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Chris HFlag for United States of America

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TS Gateway 2008 is NOT compatible with RPD 8.x protocol or greater

I've spent a year, several days and three refunded support cases only to learn from the horses mouth that, internally recognized, Microsoft RDP ver 8.x is not compatible with TS Gateway on server 2008 (Not R2).  The product is not end of life.  What this means for my organization?  NO WINDOWS 8.  NO IPAD OR IPHONE RDP.  

Hopefully this gets indexed appropriately through google and anyone going through this problem will have reference.  Stop searching.  Stop making registry edits....  Stop spending hours trying to figure out the issue.  T2 lead from MS specifically told me, IT IS NOT COMPATIBLE.  IT WILL NOT WORK!

But don't worry, they're really sorry....
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Rob Williams
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Correct: "Note This feature requires the Remote Desktop Gateway server to be running Windows Server 2008 R2 or a later version.

"The following new features in the RDC 8.1 client update ......."
http://support.microsoft.com/kb/2830477
PS-
As some possible alternatives, though I appreciate there are some disadvantages, the Remote Desktop App for Win 8/8.1 from the Windows store will work with older TS gateways:
http://apps.microsoft.com/windows/en-us/app/remote-desktop/051f560e-5e9b-4dad-8b2e-fa5e0b05a480
MAC version:
https://itunes.apple.com/ca/app/microsoft-remote-desktop/id714464092?mt=8

As will the Remote Desktop Connection Manager:
http://www.microsoft.com/en-ca/download/details.aspx?id=21101
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They finally disclosed it in 8.1.  8.0 was and still remains undisclosed.  RDP app in windows 8 does not work as you state or they state.  Microsoft has just fully refunded this last support ticket and said the only way you're getting a windows 8 computer onto your network is to buy an R2 license or do not use TS Gateway.  This isn't EOL... make it work.
I am on Win 8.1 and connect frequently to two 2008 (pre R2) servers using TS gateway and both the Remote App and Remote Desktop Connection Manager.  I do not recall trying the remote app with Win 8 (pre 8.1) but did frequently use remote desktop manager.  

However, the Remote Desktop Manager, an indispensable tool for admins, is not an ideal solution for end users and the Remote App does not support multiple monitors , so I agree neither is an ideal replacement.

Though it would be nice if it were backward compatible, I am surprised it took Microsoft that long to advise the 8.0/8.1 client wouldn't work.
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The tech, who I'm sure was thrown out on the streets of Bangladesh, said and I quote "Sir, I have at least 20 cases involving this same issue.  I could drag it out for weeks and tell you we are working on it, but we will never find a solution..."    

My head exploded.  I asked to speak with a manager, who I then used some choice profanity with.  I told the guy, I don't care that doesn't work, just don't lie to me and waste my time and money.  It just seemed tacky and lowdown.
I can appreciate your frustration.  It wouldn't be so bad if 5 minutes into the call they simply said it wouldn't work, at least you could take other steps.

If you need a work around this apparently works in most cases, though you are lowering security some to do so.  After reading your comments I was thinking there are likely others having similar issues and did some digging.
http://www.theogray.com/blog/2013/07/terminal-services-gateway-logon-attempt-failed-with-rdp-80
Other sites have also reported this works for most configurations.
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We had reviewed that last year around xmas time and still the issue persists.  My boss had bought 9000$ worth of new Surface RT computers for our producers, had to return all of them for Ipads.  Now MS force updated RDP on the ipad, doesn't work anymore....   They bought out and snuffed the I-Tap RDP program, which worked on the old RDP protocol, rebranded it into a microsoft product and then systematically poisoned it.  

Make no mistake...  This is M$ simply on the hunt for more money.
You don't sound like a Microsoft fan :-)

Why wouldn't Microsoft go after more money?  They are not a charity.  It seems to be OK when the car manufactures and cable companies do it, or me for that matter  :-)

They have added a lot of new features in the new RDP clients such as beefing up RemoteFX so I imagine it is hard to make it stay compatible with 7 year old servers, however I agree it would be nice if you could downgrade the client to RDP 7.
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It really varies...  I'm no fan of poor customer service.  I usually sing MS praises and I just bought a new computer with Windows 8.1...  

RANT>This is a systematic removal of a working product.  The acquisition of I-Tap and other companies, the renaming, re-branding and re-versioning RDP.  The fact you use the same protocol and increase the version number should validate that it was built off of version 7 and is backward compatible.... Otherwise, call it RDPv2 1.x.  </RANT

And as for your analogy:  My 62' vette still loves eating 2014 gas by the tank load.  Big oil will never fail me :D

Anyway, i just wanted to vent.  Have a good weekend.
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I mean, imagine if you couldn't drive your toyota to work tomorrow because it's incompatible with the roads or your parking space?/  This is killing me inside..
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Rob Williams
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