Windows Server 2003
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In general 12 Gb should be enough if you clean it up.
I'll find the clean up FAQ from leew
I hope this helps !
http://www.lwcomputing.com/tips/static/bootdrivesize.asp






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After this is all complete you SHOULD run a CHKDSK to check filesystem.
If you do not have Acronis, or such, you can do this with a linux liveCD.
Example take a Ubuntu LiveCD and let it boot up Once inside the desktop click start and choose run command, type in: gparted
(1) Â Resize D: to free up some space
(2) Â "Slide" D: to put the free space adjacent to C:
(3) Â Resize C:
Done :-) Â Â You can use this technique to make C: as large as you want.
Here's a bit more detail on the process:
https://www.experts-exchange.com/questions/21929035/Bootit-NG-and-Partition-resize.html
Note in particular the pictorial example of what you need to do here:
https://www.experts-exchange.com/questions/21929035/Bootit-NG-and-Partition-resize.html#17169507

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Do you have personal or server version?
If you have server version, after you watch this demo, you will definitely know how to resize your partition. All you have to do is boot the Advance recovery CD and follow the steps:
http://www.paragon-software.com/export/sites/paragonsoftware.com/images/screenshots/en/pm-server/2_redistribute_free_space.swf
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run Partition Manager and in its main interface right click on D: and choose Move\Resize.
Then in opened window catch the left border of volume with mouse left click and drag it to the right. Free 5GB space as you need and apply changes. When D: drive is not locked by running applications the operation should complete in Windows. In Partition Manager 9.0 you can see the files locking partition and close them manually.
Ok, free space is taken and located between C: and D:
Now right click on C: and choose same Move\Resize option. Then catch the right border of partition and drag it to the right so your free space block would be allocated to C: volume. Apply changes and in few moments operation will complete.
Its done. I have done this operation many times so if you have questions feel welcome to ask.
Windows Server 2003
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Windows Server 2003 was based on Windows XP and was released in four editions: Web, Standard, Enterprise and Datacenter. It also had derivative versions for clusters, storage and Microsoft’s Small Business Server. Important upgrades included integrating Internet Information Services (IIS), improvements to Active Directory (AD) and Group Policy (GP), and the migration to Automated System Recovery (ASR).