diff --git a/test/regress_ssl.c b/test/regress_ssl.c
index c772de21..5872c729 100644
--- a/test/regress_ssl.c
+++ b/test/regress_ssl.c
@@ -43,6 +43,7 @@
 #include "event2/util.h"
 #include "event2/event.h"
 #include "event2/bufferevent_ssl.h"
+#include "event2/bufferevent_struct.h"
 #include "event2/buffer.h"
 #include "event2/listener.h"
 
@@ -177,17 +178,63 @@ static int test_is_done = 0;
 static int n_connected = 0;
 static int got_close = 0;
 static int got_error = 0;
+static int got_timeout = 0;
 static int renegotiate_at = -1;
 static int stop_when_connected = 0;
 static int pending_connect_events = 0;
 static struct event_base *exit_base = NULL;
 
+enum regress_openssl_type
+{
+	REGRESS_OPENSSL_SOCKETPAIR = 1,
+	REGRESS_OPENSSL_FILTER = 2,
+	REGRESS_OPENSSL_RENEGOTIATE = 4,
+	REGRESS_OPENSSL_OPEN = 8,
+	REGRESS_OPENSSL_DIRTY_SHUTDOWN = 16,
+	REGRESS_OPENSSL_FD = 32,
+
+	REGRESS_OPENSSL_CLIENT = 64,
+	REGRESS_OPENSSL_SERVER = 128,
+
+	REGRESS_OPENSSL_FREED = 256,
+	REGRESS_OPENSSL_TIMEOUT = 512,
+};
+
+static void
+bufferevent_openssl_check_fd(struct bufferevent *bev, int filter)
+{
+	if (filter) {
+		tt_int_op(bufferevent_getfd(bev), ==, -1);
+		tt_int_op(bufferevent_setfd(bev, -1), ==, -1);
+	} else {
+		tt_int_op(bufferevent_getfd(bev), !=, -1);
+		tt_int_op(bufferevent_setfd(bev, -1), ==, 0);
+	}
+	tt_int_op(bufferevent_getfd(bev), ==, -1);
+
+end:
+	;
+}
+static void
+bufferevent_openssl_check_freed(struct bufferevent *bev)
+{
+	tt_int_op(event_pending(&bev->ev_read, EVLIST_ALL, NULL), ==, 0);
+	tt_int_op(event_pending(&bev->ev_write, EVLIST_ALL, NULL), ==, 0);
+
+end:
+	;
+}
+
 static void
 respond_to_number(struct bufferevent *bev, void *ctx)
 {
 	struct evbuffer *b = bufferevent_get_input(bev);
 	char *line;
 	int n;
+
+	enum regress_openssl_type type;
+	type = (enum regress_openssl_type)ctx;
+
 	line = evbuffer_readln(b, NULL, EVBUFFER_EOL_LF);
 	if (! line)
 		return;
@@ -201,7 +248,7 @@ respond_to_number(struct bufferevent *bev, void *ctx)
 		bufferevent_free(bev); /* Should trigger close on other side. */
 		return;
 	}
-	if (!strcmp(ctx, "client") && n == renegotiate_at) {
+	if ((type & REGRESS_OPENSSL_CLIENT) && n == renegotiate_at) {
 		SSL_renegotiate(bufferevent_openssl_get_ssl(bev));
 	}
 	++n;
@@ -226,6 +273,9 @@ done_writing_cb(struct bufferevent *bev, void *ctx)
 static void
 eventcb(struct bufferevent *bev, short what, void *ctx)
 {
+	enum regress_openssl_type type;
+	type = (enum regress_openssl_type)ctx;
+
 	TT_BLATHER(("Got event %d", (int)what));
 	if (what & BEV_EVENT_CONNECTED) {
 		SSL *ssl;
@@ -234,7 +284,7 @@ eventcb(struct bufferevent *bev, short what, void *ctx)
 		ssl = bufferevent_openssl_get_ssl(bev);
 		tt_assert(ssl);
 		peer_cert = SSL_get_peer_certificate(ssl);
-		if (0==strcmp(ctx, "server")) {
+		if (type & REGRESS_OPENSSL_SERVER) {
 			tt_assert(peer_cert == NULL);
 		} else {
 			tt_assert(peer_cert != NULL);
@@ -246,10 +296,32 @@ eventcb(struct bufferevent *bev, short what, void *ctx)
 	} else if (what & BEV_EVENT_EOF) {
 		TT_BLATHER(("Got a good EOF"));
 		++got_close;
+		if (type & REGRESS_OPENSSL_FD) {
+			bufferevent_openssl_check_fd(bev, type & REGRESS_OPENSSL_FILTER);
+		}
+		if (type & REGRESS_OPENSSL_FREED) {
+			bufferevent_openssl_check_freed(bev);
+		}
 		bufferevent_free(bev);
 	} else if (what & BEV_EVENT_ERROR) {
 		TT_BLATHER(("Got an error."));
 		++got_error;
+		if (type & REGRESS_OPENSSL_FD) {
+			bufferevent_openssl_check_fd(bev, type & REGRESS_OPENSSL_FILTER);
+		}
+		if (type & REGRESS_OPENSSL_FREED) {
+			bufferevent_openssl_check_freed(bev);
+		}
+		bufferevent_free(bev);
+	} else if (what & BEV_EVENT_TIMEOUT) {
+		TT_BLATHER(("Got timeout."));
+		++got_timeout;
+		if (type & REGRESS_OPENSSL_FD) {
+			bufferevent_openssl_check_fd(bev, type & REGRESS_OPENSSL_FILTER);
+		}
+		if (type & REGRESS_OPENSSL_FREED) {
+			bufferevent_openssl_check_freed(bev);
+		}
 		bufferevent_free(bev);
 	}
 end:
@@ -259,7 +331,8 @@ end:
 static void
 open_ssl_bufevs(struct bufferevent **bev1_out, struct bufferevent **bev2_out,
     struct event_base *base, int is_open, int flags, SSL *ssl1, SSL *ssl2,
-    evutil_socket_t *fd_pair, struct bufferevent **underlying_pair)
+    evutil_socket_t *fd_pair, struct bufferevent **underlying_pair,
+    enum regress_openssl_type type)
 {
 	int state1 = is_open ? BUFFEREVENT_SSL_OPEN :BUFFEREVENT_SSL_CONNECTING;
 	int state2 = is_open ? BUFFEREVENT_SSL_OPEN :BUFFEREVENT_SSL_ACCEPTING;
@@ -276,9 +349,13 @@ open_ssl_bufevs(struct bufferevent **bev1_out, struct bufferevent **bev2_out,
 
