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Get a free Let’s Encrypt SSL certificate for Access Anywhere and automatically renew it.

Get a free Let’s Encrypt SSL certificate for Access Anywhere and automatically renew it.

Maybe you have heard of Let’s Encrypt, the new open certificate authority where you can get a free SSL certificate that you can use with RWA and Access Anywhere on your Windows Server Essentials 2012 R2 or 2016. In this tutorial we will learn how to get the certificate and how to automatically renew it because Let’s Encrypt SSL certificates are only valid for 90 days. 

Here Why ninety-day lifetimes for certificates? - Let's Encrypt - Free SSL/TLS Certificates is explained why that is. In our setup we automatically renew certificates within 60 days so once this is set you can forget about it.

Before we can do anything we need to download a Simple ACME Client for Windows and the easiest solution I have found is ‘letsencrypt-win-simple’. This is an open source .Net solution that automates requesting new and renewing existing SSL certificates from Let’s Encrypt. You can download the latest compiled version here.

Mariette Knap Mariette Knap
Published 01/09/2017 15:02
  • Windows Server Essentials 2016
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Mariette Knap

If you have visited this page before you notice we have changed the way Lets Encrypt certificates (Let's Encrypt - Free SSL/TLS Certificates) are requested. We now use ‘Certify the Web’ from Certify Your Windows IIS Website - free SSL and https powered by Let's Encrypt. A very easy to use tool to configure Let Encrypt certificates on your server for Anywhere Access. It is completely free up to 5 certificates and for most SMB’s this is more than enough. No more wrestling with Powershell as we did in the past, lets use ‘Certify the Web’.

Get a free Let’s Encrypt SSL certificate for Access Anywhere and automatically renew it.

replied 03/14/2018 07:15
Norm Snider

I followed this procedure a year or two ago and things were working fine for quite some time.  However, in the recent months it has stopped working, which is preventing me from getting in with VPN.  Finally today, RWA stopped too.  How do I diagnose and solve the problem?  

I am being told the certificate has expired.  However, when I go into the Certify the Web app it says the last renewal was 9/6/2019 and it expires on 12/5/2019.

Any suggestions would be appreciated.

replied 10/05/2019 00:45
Last Activity 10/05/2019 00:45