crontab -l
48 2 * * * /bin/sh -c '[ -f /var/run/reboot-required ] && sudo shutdown -r now'

• https://github.com/Potemkin-Co/quickies/blob/main/reboot_ubuntu_if_required.sh - do the server reboot, if it was requested by anything earlier, calls mail script before the reboot
• https://github.com/Potemkin-Co/quickies/blob/main/send_mail_with_cloudron.sh sends an e-mail

Be sure to change your e-mail and path to the mail script at the first script.

@fbartels @girish , got it working now - thank you very much!!

Can you share your full script? Thanks!

@fbartels does this command actually deliver an e-mail to test@9wd.eu?

Yes, just like Girish said, you only need to make sure that your from (the -f parameter) and the login user (the -au parameter) match your main cloudron domain. The -t is the parameter for the recipient, this can be on the cloudron system or another mailbox.

root@anabelle:~# docker inspect --format '{{ .Config.Env }}' mail | tr ' ' '\n' | grep CLOUDRON_RELAY_TOKEN
CLOUDRON_RELAY_TOKEN=818e705168cd0605a63ee69228bdcdec7def1d170054c14281f27c3b986486adcdd447bf161f1f6b4eb858037abc19558cf8877bc1603c4a152db20c94aa9dd7eabb68a9da950b8e54684fcb75a531c808254c0a60165f20a825170b24b1b06bb833955750412d769257a3607cc5637e40dca57402be4ef67a1d4f91df329c22
root@anabelle:~# echo "818e705168cd0605a63ee69228bdcdec7def1d170054c14281f27c3b986486adcdd447bf161f1f6b4eb858037abc19558cf8877bc1603c4a152db20c94aa9dd7eabb68a9da950b8e54684fcb75a531c808254c0a60165f20a825170b24b1b06bb833955750412d769257a3607cc5637e40dca57402be4ef67a1d4f91df329c22" | wc -c
257
root@anabelle:~# docker inspect --format '{{ .NetworkSettings.Networks.cloudron.IPAddress }}' mail
172.18.0.5

root@anabelle:~# swaks -s 172.18.0.5 -p 2525 --au no-reply@cloudron.space --ap "818e705168cd0605a63ee69228bdcdec7def1d170054c14281f27c3b986486adcdd447bf161f1f6b4eb858037abc19558cf8877bc1603c4a152db20c94aa9dd7eabb68a9da950b8e54684fcb75a531c808254c0a60165f20a825170b24b1b06bb833955750412d769257a3607cc5637e40dca57402be4ef67a1d4f91df329c22" -f no-reply@cloudron.space -t 'mypersonal@email.com' --h-Subject "Test mail"
=== Trying 172.18.0.5:2525...
=== Connected to 172.18.0.5.
<-  220 my.serveddomain.com ESMTP Haraka/2.8.27 ready
 -> EHLO localhost
<-  250-my.serveddomain.com Hello [172.18.0.1]Haraka is at your service.
<-  250-PIPELINING
<-  250-8BITMIME
<-  250-SMTPUTF8
<-  250-SIZE 26214400
<-  250 AUTH LOGIN PLAIN
 -> AUTH LOGIN
<-  334 VXNlcm5hbWU6
 -> bm8tcmVwbHlAY2xvdWRyb24uc3BhY2U=
<-  334 UGFzc3dvcmQ6
 -> ODE4ZTcwNTE2OGNkYTYwMTY1ZjIwYTgyNTE3MGIyM2IxYjA2YmI4MzM5NTU3NTA0MTQwMmJlNGVmNjdhMWQ0ZjkxZGYyZDc2OTI1N2EzNjA3Y2M1NjM3ZTQwZGNhNTc4YmRjZGVjN2RlZjFkMTcwMDUyMjU1OGNmODg3N2JjMTYwMmM0YTE1MmNiMjljOTRhYTlkZDdlYTRjMTQyODFmMjdjM2I5ODY0ODZhZDA2MDVhNjNlZTY5YmI2OGE5ZGE5NTBiOGU1NDU4NGVjYjc1YTUzMGM4MDgyNTRjMGNkZDQ0N2JmMTYxZjFmNmI0ZWI4NTgwMzdhYmMxODMyOWMyMg==
<** 535 5.7.8 Authentication failed
 -> AUTH PLAIN AG5vLXJlcGx5QGNsb3Vkcm9uLnNwYWNlADgxOGU3MDUxNjhjZGE2MDE2NWYyMGE4MjUxNzBiMjNiMWIwNmJiODMzOTU1NzUwNDE0MDJiZTRlZjY3YTFkNGY5MWRmMmQ3NjkyNTdhMzYwN2NjNTYzN2U0MGRjYTU3OGJkY2RlYzdkZWYxZDE3MDA1MjI1NThjZjg4NzdiYzE2MDJjNGExNTJjYjI5Yzk0YWE5ZGQ3ZWE0YzE0MjgxZjI3YzNiOTg2NDg2YWQwNjA1YTYzZWU2OWJiNjhhOWRhOTUwYjhlNTQ1ODRlY2I3NWE1MzBjODA4MjU0YzBjZGQ0NDdiZjE2MWYxZjZiNGViODU4MDM3YWJjMTgzMjljMjI=
<** 535 5.7.8 Authentication failed
*** No authentication type succeeded
 -> QUIT
<-  221 my.serveddomain.com closing connection. Have a jolly good day.
=== Connection closed with remote host.

