diff --git a/Documentation/ldap-connector.md b/Documentation/ldap-connector.md
index 9dd3e447..174e8486 100644
--- a/Documentation/ldap-connector.md
+++ b/Documentation/ldap-connector.md
@@ -30,20 +30,28 @@ connectors:
   name: LDAP
   config:
     # Host and optional port of the LDAP server in the form "host:port".
-    # If the port is not supplied, it will be guessed based on "insecureNoSSL".
-    # 389 for insecure connections, 636 otherwise.
+    # If the port is not supplied, it will be guessed based on "insecureNoSSL",
+    # and "startTLS" flags. 389 for insecure or StartTLS connections, 636
+    # otherwise.
     host: ldap.example.com:636
 
     # Following field is required if the LDAP host is not using TLS (port 389).
     # Because this option inherently leaks passwords to anyone on the same network
     # as dex, THIS OPTION MAY BE REMOVED WITHOUT WARNING IN A FUTURE RELEASE.
+    #
     # insecureNoSSL: true
 
     # If a custom certificate isn't provide, this option can be used to turn on
     # TLS certificate checks. As noted, it is insecure and shouldn't be used outside
     # of explorative phases.
+    #
     # insecureSkipVerify: true
 
+    # When connecting to the server, connect using the ldap:// protocol then issue
+    # a StartTLS command. If unspecified, connections will use the ldaps:// protocol
+    #
+    # startTLS: true
+
     # Path to a trusted root certificate file. Default: use the host's root CA.
     rootCA: /etc/dex/ldap.ca
 
diff --git a/connector/ldap/gen-certs.sh b/connector/ldap/gen-certs.sh
new file mode 100755
index 00000000..8b0ea49b
--- /dev/null
+++ b/connector/ldap/gen-certs.sh
@@ -0,0 +1,49 @@
+#!/bin/bash -e
+
+# Stolen from the coreos/matchbox repo.
+
+echo "
+[req]
+req_extensions = v3_req
+distinguished_name = req_distinguished_name
+
+[req_distinguished_name]
+
+[ v3_req ]
+basicConstraints = CA:FALSE
+keyUsage = nonRepudiation, digitalSignature, keyEncipherment
+subjectAltName = @alt_names
+
+[alt_names]
+DNS.101 = localhost
+" > openssl.config
+
+openssl genrsa -out testdata/ca.key 2048
+openssl genrsa -out testdata/server.key 2048
+
+openssl req \
+    -x509 -new -nodes \
+    -key testdata/ca.key \
+    -days 10000 -out testdata/ca.crt \
+    -subj "/CN=ldap-tests"
+
+openssl req \
+	-new \
+	-key testdata/server.key \
+	-out testdata/server.csr \
+	-subj "/CN=localhost" \
+	-config openssl.config
+
+openssl x509 -req \
+	-in testdata/server.csr \
+	-CA testdata/ca.crt \
+	-CAkey testdata/ca.key \
+	-CAcreateserial \
+	-out testdata/server.crt \
+	-days 10000 \
+	-extensions v3_req \
+	-extfile openssl.config
+
+rm testdata/server.csr
+rm testdata/ca.srl
+rm openssl.config
diff --git a/connector/ldap/ldap.go b/connector/ldap/ldap.go
index 01c8f922..8f541c5e 100644
--- a/connector/ldap/ldap.go
+++ b/connector/ldap/ldap.go
@@ -61,6 +61,11 @@ type Config struct {
 	// Don't verify the CA.
 	InsecureSkipVerify bool `json:"insecureSkipVerify"`
 
+	// Connect to the insecure port then issue a StartTLS command to negotiate a
+	// secure connection. If unsupplied secure connections will use the LDAPS
+	// protocol.
+	StartTLS bool `json:"startTLS"`
+
 	// Path to a trusted root certificate file.
 	RootCA string `json:"rootCA"`
 
