testmsg

Generate RFC822 compliant e-mail messages for tests and send it over SMTP.

While it's easy to send test messages like echo asdf | mail you@gmail.com or via telnet mx.example.com 25 I need a tool which:

• Generates valid messages
• Messages should not look spammy or very suspicious
• Easy to use and repeat test
• Ability to customize messages
• Work well with msmtp or other full-featured SMTP client (e.g. which can send over secure SMTP connection with authentication)
• Support DKIM signatures
• Show SMTP conversation

Installation

For current user, using pipx

pipx install testmsg

or globally:

PIPX_HOME=/opt/pipx PIPX_BIN_DIR=/usr/local/bin pipx install testmsg

or (old way, better if inside virtualenv):

pip3 install testmsg

Usage example

Just generate minimal valid message, print to stdout (not sending).

$ testmsg --to you@gmail.com  --lorem 
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: quoted-printable
MIME-Version: 1.0
Subject: Sent with github.com/yaroslaff/testmsg
From: from@example.com
To: you@gmail.com

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempo=
r incididunt ut labore et dolore magna aliqua.
Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut al=
iquip ex ea commodo consequat.
Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore =
eu fugiat nulla pariatur.
Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia des=
erunt mollit anim id est laborum.

Options

You can pass options either as command-line arguments or in .env file. Example:

FROM=noreply@example.com
# Optional return-path, could be different
# RETURN=noreply@example.com

TO=me@example.net
SUBJECT="My subj"

# Only one of next three is possible at same time
# TEXT="Hello, world!"
# MSG=/tmp/helloworld.txt
LOREM=1

# add timestamp to message body
TIMESTAMP=1

# if we want to send message, set mailserver host there. Otherwise testmsg will just print to stdout
SEND=localhost

# You may override port (e.g. 587)
# PORT=25

# SMTP authentication
# If SMTPPASS given, will use SMTP authentication. Default SMTPUSER is same as FROM
# SMTPUSER=aaa@bbb.com
SMTPPASS="MySecretPassword"

# use 1 for True, anything else for False
SSL=0
STARTTLS=1

# DKIM (very very optional)
# DKIM_SELECTOR="mail"
# DKIM_PRIVKEY=/etc/ssl/private/test.example.com.pem

VERBOSE=1

To enable boolean option use value "1", to disable - any other value.

With such .env file, you can send message with just testmsg command (no options).

Sending message

To actually send message via SMTP server add --send localhost and optionally add -v for verbosity.

testmsg -v --lorem --from you@example.net --to you@gmail.com --send localhost

See below about how to use authentication and SSL/TLS and how to use with msmtp (or other smtp clients).

Customize message

Use --from, --to and --subject to override basic properties of message, use --add HEADER VALUE to add custom header(s).

To set Return-Path header (address used in MAIL FROM SMTP command) to custom value, use -r / --return, e.g. --return noreply@gmail.com.

Default message text is empty, use --text "blah blah blah" or --lorem or --msg PATH or --msg - .(to read from stdin). Add --time to add current time as an prefix to text.

Add attachments

Use --attachment (or --att) to add attachments: --att FILE1 FILE2 ...

Sign with DKIM

Generate DKIM RSA keys:

# generate private RSA key for DKIM
openssl genrsa -out example.com.pem 1024
# generate public key for DKIM
openssl rsa -in example.com.pem -out example.com.pub -pubout

Make DKIM DNS record with as SELECTOR._domainkey.example.com and verify it (here I decide to use selector mail):

$ host -t txt mail._domainkey.example.com
mail._domainkey.example.com.net descriptive text "v=DKIM1; h=sha256; k=rsa; p=MII...."

send DKIM signed message to gmail or mail-tester.com! Use --selector and --privkey arguments.

testmsg -f test@example.com -t mailbox@gmail.com --lorem --selector mail --privkey example.com.pem -v --send localhost

Use with authentication and SSL/STARTTLS SMTP servers

To use authentication, use --user and --password (or --pass) parameters. Use --ssl to use SSL-capable SMTP server (port 465), or use --starttls to use STARTTLS SMTP command. If neither --ssl nor --starttls is given, message and authentication credentials are sent over plain unencrypted connection, which is highly insecure.

If --user is not given (but --password given), testmsg will use username same as from (--from / -f) address.

Example:

testmsg -v -f test1@example.com -t somebody@example.net --lorem --pass "MyTestPass" --send mx.example.com --starttls

Use together with msmtp

Here we send with TLS and authentication (using msmtp). Username for authentication (--user) is same as FROM address. Testmsg generates valid message and msmtp sends it.

FROM=sender@example.com
TO=recipient@gmail.com

testmsg -f $FROM -t $TO --lorem | msmtp -v --host smtp.office365.com --port 587 --user $FROM --passwordeval='echo MyTestPass' -f $FROM --tls=on --auth=on $TO