diff --git a/Misc/NEWS b/Misc/NEWS
index 980cd69..a619192 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -40,6 +40,11 @@
 Library
 -------
 
+- Issue #8108: Fix the unwrap() method of SSL objects when the socket has
+  a non-infinite timeout.  Also make that method friendlier with applications
+  wanting to continue using the socket in clear-text mode, by disabling
+  OpenSSL's internal readahead.  Thanks to Darryl Miles for guidance.
+
 - Issue #8468: bz2.BZ2File() accepts str with surrogates and bytes filenames
 
 - Issue #8496: make mailcap.lookup() always return a list, rather than an
diff --git a/Modules/_ssl.c b/Modules/_ssl.c
index 5311f77..5e0f473 100644
--- a/Modules/_ssl.c
+++ b/Modules/_ssl.c
@@ -9,6 +9,9 @@
    directly.
 
    XXX should partial writes be enabled, SSL_MODE_ENABLE_PARTIAL_WRITE?
+
+   XXX integrate several "shutdown modes" as suggested in
+       http://bugs.python.org/issue8108#msg102867 ?
 */
 
 #include "Python.h"
@@ -116,6 +119,7 @@
 	SSL_CTX*	ctx;
 	SSL*		ssl;
 	X509*		peer_cert;
+	int		shutdown_seen_zero;
 
 } PySSLObject;
 
@@ -1377,7 +1381,8 @@
 
 static PyObject *PySSL_SSLshutdown(PySSLObject *self)
 {
-	int err;
+	int err, ssl_err, sockstate, nonblocking;
+	int zeros = 0;
         PySocketSockObject *sock
           = (PySocketSockObject *) PyWeakref_GetObject(self->Socket);
 
@@ -1388,13 +1393,65 @@
                 return NULL;
         }
 
-	PySSL_BEGIN_ALLOW_THREADS
-	err = SSL_shutdown(self->ssl);
-	if (err == 0) {
-		/* we need to call it again to finish the shutdown */
+        /* Just in case the blocking state of the socket has been changed */
+	nonblocking = (sock->sock_timeout >= 0.0);
+	BIO_set_nbio(SSL_get_rbio(self->ssl), nonblocking);
+	BIO_set_nbio(SSL_get_wbio(self->ssl), nonblocking);
+
+	while (1) {
+		PySSL_BEGIN_ALLOW_THREADS
+		/* Disable read-ahead so that unwrap can work correctly.
+		 * Otherwise OpenSSL might read in too much data,
+		 * eating clear text data that happens to be
+		 * transmitted after the SSL shutdown.
+		 * Should be safe to call repeatedly everytime this
+		 * function is used and the shutdown_seen_zero != 0
+		 * condition is met.
+		 */
+		if (self->shutdown_seen_zero)
+			SSL_set_read_ahead(self->ssl, 0);
 		err = SSL_shutdown(self->ssl);
+		PySSL_END_ALLOW_THREADS
+		/* If err == 1, a secure shutdown with SSL_shutdown() is complete */
+		if (err > 0)
+			break;
+		if (err == 0) {
+			/* Don't loop endlessly; instead preserve legacy
+			   behaviour of trying SSL_shutdown() only twice.
+			   This looks necessary for OpenSSL < 0.9.8m */
+			if (++zeros > 1)
+				break;
+			/* Shutdown was sent, now try receiving */
+			self->shutdown_seen_zero = 1;
+			continue;
+		}
+
+		/* Possibly retry shutdown until timeout or failure */
+		ssl_err = SSL_get_error(self->ssl, err);
+		if (ssl_err == SSL_ERROR_WANT_READ)
+			sockstate = check_socket_and_wait_for_timeout(sock, 0);
+		else if (ssl_err == SSL_ERROR_WANT_WRITE)
+			sockstate = check_socket_and_wait_for_timeout(sock, 1);
+		else
+			break;
+		if (sockstate == SOCKET_HAS_TIMED_OUT) {
+			if (ssl_err == SSL_ERROR_WANT_READ)
+				PyErr_SetString(PySSLErrorObject,
+		                                "The read operation timed out");
+			else
+				PyErr_SetString(PySSLErrorObject,
+		                                "The write operation timed out");
+			return NULL;
+		}
+		else if (sockstate == SOCKET_TOO_LARGE_FOR_SELECT) {
+			PyErr_SetString(PySSLErrorObject,
+	                                "Underlying socket too large for select().");
+			return NULL;
+		}
+		else if (sockstate != SOCKET_OPERATION_OK)
+			/* Retain the SSL error code */
+			break;
 	}
-	PySSL_END_ALLOW_THREADS
 
 	if (err < 0)
 		return PySSL_SetError(self, err, __FILE__, __LINE__);