Email Problem - Anonymous mail #3953

New Issue

OVERLORD · 2026-02-05T07:56:16+03:00

OVERLORD commented

2026-02-05 07:56:16 +03:00

Originally created by @NerdBlender on GitHub (Aug 3, 2023).

Attempted Debugging

I have read the debugging page

Searched GitHub Issues

I have searched GitHub for the issue.

Describe the Scenario

Getting this message sending a test email:

Error thrown when sending a test email: Expected response code "250" but got code "530", with message "530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM".

However manually sending an email via telnet from bash, and other emails on the system are fine.

MAIL_DRIVER=smtp
# Mail sender details
MAIL_FROM_NAME="Company BookStack"
MAIL_FROM=bookstack@company.com

# SMTP mail options
# These settings can be checked using the "Send a Test Email"
# feature found in the "Settings > Maintenance" area of the system.
# For more detailed documentation on mail options, refer to:
# https://www.bookstackapp.com/docs/admin/email-webhooks/#email-configuration
MAIL_HOST=mail.company.com
MAIL_PORT=587
MAIL_USERNAME=null
MAIL_PASSWORD=null
MAIL_ENCRYPTION=null

Exact BookStack Version

v23.06.2

Log Content

No response

PHP Version

8.2

Hosting Environment

Debian 12

Originally created by @NerdBlender on GitHub (Aug 3, 2023). ### Attempted Debugging - [X] I have read the debugging page ### Searched GitHub Issues - [X] I have searched GitHub for the issue. ### Describe the Scenario Getting this message sending a test email: Error thrown when sending a test email: Expected response code "250" but got code "530", with message "530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM". However manually sending an email via telnet from bash, and other emails on the system are fine. ```bash MAIL_DRIVER=smtp # Mail sender details MAIL_FROM_NAME="Company BookStack" MAIL_FROM=bookstack@company.com # SMTP mail options # These settings can be checked using the "Send a Test Email" # feature found in the "Settings > Maintenance" area of the system. # For more detailed documentation on mail options, refer to: # https://www.bookstackapp.com/docs/admin/email-webhooks/#email-configuration MAIL_HOST=mail.company.com MAIL_PORT=587 MAIL_USERNAME=null MAIL_PASSWORD=null MAIL_ENCRYPTION=null ``` ### Exact BookStack Version v23.06.2 ### Log Content _No response_ ### PHP Version 8.2 ### Hosting Environment Debian 12

OVERLORD added the 🐕 Support label 2026-02-05 07:56:16 +03:00

OVERLORD closed this issue

2026-02-05 07:56:18 +03:00

OVERLORD commented

2026-02-05 07:56:22 +03:00

@chris-devel0per commented on GitHub (Aug 3, 2023):

Is the

MAIL_USERNAME=null
MAIL_PASSWORD=null
MAIL_ENCRYPTION=null

null or did you just obfuscate it?

Since if it is null you should add them!

@chris-devel0per commented on GitHub (Aug 3, 2023): Is the ``` MAIL_USERNAME=null MAIL_PASSWORD=null MAIL_ENCRYPTION=null ``` null or did you just obfuscate it? Since if it is null you should add them!

OVERLORD commented

2026-02-05 07:56:26 +03:00

@NerdBlender commented on GitHub (Aug 3, 2023):

Is the
MAIL_USERNAME=null
MAIL_PASSWORD=null
MAIL_ENCRYPTION=null
null or did you just obfuscate it?

Since if it is null you should add them!

Sorry, should have said, my mailserver does not require auth as the IP is whitelisted. I assumed null would be the default if not required

@NerdBlender commented on GitHub (Aug 3, 2023): > Is the > > ``` > MAIL_USERNAME=null > MAIL_PASSWORD=null > MAIL_ENCRYPTION=null > ``` > > null or did you just obfuscate it? > > Since if it is null you should add them! Sorry, should have said, my mailserver does not require auth as the IP is whitelisted. I assumed null would be the default if not required

OVERLORD commented

2026-02-05 07:56:28 +03:00

@ssddanbrown commented on GitHub (Aug 22, 2023):

Sorry for the late response, just coming across this again now.
Based upon the code and message this seems like the SMTP server has an issue with the anonymous usage, and I can't really predict/diagnose why from my position.
BookStack should work with the anonymous options used, I tend to use similar settings in my dev environment.

@ssddanbrown commented on GitHub (Aug 22, 2023): Sorry for the late response, just coming across this again now. Based upon the code and message this seems like the SMTP server has an issue with the anonymous usage, and I can't really predict/diagnose why from my position. BookStack should work with the anonymous options used, I tend to use similar settings in my dev environment.

OVERLORD commented

2026-02-05 07:56:32 +03:00

@FlorinBuffet commented on GitHub (Feb 25, 2025):

@NerdBlender Just reading this i expect you use Postal, or what other Mailserver? Then i can test ist.

@FlorinBuffet commented on GitHub (Feb 25, 2025): @NerdBlender Just reading this i expect you use Postal, or what other Mailserver? Then i can test ist.

OVERLORD commented

2026-02-05 07:56:35 +03:00

@ssddanbrown commented on GitHub (Sep 3, 2025):

Since this is relatively old and there's been no further discussion 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 (Sep 3, 2025): Since this is relatively old and there's been no further discussion 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#3953