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Issue External Mail Authentication with STARTTLS on Exchange 2019

Natanael Sigit 41 Reputation points
2023-06-14T03:29:15.3766667+00:00

Hi all,

Currently we have one particular server that required to sending email using our domain.

I created another receive connector that have only specific scope for allowed send email from external.

What i have done, i created the TlsCertificateName under the receive connector and set the port 587.

as the Authentication i set enable TLS, Basic Authentication, Exchange Authentication

and the permission group i set at Exchange Servers, Legacy Exchange Servers, and Exchange Users

Here's when we tried to communicate via STARTTLS

220 XX**** Microsoft ESMTP MAIL Service ready at Wed, 14 Jun 2023 08:51:54 +0700

EHLO XX****

250-XX**** Hello [XXX.XXX.XXX.XXX]

250-SIZE 37748736

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-STARTTLS

250-X-ANONYMOUSTLS

250-AUTH LOGIN

250-X-EXPS GSSAPI NTLM

250-8BITMIME

250-BINARYMIME

250-CHUNKING

250-SMTPUTF8

250 XRDST

STARTTLS

220 2.0.0 SMTP server ready

EHLO XX****

Connection closed by foreign host.

Is there anything that i should fix to make the configuration work for sending email from our external server ?

Thanks

Exchange | Exchange Server | Other
Exchange | Exchange Server | Other

A robust email, calendaring, and collaboration platform developed by Microsoft, designed for enterprise-level communication and data management.Miscellaneous topics that do not fit into specific categories.

Exchange | Exchange Server | Management
Exchange | Exchange Server | Management

The administration and maintenance of Microsoft Exchange Server to ensure secure, reliable, and efficient email and collaboration services across an organization.

Exchange | Other
Exchange | Other

A powerful email and collaboration platform developed by Microsoft, designed to support enterprise-level communication and productivity. Miscellaneous topics that do not fit into specific categories.

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  1. Kai Yao 37,786 Reputation points Moderator
    2023-06-15T06:28:53.4466667+00:00

    Hi @Natanael Sigit

    After STARTTLS you got the response 220 2.0.0 SMTP server ready, which means Exchange is waiting for your server to establish the TLS negotiation.

    Please refer to rfc3207.

    After receiving a 220 response to a STARTTLS command, the client MUST start the TLS negotiation before giving any other SMTP commands.

    While since you are seeing the AUTH LOGIN option, I suppose you do not have "Offer basic authentication only after starting TLS" checked.

    If you would like to authenticate without TLS, you can also use AUTH LOGIN then input credentials encoded with base64.

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  1. Natanael Sigit 41 Reputation points
    2023-06-15T09:02:18.2133333+00:00

    Hi Kael,

    Thank you for your response. I just got the command that i need to running the negotiate of TLS.
    And the issue already resolved.

    Cheers,

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