diff --git a/configure.ac b/configure.ac
index e1950efd..701708d2 100644
--- a/configure.ac
+++ b/configure.ac
@@ -527,6 +527,33 @@ then
 
 fi
 
+#
+# TLS Locking Support within libVNCServer
+#
+
+if test "x${have_libvncserver}" = "xyes"
+then
+
+    have_vnc_tls_locking=yes
+    AC_CHECK_MEMBERS([rfbClient.LockWriteToTLS, rfbClient.UnlockWriteToTLS],
+                     [], [have_vnc_tls_locking=no],
+                     [[#include <rfb/rfbclient.h>]])
+
+    if test "x${have_vnc_tls_locking}" = "xno"
+    then
+        AC_MSG_WARN([
+      --------------------------------------------
+       This version of libvncclient lacks support
+       for TLS locking.  VNC connections that use
+       TLS may experience instability as documented
+       in GUACAMOLE-414])
+    else
+        AC_DEFINE([ENABLE_VNC_TLS_LOCKING],,
+                  [Whether support for TLS locking within VNC is enabled.])
+    fi
+
+fi
+
 #
 # FreeRDP
 #
diff --git a/src/protocols/vnc/client.c b/src/protocols/vnc/client.c
index 9cc85a18..cee1d4d5 100644
--- a/src/protocols/vnc/client.c
+++ b/src/protocols/vnc/client.c
@@ -36,6 +36,7 @@
 
 #include <guacamole/client.h>
 
+#include <pthread.h>
 #include <stdlib.h>
 #include <string.h>
 
@@ -48,6 +49,11 @@ int guac_client_init(guac_client* client) {
     guac_vnc_client* vnc_client = calloc(1, sizeof(guac_vnc_client));
     client->data = vnc_client;
 
+#ifdef ENABLE_VNC_TLS_LOCKING
+    /* Initialize the write lock */
+    pthread_mutex_init(&(vnc_client->tls_lock), NULL);
+#endif
+
     /* Init clipboard */
     vnc_client->clipboard = guac_common_clipboard_alloc(GUAC_VNC_CLIPBOARD_MAX_LENGTH);
 
@@ -125,6 +131,11 @@ int guac_vnc_client_free_handler(guac_client* client) {
     if (settings != NULL)
         guac_vnc_settings_free(settings);
 
+#ifdef ENABLE_VNC_TLS_LOCKING
+    /* Clean up TLS lock mutex. */
+    pthread_mutex_destroy(&(vnc_client->tls_lock));
+#endif
+
     /* Free generic data struct */
     free(client->data);
 
diff --git a/src/protocols/vnc/vnc.c b/src/protocols/vnc/vnc.c
index d9f9dbbb..a3ae9b12 100644
--- a/src/protocols/vnc/vnc.c
+++ b/src/protocols/vnc/vnc.c
@@ -55,6 +55,66 @@
 
 char* GUAC_VNC_CLIENT_KEY = "GUAC_VNC";
 
+#ifdef ENABLE_VNC_TLS_LOCKING
+/**
+ * A callback function that is called by the VNC library prior to writing
+ * data to a TLS-encrypted socket.  This returns the rfbBool FALSE value
+ * if there's an error locking the mutex, or rfbBool TRUE otherwise.
+ * 
+ * @param rfb_client
+ *     The rfbClient for which to lock the TLS mutex.
+ *
+ * @returns
+ *     rfbBool FALSE if an error occurs locking the mutex, otherwise
+ *     TRUE.
+ */
+static rfbBool guac_vnc_lock_write_to_tls(rfbClient* rfb_client) {
+
+    /* Retrieve the Guacamole data structures */
+    guac_client* gc = rfbClientGetClientData(rfb_client, GUAC_VNC_CLIENT_KEY);
+    guac_vnc_client* vnc_client = (guac_vnc_client*) gc->data;
+
+    /* Lock write access */
+    int retval = pthread_mutex_lock(&(vnc_client->tls_lock));
+    if (retval) {
+        guac_client_log(gc, GUAC_LOG_ERROR, "Error locking TLS write mutex: %s",
+                strerror(retval));
+        return FALSE;
+    }
+    return TRUE;
+
+}
+
+/**
+ * A callback function for use by the VNC library that is called once
+ * the client is finished writing to a TLS-encrypted socket. A rfbBool
+ * FALSE value is returned if an error occurs unlocking the mutex,
+ * otherwise TRUE is returned.
+ *
+ * @param rfb_client
+ *     The rfbClient for which to unlock the TLS mutex.
+ *
+ * @returns
+ *     rfbBool FALSE if an error occurs unlocking the mutex, otherwise
+ *     TRUE.
+ */
+static rfbBool guac_vnc_unlock_write_to_tls(rfbClient* rfb_client) {
+
+    /* Retrieve the Guacamole data structures */
+    guac_client* gc = rfbClientGetClientData(rfb_client, GUAC_VNC_CLIENT_KEY);
+    guac_vnc_client* vnc_client = (guac_vnc_client*) gc->data;
+
+    /* Unlock write access */
+    int retval = pthread_mutex_unlock(&(vnc_client->tls_lock));
+    if (retval) {
+        guac_client_log(gc, GUAC_LOG_ERROR, "Error unlocking TLS write mutex: %s",
+                strerror(retval));
+        return FALSE;
+    }
+    return TRUE;
+}
+#endif
+
 rfbClient* guac_vnc_get_client(guac_client* client) {
 
     rfbClient* rfb_client = rfbGetClient(8, 3, 4); /* 32-bpp client */
@@ -68,6 +128,12 @@ rfbClient* guac_vnc_get_client(guac_client* client) {
     rfb_client->GotFrameBufferUpdate = guac_vnc_update;
     rfb_client->GotCopyRect = guac_vnc_copyrect;
 
+#ifdef ENABLE_VNC_TLS_LOCKING
+    /* TLS Locking and Unlocking */
+    rfb_client->LockWriteToTLS = guac_vnc_lock_write_to_tls;
+    rfb_client->UnlockWriteToTLS = guac_vnc_unlock_write_to_tls;
+#endif
+
     /* Do not handle clipboard and local cursor if read-only */
     if (vnc_settings->read_only == 0) {
 
@@ -403,4 +469,3 @@ void* guac_vnc_client_thread(void* data) {
     return NULL;
 
 }
-
diff --git a/src/protocols/vnc/vnc.h b/src/protocols/vnc/vnc.h
index ce2d20af..7c189cfb 100644
--- a/src/protocols/vnc/vnc.h
+++ b/src/protocols/vnc/vnc.h
@@ -55,6 +55,13 @@ typedef struct guac_vnc_client {
      */
     pthread_t client_thread;
 
+#ifdef ENABLE_VNC_TLS_LOCKING
+    /**
+     * The TLS mutex lock for the client.
+     */
+    pthread_mutex_t tls_lock;
+#endif
+
     /**
      * The underlying VNC client.
      */