 	}
 	bufferevent_setcb(*bev1_out, respond_to_number, done_writing_cb,
-	    eventcb, (void*)"client");
+	    eventcb, (void*)(REGRESS_OPENSSL_CLIENT | (long)type));
 	bufferevent_setcb(*bev2_out, respond_to_number, done_writing_cb,
-	    eventcb, (void*)"server");
+	    eventcb, (void*)(REGRESS_OPENSSL_SERVER | (long)type));
+
+	int dirty_shutdown = type & REGRESS_OPENSSL_DIRTY_SHUTDOWN;
+	bufferevent_openssl_set_allow_dirty_shutdown(*bev1_out, dirty_shutdown);
+	bufferevent_openssl_set_allow_dirty_shutdown(*bev2_out, dirty_shutdown);
 }
 
 static void
@@ -290,18 +367,19 @@ regress_bufferevent_openssl(void *arg)
 	SSL *ssl1, *ssl2;
 	X509 *cert = getcert();
 	EVP_PKEY *key = getkey();
-	const int start_open = strstr((char*)data->setup_data, "open")!=NULL;
-	const int filter = strstr((char*)data->setup_data, "filter")!=NULL;
 	int flags = BEV_OPT_DEFER_CALLBACKS;
 	struct bufferevent *bev_ll[2] = { NULL, NULL };
 	evutil_socket_t *fd_pair = NULL;
 
+	enum regress_openssl_type type;
+	type = (enum regress_openssl_type)data->setup_data;
+
 	tt_assert(cert);
 	tt_assert(key);
 
 	init_ssl();
 
-	if (strstr((char*)data->setup_data, "renegotiate")) {
+	if (type & REGRESS_OPENSSL_RENEGOTIATE) {
 		if (SSLeay() >= 0x10001000 &&
 		    SSLeay() <  0x1000104f) {
 			/* 1.0.1 up to 1.0.1c has a bug where TLS1.1 and 1.2
@@ -317,11 +395,11 @@ regress_bufferevent_openssl(void *arg)
 	SSL_use_certificate(ssl2, cert);
 	SSL_use_PrivateKey(ssl2, key);
 
