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My own system is I think fully "up to date" as far as Apple security updates through the App Store, but the version of OpenSSL installed on my system is 0.9.8zg, a version that was current during the past year, but lost all security support as of Dec 31, 2015.

https://www.openssl.org/news/secadv/20160128.txt

I read elsewhere that, when one uses a VPN, and that VPN client comes bundled with a different, later version of OpenSSL (say, version 1.0.1r), that VPN client's version will supersede--that is, the more up-to-date version will mediate the negotiation with a network connection in a browser.

My two, related questions are:

(1) is this accurate? If so, it would seem that running a VPN with a current version of OpenSSL would nominally 'protect' the user better than a deprecated version installed on the OS, correct?

(2) If a user has no VPN, is the user then relying on the vulnerable version of OpenSSL in the OS alone for that layer of security? Or are later versions of OpenSSL somehow 'bundled' within specific applications--the browser, Skype, iTunes, etc.--just as it is 'bundled' with a VPN client?

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Having done further research, I see the following appears to answer my questions:

  • OpenSSL is just one of many SSL/TLS implementations
  • OS X does not rely solely on OpenSSL (though the deprecated version of same is still installed with the OS), but rather its own implementation called "Secure Transport"
  • Depending on the application in use (Firefox, iTunes, Mail, etc.), either OpenSSL (firefox), Secure Transport (iTunes, Mail), or yet some other SSL/TLS implementation may be utilised for the secure handshake
  • Because the VPN adds just one 'layer' of security, independent of the security implemented by the application, the TLS implementation at the VPN layer in no way affects that used at the application layer (a useful analogy is the layered 'tubes' analogy provided here:

    https://security.stackexchange.com/questions/27891/how-do-a-vpns-route-ssl-traffic-and-do-they-compromise-security

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