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Test outbound mail flow in Exchange Server 2016

You like to test outbound mail flow in Exchange Server 2016 after installing and configuring Exchange Server 2016. Maybe you did configure a send connector on the Exchange Server, and you want to test if it’s working. In this article, you will learn how to test outbound mail flow in Exchange Server 2016. It will apply to all Exchange Server versions.

Information

In previous articles, we discussed mail flow:

Before we start testing the outbound mail flow in Exchange Server, make sure you create a send connector. Otherwise, it’s not possible to send emails to the outside world. In our example, we have the send connector configured to use the MX record associated with the recipient domain.

Read more: Configure External DNS Exchange 2016 »

Send message to external recipient

Log in with an account in Outlook. Compose a new message to an external recipient. In our case, we sent an email to a recipient with a Gmail account.

Compose email

Get email header from sent message

In Gmail, go to the inbox open the message from Cristopher. Click the More button and follow with Show original.

Test outbound mail flow in Exchange Server 2016 show original

Click on the button Copy to clipboard to copy the headers. If you don’t see that button, you will see the headers on that page below. Select the headers and copy the text.

Test outbound mail flow in Exchange Server 2016 copy to clipboard

Keep reading: Setup SPF record for Exchange Server »

Message Header Analyzer

Go to Message Header Analyzer by Microsoft. Paste the copied headers from the clipboard. Click on Analyze headers.

Test outbound mail flow in Exchange Server 2016 analyze headers

Check mail flow

From Christopher’s message, we can see that the mailbox is currently hosted on a mailbox database in Exchange Server EX01-2016. The mail route went through Exchange EX01-2016 to Google mail servers.

Test outbound mail flow in Exchange Server 2016 received headers

Outbound mail flow is working great! If you like, you can remove internal Exchange Server hostnames and IP addresses from message headers.

Keep on reading: Exchange 2016 internal mail flow not working »

Conclusion

In this article, you learned how to test outbound mail flow in Exchange Server 2016. Use the Message Header Analyzer to inspect the headers. After that, you can precisely tell which route the mail took.

Did you enjoy this article? You may also like Migrate Exchange mailboxes with CSV file. Don’t forget to follow us and share this article.

ALI TAJRAN

ALI TAJRAN

ALI TAJRAN is a passionate IT Architect, IT Consultant, and Microsoft Certified Trainer. He started Information Technology at a very young age, and his goal is to teach and inspire others. Read more »

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