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I have a GPO that installs an application using the Software installation policy under Computer Configuration. I assign this GPO to the OU with our desktop/laptop computers, and my clients all install the software fine.

I have another separate OU that covers our new Server 2012 RD session hosts. Previously, we've manually installed applications on our one Terminal Server. Now we have one Broker and two Session Hosts. I'd like to take my existing GPO, assign it to the session hosts, and have it install on the next reboot after a gpupdate so I'm sure that each is identically configured.

Given this info:

  1. Should I be able to install applications via GPO to Session Hosts?
  2. Will Group Policy automatically install the applications as if I put the session host into /install mode, or do I need to do that?
  • using the Software installation policy under Computer Configuration I think Dante wrote a book about that, didn't he? In all seriousness, short of things the ICC in the Hague would classify as war crimes or crimes against humanity, I can't imagine any use for those GPOs, especially with PowerShell remoting being so easy and mature these days. – HopelessN00b Jun 10 '14 at 20:27
  • We're getting SCCM in a month or two, finally. In the meantime, I'm maintaining what we have. I know GPO software installation gets a justifiable bad rap, but it's honestly not been horrible in our environment. SCCM should improve this, but I don't have the months to spare for it. – CC. Jun 10 '14 at 20:44
  • @CC I feel your pain, as I've been in your shoes before. I really hope you can postpone all your software installation until you get SCCM running. Software installation on RDS servers can go haywire if you're not in total control (terminal services install mode for legacy apps etc). – pauska Jun 10 '14 at 21:48
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See my comment on why this is a bad idea.

That being said:

  1. Yes, it should work.
  2. Yes, the windows installer service knows that it's running on RDS and automatically kicks in installation mode (GPO installs are .MSI-only)
  • That's good to know. It is an MSI install. I'd really prefer not to install manually, but perhaps that's the better solution since it's only a couple servers. – CC. Jun 11 '14 at 17:19
  • @CC. Yeah, if it's only a couple servers, just do it manually. Automation's not gonna save you a lot of time in this case, and if it goes sideways, you'll really be hurting for it. – HopelessN00b Jun 13 '14 at 13:09
  • Ended up doing manual installs. Not letting perfect be the enemy of good here. SCCM can't come fast enough. – CC. Jun 17 '14 at 19:48

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