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Lost Between Server 2008 R2 and Server 2012 R2 (Among Other Things)

Hello all, and my apologies for what I'm sure is the newbie ignorance of the following questions. I work for a small, independent software company that sells a desktop database application for recruiters. We're looking to create a cloud version. We just signed up with Rackspace cloud servers, and I'm getting seriously lost during setup. (Been in software/IT 14 years, never in server admin, though.)

 The basics:

- Provide individual users access to a single Windows application (not the full desktop) through RemoteApp over the internet.

- Our application is a database program that uses a Microsoft Access format back end (we do not need Access itself installed), so a user or group of users would need shared, full permission access to a data folder where the database file itself is stored.

- Most of our customers are <5 users and only a few are >10 users, so my thought was to use individual cloud servers, adding new ones as necessary for demand.

- Individual user accounts on the same server would need to be restricted to only their specific data directories, multi-user clients would need a shared data directory.

I've tried setting up Server 2012 R2 for this, but it appears to not want to do Remote Desktop on the same server as Active Directory. When I attempt to set it up without Active Directory, I can't access Remote Desktop Services through Server Manager because I'm not logged in as a “domain user”. I also tried to get it going under Server 2008 R2 (which doesn't seem to require AD), but the available documentation on-line is spotty at best.

Given those (I hope) simple requirements, can anyone who knows more about Windows Server than me (which would, I think, be all of you) recommend an OS version and what roles should be installed? Or recommend a good server admin book that covers cloud deployments like Rackspace well? Tech support is the least fun part of my job, and I hate getting those kind of open ended questions, but right now I'm lost.

Thanks much.

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  • UPDATE 07/22/2016 : It looks like Jeff was able to respond first.  I would recommend going with his input as he is the more experienced administrator.


    As you have found, without an Active Directory domain, setting up remote desktop services on a single Windows 2012 server is almost impossible.  I have read that it might be possible via PowerShell but I have not found solid documentation at this time.  

    I too recall the days when you could task a server to play the part of several roles.  Many of the older Microsoft TechNet deployment guides are still online available for reference.

    I wish you luck with your project. If you have any questions or concerns, please don't hesitate to get in touch with us.

    High regards,

    Bill Hertzing
    Cloud Launch Manager

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