@@ -238,9 +243,18 @@ func (c *ldapConnector) do(ctx context.Context, f func(c *ldap.Conn) error) erro
 		conn *ldap.Conn
 		err  error
 	)
-	if c.InsecureNoSSL {
+	switch {
+	case c.InsecureNoSSL:
 		conn, err = ldap.Dial("tcp", c.Host)
-	} else {
+	case c.StartTLS:
+		conn, err = ldap.Dial("tcp", c.Host)
+		if err != nil {
+			return fmt.Errorf("failed to connect: %v", err)
+		}
+		if err := conn.StartTLS(c.tlsConfig); err != nil {
+			return fmt.Errorf("start TLS failed: %v", err)
+		}
+	default:
 		conn, err = ldap.DialTLS("tcp", c.Host, c.tlsConfig)
 	}
 	if err != nil {
diff --git a/connector/ldap/ldap_test.go b/connector/ldap/ldap_test.go
index 9e78c346..cd4d69ee 100644
--- a/connector/ldap/ldap_test.go
+++ b/connector/ldap/ldap_test.go
@@ -21,6 +21,15 @@ import (
 
 const envVar = "DEX_LDAP_TESTS"
 
+// connectionMethod indicates how the test should connect to the LDAP server.
+type connectionMethod int32
+
+const (
+	connectStartTLS connectionMethod = iota
+	connectLDAPS
+	connectLDAP
+)
+
 // subtest is a login test against a given schema.
 type subtest struct {
 	// Name of the sub-test.
@@ -110,7 +119,7 @@ userpassword: bar
 		},
 	}
 
-	runTests(t, schema, c, tests)
+	runTests(t, schema, connectLDAP, c, tests)
 }
 
 func TestGroupQuery(t *testing.T) {
@@ -198,7 +207,7 @@ member: cn=jane,ou=People,dc=example,dc=org
 		},
 	}
 
-	runTests(t, schema, c, tests)
+	runTests(t, schema, connectLDAP, c, tests)
 }
 
 func TestGroupsOnUserEntity(t *testing.T) {
@@ -295,7 +304,93 @@ gidNumber: 1002
 			},
 		},
 	}
-	runTests(t, schema, c, tests)
+	runTests(t, schema, connectLDAP, c, tests)
+}
+
+func TestStartTLS(t *testing.T) {
+	schema := `
+dn: dc=example,dc=org
+objectClass: dcObject
+objectClass: organization
+o: Example Company
+dc: example
+
+dn: ou=People,dc=example,dc=org
+objectClass: organizationalUnit
+ou: People
+
+dn: cn=jane,ou=People,dc=example,dc=org
+objectClass: person
+objectClass: inetOrgPerson
+sn: doe
+cn: jane
+mail: janedoe@example.com
+userpassword: foo
+`
+	c := &Config{}
+	c.UserSearch.BaseDN = "ou=People,dc=example,dc=org"
+	c.UserSearch.NameAttr = "cn"
+	c.UserSearch.EmailAttr = "mail"
+	c.UserSearch.IDAttr = "DN"
+	c.UserSearch.Username = "cn"
+
+	tests := []subtest{
+		{
+			name:     "validpassword",
+			username: "jane",
+			password: "foo",
+			want: connector.Identity{
+				UserID:        "cn=jane,ou=People,dc=example,dc=org",
+				Username:      "jane",
+				Email:         "janedoe@example.com",
+				EmailVerified: true,
+			},
+		},
+	}
+	runTests(t, schema, connectStartTLS, c, tests)
+}
+
+func TestLDAPS(t *testing.T) {
+	schema := `
+dn: dc=example,dc=org
+objectClass: dcObject
+objectClass: organization
+o: Example Company
+dc: example
+
+dn: ou=People,dc=example,dc=org
+objectClass: organizationalUnit
+ou: People
+
+dn: cn=jane,ou=People,dc=example,dc=org
+objectClass: person
+objectClass: inetOrgPerson
+sn: doe
+cn: jane
+mail: janedoe@example.com
+userpassword: foo
+`
+	c := &Config{}
+	c.UserSearch.BaseDN = "ou=People,dc=example,dc=org"
+	c.UserSearch.NameAttr = "cn"
+	c.UserSearch.EmailAttr = "mail"
+	c.UserSearch.IDAttr = "DN"
+	c.UserSearch.Username = "cn"
+
+	tests := []subtest{
+		{
+			name:     "validpassword",
+			username: "jane",
+			password: "foo",
+			want: connector.Identity{
+				UserID:        "cn=jane,ou=People,dc=example,dc=org",
+				Username:      "jane",
+				Email:         "janedoe@example.com",
+				EmailVerified: true,
+			},
+		},
+	}
+	runTests(t, schema, connectLDAPS, c, tests)
 }
 
