SMTP sendEmail error

[vitis586]

Hi guys,

I finally got it kind of a running now I am struggling with SMTP. I have all the keys in the .env file.

# E-mail settings
# Configures the global From: header whilst sending emails.
EMAIL_FROM=noreply@example.cz

# Configure SMTP settings (@see https://nodemailer.com/smtp/).
EMAIL_SERVER_HOST=smtp.eu.mailgun.org
EMAIL_SERVER_PORT=465
EMAIL_SERVER_USER=postmaster@example.cz
EMAIL_SERVER_PASSWORD=pass

It seems that the container is not picking the EMAIL_FROM from the .env because the SMTP server refuses to sent mail from notifications@example.com which I understand as I have SPF set up. I already tried starting over - deleting database and renew the secrets.

@calcom/web:start: sendEmail Error: Mail command failed: 550 5.1.0 <notifications@example.com> sender rejected
@calcom/web:start:     at SMTPConnection._formatError (/calcom/node_modules/nodemailer/lib/smtp-connection/index.js:787:19)
@calcom/web:start:     at SMTPConnection._actionMAIL (/calcom/node_modules/nodemailer/lib/smtp-connection/index.js:1569:34)
@calcom/web:start:     at SMTPConnection.<anonymous> (/calcom/node_modules/nodemailer/lib/smtp-connection/index.js:1044:18)
@calcom/web:start:     at SMTPConnection._processResponse (/calcom/node_modules/nodemailer/lib/smtp-connection/index.js:950:20)
@calcom/web:start:     at SMTPConnection._onData (/calcom/node_modules/nodemailer/lib/smtp-connection/index.js:752:14)
@calcom/web:start:     at SMTPConnection._onSocketData (/calcom/node_modules/nodemailer/lib/smtp-connection/index.js:191:44)
@calcom/web:start:     at TLSSocket.emit (node:events:513:28)
@calcom/web:start:     at addChunk (node:internal/streams/readable:324:12)
@calcom/web:start:     at readableAddChunk (node:internal/streams/readable:297:9)
@calcom/web:start:     at Readable.push (node:internal/streams/readable:234:10)
@calcom/web:start:     at TLSWrap.onStreamRead (node:internal/stream_base_commons:190:23) {
@calcom/web:start:   code: 'EENVELOPE',
@calcom/web:start:   response: '550 5.1.0 <notifications@example.com> sender rejected',
@calcom/web:start:   responseCode: 550,
@calcom/web:start:   command: 'MAIL FROM'
@calcom/web:start: }

I looked for similar issues and only found https://github.com/calcom/docker/issues/80 being somewhat close but that was closed due to inactivity.

[vitis586]

No idea why, but I had to move the EMAIL_FROM from the .env to the container variables. So this is how my sender looks in .env:

# E-mail settings
# Configures the global From: header whilst sending emails.
#EMAIL_FROM=noreply@example.cz

The rest of the email config is still in .env stayed in the .env

# Configure SMTP settings (@see https://nodemailer.com/smtp/).
EMAIL_SERVER_HOST=smtp.eu.mailgun.org
EMAIL_SERVER_PORT=465
EMAIL_SERVER_USER=postmaster@example.cz
EMAIL_SERVER_PASSWORD=pass

I had to do the same with the database connection details so that is where I got my idea from.

[krumware]

Can you help me understand what you mean by the container variables versus the .env in your case? What's your method of running/orchestrating the image? Are you relying on your .env being packaged with the image, versus provided the .env vars at runtime via docker-compose or other orchestrator?

Should help us provide better guidance overall!

[vitis586]

Sure. Let me try. I am running containers in Docker on Unraid so there is no Compose available. When starting a container there is a form that you fill in and that is then composed into a docker run command:

docker run
  -d
  --name='calcom'
  --net='proxynet'
  -e TZ="Europe/Budapest"
  -e HOST_OS="Unraid"
  -e HOST_HOSTNAME="ClearSky"
  -e HOST_CONTAINERNAME="calcom"
  -e 'DATABASE_URL'='postgresql://calcom:pass@clearsky.hloub/calcom'
  -e 'EMAIL_FROM'='noreply@example.cz'
  -e 'NEXTAUTH_URL'='https://booking.example.cz'
  -l net.unraid.docker.managed=dockerman
  -l net.unraid.docker.webui='http://[IP]:[PORT:3000]'
  -l net.unraid.docker.icon='https://i.imgur.com/mwmNzNQ.png'
  -p '3003:3000/tcp'
  -v '/mnt/cache/appdata/calcom/':'/cal':'rw'
  --env-file /mnt/cache/appdata/calcom/.env 'calcom/cal.com:latest' 

I am running the latest Cal.com version. As you can see, some of the environment variables are passed directly and some through the .env file. There might be a term for this, but you get the point. Initially I had everything in the .env file because it is what the image authors suggested. The container could not connect to database when I had the connection detail in the .env file so I moved those details to the DATABASE_URL variable and that worked. I did the same now with the EMAIL_FROM.

To answer your question directly. I am actually doing both - relying on .env passed as an extra parameter and providing the env variables at runtime. I do not know why it is working that way for me. I wanted to have everything in place but it was not working for me.

I hope I got it right. I am doing this for years now but still only scratching the surface. I am still sorting one last issue. I cannot log in at all after logging out. I am getting just [ERROR] (next-collect/server) - Invalid URL TypeError [ERR_INVALID_URL]: Invalid URL. I am able to pass the login screen with a private browser window (empty browser profile) but then I am not passing the 2FA with the same error code.