http://bugs.winehq.org/show_bug.cgi?id=31159
--- Comment #11 from Juan Lang juan.lang@gmail.com 2012-07-14 09:31:07 CDT --- Perfect, thanks for the details. (And I'm sorry it's wearing you down.)
There's a bug having to do with secur32 and certificate caching, bug 27168, and I wouldn't be surprised if there's a similar bug with wininet. You could have a look if attachment 36923 has any impact.
I'll have another look at the log in the meanwhile to see if there's anything that sticks out.