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We're planning on installing WordPress on Windows Server 2008 to be consistent with the rest of our servers and leverage administrative expertise.

The server will not be running anything else. Are there any gotcha's to be had for Wordpress on Windows versus Linux (outside of server licensing costs)?

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I've installed WordPress on my virtual server running Windows Server 2008 R2. Installation was easy, no troubles. I installed PHP using Web Platform Installer. PHP 5.3 performs well on IIS7 and you can also use WP super cache to increase performance. There haven't been any downsides for me so far :)

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Maybe this is slightly unrelated to the original question, but what about permalinks? On the few installations I've done on Windows servers, I've had no luck getting anything but the most basic permalink structure up and running. In contrast, WP interacts with mod_rewrite on Apache almost seamlessly. Is there a workaround for that? –  goldenapples Sep 3 '10 at 12:00
    
@goldenapples You can install ISAPI_Rewrite on IIS and have it take care of your permalink needs. –  KalenGi Sep 9 '10 at 1:57
    
@Mika Kolari: Any specs of the Linux system to share you compare against? Or is this windows only? –  hakre Sep 9 '10 at 2:06
    
I've had issues with mailing items but have been able to overcome them with wp-mail plugin –  curtismchale Sep 9 '10 at 2:07
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I had issues when I was developing a plugin on Windows with unicode. It had something to do with replacing whitespace with preg_replace. When I switched to Linux, the issue went away... –  jjeaton Oct 9 '10 at 2:35
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Given the way that Linux and Windows are licensed, using Linux would cut on the OS licensing costs, and Linux would make a better use of the CPU as you would only load the modules and process you need, with greater flexibility than Windows.

Also, you can run a server-only Linux, which is not possible under Windows, as well as running a headless computer, which you can access using a simple SSH connection. You may want to take a look at DistroWatch:

http://www.distrowatch.com

They will list all the major distros as well as those that are geared towards server configuration. The LAMP (Linux Apache MySQL PHP) configuration is what you are looking for.

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You can absolutely run a headless windows server, with ssh support if you so choose so. However the server implementation in windows already prioritizes service processes over the desktop/gui components by default so it's not really much of an advantage to disable the "head". Additionally Remote Desktop is the "windows way of doing things" so for those without ssh / command line knowledge it's a suitable and performant solution. –  Marcus Pope Aug 16 '12 at 19:42
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WordPress doesn't interact with the operational system in any way, so it doesn't really matter. You need DB and web-server so your question would be for instance "do Apache and MySQL behave better on Linux" or "Is Apache faster on Linux, than (IIS) on Windows?".

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Although wordpress could use, for example, certain features of PHP/apache that are much better optimised on one OS or the other. –  Bobby Jack Sep 3 '10 at 13:00
    
Which is yet a matter of behavior of your environment and compatibility OS <-> web-server <-> database server. –  vlood Sep 3 '10 at 14:53
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In any case, in Windows, you are not forced to use IIS7 , can use other options. I would advice to check BitNami WordPress installer. You can even have a sort of LAMP in windows: http://bitnami.org/stack/wampstack , and install apps like WordPress as modules, which will use WAMP as common base.

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protected by toscho Aug 16 '12 at 19:24

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