diff --git a/common/trans.c b/common/trans.c
index 7a98986c..eb451073 100644
--- a/common/trans.c
+++ b/common/trans.c
@@ -32,6 +32,11 @@
 
 #define MAX_SBYTES 0
 
+/** Time between polls of is_term when connecting */
+#define CONNECT_TERM_POLL_MS 3000
+/** Time we wait before another connect() attempt if one fails immediately */
+#define CONNECT_DELAY_ON_FAIL_MS 2000
+
 /*****************************************************************************/
 int
 trans_tls_recv(struct trans *self, char *ptr, int len)
@@ -96,6 +101,7 @@ trans_create(int mode, int in_size, int out_size)
 
     if (self != NULL)
     {
+        self->sck = -1;
         make_stream(self->in_s);
         init_stream(self->in_s, in_size);
         make_stream(self->out_s);
@@ -129,12 +135,12 @@ trans_delete(struct trans *self)
     free_stream(self->in_s);
     free_stream(self->out_s);
 
-    if (self->sck > 0)
+    if (self->sck >= 0)
     {
         g_tcp_close(self->sck);
     }
 
-    self->sck = 0;
+    self->sck = -1;
 
     if (self->listen_filename != 0)
     {
@@ -671,143 +677,182 @@ trans_write_copy(struct trans *self)
 }
 
 /*****************************************************************************/
+
+/* Shim to apply the function signature of g_tcp_connect()
+ * to g_tcp_local_connect()
+ */
+static int
+local_connect_shim(int fd, const char *server, const char *port)
+{
+    return g_tcp_local_connect(fd, port);
+}
+
+/**************************************************************************//**
+ * Waits for an asynchronous connect to complete.
+ * @param self - Transport object
+ * @param start_time Start time of connect (from g_time3())
+ * @param timeout Total wait timeout
+ * @return 0 - connect succeeded, 1 - Connect failed
+ *
+ * If the transport is set up for checking a termination object, this
+ * on a regular basis.
+ */
+static int
+poll_for_async_connect(struct trans *self, int start_time, int timeout)
+{
+    int rv = 1;
+    int ms_remaining = timeout - (g_time3() - start_time);
+
+    while (ms_remaining > 0)
+    {
+        int poll_time = ms_remaining;
+        /* Lower bound for waititng for a result */
+        if (poll_time < 100)
+        {
+            poll_time = 100;
+        }
+        /* Limit the wait time if we need to poll for termination */
+        if (self->is_term != NULL && poll_time > CONNECT_TERM_POLL_MS)
+        {
+            poll_time = CONNECT_TERM_POLL_MS;
+        }
+
+        if (g_tcp_can_send(self->sck, poll_time))
+        {
+            /* Connect has finished - return the socket status */
+            rv = g_sck_socket_ok(self->sck) ? 0 : 1;
+            break;
+        }
+
+        /* Check for program termination */
+        if (self->is_term != NULL && self->is_term())
+        {
+            break;
+        }
+
+        ms_remaining = timeout - (g_time3() - start_time);
+    }
+    return rv;
+}
+
+/*****************************************************************************/
+
 int
 trans_connect(struct trans *self, const char *server, const char *port,
               int timeout)
 {
+    int start_time = g_time3();
     int error;
-    int now;
-    int start_time;
+    int ms_before_next_connect;
 
-    start_time = g_time3();
+    /*
+     * Function pointers which we use in the main loop to avoid
+     * having to switch on the socket mode */
+    int (*f_alloc_socket)(void);
+    int (*f_connect)(int fd, const char *server, const char *port);
 
-    if (self->sck != 0)
+    switch (self->mode)
     {
-        g_tcp_close(self->sck);
-        self->sck = 0;
+        case TRANS_MODE_TCP:
+            f_alloc_socket = g_tcp_socket;
+            f_connect = g_tcp_connect;
+            break;
+
+        case TRANS_MODE_UNIX:
+            f_alloc_socket = g_tcp_local_socket;
+            f_connect = local_connect_shim;
+            break;
+
+        default:
+            LOG(LOG_LEVEL_ERROR, "Bad socket mode %d", self->mode);
+            return 1;
     }
 
