The problem is not building openssl, the problem is providing access to some database of root certificates for the custom built openssl. homebrew includes a script that exports the apple certificates into a form useable by openssl. That solution is a horrible hack -- for obvious reasons.
I am looking into bundling the mozilla root certificate db with calibre for use on OS X. This is less than ideal, it means that the root cert store can get out of date unless the user updates calibre and the user cannot use the system keychain to manage the root certificates calibre uses -- but such is the price of using Appleware.
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