RWW (internal error 50331656)

Searching for "internal error 50331656" reveals a discussion on an external site that points this issue as possibly being caused by a lack of a certificate assigned to the terminal service gateway.

Just back from holidays and back investigating issue and I can confirm there is a certificate assigned to terminal service gateway.
An external site discusses editing workstation registry key HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\TermService\Parameters but I can't find the external site that discusses the lack of a certificate, can you please add the link to a comment and I will investigate further.

Is this internal error seen on a single workstation trying to connect or is it on all workstations?

Check whether the certificate chain is valid

use yahoo to search for "internal error 50331656" within results search for chicago.

Not sure whether a link to that forum should be posted here.

The issue with this deals with the cryptographic system either missing on the server or on the workstation, if all workstations are having issues, one would look at the server first, if only one workstation has issues, one would look at the workstations affected.

Double check the certificate and look at its signing chain to make sure that while the certificate you have loaded is valid, one of the signing in the chain may have expired.
Or an updated intermediary needs to be loaded.

If on a single workstation, it may have issues with the cryptographic system, missing the CA/trusted certificate, etc.

Not sure you want to keep your comment since it is not a solution it is a confirmation that the issue is limited to the home system being used. .......

I think the steps trying to determine and the link to check on the cryptgraphic system on the home system is the way to go, I believe there might be a fixit from MS dealing with crypto system, though not sure.

Will continue to troubleshoot and investigate internally