 // runTests runs a set of tests against an LDAP schema. It does this by
@@ -305,7 +400,7 @@ gidNumber: 1002
 // machine's PATH.
 //
 // The DEX_LDAP_TESTS must be set to "1"
-func runTests(t *testing.T, schema string, config *Config, tests []subtest) {
+func runTests(t *testing.T, schema string, connMethod connectionMethod, config *Config, tests []subtest) {
 	if os.Getenv(envVar) != "1" {
 		t.Skipf("%s not set. Skipping test (run 'export %s=1' to run tests)", envVar, envVar)
 	}
@@ -316,6 +411,11 @@ func runTests(t *testing.T, schema string, config *Config, tests []subtest) {
 		}
 	}
 
+	wd, err := os.Getwd()
+	if err != nil {
+		t.Fatal(err)
+	}
+
 	tempDir, err := ioutil.TempDir("", "")
 	if err != nil {
 		t.Fatal(err)
@@ -324,7 +424,13 @@ func runTests(t *testing.T, schema string, config *Config, tests []subtest) {
 
 	configBytes := new(bytes.Buffer)
 
-	if err := slapdConfigTmpl.Execute(configBytes, tmplData{tempDir, includes(t)}); err != nil {
+	data := tmplData{
+		TempDir:  tempDir,
+		Includes: includes(t, wd),
+	}
+	data.TLSCertPath, data.TLSKeyPath = tlsAssets(t, wd)
+
+	if err := slapdConfigTmpl.Execute(configBytes, data); err != nil {
 		t.Fatal(err)
 	}
 
@@ -344,7 +450,7 @@ func runTests(t *testing.T, schema string, config *Config, tests []subtest) {
 	cmd := exec.Command(
 		"slapd",
 		"-d", "any",
-		"-h", "ldap://localhost:10363/ ldaps://localhost:10636/ ldapi://"+socketPath,
+		"-h", "ldap://localhost:10389/ ldaps://localhost:10636/ ldapi://"+socketPath,
 		"-f", configPath,
 	)
 	cmd.Stdout = slapdOut
@@ -385,18 +491,30 @@ func runTests(t *testing.T, schema string, config *Config, tests []subtest) {
 		wg.Wait()
 	}()
 
-	// Wait for slapd to come up.
-	time.Sleep(100 * time.Millisecond)
+	// Try a few times to connect to the LDAP server. On slower machines
+	// it can take a while for it to come up.
+	connected := false
+	wait := 100 * time.Millisecond
+	for i := 0; i < 5; i++ {
+		time.Sleep(wait)
 
-	ldapadd := exec.Command(
-		"ldapadd", "-x",
-		"-D", "cn=admin,dc=example,dc=org",
-		"-w", "admin",
-		"-f", schemaPath,
-		"-H", "ldap://localhost:10363/",
-	)
-	if out, err := ldapadd.CombinedOutput(); err != nil {
-		t.Errorf("ldapadd: %s", out)
+		ldapadd := exec.Command(
+			"ldapadd", "-x",
+			"-D", "cn=admin,dc=example,dc=org",
+			"-w", "admin",
+			"-f", schemaPath,
+			"-H", "ldap://localhost:10389/",
+		)
+		if out, err := ldapadd.CombinedOutput(); err != nil {
+			t.Logf("ldapadd: %s", out)
+			wait = wait * 2 // backoff
+			continue
+		}
+		connected = true
+		break
+	}
+	if !connected {
+		t.Errorf("ldapadd command failed")
 		return
 	}
 
@@ -405,8 +523,19 @@ func runTests(t *testing.T, schema string, config *Config, tests []subtest) {
 
 	// We need to configure host parameters but don't want to overwrite user or
 	// group search configuration.
-	c.Host = "localhost:10363"
-	c.InsecureNoSSL = true
+	switch connMethod {
+	case connectStartTLS:
+		c.Host = "localhost:10389"
+		c.RootCA = "testdata/ca.crt"
+		c.StartTLS = true
+	case connectLDAPS:
+		c.Host = "localhost:10636"
+		c.RootCA = "testdata/ca.crt"
+	case connectLDAP:
+		c.Host = "localhost:10389"
+		c.InsecureNoSSL = true
+	}
+
 	c.BindDN = "cn=admin,dc=example,dc=org"
 	c.BindPW = "admin"
 
