Single Client Computer Suddenly Cannot Connect to Remote Web Access on 2012 R2 Essentials Server

John N
John N used Ask the Experts™
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We manage a law firm's computer network.  The server operating system is Windows Server Essentials 2012 R2.  We installed the new network in 2015, and overall it has worked very well.

One of the senior partners at the firm lives a long distance from the office.  As a result, he relies on the Remote Web Access (Anywhere Access) to work remotely.  His desktop computer has Windows 10 and he uses Google Chrome as his primary web browser.

Until recently, the RWA system has worked very well for him.  Recently, though, he has been unable to connect to Remote Web Access.  Instead his attempt to do through with Chrome results in a timeout error and failure.  Please note that he has used Chrome for this function since 2015 and it has worked consistently and reliably.  Also, he is able to connect to many other web address without problem.

We tested connecting to their Remote Web Access system from our office, using various browsers, computer and operating systems (Windows 10 and 7) and in every case we have connected easily to RWA.  The only time we experienced the timeout error with Chrome was when we incorrectly typed the RWA address.  Once that was fixed, everything worked perfectly.

Given this background and recent problem, does anyone have any ideas how we can fix this?  Thanks very much for your help.
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Sounds like a possible issue with his "home" connection and/or PC

Any firewalls in play which could be blocking his "home" IP? (or vise versa) etc??

Have you checked his "home" PC and modem/service to make sure there weren't any issues?

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Commented:
Thanks for your suggestions.  When asked, the user indicated that he experiences no other problems with Internet connection or web site access other than the one described above.

Also, nothing has changed in terms of IP blocking or firewall changes (and this remote access function has bee working perfectly for him for over five years now with the same firewall settings).
Commented:
We were able to get the remote machine to connect to RWA by using a different web browser.  Initially we tried Chrome again, but it failed as noted above.  Next we tried Internet Explorer and Microsoft Edge.  On the first pass, neither of them worked either.  However, when we tried IE again, it worked, as did Edge and Chrome!  My theory is that somehow an invalid DNS entry linked the RWA site to the wrong IP address (which explains the recurring timeout problem with Chrome).  Apparently that was fixed by a later run with IE and then all three browsers worked (probably a common file used by all three of them).

If anyone has a different theory, please write back.  Thanks.

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