diff --git a/caddyhttp/proxy/reverseproxy.go b/caddyhttp/proxy/reverseproxy.go
index d32be7cdb..021025a05 100644
--- a/caddyhttp/proxy/reverseproxy.go
+++ b/caddyhttp/proxy/reverseproxy.go
@@ -349,9 +349,14 @@ func newConnHijackerTransport(base http.RoundTripper) *connHijackerTransport {
 		MaxIdleConnsPerHost: -1,
 	}
 	if b, _ := base.(*http.Transport); b != nil {
+		tlsClientConfig := b.TLSClientConfig
+		if tlsClientConfig.NextProtos != nil {
+			tlsClientConfig = cloneTLSClientConfig(tlsClientConfig)
+			tlsClientConfig.NextProtos = nil
+		}
+
 		t.Proxy = b.Proxy
-		t.TLSClientConfig = cloneTLSClientConfig(b.TLSClientConfig)
-		t.TLSClientConfig.NextProtos = nil
+		t.TLSClientConfig = tlsClientConfig
 		t.TLSHandshakeTimeout = b.TLSHandshakeTimeout
 		t.Dial = b.Dial
 		t.DialTLS = b.DialTLS
@@ -363,19 +368,15 @@ func newConnHijackerTransport(base http.RoundTripper) *connHijackerTransport {
 
 	dial := getTransportDial(t)
 	dialTLS := getTransportDialTLS(t)
-
 	t.Dial = func(network, addr string) (net.Conn, error) {
 		c, err := dial(network, addr)
 		hj.Conn = c
 		return &hijackedConn{c, hj}, err
 	}
-
-	if dialTLS != nil {
-		t.DialTLS = func(network, addr string) (net.Conn, error) {
-			c, err := dialTLS(network, addr)
-			hj.Conn = c
-			return &hijackedConn{c, hj}, err
-		}
+	t.DialTLS = func(network, addr string) (net.Conn, error) {
+		c, err := dialTLS(network, addr)
+		hj.Conn = c
+		return &hijackedConn{c, hj}, err
 	}
 
 	return hj
@@ -390,27 +391,35 @@ func getTransportDial(t *http.Transport) func(network, addr string) (net.Conn, e
 	return defaultDialer.Dial
 }
 
-// getTransportDial returns a TLS Dialer if TLSClientConfig is non-nil
+// getTransportDial always returns a TLS Dialer
 // and defaults to the existing t.DialTLS.
 func getTransportDialTLS(t *http.Transport) func(network, addr string) (net.Conn, error) {
 	if t.DialTLS != nil {
 		return t.DialTLS
 	}
-	if t.TLSClientConfig == nil {
-		return nil
-	}
 
 	// newConnHijackerTransport will modify t.Dial after calling this method
 	// => Create a backup reference.
 	plainDial := getTransportDial(t)
 
+	// The following DialTLS implementation stems from the Go stdlib and
+	// is identical to what happens if DialTLS is not provided.
+	// Source: https://github.com/golang/go/blob/230a376b5a67f0e9341e1fa47e670ff762213c83/src/net/http/transport.go#L1018-L1051
 	return func(network, addr string) (net.Conn, error) {
 		plainConn, err := plainDial(network, addr)
 		if err != nil {
 			return nil, err
 		}
 
-		tlsConn := tls.Client(plainConn, t.TLSClientConfig)
+		tlsClientConfig := t.TLSClientConfig
+		if tlsClientConfig == nil {
+			tlsClientConfig = &tls.Config{}
+		}
+		if !tlsClientConfig.InsecureSkipVerify && tlsClientConfig.ServerName == "" {
+			tlsClientConfig.ServerName = stripPort(addr)
+		}
+
+		tlsConn := tls.Client(plainConn, tlsClientConfig)
 		errc := make(chan error, 2)
 		var timer *time.Timer
 		if d := t.TLSHandshakeTimeout; d != 0 {
@@ -429,16 +438,12 @@ func getTransportDialTLS(t *http.Transport) func(network, addr string) (net.Conn
 			plainConn.Close()
 			return nil, err
 		}
-		if !t.TLSClientConfig.InsecureSkipVerify {
-			serverName := t.TLSClientConfig.ServerName
-			if serverName == "" {
-				serverName = addr
-				idx := strings.LastIndex(serverName, ":")
-				if idx != -1 {
-					serverName = serverName[:idx]
-				}
+		if !tlsClientConfig.InsecureSkipVerify {
+			hostname := tlsClientConfig.ServerName
+			if hostname == "" {
+				hostname = stripPort(addr)
 			}
-			if err := tlsConn.VerifyHostname(serverName); err != nil {
+			if err := tlsConn.VerifyHostname(hostname); err != nil {
 				plainConn.Close()
 				return nil, err
 			}
@@ -448,6 +453,22 @@ func getTransportDialTLS(t *http.Transport) func(network, addr string) (net.Conn
 	}
 }
 
+// stripPort returns address without its port if it has one and
+// works with IP addresses as well as hostnames formatted as host:port.
+//
+// IPv6 addresses (excluding the port) must be enclosed in
+// square brackets similar to the requirements of Go's stdlib.
+func stripPort(address string) string {
+	// Keep in mind that the address might be a IPv6 address
+	// and thus contain a colon, but not have a port.
+	portIdx := strings.LastIndex(address, ":")
+	ipv6Idx := strings.LastIndex(address, "]")
+	if portIdx > ipv6Idx {
+		address = address[:portIdx]
+	}
+	return address
+}
+
 type tlsHandshakeTimeoutError struct{}
 
 func (tlsHandshakeTimeoutError) Timeout() bool   { return true }