Jay Taylor's notes

Since msmtp version 1.8.6 you can place your user configuration either at ~/.msmtprc or $XDG_CONFIG_HOME/msmtp/config. The following is an example of a msmtp configuration (the file is based on the per-user example file located at /usr/share/doc/msmtp/msmtprc-user.example; the system configuration file belongs at /etc/msmtprc and its corresponding example file is located at /usr/share/doc/msmtp/msmtprc-system.example).

Tip: If using Gmail you will need to either:

Use OAuth, via #OAuth2 Setup.
If you use two factor authentication: create an app password.

~/.msmtprc

# Set default values for all following accounts.
defaults
auth           on
tls            on
tls_trust_file /etc/ssl/certs/ca-certificates.crt
logfile        ~/.msmtp.log

# Gmail
account        gmail
host           smtp.gmail.com
port           465
tls_starttls   off
from           username@gmail.com
user           username
password       plain-text-password

# A freemail service
account        freemail
host           smtp.freemail.example
from           joe_smith@freemail.example
...

# Set a default account
account default: gmail

Note: If you are using SSL/TLS and receive a "Server sent empty reply" error message, see #Server sent empty reply.

The user configuration file must be explicitly readable/writeable by its owner or msmtp will fail:

$ chmod 600 ~/.msmtprc

To avoid saving the password in plain text in the configuration file, use passwordeval to launch an external program, or see the #Password management section below. This example using Gnu PG is commonly used to perform decryption of a password:

echo -e "passwordn" | gpg --encrypt -o .msmtp-gmail.gpg # enter id (email...)

Warning: Most shells save command history(e.g. .bash_history .zhistory). To avoid this, use gpg with shell stdin: gpg --encrypt -o .msmtp-gmail.gpg -r <email> -. The ending dash is not a typo, rather it causes gpg to use stdin. After running that snippet of code, type in your password, press enter, and press Control-d so gpg can encrypt your password.

~/.msmtprc

passwordeval    "gpg --quiet --for-your-eyes-only --no-tty --decrypt ~/.msmtp-gmail.gpg"

1 "." counter(h3-section)OAuth2 Setup

OAuth2 can be used to securely authenticate msmtp when basic username/password authentication is unsupported by the site configuration or otherwise undesirable.

Note: this post explains the now extremely limited functionality permitted for Gmail.

1 "." counter(h3-section) "." counter(h4-section)oama

msmtp alone lacks the ability to renew or authorize OAuth2 credentials. A comprehensive solution is using the oama utility which provides IMAP/SMTP clients with renewal capabilities and authorization of OAuth2 credentials.

To use oama, install oama-bin^AUR and configure msmtp to use it:

   # account at Google with oauth2 access                                    
   account YOUR_EMAIL_NAME@gmail.com
   from YOUR_EMAIL_NAME@gmail.com
   user YOUR_EMAIL_NAME@gmail.com
   auth oauthbearer
   passwordeval oama access YOUR_EMAIL_NAME@gmail.com
   host smtp.gmail.com
   port 587
   tls on
   tls_trust_file /etc/ssl/certs/ca-certificates.crt

Access token renewal happens automatically in the background transparent to the user.

3Using the mail command

To send mails using the mail command you must install the package s-nail, which also provides the mailx command. You will also need to provide a sendmail-compatible MTA, either by installing msmtp-mta (which symlinks sendmail to msmtp) or by editing /etc/mail.rc to set the sendmail path:

/etc/mail.rc

set mta=/usr/bin/msmtp

A .msmtprc file will need to be in the home of every user who wants to send mail or alternatively the system wide /etc/msmtprc can be used.

msmtp also understands aliases. Add the following line to the defaults section of msmtprc or your local configuration file:

/etc/msmtprc

aliases               /etc/aliases

and create an aliases file in /etc

/etc/aliases

# Example aliases file
     
# Send root to Joe and Jane
root: joe_smith@example.com, jane_chang@example.com
   
# Send everything else to admin
default: admin@domain.example

4Test functionality

The account option (--account=,-a) tells which account to use as sender:

$ echo "hello there username." | msmtp -a default username@domain.com

Or, send both a subject and a body:

$ printf "Subject: Testnnhello there username." | msmtp -a default username@domain.com

Or, with the addresses in a file:

To: username@domain.com
From: username@gmail.com
Subject: A test

Hello there.