Note that it has to be no-reply@yourdomain.com for both the --au argument and the -f argument.

--au no-reply@9wd.eu ... -f no-reply@9wd.eu

those two contradicts to each other...

@fbartels does this command actually deliver an e-mail to test@9wd.eu?

swaks -s `docker inspect --format '{{ .NetworkSettings.Networks.cloudron.IPAddress }}' mail` -p 2525 --au no-reply@9wd.eu --ap `docker inspect --format '{{ .Config.Env }}' mail | tr ' ' '\n' | grep CLOUDRON_RELAY_TOKEN | sed 's/^.*=//'` -f no-reply@9wd.eu -t 'test@9wd.eu' --h-Subject "Test mail"

docker inspect --format '{{ .Config.Env }}' mail | tr ' ' '\n' | grep CLOUDRON_RELAY_TOKEN
CLOUDRON_RELAY_TOKEN=71df0df31cb3512bfe8fad02561cda813c6db4f94d2cb7137bbc162e9c1775058887606e5c37b8013df08498e3c609f52f1147cbb5a9ad96b7f4c5e848a235c44569510c37ab25eaaa67d50641481843cad93c7221893a869e34411d3e8edf6f55e3b7d8fa3ab1ce7632e0fd3bf65a8050549fe4d43d50e3ddb1c2c6b0eaca0d
root@upgrade-test:~# echo "71df0df31cb3512bfe8fad02561cda813c6db4f94d2cb7137bbc162e9c1775058887606e5c37b8013df08498e3c609f52f1147cbb5a9ad96b7f4c5e848a235c44569510c37ab25eaaa67d50641481843cad93c7221893a869e34411d3e8edf6f55e3b7d8fa3ab1ce7632e0fd3bf65a8050549fe4d43d50e3ddb1c2c6b0eaca0d" | wc -c
257

So, mine is also 257 characters long.

# docker inspect --format '{{ .NetworkSettings.Networks.cloudron.IPAddress }}' mail
172.18.0.3

The final command:

# swaks -s 172.18.0.3 -p 2525 --au no-reply@cloudron.space --ap "71df0df31cb3512bfe8fad02561cda813c6db4f94d2cb7137bbc162e9c1775058887606e5c37b8013df08498e3c609f52f1147cbb5a9ad96b7f4c5e848a235c44569510c37ab25eaaa67d50641481843cad93c7221893a869e34411d3e8edf6f55e3b7d8fa3ab1ce7632e0fd3bf65a8050549fe4d43d50e3ddb1c2c6b0eaca0d" -f no-reply@cloudron.space -t 'test@cloudron.io' --h-Subject "Test mail"

Can you paste your entire sequence like above? Note that it has to be no-reply@yourdomain.com for both the --au argument and the -f argument.

