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We set up a new 2016 standard server with essentials role a few months back and set up anywhere access using the free remotewebaccess.com domain which has worked fine for us on previous windows versions however it seems that on server 2016 standard there's a common problem which appears to be with the certificates which means that the server has to be restarted every 24 hours otherwise the anywhere access stops working. My research into this so far seems to indicated that the only solution is to not use remotewebaccess.com.
I've had a brief look at your tutorial about using Lets Encrypt certificates but I was wondering if you have any experience with setting this up after previously using remotewebaccess.com? In particular for remote workers as I'm assuming that as soon as we complete that tutorial the remote workers will no longer be able to connect via anywhere access? How do we get those remote workers updated with the correct information, would it be a matter of running the connect computer wizard again?
Using remotewebaccess.com and Let's Encrypt may not work because you do not own the domain. Though I think it would technically be possible to run Certify the Web for someone.remotewebaccess.com and generate a certificate I don't think it is a good idea because you don't own it.
Get your self an FQDN like yourcompany.com and get a static IP address for your Internet connection. Remote users would need to change the URL they connect to, like https://remote.yourdomain.com/remote and the VPN connection on the client must also be changed to remote.yourdomain.com.