diff --git a/modules/caddyhttp/app.go b/modules/caddyhttp/app.go
index 64cc5401b..67f9d1d68 100644
--- a/modules/caddyhttp/app.go
+++ b/modules/caddyhttp/app.go
@@ -343,6 +343,11 @@ func (app *App) Start() error {
 				// enable TLS if there is a policy and if this is not the HTTP port
 				useTLS := len(srv.TLSConnPolicies) > 0 && int(listenAddr.StartPort+portOffset) != app.httpPort()
 				if useTLS {
+					// create HTTP redirect wrapper, which detects if
+					// the request had HTTP bytes on the HTTPS port, and
+					// triggers a redirect if so.
+					ln = &httpRedirectListener{Listener: ln}
+
 					// create TLS listener
 					tlsCfg := srv.TLSConnPolicies.TLSConfig(app.ctx)
 					ln = tls.NewListener(ln, tlsCfg)
diff --git a/modules/caddyhttp/httpredirectlistener.go b/modules/caddyhttp/httpredirectlistener.go
new file mode 100644
index 000000000..38225a3d2
--- /dev/null
+++ b/modules/caddyhttp/httpredirectlistener.go
@@ -0,0 +1,114 @@
+// Copyright 2015 Matthew Holt and The Caddy Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package caddyhttp
+
+import (
+	"bufio"
+	"fmt"
+	"net"
+	"net/http"
+	"sync"
+)
+
+// httpRedirectListener is listener that checks the first few bytes
+// of the request when the server is intended to accept HTTPS requests,
+// to respond to an HTTP request with a redirect.
+type httpRedirectListener struct {
+	net.Listener
+}
+
+// Accept waits for and returns the next connection to the listener,
+// wrapping it with a httpRedirectConn.
+func (l *httpRedirectListener) Accept() (net.Conn, error) {
+	c, err := l.Listener.Accept()
+	if err != nil {
+		return nil, err
+	}
+
+	return &httpRedirectConn{
+		Conn: c,
+		r:    bufio.NewReader(c),
+	}, nil
+}
+
+type httpRedirectConn struct {
+	net.Conn
+	once sync.Once
+	r    *bufio.Reader
+}
+
+// Read tries to peek at the first few bytes of the request, and if we get
+// an error reading the headers, and that error was due to the bytes looking
+// like an HTTP request, then we perform a HTTP->HTTPS redirect on the same
+// port as the original connection.
+func (c *httpRedirectConn) Read(p []byte) (int, error) {
+	var errReturn error
+	c.once.Do(func() {
+		firstBytes, err := c.r.Peek(5)
+		if err != nil {
+			return
+		}
+
+		// If the request doesn't look like HTTP, then it's probably
+		// TLS bytes and we don't need to do anything.
+		if !firstBytesLookLikeHTTP(firstBytes) {
+			return
+		}
+
+		// Parse the HTTP request, so we can get the Host and URL to redirect to.
+		req, err := http.ReadRequest(c.r)
+		if err != nil {
+			return
+		}
+
+		// Build the redirect response, using the same Host and URL,
+		// but replacing the scheme with https.
+		headers := make(http.Header)
+		headers.Add("Location", "https://"+req.Host+req.URL.String())
+		resp := &http.Response{
+			Proto:      "HTTP/1.0",
+			Status:     "308 Permanent Redirect",
+			StatusCode: 308,
+			ProtoMajor: 1,
+			ProtoMinor: 0,
+			Header:     headers,
+		}
+
+		err = resp.Write(c.Conn)
+		if err != nil {
+			errReturn = fmt.Errorf("couldn't write HTTP->HTTPS redirect")
+			return
+		}
+
+		errReturn = fmt.Errorf("redirected HTTP request on HTTPS port")
+		c.Conn.Close()
+	})
+
+	if errReturn != nil {
+		return 0, errReturn
+	}
+
+	return c.r.Read(p)
+}
+
+// firstBytesLookLikeHTTP reports whether a TLS record header
+// looks like it might've been a misdirected plaintext HTTP request.
+func firstBytesLookLikeHTTP(hdr []byte) bool {
+	switch string(hdr[:5]) {
+	case "GET /", "HEAD ", "POST ", "PUT /", "OPTIO":
+		return true
+	}
+	return false
+}