Is there a flag, available today, that can be set that tells courier to _try_ TLS?
No, and I believe that Sam has made a good case for that in the past.
TLS is a security measure. If a security measure is optional, and users will never know whether it works or not, then it's not at all worth having. If you don't care whether or not TLS works, then there's no reason to even specify that Courier should _try_ it.
I recommend that you simply turn it off completely, and if you have a specific domain that you want to secure mail for, set up the TLS requirement in the esmtproutes file.
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