diff --git a/src/etc/inc/system.inc b/src/etc/inc/system.inc
index 50ce99cea..35fcbe87f 100644
--- a/src/etc/inc/system.inc
+++ b/src/etc/inc/system.inc
@@ -673,6 +673,8 @@ EOD;
         }
     }
 
+    // deploy certificates (separate caller in case we ever remove clog, in which case we can move all to configd)
+    mwexecf("/usr/local/opnsense/scripts/syslog/generate_certs");
     if (!empty($config['syslog']['disable_clog'])) {
         // non legacy mode
         if (isvalidpid('/var/run/syslog.pid')) {
diff --git a/src/opnsense/mvc/app/controllers/OPNsense/Syslog/forms/dialogDestination.xml b/src/opnsense/mvc/app/controllers/OPNsense/Syslog/forms/dialogDestination.xml
index 484c9040e..36ad7bd96 100644
--- a/src/opnsense/mvc/app/controllers/OPNsense/Syslog/forms/dialogDestination.xml
+++ b/src/opnsense/mvc/app/controllers/OPNsense/Syslog/forms/dialogDestination.xml
@@ -39,6 +39,16 @@
     <label>Port</label>
     <type>text</type>
   </field>
+  <field>
+    <id>destination.certificate</id>
+    <style>transport_type_tls4 transport_type_tls6 transport_type</style>
+    <label>Certificate</label>
+    <type>dropdown</type>
+    <help><![CDATA[Transport certificate to use, please make sure to check the general system log when experiencing issues.
+      Error messages can be a bit cryptic from time to time, in which case <a href="https://support.oneidentity.com/kb/263658/common-issues-of-tls-encrypted-message-transfer">this</a> is a good
+      resource for tracking common issues.]]>
+    </help>
+  </field>
   <field>
     <id>destination.description</id>
     <label>Description</label>
diff --git a/src/opnsense/mvc/app/models/OPNsense/Syslog/Syslog.php b/src/opnsense/mvc/app/models/OPNsense/Syslog/Syslog.php
index c5f11c409..2fb911dd5 100644
--- a/src/opnsense/mvc/app/models/OPNsense/Syslog/Syslog.php
+++ b/src/opnsense/mvc/app/models/OPNsense/Syslog/Syslog.php
@@ -51,14 +51,26 @@ class Syslog extends BaseModel
                 $parentNode = $node->getParentNode();
                 $ptagname = $parentNode->getInternalXMLTagName();
                 $tagname = $node->getInternalXMLTagName();
-                if ($ptagname == 'destination' && in_array($tagname, array('hostname', 'transport'))) {
-                    // protocol family check
-                    if (in_array((string)$parentNode->transport, array('udp4', 'udp6', 'tcp4', 'tcp6'))) {
-                        $ipproto = ((string)$parentNode->transport)[3];
-                        $hostproto = strpos((string)$parentNode->hostname, ":") === false ? "4" : "6";
-                        if (Util::isIpAddress((string)$parentNode->hostname) && $ipproto != $hostproto) {
+                $transport = (string)$parentNode->transport;
+                if ($ptagname == 'destination') {
+                    if (in_array($tagname, array('hostname', 'transport'))) {
+                        // protocol family check
+                        if (in_array($transport, ['udp4', 'udp6', 'tcp4', 'tcp6', 'tls4', 'tls6'])) {
+                            $ipproto = ((string)$parentNode->transport)[3];
+                            $hostproto = strpos((string)$parentNode->hostname, ":") === false ? "4" : "6";
+                            if (Util::isIpAddress((string)$parentNode->hostname) && $ipproto != $hostproto) {
+                                $messages->appendMessage(new Message(
+                                    gettext("Transport protocol does not match address in hostname"),
+                                    $key
+                                ));
+                            }
+                        }
+                    }
+                    if (in_array($tagname, ['certificate', 'transport']) && in_array($transport, ['tls4', 'tls6'])) {
+                        // certificate availability
+                        if (empty((string)$parentNode->certificate)) {
                             $messages->appendMessage(new Message(
-                                gettext("Transport protocol does not match address in hostname"),
+                                gettext("A certificate is required for tls types"),
                                 $key
                             ));
                         }
diff --git a/src/opnsense/mvc/app/models/OPNsense/Syslog/Syslog.xml b/src/opnsense/mvc/app/models/OPNsense/Syslog/Syslog.xml
index d2362c0cf..6ed227d99 100644
--- a/src/opnsense/mvc/app/models/OPNsense/Syslog/Syslog.xml
+++ b/src/opnsense/mvc/app/models/OPNsense/Syslog/Syslog.xml
@@ -22,6 +22,8 @@
                       <tcp4>TCP(4)</tcp4>
                       <udp6>UDP(6)</udp6>
                       <tcp6>TCP(6)</tcp6>
+                      <tls4>TLS(4)</tls4>
+                      <tls6>TLS(6)</tls6>
                   </OptionValues>
                 </transport>
                 <program type="JsonKeyValueStoreField">
@@ -80,6 +82,10 @@
                 <hostname type="HostnameField">
                     <Required>Y</Required>
                 </hostname>
+                <certificate type="CertificateField">
+                    <Required>N</Required>
+                    <ValidationMessage>Please select a valid certificate from the list</ValidationMessage>
+                </certificate>
                 <port type="PortField">
                     <Required>Y</Required>
                     <default>514</default>
diff --git a/src/opnsense/mvc/app/views/OPNsense/Syslog/index.volt b/src/opnsense/mvc/app/views/OPNsense/Syslog/index.volt
index ee5fa2ac4..5f80efa2e 100644
--- a/src/opnsense/mvc/app/views/OPNsense/Syslog/index.volt
+++ b/src/opnsense/mvc/app/views/OPNsense/Syslog/index.volt
@@ -48,6 +48,17 @@
          */
         $("#reconfigureAct").SimpleActionButton();
         updateServiceControlUI('syslog');
+
+        $("#destination\\.transport").change(function(){
+            let transport_type = $(this).val();
+            $(".transport_type").each(function(){
+                if ($(this).hasClass("transport_type_" + transport_type)) {
+                    $(this).closest("tr").show();
+                } else {
+                    $(this).closest("tr").hide();
+                }
+            });
+        });
     });
 