-	if (! start_open)
+	if (!(type & REGRESS_OPENSSL_OPEN))
 		flags |= BEV_OPT_CLOSE_ON_FREE;
 
-	if (!filter) {
-		tt_assert(strstr((char*)data->setup_data, "socketpair"));
+	if (!(type & REGRESS_OPENSSL_FILTER)) {
+		tt_assert(type & REGRESS_OPENSSL_SOCKETPAIR);
 		fd_pair = data->pair;
 	} else {
 		bev_ll[0] = bufferevent_socket_new(data->base, data->pair[0],
@@ -331,15 +409,15 @@ regress_bufferevent_openssl(void *arg)
 	}
 
 	open_ssl_bufevs(&bev1, &bev2, data->base, 0, flags, ssl1, ssl2,
-	    fd_pair, bev_ll);
+	    fd_pair, bev_ll, type);
 
-	if (!filter) {
+	if (!(type & REGRESS_OPENSSL_FILTER)) {
 		tt_int_op(bufferevent_getfd(bev1), ==, data->pair[0]);
 	} else {
 		tt_ptr_op(bufferevent_get_underlying(bev1), ==, bev_ll[0]);
 	}
 
-	if (start_open) {
+	if (type & REGRESS_OPENSSL_OPEN) {
 		pending_connect_events = 2;
 		stop_when_connected = 1;
 		exit_base = data->base;
@@ -351,23 +429,47 @@ regress_bufferevent_openssl(void *arg)
 		bufferevent_free(bev2);
 		bev1 = bev2 = NULL;
 		open_ssl_bufevs(&bev1, &bev2, data->base, 1, flags, ssl1, ssl2,
-		    fd_pair, bev_ll);
+		    fd_pair, bev_ll, type);
 	}
 
-	bufferevent_enable(bev1, EV_READ|EV_WRITE);
-	bufferevent_enable(bev2, EV_READ|EV_WRITE);
+	if (!(type & REGRESS_OPENSSL_TIMEOUT)) {
+		bufferevent_enable(bev1, EV_READ|EV_WRITE);
+		bufferevent_enable(bev2, EV_READ|EV_WRITE);
 
-	evbuffer_add_printf(bufferevent_get_output(bev1), "1\n");
+		evbuffer_add_printf(bufferevent_get_output(bev1), "1\n");
 
-	event_base_dispatch(data->base);
+		event_base_dispatch(data->base);
 
-	tt_assert(test_is_done == 1);
-	tt_assert(n_connected == 2);
+		tt_assert(test_is_done == 1);
+		tt_assert(n_connected == 2);
 
-	/* We don't handle shutdown properly yet.
-	   tt_int_op(got_close, ==, 1);
-	   tt_int_op(got_error, ==, 0);
-	*/
+		/* We don't handle shutdown properly yet */
+		if (type & REGRESS_OPENSSL_DIRTY_SHUTDOWN) {
+			tt_int_op(got_close, ==, 1);
+			tt_int_op(got_error, ==, 0);
+		} else {
+			tt_int_op(got_error, ==, 1);
+		}
+		tt_int_op(got_timeout, ==, 0);
+	} else {
+		struct timeval t = { 2 };
+
+		bufferevent_enable(bev1, EV_READ|EV_WRITE);
+		bufferevent_disable(bev2, EV_READ|EV_WRITE);
+
+		bufferevent_set_timeouts(bev1, &t, &t);
+
+		evbuffer_add_printf(bufferevent_get_output(bev1), "1\n");
+
+		event_base_dispatch(data->base);
+
+		tt_assert(test_is_done == 0);
+		tt_assert(n_connected == 0);
+
+		tt_int_op(got_close, ==, 0);
+		tt_int_op(got_error, ==, 0);
+		tt_int_op(got_timeout, ==, 1);
+	}
 end:
 	return;
 }
@@ -391,7 +493,7 @@ acceptcb(struct evconnlistener *listener, evutil_socket_t fd,
 		BEV_OPT_CLOSE_ON_FREE|BEV_OPT_DEFER_CALLBACKS);
 
 	bufferevent_setcb(bev, respond_to_number, NULL, eventcb,
-	    (void*)"server");
+	    (void*)(REGRESS_OPENSSL_SERVER));
 
 	bufferevent_enable(bev, EV_READ|EV_WRITE);
 
