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Do you know how I can resolve The problem below?

This scenario was normally working few months...

Exchange 2016

SMTP client is trying to send email by port 25 using TLS and Basic auth. Recive connector authenticate user and make proxy to Reciver Client Proxy.

Client Proxy quit connection and provide information:

Setting up client proxy session failed with error: 451 4.4.0 Primary target IP address responded with: ""451 4.5.0 Require XAnonymousTls to send mail.

I can't find solution for that.

1 Answer 1

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Do you configure relay connector? If yes, you could recreate new one as the following article: How to create Anonymous relay for applications in Exchange 2016 From http://msexchangeguru.com/2015/10/07/how-to-create-anonymous-relay-for-applications-in-exchange-2016/

You mentioned this working before, did you change any settings recently? If not, you could test the followings: 1. Check the clock on both servers and domain controllers that might be used to authenticate the servers. All clocks should be synchronized to within 5 minutes of one other. 2. Force replication between domain controllers to see if there is a replication issue.

And you also could check SMTP log for this connector.

Reference: https://social.technet.microsoft.com/Forums/en-US/c5502895-8a9e-41a7-a6b7-d4f181178913/451-450-require-ehlo-options-to-match?forum=exchangesvrsecuremessaginglegacy

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