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SMTP Error: Could not authenticate.

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Hi,

using your plugin, for a good number of years now it has been working successfully sending mail via Office 365 but recently (in fact this goes back to Nov last year on a low traffic site so I haven’t noticed) it now gives an error of SMTP Error: Could not authenticate.

All details are 100% correct. ‘Authenticated SMTP’ under User > Mail > Manage email apps is already checked. This is happening on multiple sites after checking. This particular one has two factor authentication set so I tried using the app password instead but same error. The other sites without two factor give the same error.

The log is:

Versions:
WordPress: 5.9
WordPress MS: No
PHP: 7.3.33
WP Mail SMTP: 3.2.1

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 1.1.1l FIPS 24 Aug 2021

Debug:
Email Source: WP Mail SMTP
Mailer: Other SMTP
SMTP Error: Could not authenticate.

SMTP Debug:
2022-01-27 18:14:13 Connection: opening to smtp.office365.com:587, timeout=300, options=array()

2022-01-27 18:14:13 Connection: opened

2022-01-27 18:14:13 SERVER -> CLIENT: 220 LO2P265CA0329.outlook.office365.com Microsoft ESMTP MAIL Service ready at Thu, 27 Jan 2022 18:14:13 +0000

2022-01-27 18:14:13 CLIENT -> SERVER: EHLO sound-of-faz.com

2022-01-27 18:14:13 SERVER -> CLIENT: 250-LO2P265CA0329.outlook.office365.com Hello [35.214.11.101]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-STARTTLS250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8

2022-01-27 18:14:13 CLIENT -> SERVER: STARTTLS

2022-01-27 18:14:13 SERVER -> CLIENT: 220 2.0.0 SMTP server ready

2022-01-27 18:14:13 CLIENT -> SERVER: EHLO sound-of-faz.com

2022-01-27 18:14:13 SERVER -> CLIENT: 250-LO2P265CA0329.outlook.office365.com Hello [35.214.11.101]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-AUTH LOGIN XOAUTH2250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8

2022-01-27 18:14:13 CLIENT -> SERVER: AUTH LOGIN

2022-01-27 18:14:13 SERVER -> CLIENT: 334 VXNlcm5hbWU6

2022-01-27 18:14:13 CLIENT -> SERVER: [credentials hidden]

2022-01-27 18:14:13 SERVER -> CLIENT: 334 UGFzc3dvcmQ6

2022-01-27 18:14:13 CLIENT -> SERVER: [credentials hidden]

2022-01-27 18:14:19 SERVER -> CLIENT: 535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [LO2P265CA0329.GBRP265.PROD.OUTLOOK.COM]

2022-01-27 18:14:19 SMTP ERROR: Password command failed: 535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [LO2P265CA0329.GBRP265.PROD.OUTLOOK.COM]

SMTP Error: Could not authenticate.

2022-01-27 18:14:19 CLIENT -> SERVER: QUIT

2022-01-27 18:14:19 SERVER -> CLIENT: 221 2.0.0 Service closing transmission channel

2022-01-27 18:14:19 Connection: closed

SMTP Error: Could not authenticate.

I have read all other threads which suggest doing what I’ve already tried above so am a bit of a loss.

Thanks in advance.


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