I've been dealing with spats of SSL issues recently too. I eventually
also settled on making Satchmo as ignorant as possible and performing
rewriting on the server. In my opinion, this should become the
standard methodology; the current internal method for handling SSL is
pretty broken, as we can see by almost everyone in this thread
admitting to just using the web server's rewrite to ensure the right
mode is used.

Since I'm using basic PayPal, however, a redirect causes the loss of
POSTed data, which means that Satchmo does not fully register a given
sale. To work around this, I went into the lookup_url method and set
ssl as always True (not default True, always True). I'm hoping that
makes PayPal work correctly by avoiding the redirect that drops pp's
post data, but I haven't tested because the test interface usually
works, even without the post, but the real payments don't work; I'm
assuming here because they don't have the POST attached. So hopefully
that will fix that.

There is really no need to be weird about this or handle it internally
beyond URL writing; Satchmo should allow us to specify which links
should be printed with https:// prefixes, and otherwise let us deal
with things like redirecting on the web server. Since we currently
have to eat the SSL variable to avoid errors or redirect loops if we
are using web server rewriting/redirection, it does not get passed
correctly to the application. There should be a global toggle that is
respected regardless of anything else.

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