Remote Desktop hanging on "Configuring Remote Session"

I've got a couple of Windows 10 Enterprise VMs which are used for connecting to remote customer sites.  They have pretty much no 3rd party software on there, we just connect to remote sites via a VPN then Remote Desktop in the systems.

This has all been working fine for years, but some time in the last month or so (I think) the RDP sessions take ages to connect.  The VPN will connect fine, and I can ping the machines no problem, but when I RDP in it just hangs on "Configuring Remote Session" and then a couple of minutes later it fails.

Typically, if I retry connecting straight away after it fails then it will connect almost straight away (if I leave it a few minutes then it continues to hang and fail).

This is happening on more than one Win 10 Ent system, and when connecting to completely different sites, so I don't think it's network related.  Seems like it may be a Win 10 update that's caused it.  Current build is 10586 1232.

Anyone else having this issue, or know how to resolve it?
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You should first compare the behavior to that when connecting to clients in your LAN.
Your windows version needs to be updated, 10586 is out of service since october.

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Cliff GaliherCommented:
It wouldn't surprise me if an update (not on your enterprise, but on the clients) broke things.  If you are diligent in patching clients then it is quite possible.   I can't put my finger on anything specifically, but Microsoft is regularly patching security flaws and several of those impact RDP, at least indirectly.   Thought I haven't heard of any RDP-breaking patches, if MS released a patch that fixes an recently, and 10586 did not get a matching patch since it is out of support, you could have issues from then on.  That's my initial instinct at this point.
JohnBusiness Consultant (Owner)Commented:
The only issue I have had with RDP is with V1709 and the Local Printer resources has to be unchecked. Other than that, yes, your Windows 10 version is very old.
Cliff GaliherCommented:
That 1709 bug should be fixed with the latest CU. Just as an aside.
fred2k3Author Commented:
Yes, Windows was out of date - it turned out that the version of Symantec Endpoint protection I had installed was causing issues with Windows updates.  Thanks all for input.
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