Office 365 SMTP authentication failing, even with correct account information

Anonymous
2020-02-10T16:38:43+00:00

On my Wordpress site I've run into a problem in the last day or so, where emails simply fail to send. Before today it was running flawlessly for two months. The account information/password/username etc have not changed in that two months.

I'm using a Wordpress plugin called WP Mail SMTP to facilitate the sending of all outgoing emails. The error log I'm getting from the email test on that is as follows:

Versions:

WordPress: 5.3.2

WordPress MS: No

PHP: 7.3.14-5+0~20200202.52+debian9~1.gbpa71879

WP Mail SMTP: 1.8.1

Params:

Mailer: smtp

Constants: No

ErrorInfo: SMTP Error: Could not authenticate.

Host: smtp.office365.com

Port: 587

SMTPSecure: tls

SMTPAutoTLS: bool(true)

SMTPAuth: bool(true)

Server:

OpenSSL: OpenSSL 1.1.1d 10 Sep 2019

SMTP Debug:

2020-02-10 16:36:56 Connection: opening to smtp.office365.com:587, timeout=300, options=array ()

2020-02-10 16:36:56 Connection: opened

2020-02-10 16:36:56 SERVER -> CLIENT: 220 LNXP123CA0008.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 10 Feb 2020 16:36:55 +0000

2020-02-10 16:36:56 CLIENT -> SERVER: EHLO www.*****.com

2020-02-10 16:36:56 SERVER -> CLIENT: 250-LNXP123CA0008.outlook.office365.com Hello [***]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-STARTTLS250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8

2020-02-10 16:36:56 CLIENT -> SERVER: STARTTLS

2020-02-10 16:36:56 SERVER -> CLIENT: 220 2.0.0 SMTP server ready

2020-02-10 16:36:56 CLIENT -> SERVER: EHLO www.zestpromotional.com

2020-02-10 16:36:56 SERVER -> CLIENT: 250-LNXP123CA0008.outlook.office365.com Hello [***]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-AUTH LOGIN XOAUTH2250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8

2020-02-10 16:36:56 CLIENT -> SERVER: AUTH LOGIN

2020-02-10 16:36:56 SERVER -> CLIENT: 334 VXNlcm5hbWU6

2020-02-10 16:36:56 CLIENT -> SERVER: c2FsZXNAemVzdHByb21vdGlvbmFsLmNvbQ==

2020-02-10 16:36:56 SERVER -> CLIENT: 334 UGFzc3dvcmQ6

2020-02-10 16:36:56 CLIENT -> SERVER: QmFkMzM4MzA=

2020-02-10 16:37:02 SERVER -> CLIENT: 535 5.7.3 Authentication unsuccessful [LNXP123CA0008.GBRP123.PROD.OUTLOOK.COM]

2020-02-10 16:37:02 SMTP ERROR: Password command failed: 535 5.7.3 Authentication unsuccessful [LNXP123CA0008.GBRP123.PROD.OUTLOOK.COM]

SMTP Error: Could not authenticate.

2020-02-10 16:37:02 CLIENT -> SERVER: QUIT

2020-02-10 16:37:02 SERVER -> CLIENT: 221 2.0.0 Service closing transmission channel

2020-02-10 16:37:02 Connection: closed

SMTP Error: Could not authenticate.

Does anyone have any ideas at all? I'm completely at a loss here.

Microsoft 365 and Office | Subscription, account, billing | For home | Windows

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  1. Anonymous
    2020-09-08T22:49:51+00:00

    I can't get these powershell permissions to take as I don't have the right role to execute cmdlet Get-TransportConfig. This is super frustrating as the SMTP server fails the authentication of the user every time. Opening a support ticket with MSFT as we've had no email on Wordpress now for four weeks. Ugh.

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  2. Anonymous
    2020-09-26T21:51:21+00:00

    I don't believe that i post solution thatch work onmicrosoft.com only accept solution should be slc /scannowYou have to enable Authenticated SMTP then wait 3 minutes.Open the Microsoft 365 admin center and go to Users > Active users.

    Select the user, and in the flyout that appears, click Mail.
    
    In the Email apps section, click Manage email apps.
    
    Verify the Authenticated SMTP setting: unchecked = disabled, checked = enabled.
    
    When you're finished, click Save changes.
    

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  3. Anonymous
    2020-10-05T16:05:09+00:00
    I don't believe that i post solution thatch work onmicrosoft.com only accept solution should be slc /scannowYou have to enable Authenticated SMTP then wait 3 minutes.Open the Microsoft 365 admin center and go to Users > Active users.
    
    Select the user, and in the flyout that appears, click Mail.
    
    In the Email apps section, click Manage email apps.
    
    Verify the Authenticated SMTP setting: unchecked = disabled, checked = enabled.
    
    When you're finished, click Save changes.
    

    This solve my problem..

    When my admin entered the screen, this option was already checked in my account, so he deselected, saved, closed the screen (I don't know if it is necessary), entered again, selected again and saved.

    I waited 5 minutes, and updated the configuration in gmail.

    And work

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  4. Anonymous
    2020-10-24T17:45:41+00:00

    @all i think this ist the solution:

    I had the same Problems, old offic365 accounts work, new accounts did not work. After searching for 5 hours i get a solution:

    In the old accounts SmtpClientAuthenticationDisabled is false by default on online Exchange, in the new accounts it is True by default.

    I had to set it to false by exchange online powershell and also hat do go to e-mail-apps and set the hook to authenticated smtp

    after that it worked. Here you can read what is to do by exchange powershell:

    https://docs.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission

    Steps in Powershell:

    $UserCredential = Get-Credential

    $Session = New-PSSession -ConfigurationName Microsoft.Exchange -ConnectionUri https://outlook.office365.com/powershell-liveid/ -Credential $UserCredential -Authentication Basic -AllowRedirection

    Import-PSSession $Session -DisableNameChecking

    Take a look if it is True: Get-TransportConfig  (if there is True set to false)

    Set-TransportConfig -SmtpClientAuthenticationDisabled $false

    Take a look again if it works: Get-TransportConfig

    Remove-PSSession $Session

    In Admin Center --> acitve Users --> click the user --> email-apps --> click the hook --> authenticated smtp

    With this combination it worked for me. Hope this can help you all

    This was exactly what I was looking for, it was hard to find. I would like to add that in my case, I had to not only do this but also do it at the user account explicitly because it had already been created with the previous global defaults. Thanks a lot.

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  5. Anonymous
    2020-11-14T08:40:19+00:00

    Everything was checked but had to go open the window and then click save changes without changing anything and now SMTP works.

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