@@ -488,10 +617,16 @@ type tmplData struct {
 	TempDir string
 	// List of schema files to include.
 	Includes []string
+	// TLS assets for LDAPS.
+	TLSKeyPath  string
+	TLSCertPath string
 }
 
 // Config template copied from:
 // http://www.zytrax.com/books/ldap/ch5/index.html#step1-slapd
+//
+// TLS instructions found here:
+// http://www.openldap.org/doc/admin24/tls.html
 var slapdConfigTmpl = template.Must(template.New("").Parse(`
 {{ range $i, $include := .Includes }}
 include {{ $include }}
@@ -511,6 +646,9 @@ rootpw admin
 # change path as necessary
 directory	{{ .TempDir }}
 
+TLSCertificateFile {{ .TLSCertPath }}
+TLSCertificateKeyFile {{ .TLSKeyPath }}
+
 # Indices to maintain for this directory
 # unique id so equality match only
 index	uid	eq
@@ -534,11 +672,18 @@ cachesize 10000
 checkpoint 128 15
 `))
 
-func includes(t *testing.T) (paths []string) {
-	wd, err := os.Getwd()
-	if err != nil {
-		t.Fatalf("getting working directory: %v", err)
+func tlsAssets(t *testing.T, wd string) (certPath, keyPath string) {
+	certPath = filepath.Join(wd, "testdata", "server.crt")
+	keyPath = filepath.Join(wd, "testdata", "server.key")
+	for _, p := range []string{certPath, keyPath} {
+		if _, err := os.Stat(p); err != nil {
+			t.Fatalf("failed to find TLS asset file: %s %v", p, err)
+		}
 	}
+	return
+}
+
+func includes(t *testing.T, wd string) (paths []string) {
 	for _, f := range includeFiles {
 		p := filepath.Join(wd, "testdata", f)
 		if _, err := os.Stat(p); err != nil {
diff --git a/connector/ldap/testdata/ca.crt b/connector/ldap/testdata/ca.crt
new file mode 100644
index 00000000..1bfd9697
--- /dev/null
+++ b/connector/ldap/testdata/ca.crt
@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----
+MIIC/TCCAeWgAwIBAgIJAIrt+AlVUsXKMA0GCSqGSIb3DQEBCwUAMBUxEzARBgNV
+BAMMCmxkYXAtdGVzdHMwHhcNMTcwNDEyMjAxNzI5WhcNNDQwODI4MjAxNzI5WjAV
+MRMwEQYDVQQDDApsZGFwLXRlc3RzMIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIB
+CgKCAQEAzKJkt2WsALUDA3tQsedx7UJKIxis05+dU5FbBxf/BMSch8gCNh/cWErH
+IDljWGwLKbc9UefIz3BzbcNBPLgLGMp7t9Pf9HCBNf7lShLZB2BEGpgpCpd0urox
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+2xBbV4rf5FNvYaE2Bg0wHwYDVR0jBBgwFoAUnfj9sAq42xBbV4rf5FNvYaE2Bg0w
+DAYDVR0TBAUwAwEB/zANBgkqhkiG9w0BAQsFAAOCAQEAFGnBH1qpLJLvrLWKNI5w
+u8pFYO3RGqmfJ3BGf60MQxdUaTIUNQxPfPATbth7t8GRJwpWESRDlaXWq9fM9rkt
+fbmuqjAMGTFloNd9ra6e2F0CKjwZWcn/3eG/mVw/5d1Ku9Ow8luKrZuzNzVJd13r
+hoNc1wYXN0pHWkNiRUuR/E4fE/sn+tYOpJ4XYQvKAcSrNrq8m5O9VG5gLvlTeNno
+6q9hBy+5XKYUdHlzbAGm9QL0e1R45Mu4qxcFluKEmzS1rXlLsLs4/pqHgreXlYgL
+f7K0cFvaJGnFRKaxa6Bpf1EPNtqSc/pQZh01Ww8CUu1xh2+5KufgJQjAHVG3a1ow
+dQ==
