Not working: Use correlation to track email conversations

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Posted on by Robert50

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In my personal options, I've selected "Email messages in response to Dynamics 365 email" I then send an email to my self from an external domain. Once I receive the email in outlook, I click the D365 app icon and then click the chain link icon next to the contact name. The message correctly shows up in CRM under activities for the contact.

However, if I reply to the now tracked email, my reply never makes it to CRM unless I manually click track the email in the same way I did for the incoming message. Why isn't my reply being tracked?

Based on my options chosen, coloration and smart matching should causes the response to be tracked as well, correct?