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If you are wondering if Simple:Press will work using Windows Azure and IIS I can tell you that it definitely does!
I recently created a WordPress site using the Windows Azure website then installed Simple:Press without issue.
If you are familiar with Azure you know you can create a website using the gallery. This is what I did and created a basic WordPress install. I then uploaded Simple:Press and activated it in the standard way. It installed fine and once I created some groups and forums it all worked as expected.
What it is currently running is:
- IIS 8
- PHP Version: 5.4.23
- MySQL – Version: 5.5.21
Also, if needed, it very easy to access the WP files via FTP and you can also use an external database without issue. You can also change the default php setting using a .user.ini file.
In my tests everything worked fine right out of the box but if you have special needs then you should be able to setup anything you need.
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