2023-08-14

Error - Thunderbird SMTP login to server smtp.office.365.com failed

Error - SMTP login to server smtp.office.365.com failed
Error - Unable to authenticate to Outgoing server (SMTP) smtp.office.365.com.  Check the password and verify the 'Authentication method' in 'Account Settings | Outgoing server (SMTP)

Summary: 
A change is required in a default O365 setting.
This example uses GoDaddy, which is hosting my O365 email.  Your email provider will have similar steps.

(O365 / Office.com will not host your email directly, they always go through a third-party)
Note:  O365 has been renamed to "Microsoft 365".  Microsoft has a branding problem.

Symptoms:
Thunderbird email client (version 115 and newer) displays ~ messages.
Receiving emails is not a problem. 
Error appears only when sending.

This can happen with other email clients, other email providers.
The email client must be capable of logging into O365 new OAuth2 authentication methods (with Mozilla Thunderbird, version 85 or newer). 

Solution:

Assuming you are using IMAP email.
Assuming you are using GoDaddy.com (suspect other email providers follow similar steps)

Confirm these SMTP email settings

Likely already correct:

A.  In Thunderbird, "Account Settings", "Server Settings"

     Confirm:  Server Name:  outlook.office365.com   Port 993
     Confirm:  Connection Security:  SSL/TLS
     Confirm:  Authentication method: OAuth2

B.  In "Account Settings", "Outgoing Server (SMTP)"
 
    "Edit"
    Confirm server name:  smtp.office365.com
    Port 587
    Connection Security: STARTTLS
    Authentication method:  OAuth2

    Note: By design, with OAuth2, there is not a typed password

Change this O365 Email setting:

1. Login to GoDaddy
2. At the Email Dashboard, in "Account Information", click "Advanced Settings"

3.  Enable (turn on) "SMTP Authentication"

4.  Important:  Wait (apx 24 hrs) before this change takes effect.   Yes, you must wait.

5.  Testing:  The next day, open Thunderbird: Send a test email.


Other sites, other articles, recommend turning off SSL/TLS.  No.  Don't do that.  Others recommend using a user-ID/password for the SMTP login (turning off OAuth2).  No, don't do that either.  While these workarounds will solve the problem, they miss the point -- fixing the symptoms, and causing other security problems.

You will not need an Windows app password, as suggested by other sites.

I would appreciate comments on how to do this with other, non-GoDaddy email providers.

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