-    if (self->mode == TRANS_MODE_TCP) /* tcp */
+    while (1)
     {
-        self->sck = g_tcp_socket();
+        /* Check the program isn't terminating */
+        if (self->is_term != NULL && self->is_term())
+        {
+            error = 1;
+            break;
+        }
+
+        /* Allocate a new socket */
+        if (self->sck >= 0)
+        {
+            g_tcp_close(self->sck);
+        }
+        self->sck = f_alloc_socket();
+
         if (self->sck < 0)
         {
-            self->status = TRANS_STATUS_DOWN;
-            return 1;
+            error = 1;
+            break;
         }
+
+        /* Try to connect asynchronously */
         g_tcp_set_non_blocking(self->sck);
-        while (1)
+        error = f_connect(self->sck, server, port);
+        if (error == 0)
         {
-            error = g_tcp_connect(self->sck, server, port);
-            if (error == 0)
+            /* Connect was immediately successful */
+            break;
+        }
+
+        if (g_tcp_last_error_would_block(self->sck))
+        {
+            /* Async connect is in progress */
+            if (poll_for_async_connect(self, start_time, timeout) == 0)
             {
+                /* Async connect was successful */
+                error = 0;
                 break;
             }
-            else
+            /* No need to wait any more before the next connect attempt */
+            ms_before_next_connect = 0;
+        }
+        else
+        {
+            /* Connect failed immediately. Wait a bit before the next
+             * attempt */
+            ms_before_next_connect = CONNECT_DELAY_ON_FAIL_MS;
+        }
+
+        /* Have we reached the total timeout yet? */
+        int ms_left = timeout - (g_time3() - start_time);
+        if (ms_left <= 0)
+        {
+            error = 1;
+            break;
+        }
+
+        /* Sleep a bit before trying again */
+        if (ms_before_next_connect > 0)
+        {
+            if (ms_before_next_connect > ms_left)
             {
-                if (timeout < 1)
-                {
-                    self->status = TRANS_STATUS_DOWN;
-                    return 1;
-                }
-                now = g_time3();
-                if (now - start_time < timeout)
-                {
-                    g_sleep(100);
-                }
-                else
-                {
-                    self->status = TRANS_STATUS_DOWN;
-                    return 1;
-                }
-                if (self->is_term != NULL)
-                {
-                    if (self->is_term())
-                    {
-                        self->status = TRANS_STATUS_DOWN;
-                        return 1;
-                    }
-                }
+                ms_before_next_connect = ms_left;
             }
+            g_sleep(ms_before_next_connect);
         }
     }
-    else if (self->mode == TRANS_MODE_UNIX) /* unix socket */
+
+    if (error != 0)
     {
-        self->sck = g_tcp_local_socket();
-        if (self->sck < 0)
+        if (self->sck >= 0)
         {
-            self->status = TRANS_STATUS_DOWN;
-            return 1;
-        }
-        g_tcp_set_non_blocking(self->sck);
-        while (1)
-        {
-            error = g_tcp_local_connect(self->sck, port);
-            if (error == 0)
-            {
-                break;
-            }
-            else
-            {
-                if (timeout < 1)
-                {
-                    self->status = TRANS_STATUS_DOWN;
-                    return 1;
-                }
-                now = g_time3();
-                if (now - start_time < timeout)
-                {
-                    g_sleep(100);
-                }
-                else
-                {
-                    self->status = TRANS_STATUS_DOWN;
-                    return 1;
-                }
-                if (self->is_term != NULL)
-                {
-                    if (self->is_term())
-                    {
-                        self->status = TRANS_STATUS_DOWN;
-                        return 1;
-                    }
-                }
-            }
+            g_tcp_close(self->sck);
+            self->sck = -1;
         }
+        self->status = TRANS_STATUS_DOWN;
     }
     else
     {
-        self->status = TRANS_STATUS_DOWN;
-        return 1;
+        self->status = TRANS_STATUS_UP; /* ok */
+        self->type1 = TRANS_TYPE_CLIENT; /* client */
     }
 
-    if (error == -1)
-    {
-        if (g_tcp_last_error_would_block(self->sck))
-        {
-            now = g_time3();
-            if (now - start_time < timeout)
-            {
-                timeout = timeout - (now - start_time);
-            }
-            else
-            {
-                timeout = 0;
-            }
-            if (g_tcp_can_send(self->sck, timeout))
-            {
-                self->status = TRANS_STATUS_UP; /* ok */
-                self->type1 = TRANS_TYPE_CLIENT; /* client */
-                return 0;
-            }
-        }
-
-        return 1;
-    }
-
-    self->status = TRANS_STATUS_UP; /* ok */
-    self->type1 = TRANS_TYPE_CLIENT; /* client */
-    return 0;
+    return error;
 }
 