$ cat test.mail | msmtp -a default <username>@domain.com

Tip: You can use --read-envelope-from instead of -a default to automatically choose account by the From: field in a message you are going to send. You can also use --read-recipients,-t to read recipient addresses from the To, Cc, and Bcc headers of the mail in addition to the recipients given on the command line.

5Cronie default email client

This article or section is out of date.

Reason: Arch uses systemd/Timers instead of cronie (Discuss in Talk:Msmtp)

To make Cronie use msmtp rather than sendmail, make sure msmtp-mta is installed, or edit the cronie.service systemd unit:

/etc/systemd/system/cronie.service.d/msmtp.conf

[Service]
ExecStart=
ExecStart=/usr/bin/crond -n -m '/usr/bin/msmtp -t'

Then you must tell cronie or msmtp what your email address is. One way to accomplish this is by adding it to the msmtp configuration:

Add to /etc/msmtprc:
```
aliases /etc/aliases
```
Create /etc/aliases:
```
your_username: email@address.com
```

Alternatively, you can add it directly to the crontab:

Add a MAILTO line to the crontab:
```
MAILTO=email@address.com
```
Add a MAILFROM line to the crontab:
```
MAILFROM=email@address-from-msmtp.com
```

The last part is necessary to prevent this error:

sendmail: server message: 550 5.7.1 Rejected due to unmatching envelope and header sender.

6Password management

Passwords for msmtp can be stored in plaintext, encrypted files, or a keyring.

2 "." counter(h3-section)GNOME Keyring

Storing passwords in GNOME Keyring is supported natively in msmtp. Setup the keyring as described on the linked wiki page and install libsecret. Then, store a password by running:

secret-tool store --label=msmtp host smtp.your.domain service smtp user yourusername

msmtp should now find the password automatically.

3 "." counter(h3-section)GnuPG

The password directive may be omitted. In that case, if the account in question has auth set to a legitimate value other than off, invoking msmtp from an interactive shell will ask for the password before sending mail. msmtp will not prompt if it has been called by another type of application, such as Mutt. For such cases, the --passwordeval parameter can be used to call an external keyring tool like GnuPG.

To do this, set up GnuPG, including gpg-agent to avoid having to enter the password every time. Then, create an encrypted password file for msmtp, as follows. Create a secure directory with 700 permissions located on a tmpfs to avoid writing the unencrypted password to the disk. In that directory create a plain text file with the mail account password. Then, encrypt the file with your private key:

$ gpg --default-recipient-self -e /path/to/plain/password

Remove the plain text file and move the encrypted file to the final location, e.g. ~/.mail/.msmtp-credentials.gpg. In ~/.msmtprc add:

~/.msmtprc

passwordeval  "gpg --quiet --for-your-eyes-only --no-tty --decrypt ~/.mail/.msmtp-credentials.gpg"

Normally this is sufficient for a GUI password prompt to appear when, for example, sending a message from Mutt. If gpg prompt for the passphrase cannot be issued, then start the gpg-agent before. A simple hack to start the agent is to execute a external command in your muttrc using the backtick `command` syntax. For example, you can put something like the following in your muttrc:

muttrc

set my_msmtp_pass=`gpg -d mypwfile.gpg`

Mutt will execute this when it starts, gpg-agent will cache your password, msmtp will be happy and you can send mail.

Note: If you do this, you will have to restart mutt after gpg-agent clears the password to start sending emails again.

An alternative is to place passwords in ~/.netrc, a file that can act as a common pool for msmtp, OfflineIMAP, and associated tools.

4 "." counter(h3-section)pass

You may store your credentials inside of the pass password manager.

If you are using your main password (which is customarily stored in the first line of your pass file) to login into your SMTP server, you can add the following to your .msmptrc:

~/.msmtprc

passwordeval   "pass your_email_password_entry | head -n1"

If you are using Gmail, and have set up an app password, the following configuration will suit you better. Save your app password inside your pass password file, but with a msmtp: prefix:

your_email_password_entry

your_main_password

login: your_username
url: the_url_of_your_email
msmtp: your_msmtp_app_password

Then add the following to your .msmptrc:

~/.msmtprc

passwordeval   "pass your_email_password_entry | awk '/^msmtp:/ { print $2; }'"

In either case, trying to send an email with msmtp will trigger pass, which may ask you for your pass master password if you have not entered it recently.

7Miscellaneous

5 "." counter(h3-section)Using msmtp offline

Although msmtp is great, it requires that you be online to use it. This is not ideal for people on laptops with intermittent connections to the Internet or dialup users. Several scripts have been written to remedy this fact, collectively called msmtpqueue.

