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I just limited all my SSL ciphers to TLS 1.X and TLS1_RSA_AES and my up-to-date OSX machine is no longer able to connect to the server via Outlook 2011.

I can use Safari to connect to the same host, so this is probably an app-specific issue.

How do I, in OSX, figure out what TLS cipher and protocol is being used to connect to a given host?

This is necessary to remove security risks with SSL3, BEAST, CRIME, POODLE, and other security risks.

Ideally I will remove all ciphers locally that use RC4 and other risky protocol negotiations.

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As you already remarked, the use of ciphers and protocol version is application specific. The easiest way to check which ciphers and protocol version is currently used by an application is to either use wireshark to sniff and look at the TLS handshake (ClientHello contains the cipher offers) or to use some server which displays these information from the SSL handshake, like SSLLabs.

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