Nathan M wrote:
Traditionally this server has only accepted plaintext authentications;
however, we want to change that and enable TLS/SSL.  The challenge is
the server has hundreds of IP addresses it binds to to listen on ports
110/143.

It may be 3am, but I'm pretty sure that this is the part of your setup that doesn't make sense. Why does your POP/IMAP server need to be accessed via so many addresses?

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