Thank you Mike. I went ahead with the manual domain configuration and have made progress. I’ve got my domain and records published. I can get to a generic Windows Server Internet Information Services screen when navigating to my top level domain and remote subdomain from outside my home network (at work for example). Dynamic DNS seems to be working. I have also just purchased an SSL certificate and installed it on the server. I am left with only a single error now when trying to complete Anywhere Access configuration. See attached. I have checked via various online port checking websites (from the server) that ports 443 and 80 are open/accessible (I have forwarded them to the server static IP in my router). I don’t know how else to troubleshoot this error. Would you have any suggestions?

Thank you Mike.  Yes, I discovered that notice after further research.

I think I buried the lead though.  Seemingly irrelevant to this benign error (I am looking for any “smoking gun” 🙂 ), I am unable to get to the remote web access login screen:

1. from any other computer (on the LAN or outside the LAN)
2. from the expected web address format from within the server’s browser itself

I’ve been troubleshooting as best as my skills/research allow, and I suspect there must be something going on with IIS bindings (maybe?). I’ve tried to document different access scenarios in the attached screenshots.  Note: all of these screenshots are working directly from the server’s browser (not a different computer on the LAN). I can never get anywhere via “customdomain.com” nor “remote.customdomain.com”. I can only get somewhere using other addresses with “/remote” appended (which is not behavior I expected from the tutorial). None of these other methods however allow me to get the web access logon from another machine. Using the same addresses from another machine on the LAN always results in a 403-Forbidden: Access is Denied. I also notice that Edge (on the server) always reports the connections are not secure, as if the SSL certificate is not present.

Any suggestions?

Thank you very much Mike! Admittedly, I had been mucking about with the bindings, as I didn’t understand why there was originally (after the essentials anywhere access wizard process) a second HTTPS port 443 binding with a certificate pointing back at my SERVERNAME.  So I deleted that one and redid the http and https, thinking that’s all I needed.  Understood now, I should have let Essentials wizard handle it.

I ran the repair functionality from anywhere access and it re-established the original bindings.  A strange thing though, the http/port 80 binding still shows as lowercase. Any idea the impact of this? I can’t tell any negative consequence so far.

I don’t know why I didn’t detect it, but until you’ve pointed it out just now I never noticed the need to append /remote to the end of the URL when trying to navigate to the web access logon page.  Must’ve been when I kept reading that sample URL I just figured remote.vanitydomain.com would do the job.  The /remote suffix is never entered anywhere else in the Essentials wizard steps on essentials (just looking for excuses to explain why I missed it 🙂 ).  I have now been able to navigate to the web access logon page from the server’s browser, from a MAC laptop on the LAN and from my iPhone not on the LAN.  All is working now.

One final question; I notice then when I type remote.vanitydomain.com/remote from the Edge browser on the server, it automatically appends the https:// to the beginning of the URL and navigates straight away to the web access logon screen. Almost so fast I miss the URL updating itself.  When I try the same action from Safari on my MAC laptop (still on the LAN), I get a 403 forbidden access error, and the https:// has not automatically been appended to the beginning of the URL.  However when I specifically type https://remote.vanitydomain.com/remote from either the MAC or iPhone browsers, it navigates perfectly to the web access logon screen (and indicates its a secure connection).  Would you think this is just a “feature” difference between Edge and Safari browsers?

Ideally, I’d love to be able to type remote.vanitydomain.com from any browser, and get to the web access logon screen.  I am gathering from your last post, that it is not possible to manually create a redirection on the server from this to https://remote.vanitydomain/com/remote without breaking something else in Essentials? Is there anything with CNAME records that could help?