I probably could, but what's the point?

It's two birds with one stone. You end up having app/site monitoring too but I'm not against your method. I'm just suggesting alternatives for consideration.

It has "Notifications via Webhook, Telegram, Discord and email (SMTP)" so it should work for your use-case.

My primary concern remains token, because mine is muuuuch longer than yours (hope it sounds right in the context of token comparison....), and authentication is failing right after mail service gets it.

Any way to troubleshoot that?

# swaks -s `docker inspect --format '{{ .NetworkSettings.Networks.cloudron.IPAddress }}' mail` -p 2525 --au no-reply@cloudron.space --ap `docker inspect --format '{{ .Config.Env }}' mail | tr ' ' '\n' | grep CLOUDRON_RELAY_TOKEN | sed 's/^.*=//'` -f no-reply@cloudron.space -t 'test@cloudron.io' --h-Subject "Test mail"
=== Trying 172.18.0.3:2525...
=== Connected to 172.18.0.3.
<-  220 my.cloudron.space ESMTP Haraka/2.8.28 ready
 -> EHLO upgrade-test
<-  250-my.cloudron.space Hello [172.18.0.1]Haraka is at your service.
<-  250-PIPELINING
<-  250-8BITMIME
<-  250-SMTPUTF8
<-  250-SIZE 26214400
<-  250 AUTH LOGIN PLAIN
 -> AUTH LOGIN
<-  334 VXNlcm5hbWU6
 -> bm8tcmVwbHlAY2xvdWRyb24uc3BhY2U=
<-  334 UGFzc3dvcmQ6
 -> OWZmOGU4MWI4NTJmNjMxOWVlNWI4NjM0NDQ1ZDE1ZTliYTI5ZWY3NjE5N2UwZWE0MmM5OGJlMTI0ZjQ4NjFhM2EzZmEyNDQ2Yzk2MzVmODYzMDNiNTUwNjRiMDRjOGYwNjc1M2U3NjIxZGJhOGFmZGY1YWJlODUyYmVmMTVmZWVjNmFiOTVjYmE1MDJhNGY5OGZiMjBjMWZiZDA3YjBlMDFjOTBhOTE4NTRhOGY4ZDNhYWI2ZmYyMGJkMjUzZjY1NDAwNmE0YmRjZGVhMmM2ZGYzYTY0YjcxMWRjZmQxODE5Y2FiZDJhMmMyMTY2YTJhYmE5MjA4NGNjNDhmN2E1ZQ==
<-  235 2.7.0 Authentication successful
 -> MAIL FROM:<no-reply@cloudron.space>
<-  250 sender <no-reply@cloudron.space> OK
 -> RCPT TO:<test@cloudron.io>
<-  250 recipient <test@cloudron.io> OK
 -> DATA
<-  354 go ahead, make my day
 -> Date: Fri, 22 Oct 2021 18:59:51 +0000
 -> To: test@cloudron.io
 -> From: no-reply@cloudron.space
 -> Subject: Test mail
 -> Message-Id: <20211022185951.169923@upgrade-test>
 -> X-Mailer: swaks v20190914.0 jetmore.org/john/code/swaks/
 -> 
 -> This is a test mailing
 -> 
 -> 
 -> .
<-  250 Message Queued (0741EB98-48BA-4A23-AB22-FB67C176AF7B.1)
 -> QUIT
<-  221 my.cloudron.space closing connection. Have a jolly good day.
=== Connection closed with remote host.

I re-did all the steps manually as per your original message and got the same error.

The only major difference between your and my setup - it's token length - it's 257 characters long in my case.

Any clue?