@@ -435,7 +537,7 @@ regress_bufferevent_openssl_connect(void *arg)
 	tt_assert(bev);
 
 	bufferevent_setcb(bev, respond_to_number, NULL, eventcb,
-	    (void*)"client");
+	    (void*)(REGRESS_OPENSSL_CLIENT));
 
 	tt_assert(getsockname(evconnlistener_get_fd(listener),
 		(struct sockaddr*)&ss, &slen) == 0);
@@ -453,22 +555,69 @@ end:
 }
 
 struct testcase_t ssl_testcases[] = {
-
-	{ "bufferevent_socketpair", regress_bufferevent_openssl, TT_ISOLATED,
-	  &basic_setup, (void*)"socketpair" },
+#define T(a) ((void *)(a))
+	{ "bufferevent_socketpair", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup, T(REGRESS_OPENSSL_SOCKETPAIR) },
 	{ "bufferevent_filter", regress_bufferevent_openssl,
-	  TT_ISOLATED,
-	  &basic_setup, (void*)"filter" },
+	  TT_ISOLATED, &basic_setup, T(REGRESS_OPENSSL_FILTER) },
 	{ "bufferevent_renegotiate_socketpair", regress_bufferevent_openssl,
-	  TT_ISOLATED,
-	  &basic_setup, (void*)"socketpair renegotiate" },
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_RENEGOTIATE) },
 	{ "bufferevent_renegotiate_filter", regress_bufferevent_openssl,
-	  TT_ISOLATED,
-	  &basic_setup, (void*)"filter renegotiate" },
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_FILTER | REGRESS_OPENSSL_RENEGOTIATE) },
 	{ "bufferevent_socketpair_startopen", regress_bufferevent_openssl,
-	  TT_ISOLATED, &basic_setup, (void*)"socketpair open" },
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_OPEN) },
 	{ "bufferevent_filter_startopen", regress_bufferevent_openssl,
-	  TT_ISOLATED, &basic_setup, (void*)"filter open" },
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_FILTER | REGRESS_OPENSSL_OPEN) },
+
+	{ "bufferevent_socketpair_dirty_shutdown", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_DIRTY_SHUTDOWN) },
+	{ "bufferevent_filter_dirty_shutdown", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_FILTER | REGRESS_OPENSSL_DIRTY_SHUTDOWN) },
+	{ "bufferevent_renegotiate_socketpair_dirty_shutdown",
+	  regress_bufferevent_openssl,
+	  TT_ISOLATED,
+	  &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_RENEGOTIATE | REGRESS_OPENSSL_DIRTY_SHUTDOWN) },
+	{ "bufferevent_renegotiate_filter_dirty_shutdown",
+	  regress_bufferevent_openssl,
+	  TT_ISOLATED,
+	  &basic_setup,
+	  T(REGRESS_OPENSSL_FILTER | REGRESS_OPENSSL_RENEGOTIATE | REGRESS_OPENSSL_DIRTY_SHUTDOWN) },
+	{ "bufferevent_socketpair_startopen_dirty_shutdown",
+	  regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_OPEN | REGRESS_OPENSSL_DIRTY_SHUTDOWN) },
+	{ "bufferevent_filter_startopen_dirty_shutdown",
+	  regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_FILTER | REGRESS_OPENSSL_OPEN | REGRESS_OPENSSL_DIRTY_SHUTDOWN) },
+
+	{ "bufferevent_socketpair_fd", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_FD) },
+	{ "bufferevent_socketpair_freed", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_FREED) },
+	{ "bufferevent_socketpair_freed_fd", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_FREED | REGRESS_OPENSSL_FD) },
+	{ "bufferevent_filter_freed_fd", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_FILTER | REGRESS_OPENSSL_FREED | REGRESS_OPENSSL_FD) },
+
+	{ "bufferevent_socketpair_timeout", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_TIMEOUT) },
+	{ "bufferevent_socketpair_timeout_freed_fd", regress_bufferevent_openssl,
+	  TT_ISOLATED, &basic_setup,
+	  T(REGRESS_OPENSSL_SOCKETPAIR | REGRESS_OPENSSL_TIMEOUT | REGRESS_OPENSSL_FREED | REGRESS_OPENSSL_FD) },
+#undef T
 
 	{ "bufferevent_connect", regress_bufferevent_openssl_connect,
 	  TT_FORK|TT_NEED_BASE, &basic_setup, NULL },