 /*****************************************************************************/
@@ -818,7 +863,7 @@ trans_connect(struct trans *self, const char *server, const char *port,
 int
 trans_listen_address(struct trans *self, const char *port, const char *address)
 {
-    if (self->sck != 0)
+    if (self->sck >= 0)
     {
         g_tcp_close(self->sck);
     }
diff --git a/common/trans.h b/common/trans.h
index 9810cefd..c6b6c4bb 100644
--- a/common/trans.h
+++ b/common/trans.h
@@ -147,6 +147,20 @@ int
 trans_write_copy(struct trans *self);
 int
 trans_write_copy_s(struct trans *self, struct stream *out_s);
+/**
+ * Connect the transport to the specified destination
+ *
+ * @param self Transport
+ * @param server Destination server (TCP transports only)
+ * @param port TCP port, or UNIX socket to connect to
+ * @param timeout in milli-seconds for the operation
+ * @return 0 for success
+ *
+ * Multiple connection attempts may be made within the timeout period.
+ *
+ * If the operation is successful, 0 is returned and self->status will
+ * be TRANS_STATUS_UP
+ */
 int
 trans_connect(struct trans *self, const char *server, const char *port,
               int timeout);
diff --git a/libipm/scp.c b/libipm/scp.c
index 4e1426a3..b3f4fbf6 100644
--- a/libipm/scp.c
+++ b/libipm/scp.c
@@ -74,8 +74,6 @@ scp_connect(const char *host, const  char *port,
     struct trans *t;
     if ((t = trans_create(TRANS_MODE_TCP, 128, 128)) != NULL)
     {
-        int index;
-
         if (host == NULL)
         {
             host = "localhost";
@@ -88,18 +86,7 @@ scp_connect(const char *host, const  char *port,
 
         t->is_term = term_func;
 
-        /* try to connect up to 4 times
-         *
-         * term_func can be NULL, so check before calling it */
-        index = 4;
-        while (trans_connect(t, host, port, 3000) != 0 &&
-                !(term_func && term_func()) &&
-                --index > 0)
-        {
-            g_sleep(1000);
-            LOG_DEVEL(LOG_LEVEL_DEBUG, "Connect failed. Trying again...");
-        }
-
+        trans_connect(t, host, port, 3000);
         if (t->status != TRANS_STATUS_UP)
         {
             trans_delete(t);
diff --git a/libxrdp/xrdp_mcs.c b/libxrdp/xrdp_mcs.c
index 83b5e760..4d86aee0 100644
--- a/libxrdp/xrdp_mcs.c
+++ b/libxrdp/xrdp_mcs.c
@@ -1383,7 +1383,7 @@ close_rdp_socket(struct xrdp_mcs *self)
         {
             trans_shutdown_tls_mode(self->iso_layer->trans);
             g_tcp_close(self->iso_layer->trans->sck);
-            self->iso_layer->trans->sck = 0 ;
+            self->iso_layer->trans->sck = -1;
             LOG_DEVEL(LOG_LEVEL_DEBUG, "xrdp_mcs_disconnect - socket closed");
             return;
         }
diff --git a/mc/mc.h b/mc/mc.h
index 990ce7a5..879c298c 100644
--- a/mc/mc.h
+++ b/mc/mc.h
@@ -57,7 +57,7 @@ struct mod
     int (*server_set_cursor)(struct mod *v, int x, int y, char *data, char *mask);
     int (*server_palette)(struct mod *v, int *palette);
     int (*server_msg)(struct mod *v, const char *msg, int code);
-    int (*server_is_term)(struct mod *v);
+    int (*server_is_term)(void);
     int (*server_set_clip)(struct mod *v, int x, int y, int cx, int cy);
     int (*server_reset_clip)(struct mod *v);
     int (*server_set_fgcolor)(struct mod *v, int fgcolor);
diff --git a/neutrinordp/xrdp-neutrinordp.h b/neutrinordp/xrdp-neutrinordp.h
index cbedb08b..55601c08 100644
--- a/neutrinordp/xrdp-neutrinordp.h
+++ b/neutrinordp/xrdp-neutrinordp.h
@@ -109,7 +109,7 @@ struct mod
     int (*server_set_pointer)(struct mod *v, int x, int y, char *data, char *mask);
     int (*server_palette)(struct mod *v, int *palette);
     int (*server_msg)(struct mod *v, const char *msg, int code);
-    int (*server_is_term)(struct mod *v);
+    int (*server_is_term)(void);
     int (*server_set_clip)(struct mod *v, int x, int y, int cx, int cy);
     int (*server_reset_clip)(struct mod *v);
     int (*server_set_fgcolor)(struct mod *v, int fgcolor);
diff --git a/vnc/vnc.h b/vnc/vnc.h
index f4ce44b4..5cf65391 100644
--- a/vnc/vnc.h
+++ b/vnc/vnc.h
@@ -102,7 +102,7 @@ struct vnc
     int (*server_set_cursor)(struct vnc *v, int x, int y, char *data, char *mask);
     int (*server_palette)(struct vnc *v, int *palette);
     int (*server_msg)(struct vnc *v, const char *msg, int code);
-    int (*server_is_term)(struct vnc *v);
+    int (*server_is_term)(void);
     int (*server_set_clip)(struct vnc *v, int x, int y, int cx, int cy);
     int (*server_reset_clip)(struct vnc *v);
     int (*server_set_fgcolor)(struct vnc *v, int fgcolor);
diff --git a/xrdp/xrdp.h b/xrdp/xrdp.h
index 36d8f87a..88ec8814 100644
--- a/xrdp/xrdp.h
+++ b/xrdp/xrdp.h
@@ -477,8 +477,6 @@ server_palette(struct xrdp_mod *mod, int *palette);
 int
 server_msg(struct xrdp_mod *mod, const char *msg, int code);
 int
-server_is_term(struct xrdp_mod *mod);
-int
 server_set_clip(struct xrdp_mod *mod, int x, int y, int cx, int cy);
 int
 server_reset_clip(struct xrdp_mod *mod);
diff --git a/xrdp/xrdp_mm.c b/xrdp/xrdp_mm.c
index 796d997f..fa3f9396 100644
--- a/xrdp/xrdp_mm.c
+++ b/xrdp/xrdp_mm.c
@@ -415,7 +415,7 @@ xrdp_mm_setup_mod1(struct xrdp_mm *self)
             self->mod->server_set_pointer_ex = server_set_pointer_ex;
             self->mod->server_palette = server_palette;
             self->mod->server_msg = server_msg;
-            self->mod->server_is_term = server_is_term;
+            self->mod->server_is_term = g_is_term;
             self->mod->server_set_clip = server_set_clip;
             self->mod->server_reset_clip = server_reset_clip;
             self->mod->server_set_fgcolor = server_set_fgcolor;
@@ -2356,8 +2356,6 @@ xrdp_mm_sesman_connect(struct xrdp_mm *self, const char *ip)
 static int
 xrdp_mm_chansrv_connect(struct xrdp_mm *self, const char *ip, const char *port)
 {
-    int index;
-
     if (self->wm->client_info->channels_allowed == 0)
     {
         LOG(LOG_LEVEL_DEBUG, "%s: "
@@ -2387,22 +2385,8 @@ xrdp_mm_chansrv_connect(struct xrdp_mm *self, const char *ip, const char *port)
     self->chan_trans->no_stream_init_on_data_in = 1;
     self->chan_trans->extra_flags = 0;
 
