We've currently reviving the STARTTLS Everywhere
(https://github.com/EFForg/starttls-everywhere) project at EFF. Some
of the features it currently has:

* Know about a set of major email domains that are guaranteed to
support STARTTLS, and what mx domains they point to
* Know about the minimum TLS version that those domains are guaranteed
to support
* Preliminary integration with the letsencrypt python client, allowing
automated installation of a valid cert from Let's Encrypt

The code can currently transform all of the above into tweaks to a
postfix configuration.  However we quickly ran into what seems to be a
bug while trying to pin TLS versions via a policy map file:

https://github.com/EFForg/starttls-everywhere/issues/20

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