By strange coincidence, I got the same error tonight, using web2py 
v.2.9.12-stable on the latest version of pypy (python written in python). 
 In my case, I'm pretty sure it is a file handle leak caused by my code 
which handles scheduled insertion of files into the database.  If pypy were 
dramatically faster at something, I'd pursue it, but my initial tests did 
not show a dramatic improvement so I'll probably just deploy on regular 
Python.

Just thought I'd mention it in case you're using some weird version of 
Python on your mac.  Speaking of which, is there some reason you're using 
Python 2.5 instead of a version, say, something like five years newer?

-- 
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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