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I'm tinkering with a Server 2008 R2 server that has a 16 GB C: drive. After running Windows update, I only have 340 MB of free space left. C:\Windows\Assembly is taking up 8 GB and C:\Windows\Installer is takiing up 2 GB.

What is the best way to make more room on my C: drive?

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What a question? Make C: bigger! Use Gparted for it. – mailq Sep 19 '11 at 20:31
Expand the volume?!? Seriously there are not a lot of file you can delete under \Windows. But I'd suggest running WinDirstat top find any big files to see if there are any to delete. – uSlackr Sep 19 '11 at 20:32
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No need to use GParted to expand the volume. Windows server 2008 can do this natively if there is room to expand into – uSlackr Sep 19 '11 at 20:33
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The minimum disk space requirement is 32GB. What do you expect, seriously? – Ben Pilbrow Sep 19 '11 at 20:34
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@mailq: you can extend the system/boot volume in W2K8 (under the correct circumstances), I've done it many times. blogs.technet.com/b/mghazai/archive/2009/02/24/… – joeqwerty Sep 19 '11 at 21:09
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Honestly? 16 GB for C: on Server 2008 R2 is woefully insufficient, as you've already noticed. Extend it with something or, since you're just tinkering with this server, buy a bigger disk and put it in. MS recommends at least 40 GB.

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(ah, missed the part about only allocating 16GB to the C: partition to begin with. that'll cause problems. my response is for more general space issues not related to what amounts to a misconfiguration.)

The first thing to do is to step back and decide whether or not this makes sense. Do you likely have a full drive's worth of actual data + applications or is something, somewhere going unchecked and causing issues for you.

If you feel that it does makes sense, then there's not a whole lot you can do besides move some of that data off of the drive. Sure, you can compress some folders and their contents and that might gain you a bit, but it's not going to solve the problem in the long run.

If you don't think that you should have a full hard drive at this point, you'll need to do some more research. Among other possibilities, there might be some extremely verbose logging that is causing the space issues.

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