously-set error.
+func SetTLSConnectionError(host string, err error) {
+	mu.Lock()
+	defer mu.Unlock()
+	if err == nil {
+		delete(tlsConnectionErrors, host)
+	} else {
+		tlsConnectionErrors[host] = err
+	}
+}
+
 func RegisterDebugHandler(typ string, h http.Handler) {
 	mu.Lock()
 	defer mu.Unlock()
@@ -476,6 +489,9 @@ func overallErrorLocked() error {
 	if err := envknob.ApplyDiskConfigError(); err != nil {
 		errs = append(errs, err)
 	}
+	for serverName, err := range tlsConnectionErrors {
+		errs = append(errs, fmt.Errorf("TLS connection error for %q: %w", serverName, err))
+	}
 	if e := fakeErrForTesting(); len(errs) == 0 && e != "" {
 		return errors.New(e)
 	}

net/tlsdial/tlsdial.go

@@ -11,9 +11,11 @@
 package tlsdial
 
 import (
+	"bytes"
 	"crypto/tls"
 	"crypto/x509"
 	"errors"
+	"fmt"
 	"log"
 	"os"
 	"sync"
@@ -21,6 +23,7 @@
 	"time"
 
 	"tailscale.com/envknob"
+	"tailscale.com/health"
 )
 
 var counterFallbackOK int32 // atomic
@@ -33,6 +36,11 @@
 
 var debug = envknob.RegisterBool("TS_DEBUG_TLS_DIAL")
 
+// tlsdialWarningPrinted tracks whether we've printed a warning about a given
+// hostname already, to avoid log spam for users with custom DERP servers,
+// Headscale, etc.
+var tlsdialWarningPrinted sync.Map // map[string]bool
+
 // Config returns a tls.Config for connecting to a server.
 // If base is non-nil, it's cloned as the base config before
 // being configured and returned.
@@ -66,6 +74,16 @@ func Config(host string, base *tls.Config) *tls.Config {
 	// (with the baked-in fallback root) in the VerifyConnection hook.
 	conf.InsecureSkipVerify = true
 	conf.VerifyConnection = func(cs tls.ConnectionState) error {
+		// Perform some health checks on this certificate before we do
+		// any verification.
+		if certIsSelfSigned(cs.PeerCertificates[0]) {
+			// Self-signed certs are never valid.
+			health.SetTLSConnectionError(cs.ServerName, fmt.Errorf("certificate is self-signed"))
+		} else {
+			// Ensure we clear any error state for this ServerName.
+			health.SetTLSConnectionError(cs.ServerName, nil)
+		}
+
 		// First try doing x509 verification with the system's
 		// root CA pool.
 		opts := x509.VerifyOptions{
@@ -79,18 +97,27 @@ func Config(host string, base *tls.Config) *tls.Config {
 		if debug() {
 			log.Printf("tlsdial(sys %q): %v", host, errSys)
 		}
-		if errSys == nil {
+
-			return nil
+		// Always verify with our baked-in Let's Encrypt certificate,
+		// so we can log an informational message. This is useful for
+		// detecting SSL MiTM.
+		opts.Roots = bakedInRoots()
+		_, bakedErr := cs.PeerCertificates[0].Verify(opts)
+		if debug() {
+			log.Printf("tlsdial(bake %q): %v", host, bakedErr)
+		} else if bakedErr != nil {
+			if _, loaded := tlsdialWarningPrinted.LoadOrStore(host, true); !loaded {
+				if errSys == nil {
+					log.Printf("tlsdial: warning: server cert for %q is not a Let's Encrypt cert", host)
+				} else {
+					log.Printf("tlsdial: error: server cert for %q failed to verify and is not a Let's Encrypt cert", host)
+				}
+			}
 		}
 
-		// If that failed, because the system's CA roots are old
+		if errSys == nil {
-		// or broken, fall back to trying LetsEncrypt at least.
+			return nil
-		opts.Roots = bakedInRoots()
+		} else if bakedErr == nil {
-		_, err := cs.PeerCertificates[0].Verify(opts)
-		if debug() {
-			log.Printf("tlsdial(bake %q): %v", host, err)
-		}
-		if err == nil {
 			atomic.AddInt32(&counterFallbackOK, 1)
 			return nil
 		}
@@ -99,6 +126,12 @@ func Config(host string, base *tls.Config) *tls.Config {
 	return conf
 }
 
+func certIsSelfSigned(cert *x509.Certificate) bool {
+	// A certificate is determined to be self-signed if the certificate's
+	// subject is the same as its issuer.
+	return bytes.Equal(cert.RawSubject, cert.RawIssuer)
+}
+
 // SetConfigExpectedCert modifies c to expect and verify that the server returns
 // a certificate for the provided certDNSName.
 //