+-----END CERTIFICATE-----
diff --git a/connector/ldap/testdata/ca.key b/connector/ldap/testdata/ca.key
new file mode 100644
index 00000000..551bd7f2
--- /dev/null
+++ b/connector/ldap/testdata/ca.key
@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----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++jKKAQXmzZzRMYLMLsWDoQKBgAnrCcoyX5VivG7ka9jqlhQcmdBxFAt7KYkj1ZDM
+Ud6U7qIRcYIEUd95JbNl4jzhj0WEtAqGIfWhgUvE9ADzQAiWQLt+1v9ii9lwGFe0
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+FYI3AoGBAMacjjbPjjfOXxBRhRz1rEDTrIStDj5KM4fgslKVGysqpH/mw7gSC8SK
+qn0anL2s3SAe9PQpOzM3pFFRZx4XMOk4ojYRZtp3FjPFDRnYuYzkfkbU7eV04awO
+6nrua8KNLNK+ir9iCi46tP6Zr3F81zWGUoVArVUgCRDbA9e0swB0
+-----END RSA PRIVATE KEY-----
diff --git a/connector/ldap/testdata/server.crt b/connector/ldap/testdata/server.crt
new file mode 100644
index 00000000..a4b8358f
--- /dev/null
+++ b/connector/ldap/testdata/server.crt
@@ -0,0 +1,18 @@
+-----BEGIN CERTIFICATE-----
+MIIC3DCCAcSgAwIBAgIJANsmsx7hUWnHMA0GCSqGSIb3DQEBCwUAMBUxEzARBgNV
+BAMMCmxkYXAtdGVzdHMwHhcNMTcwNDEyMjAxNzI5WhcNNDQwODI4MjAxNzI5WjAU
+MRIwEAYDVQQDDAlsb2NhbGhvc3QwggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEK
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+BAQDAgXgMBQGA1UdEQQNMAuCCWxvY2FsaG9zdDANBgkqhkiG9w0BAQsFAAOCAQEA
+RZp/fNjoQNaO6KW0Ay0aaPW6jPrcqGjzFgeIXaw/0UaWm5jhptWtjOAILV+afIrd
+4cKDg65o4xRdQYYbqmutFMAO/DeyDyMi3IL60qk0osipPDIORx5Ai2ZBQvUsGtwV
+np9UwQGNO5AGeR9N5kndyldbpxaIJFhsKOV8uRSi+4PRbMH3G0kJIX6wwZU4Ri/k
+3lWJQfqULH0vtMQCWSJuaYHxWYFq4AM+H/zpLwg1WG2eKVgSMWotxMRi5LOFSBbG
+XuOxAb0SNBcXl6kjRYbQyHBxIJMsB1lk64g7dTJqXuYFUwmIGL/vTr6PL6EKYk65
+/aWO8cvwXOrYaf9umgcqvg==
+-----END CERTIFICATE-----
diff --git a/connector/ldap/testdata/server.key b/connector/ldap/testdata/server.key
new file mode 100644
index 00000000..20fd6520
--- /dev/null
+++ b/connector/ldap/testdata/server.key
@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEpAIBAAKCAQEA5VhguV/01oMrBIpjO59IUpF0QiE8ABcShtAuBHqaZi+NgwXI
+0GtMaxJURYeexAWZbW0n70zAwWQMoceaGSqBEw38MuYxc3+C+D2s0pL35+Klpgp6
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+CPk1BRPhAoGBAPf8TMTr+l8MHRuVXEx52E1dBH46ZB8bMfvwb7cZ31Fn0EEmygCj
+wP9eKZ8MKmHVBbU6CbxYQMICTTwRrw9H0tNoaZBwzWMz/JDHcACfsPKtfrX8T4UQ
+wmVwbLctdC1Cbaxn1jYeSLoLfSe8IGPDnLpsMCzpRcQIgPS+gO69zr8vAoGBAOzB
+254TKd2OQPnvUvmAVYGRYyTu/+ShH9fZyDJYtjhQbuxt6eqh3poneWJOW+KPlqDd
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++TZ6MDU/eyJRq7Mc5SQrssziJidS3cU21b560xvLAoGBAPYpZY9Ia7Uz0iUSY5eq
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+KVyRIuiYNmgOXGpaFpMXSw718N4U7jWW7lqUxK2rvEupFhaL52oJFQ==
+-----END RSA PRIVATE KEY-----