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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48 answers

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  1. Anonymous
    2021-05-26T20:28:35+00:00

    We were able to resolve this by changing multifactor authentication default settings in azure directory property setting to “No”.

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  2. Anonymous
    2021-06-25T06:05:07+00:00

    Hi there, from what I've read from this thread, I can not use office365 SMTP anymore, an I write?!

    I want to use it in my project so if yes, what should I do to have a n email from one of my domains that I'll use for SMTP in the website. Or even what is the best replacement for this SMTP Service.

    This is what I get in the website.

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  3. Anonymous
    2021-07-06T10:45:48+00:00

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    5 people found this answer helpful.
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