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We're about to fork out more than $20,000 in new Windows Server 2008 R2 licenses and CALs, and are in the position of deciding if we're going to purchase Software Assurance or not.

I've tried to search for a Windows Server roadmap, but all I can find is some seriously non-commital data here.

Is there any other data from Microsoft that we can use to evaluate whether it's worth while purchasing SA on the basis of major server OS releases in the next 3 years?

Basically, I'd be pretty upset if I had purchased SA in 2003 because there wasn't any use for it until 2008 and we don't want to find ourselves in that situation.

Worth noting that adding SA to the licenses increases the cost to $30,000 so it's a fairly big jump

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up vote 4 down vote accepted

Microsoft has had a fairly well established pattern of releasing a new server OS shortly after the release of their desktop OS. Windows 8 has been revealed by Balmer to be slated for 2012, so I imagine we'll see a new server OS in 2012 or 2013 (barring any Vista-style delays). I think you're safe in assuming you'll get something out of it. There's at least one guy who thinks he can give it a more definite date.

As for a roadmap...haven't seen one yet. Based on the recent server releases from Microsoft, I just assume that I"m going to drool over it when it comes :-)

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Windows 8: RTM: Friday, July 1, 2011 yeah, I think they're going to have to push pretty hard to reach that deadline... – Mark Henderson Jun 8 '11 at 4:05
Well...Apple announced Lion a month before release...And everybody wants to be like Apple now :-) – Jason Berg Jun 8 '11 at 4:07
The other thing is that almost all of that $20,000 is RDS CALs, so even if we did upgrade our OS's, our TS would most likely stay as they are for a much, much, much longer period... thanks for the confirmation though – Mark Henderson Jun 8 '11 at 4:07

For the server licenses, we've never purchased SA, but then we tend to keep servers in production for a long time and run with a mix of OSes. So we've always managed to roll out new versions of the OS on new hardware.

For CALs, it's been a mixed bag. For the amount of money you're talking about, you have more users than we do, so I don't think our CAL strategy of "sometimes SA, sometimes not" would work for you - too tough to keep track of what you've got.

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Our thinking was along the same line as yours. SA for CALs, not for OS licenses, because it's pretty rare that we'll upgrade the OS on a particular server once it's in production, but its nice to know that your CALs can be if the situation calls for it... – Mark Henderson Jun 8 '11 at 5:51
(also, with the price of RDS CAL's combined with a regular Windows CAL, it's not too hard to hit $20,000 - at least in $AU anyway) – Mark Henderson Jun 8 '11 at 5:51

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