365 test email error

[gzelasco]

We have installed Snipe-IT 8.0.4 on a Hyper-V virtual machine and it works correctly
OS Ubuntu 24.04.2
Snipe version: 8.0.4 build 17611 (gfab1a6c33)
PHP version: 8.3.6
Laravel: 11.4.1
Database: maria-db v.15.1 distrib. 10.11.11

However, we are having difficulties configuring an email 365 account in Snipe-IT.

Following the online documentation, we configured the outgoing e-mail section in the .env file as follows:

MAIL_MAILER=smtp
MAIL_HOST=smtp.office365.com
MAIL_PORT=587
MAIL_USERNAME=[email protected]
MAIL_PASSWORD=[app password]
MAIL_FROM_ADDR=[email protected]
MAIL_FROM_NAME=SnipeIT
MAIL_REPLYTO_ADDR=[email protected]
MAIL_REPLYTO_NAME=SnipeIT
MAIL_AUTO_EMBED_METHOD='attachment'
MAIL_TLS_VERIFY_PEER=true

on test email send our fiddler reports the following error:

2cc
{"message":"Failed to authenticate on SMTP server with username "[email protected]" using the following authenticators: "LOGIN", "XOAUTH2". Authenticator "LOGIN" returned "Expected response code "235" but got code "535", with message "535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [ZR0P278CA0099.CHEP278.PROD.OUTLOOK.COM 2025-05-21T06:49:31.892Z 08DD97430B9575EB]".". Authenticator "XOAUTH2" returned "Expected response code "235" but got code "535", with message "535 5.7.3 Authentication unsuccessful [ZR0P278CA0099.CHEP278.PROD.OUTLOOK.COM 2025-05-21T06:49:42.127Z 08DD97430B9575EB]"."."}
0

- The 365 email account [email protected] is active with MFA enabled. 
- Password is an App Password
- SMTP AUTH is enabled

We've run tests also with user password (without MFA enabled) but unsuccesfully

Someone can help us please ?

Thank you very much

[gzelasco]

Hi all, any news about our case ?
I saw new 8.1.15 version. Maybe our issue has been addressed ?
Thank you

[gzelasco]

Hi all. Since we are stuck without a solution we ask you if there is a way to avoid authentication. We intend to connect to SMTP server in anonymous mode (no need to authenticate the connection). Thank you

[snipe]

I believe we have many users who are using Office 365 to send email, but it's generally a hassle to set up IIRC. You might take a look at some of these links.

• https://learn.microsoft.com/en-us/answers/questions/512954/535-5-7-139-authentication-unsuccessful
• https://www.reddit.com/r/Office365/comments/155y79v/comment/jswyhig/
• https://learn.microsoft.com/en-us/Exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-microsoft-365-or-office-365#settings-for-direct-send

535 5.7.139 Authentication unsuccessful - Microsoft Q&A

We are receiving the following error using the Office 365 SMTP server to send mails: 535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Same issue with MFA (+ App password) and without…

How to set up a multifunction device or application to send email using Microsoft 365 or Office 365

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[gzelasco]

Thanks snipe for suggestions.
We have already seen that information. These are all steps or verifications that we have already tested (unsuccessfully).
That is why we are asking if there is a way for an anonymous SMTP connection. In our opinion the only way out of the empasse