-    /* try to connect up to 4 times */
-    for (index = 0; index < 4; index++)
-    {
-        if (trans_connect(self->chan_trans, ip, port, 3000) == 0)
-        {
-            break;
-        }
-        if (g_is_term())
-        {
-            break;
-        }
-        g_sleep(1000);
-        LOG(LOG_LEVEL_WARNING, "xrdp_mm_chansrv_connect: connect failed "
-            "trying again...");
-    }
-
+    /* try to connect for up to 10 seconds */
+    trans_connect(self->chan_trans, ip, port, 10 * 1000);
     if (self->chan_trans->status != TRANS_STATUS_UP)
     {
         LOG(LOG_LEVEL_ERROR, "xrdp_mm_chansrv_connect: error in "
@@ -3368,13 +3352,6 @@ server_msg(struct xrdp_mod *mod, const char *msg, int code)
     return xrdp_wm_log_msg(wm, LOG_LEVEL_DEBUG, "%s", msg);
 }
 
-/*****************************************************************************/
-int
-server_is_term(struct xrdp_mod *mod)
-{
-    return g_is_term();
-}
-
 /*****************************************************************************/
 int
 server_set_clip(struct xrdp_mod *mod, int x, int y, int cx, int cy)
diff --git a/xrdp/xrdp_types.h b/xrdp/xrdp_types.h
index feec7184..8ec731fa 100644
--- a/xrdp/xrdp_types.h
+++ b/xrdp/xrdp_types.h
@@ -74,7 +74,9 @@ struct xrdp_mod
                               char *data, char *mask);
     int (*server_palette)(struct xrdp_mod *v, int *palette);
     int (*server_msg)(struct xrdp_mod *v, const char *msg, int code);
-    int (*server_is_term)(struct xrdp_mod *v);
+    /* This one can be assigned directly into the is_term member of
+     * a struct trans */
+    int (*server_is_term)(void);
     int (*server_set_clip)(struct xrdp_mod *v, int x, int y, int cx, int cy);
     int (*server_reset_clip)(struct xrdp_mod *v);
     int (*server_set_fgcolor)(struct xrdp_mod *v, int fgcolor);
diff --git a/xup/xup.c b/xup/xup.c
index e67d9477..ca36efc7 100644
--- a/xup/xup.c
+++ b/xup/xup.c
@@ -148,8 +148,7 @@ int
 lib_mod_connect(struct mod *mod)
 {
     int error;
-    int i;
-    int use_uds;
+    int socket_mode;
     struct stream *s;
     char con_port[256];
 
