[GH-ISSUE #804] SMTP with fastmail not working #567

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opened 2026-02-25 23:42:53 +03:00 by kerem · 4 comments

kerem commented

2026-02-25 23:42:53 +03:00

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Originally created by @ramlev on GitHub (Mar 17, 2023).
Original GitHub issue: https://github.com/healthchecks/healthchecks/issues/804

I have installed healthchecks on my own server with docker, and i cannot get the smtp to work.

I have these settings in the environment section in docker-compose.yml

- EMAIL_HOST=smtp.fastmail.com
- EMAIL_PORT=465
- EMAIL_HOST_USER=me@host.com
- EMAIL_HOST_PASSWORD=my-secret-smtp-password
- EMAIL_USE_TLS=False
- EMAIL_USE_SSL=True

and i dont get any email when trying to enable OTP or any email reports, what am i doing wrong

Originally created by @ramlev on GitHub (Mar 17, 2023). Original GitHub issue: https://github.com/healthchecks/healthchecks/issues/804 I have installed healthchecks on my own server with docker, and i cannot get the smtp to work. I have these settings in the environment section in docker-compose.yml ``` - EMAIL_HOST=smtp.fastmail.com - EMAIL_PORT=465 - EMAIL_HOST_USER=me@host.com - EMAIL_HOST_PASSWORD=my-secret-smtp-password - EMAIL_USE_TLS=False - EMAIL_USE_SSL=True ``` and i dont get any email when trying to enable OTP or any email reports, what am i doing wrong

kerem closed this issue

2026-02-25 23:42:53 +03:00

kerem commented

2026-02-25 23:42:53 +03:00

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@KiwiActinidia commented on GitHub (Mar 19, 2023):

I have the same problem with a self-hosted email server

@KiwiActinidia commented on GitHub (Mar 19, 2023): I have the same problem with a self-hosted email server

kerem commented

2026-02-25 23:42:53 +03:00

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@cuu508 commented on GitHub (Apr 3, 2023):

@ramlev can you test if these credentials work for sending email from the same machine, but from any software other than Healthchecks?

@cuu508 commented on GitHub (Apr 3, 2023): @ramlev can you test if these credentials work for sending email from the same machine, but from any software other than Healthchecks?

kerem commented

2026-02-25 23:42:53 +03:00

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@ramlev commented on GitHub (Apr 3, 2023):

It does

@ramlev commented on GitHub (Apr 3, 2023): It does

kerem commented

2026-02-25 23:42:53 +03:00

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@cuu508 commented on GitHub (Apr 3, 2023):

When you send email (let's say, during signup), do you see any error messages in docker-compose output?

Is the DEFAULT_FROM_EMAIL env var set to the same value as EMAIL_HOST_USER? I just tested with Fastmail credentials and initially got this error in docker-compose logs:

smtplib.SMTPDataError: (551, b'5.7.1 Not authorised to send from this header address')

This was because the DEFAULT_FROM_EMAIL was set to an incorrect value that Fastmail refused to send emails from. Once I fixed that, I received email from Fastmail in Gmail inbox using these settings:

DEFAULT_FROM_EMAIL=me@example.org
EMAIL_HOST=smtp.fastmail.com
EMAIL_HOST_PASSWORD=myapppassword
EMAIL_HOST_USER=me@example.org
EMAIL_PORT=465
EMAIL_USE_TLS=False
EMAIL_USE_SSL=True

@cuu508 commented on GitHub (Apr 3, 2023): When you send email (let's say, during signup), do you see any error messages in docker-compose output? Is the `DEFAULT_FROM_EMAIL` env var set to the same value as `EMAIL_HOST_USER`? I just tested with Fastmail credentials and initially got this error in docker-compose logs: ``` smtplib.SMTPDataError: (551, b'5.7.1 Not authorised to send from this header address') ``` This was because the `DEFAULT_FROM_EMAIL` was set to an incorrect value that Fastmail refused to send emails from. Once I fixed that, I received email from Fastmail in Gmail inbox using these settings: ``` DEFAULT_FROM_EMAIL=me@example.org EMAIL_HOST=smtp.fastmail.com EMAIL_HOST_PASSWORD=myapppassword EMAIL_HOST_USER=me@example.org EMAIL_PORT=465 EMAIL_USE_TLS=False EMAIL_USE_SSL=True ```