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Issues with Sending email when TLS is on.

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Hey Guys,

Having an odd issue, I can send emails anonymously via port 25, but whenever i try to use TLS or AutoTLS i get an issue. See error below, I thought possibly a cert but the cert is valid and I don’t see any errors on the exchange server log.

Versions:
WordPress: 5.2.1
WordPress MS: No
PHP: 7.2.18
WP Mail SMTP: 1.4.2

Params:
Mailer: smtp
Constants: No
ErrorInfo: SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting
Host: mail.xxxxxxxxxxx.com
Port: 25
SMTPSecure: string(0) “”
SMTPAutoTLS: bool(true)
SMTPAuth: bool(false)

Server:
OpenSSL: OpenSSL 1.0.2r 26 Feb 2019
SMTP Debug:

2019-05-30 19:47:42 Connection: opening to mail.xxxxxxxxxxx.com:25, timeout=300, options=array (
)
2019-05-30 19:47:42 Connection: opened
2019-05-30 19:47:42 SERVER -> CLIENT: 220 dmz.xxxxxxxxxxx.com Microsoft ESMTP MAIL Service ready at Thu, 30 May 2019 12:47:41 -0700
2019-05-30 19:47:42 CLIENT -> SERVER: EHLO domain.com
2019-05-30 19:47:42 SERVER -> CLIENT: 250-dmz.xxxxxxxxxxx.com Hello [x.x.x.x]
250-SIZE 37748736
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-X-EXPS NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250-XEXCH50
250 XSHADOW
2019-05-30 19:47:42 CLIENT -> SERVER: STARTTLS
2019-05-30 19:47:42 SERVER -> CLIENT: 220 2.0.0 SMTP server ready
2019-05-30 19:47:42 SMTP Error: Could not connect to SMTP host.
2019-05-30 19:47:42 CLIENT -> SERVER: QUIT
2019-05-30 19:47:42 SERVER -> CLIENT:
2019-05-30 19:47:42 SMTP ERROR: QUIT command failed:
2019-05-30 19:47:42 Connection: closed
2019-05-30 19:47:42 SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting


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