O365 - 5.7.57 SMTP; Client was not authenticated

As a newbie, I have had to remove dots from URL’s… :roll_eyes:

The full error is -

The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [DB9PR06CA0026.eurprd06 prod outlook com]

I am using smtp office365 com (and have also used the MX server - mydomain mail protection outlook com)

I am authenticating using the same credentials I use to login to O365. I have STARTTLS enabled. The port is 587

I have also created an app password as I thought 2FA might be getting in the way.

I have also (temporarily) removed enforced 2FA off my O365 login.

Any ideas?

This is a deal breaker for me.

Hi @Tx2

Welcome to the forum!

Sorry to hear you’re experiencing some issues with the SMTP.

Do you have any aliases set up on the email account you’re trying to use? Does the “from email” differ from the login address, and if so, is it an alias?

Yes, many aliases exist on the account, but I have tried using both an alias, and the ‘primary’ account. I’ve tried every which way.

Using the primary account on both FROM and LOGIN address made no difference.

It works if I use my Gmail account, but I don’t really want to send professional correspondence from a Gmail address.

These two are contradictory - if you have 2FA switched on then you need to use an app password, if you have 2FA switched off then you need to use your normal login password.

Let me clarify.
I had 2FA on and USED an app password.
That didn’t work, so I turned 2FA OFF, and used my normal password.
That didn’t work, so rather than waste any more time, I’m looking at other products now.

Sorry to hear that @Tx2. Just to clarify - we’re not doing anything special with the SMTP connection, this is just a standard connection.

Providing all the details are correct, it should work fine.

If you do decide to stay with QuickFile, then please let us know and we can look into it further.

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