How to install and configure MSMTP on OSX?

user_5122006 0
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Following the instructions on ArchLinux to install and configure msmtp does not work. The file /etc/ssl/certs/ca-certificates.crt or anything like it is missing, and trying to use msmtp to send mail will result in a certificate error.

What is an alternate configuration for OSX High Sierra so that msmtp can be used to send mail like in the tutorial?

Note: I answered this question for myself some time ago and decided it's useful and worth sharing, so I created this question and answer. It would be nice if someone with more knowledge of certificates and fingerprints could provide a higher quality answer with more detail and background information about the difference between using a certificate or a fingerprint, for example.

Note years later: I know it's a self answered Q/A but this has 1k views so maybe remember to upvote a useful Q/A.

msmtp macos-high-sierra macos
1 Answers

You can use the tls_fingerprint field in ~/.msmtprc instead of tls_trust_file. To generate the field value for tls_fingerprint, you can run the command

msmtp --serverinfo --tls --tls-certcheck=off --host=smtp.gmail.com --port=587 | egrep -o "([0-9A-Za-z]{2}:){31}[0-9A-Za-z]{2}"

tls_fingerprint and tls_trust_file are mutually exclusive, so do not try to use both, or msmtp will have a configuration error.

Here is a script you can run to install and configure msmtp for use with a gmail account on either Ubuntu 18 or Mac OSX High Sierra.

user_51220060
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