Mail sendinng fails with exim #1953

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OVERLORD · 2026-02-05T02:18:49+03:00

OVERLORD commented

2026-02-05 02:18:49 +03:00

Originally created by @bash-stack on GitHub (Nov 23, 2020).

Describe the bug
fails to send via exim4

Steps To Reproduce
Steps to reproduce the behavior:

Go to '...'
console , install recent version ,
enable smtp in env file
Click on '....'
send test mail under settings>maintainance
See error on top right

Error thrown when sending a test email: Expected response code 250 but got code "501", with message "501 Syntactically invalid HELO argument(s) "

Expected behavior
SEND MAIL

Your Configuration (please complete the following information):

Exact BookStack Version (Found in settings): BookStack v0.30.4
PHP Version: 7.4
Hosting Method (Nginx/Apache/Docker): docker->nginx->nginx

Additional context
Add any other context about the problem here.

Originally created by @bash-stack on GitHub (Nov 23, 2020). **Describe the bug** fails to send via exim4 **Steps To Reproduce** Steps to reproduce the behavior: 1. Go to '...' console , install recent version , enable smtp in env file 2. Click on '....' send test mail under settings>maintainance 4. See error on top right ` Error thrown when sending a test email: Expected response code 250 but got code "501", with message "501 Syntactically invalid HELO argument(s) "` **Expected behavior** SEND MAIL **Your Configuration (please complete the following information):** - Exact BookStack Version (Found in settings): BookStack v0.30.4 - PHP Version: 7.4 - Hosting Method (Nginx/Apache/Docker): docker->nginx->nginx **Additional context** Add any other context about the problem here.

OVERLORD added the 🐕 Support label 2026-02-05 02:18:49 +03:00

OVERLORD closed this issue

2026-02-05 02:18:51 +03:00

OVERLORD commented

2026-02-05 02:18:55 +03:00

@ssddanbrown commented on GitHub (Nov 26, 2020):

Hi @bash-stack,
Unfortunately I don't have much experiencing with exim.
Looks like this is a fairly common issue there.
Might be worth going through the causes listed here for validation: https://confluence.atlassian.com/confkb/getting-501-syntactically-invalid-helo-argument-error-when-sending-mail-from-confluence-226790155.html

Do you have other services using exim to confirm if this is a specific issue to your BookStack instance?
What host/container is exim located in relation to bookstack?
Can you share all possible, non-private, mail configuration set?

@ssddanbrown commented on GitHub (Nov 26, 2020): Hi @bash-stack, Unfortunately I don't have much experiencing with exim. Looks like this is a fairly common issue there. Might be worth going through the causes listed here for validation: https://confluence.atlassian.com/confkb/getting-501-syntactically-invalid-helo-argument-error-when-sending-mail-from-confluence-226790155.html - Do you have other services using exim to confirm if this is a specific issue to your BookStack instance? - What host/container is exim located in relation to bookstack? - Can you share all possible, non-private, mail configuration set?

OVERLORD commented

2026-02-05 02:18:58 +03:00

@ssddanbrown commented on GitHub (Feb 12, 2021):

Since there's been no follow-up I'm going to close this. If the issue remains and is something you still require to be fixed please open a new issue, referencing this one.

@ssddanbrown commented on GitHub (Feb 12, 2021): Since there's been no follow-up I'm going to close this. If the issue remains and is something you still require to be fixed please open a new issue, referencing this one.

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Reference: starred/BookStack#1953