The scripts are installed under /usr/share/doc/msmtp/msmtpqueue. You might want to copy the scripts to a convenient location on your computer, (/usr/local/bin is a good choice).

Finally, change your MUA to use msmtp-enqueue.sh instead of msmtp when sending e-mail. By default, queued messages will be stored in ~/.msmtpqueue. To change this location, change the QUEUEDIR=$HOME/.msmtpqueue line in the scripts (or delete the line, and export the QUEUEDIR variable in .bash_profile like so: export QUEUEDIR="$XDG_DATA_HOME/msmtpqueue").

When you want to send any mail that you have created and queued up run:

$ /usr/local/bin/msmtp-runqueue.sh

Adding /usr/local/bin to your PATH can save you some keystrokes if you are doing it manually. The README file that comes with the scripts has some handy information, reading it is recommended.

6 "." counter(h3-section)Vim syntax highlighting

The msmtp source distribution includes an msmtprc syntax-highlighting script for Vim, which is available at /usr/share/vim/vimfiles/syntax/msmtp.vim. The filetype is not detected automatically. The easiest way to enable it is by adding a modeline at the top or bottom of the file(s), i.e.:

# vim:filetype=msmtp

7 "." counter(h3-section)Send mail with PHP using msmtp

Look for sendmail_path option in your php.ini and edit like this:

sendmail_path = "/usr/bin/msmtp -C /path/to/your/config -t"

Note that you can not use a user configuration file (ie: one under ~/) if you plan on using msmtp as a sendmail replacement with php or something similar. In that case just create /etc/msmtprc, and remove your user configuration (or not if you plan on using it for something else). Also make sure it is readable by whatever you are using it with (php, django, etc...).

From the msmtp manual: Accounts defined in the user configuration file override accounts from the system configuration file. The user configuration file must have no more permissions than user read/write

So it is impossible to have a conf file under ~/ and have it still be readable by the php user.

To test it place this file in your php enabled server or using php-cli.

<?php
mail("your@email.com", "Test email from PHP", "msmtp as sendmail for PHP");
?>

php-fpm will fail to send mails and logs the warning: PHP Warning: mail(mail.log): failed to open stream unless you set the permissions of your /etc/msmtprc to user read/write (600).

8Troubleshooting

8 "." counter(h3-section)Issues with TLS

If you see the following message:

msmtp: TLS certificate verification failed: the certificate hasn't got a known issuer

It probably means your tls_trust_file is not right.

Just follow the fine manual. It explains you how to find out the server certificate issuer of a given smtp server. Then you can explore the /usr/share/ca-certificates/ directory to find out if by any chance, the certificate you need is there. If not, you will have to get the certificate on your own. If you are using your own certificate, you can make msmtp trust it by adding the following to your ~/.msmtprc:

tls_fingerprint <SHA1 (recommended) or MD5 fingerprint of the certificate>

If you are trying to send mail through Gmail and are receiving this error, have a look at this thread or just use the second Gmail example above.

If you are completely desperate, but are 100% sure you are communicating with the right server, you can always temporarily disable the cert check:

$ msmtp --tls-certcheck off

If you see the following message:

msmtp: TLS handshake failed: the operation timed out

You may be affected by this bug. Recompile with --with-ssl=openssl (msmtp is compiled with GnuTLS by default).

9 "." counter(h3-section)Server sent empty reply

If you get a "server sent empty reply" error, this probably means the mail server does not support STARTTLS over port 587, but requires TLS over port 465.

To let msmtp use TLS over port 465, add the following line to ~/.msmtprc:

tls_starttls off

2 "." counter(h3-section) "." counter(h4-section)Zoho SMTP server

It can also happen on Zoho SMTP servers when the mail has no blank line between mail headers and mail body (see Debian bug #917260). The solution to this is to add an extra space in between:

"test-headernntest-body"

10 "." counter(h3-section)Issues with GSSAPI

If you get the following error

GNU SASL: GSSAPI error in client while negotiating security context in gss_init_sec_context() in SASL library.  This is most likely due insufficient credentials or malicious interactions.

Try changing your auth setting to plain, instead of gssapi in your .msmtprc file [1]:

auth plain

11 "." counter(h3-section)Envelope not accepted

In the case of

msmtp: envelope from address mail@server not accepted by the server
msmtp: server message: 530 5.5.1 Authentication Required.
msmtp: could not send mail (account default from /etc/msmtprc)

Try enabling authentication with

auth on

or any other method.

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This page was last edited on 5 October 2024, at 08:21.
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