I have a similar set up, but do not use connection pooling. When the MSSQL 
server is rebooting, any requests by web2py will predictably return an error 
about not being able to connect, but when the MSSQL server becomes available 
again, web2py starts working again, no restart required. So I suspect that 
connection pooling is the culprit. I have never used connection pooling 
before (never needed it), so I wouldn't even know where to begin in 
debugging that part of the code, sorry.

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