Ok, Simone is a legend. He found that a recent change in Microsoft's 
wfastcgi.py was causing the problem. He suggested a fix requiring IIS's URL 
rewrite module, which I have tested and it works. I've moved from apache to 
IIS now and I'll see how it goes over the coming week. 

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Resources:
- http://web2py.com
- http://web2py.com/book (Documentation)
- http://github.com/web2py/web2py (Source code)
- https://code.google.com/p/web2py/issues/list (Report Issues)
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