@@ -171,82 +170,47 @@ lib_mod_connect(struct mod *mod)
 
     make_stream(s);
     g_sprintf(con_port, "%s", mod->port);
-    use_uds = 0;
-
-    if (con_port[0] == '/')
-    {
-        use_uds = 1;
-    }
 
     error = 0;
     mod->sck_closed = 0;
-    i = 0;
 
-    if (use_uds)
+    if (con_port[0] == '/')
     {
+        socket_mode = TRANS_MODE_UNIX;
         LOG(LOG_LEVEL_INFO, "lib_mod_connect: connecting via UNIX socket");
-        mod->trans = trans_create(TRANS_MODE_UNIX, 8 * 8192, 8192);
-        if (mod->trans == 0)
-        {
-            free_stream(s);
-            return 1;
-        }
     }
     else
     {
+        socket_mode = TRANS_MODE_TCP;
         LOG(LOG_LEVEL_INFO, "lib_mod_connect: connecting via TCP socket");
-        mod->trans = trans_create(TRANS_MODE_TCP, 8 * 8192, 8192);
-        if (mod->trans == 0)
-        {
-            free_stream(s);
-            return 1;
-        }
     }
 
+    mod->trans = trans_create(socket_mode, 8 * 8192, 8192);
+    if (mod->trans == 0)
+    {
+        free_stream(s);
+        return 1;
+    }
     mod->trans->si = mod->si;
     mod->trans->my_source = XRDP_SOURCE_MOD;
+    mod->trans->is_term = mod->server_is_term;
 
-    while (1)
+    /* Give the X server a bit of time to start */
+    if (trans_connect(mod->trans, mod->ip, con_port, 30 * 1000) == 0)
     {
-
-        /* mod->server_msg(mod, "connecting...", 0); */
-
-        error = -1;
-        if (trans_connect(mod->trans, mod->ip, con_port, 3000) == 0)
-        {
-            LOG_DEVEL(LOG_LEVEL_INFO, "lib_mod_connect: connected to Xserver "
-                      "(Xorg or X11rdp) sck %lld",
-                      (long long) (mod->trans->sck));
-            error = 0;
-        }
-
-        if (error == 0)
-        {
-            break;
-        }
-
-        if (mod->server_is_term(mod))
-        {
-            break;
-        }
-
-        i++;
-
-        if (i >= 60)
-        {
-            mod->server_msg(mod, "connection problem, giving up", 0);
-            break;
-        }
-
-        g_sleep(500);
+        LOG_DEVEL(LOG_LEVEL_INFO, "lib_mod_connect: connected to Xserver "
+                  "(Xorg or X11rdp) sck %lld",
+                  (long long) (mod->trans->sck));
+    }
+    else
+    {
+        mod->server_msg(mod, "connection problem, giving up", 0);
+        error = 1;
     }
 
-    if (error == 0)
+    if (error == 0 && socket_mode == TRANS_MODE_UNIX)
     {
-        if (use_uds)
-        {
-            lib_mod_log_peer(mod);
-        }
+        lib_mod_log_peer(mod);
     }
 
     if (error == 0)
diff --git a/xup/xup.h b/xup/xup.h
index 767c459d..4f4b415b 100644
--- a/xup/xup.h
+++ b/xup/xup.h
@@ -70,7 +70,7 @@ struct mod
     int (*server_set_cursor)(struct mod *v, int x, int y, char *data, char *mask);
     int (*server_palette)(struct mod *v, int *palette);
     int (*server_msg)(struct mod *v, const char *msg, int code);
-    int (*server_is_term)(struct mod *v);
+    int (*server_is_term)(void);
     int (*server_set_clip)(struct mod *v, int x, int y, int cx, int cy);
     int (*server_reset_clip)(struct mod *v);
     int (*server_set_fgcolor)(struct mod *v, int fgcolor);