 </script>
diff --git a/src/opnsense/scripts/syslog/generate_certs b/src/opnsense/scripts/syslog/generate_certs
new file mode 100755
index 000000000..ac8730ce2
--- /dev/null
+++ b/src/opnsense/scripts/syslog/generate_certs
@@ -0,0 +1,63 @@
+#!/usr/local/bin/php
+<?php
+
+/*
+ * Copyright (C) 2021 Deciso B.V.
+ * All rights reserved.
+ *
+ * Redistribution and use in source and binary forms, with or without
+ * modification, are permitted provided that the following conditions are met:
+ *
+ * 1. Redistributions of source code must retain the above copyright notice,
+ *    this list of conditions and the following disclaimer.
+ *
+ * 2. Redistributions in binary form must reproduce the above copyright
+ *    notice, this list of conditions and the following disclaimer in the
+ *    documentation and/or other materials provided with the distribution.
+ *
+ * THIS SOFTWARE IS PROVIDED ``AS IS'' AND ANY EXPRESS OR IMPLIED WARRANTIES,
+ * INCLUDING, BUT NOT LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY
+ * AND FITNESS FOR A PARTICULAR PURPOSE ARE DISCLAIMED. IN NO EVENT SHALL THE
+ * AUTHOR BE LIABLE FOR ANY DIRECT, INDIRECT, INCIDENTAL, SPECIAL, EXEMPLARY,
+ * OR CONSEQUENTIAL DAMAGES (INCLUDING, BUT NOT LIMITED TO, PROCUREMENT OF
+ * SUBSTITUTE GOODS OR SERVICES; LOSS OF USE, DATA, OR PROFITS; OR BUSINESS
+ * INTERRUPTION) HOWEVER CAUSED AND ON ANY THEORY OF LIABILITY, WHETHER IN
+ * CONTRACT, STRICT LIABILITY, OR TORT (INCLUDING NEGLIGENCE OR OTHERWISE)
+ * ARISING IN ANY WAY OUT OF THE USE OF THIS SOFTWARE, EVEN IF ADVISED OF THE
+ * POSSIBILITY OF SUCH DAMAGE.
+ */
+
+require_once("config.inc");
+require_once("certs.inc");
+require_once("legacy_bindings.inc");
+
+use OPNsense\Core\Config;
+
+$instances = [];
+$configObj = Config::getInstance()->object();
+@mkdir("/usr/local/etc/syslog-ng/cert.d", 0700, true);
+foreach ((new OPNsense\Syslog\Syslog())->destinations->destination->iterateItems() as $id => $item) {
+    if (in_array($item->transport, ['tls4', 'tls6']) && !empty($configObj->cert) && (string)$item->enabled == "1"){
+        $dest_key = str_replace("-", "", $id);
+        $instances[] = $dest_key;
+        $cert_refid = (string)$item->certificate;
+        foreach ($configObj->cert as $cert) {
+            if ($cert_refid == (string)$cert->refid) {
+                file_put_contents("/usr/local/etc/syslog-ng/cert.d/{$dest_key}.key", base64_decode((string)$cert->prv));
+                file_put_contents("/usr/local/etc/syslog-ng/cert.d/{$dest_key}.crt", base64_decode((string)$cert->crt));
+                $cert = (array)$cert;
+                $ca = ca_chain($cert);
+                file_put_contents("/usr/local/etc/syslog-ng/cert.d/{$dest_key}.ca", (string)$ca);
+            }
+        }
+    }
+}
+
+// cleanup old/unused certs
+foreach (glob("/usr/local/etc/syslog-ng/cert.d/*") as $filename) {
+    $instance = explode(".", basename($filename))[0];
+    $ext = pathinfo($filename)['extension'];
+    if (!in_array($instance, $instances) && in_array($ext, ['crt', 'key', 'ca'])) {
+        unlink($filename);
+    }
+}
diff --git a/src/opnsense/service/templates/OPNsense/Syslog/syslog-ng-destinations.conf b/src/opnsense/service/templates/OPNsense/Syslog/syslog-ng-destinations.conf
index 047d176db..5c0c8569f 100644
--- a/src/opnsense/service/templates/OPNsense/Syslog/syslog-ng-destinations.conf
+++ b/src/opnsense/service/templates/OPNsense/Syslog/syslog-ng-destinations.conf
@@ -30,7 +30,20 @@ destination d_{{dest_key}} {
         ip-protocol({{destination.transport[3]}})
         persist-name("{{dest_key}}")
     );
-{%            endif %}
+{%           elif destination.transport in ['tls4', 'tls6'] %}
+    network(
+        "{{destination.hostname}}"
+        transport("tls")
+        port({{destination.port}})
+        ip-protocol({{destination.transport[3]}})
+        persist-name("{{dest_key}}")
+        tls(
+                ca-file("/usr/local/etc/syslog-ng/cert.d/{{dest_key}}.ca")
+                key-file("/usr/local/etc/syslog-ng/cert.d/{{dest_key}}.key")
+                cert-file("/usr/local/etc/syslog-ng/cert.d/{{dest_key}}.crt")
+        )
+    );
+{%           endif %}
 };
 
 log {