I've got problem with some undelivered emails. Got many queues in my on-prem, which are tracking all of incoming emails. But some ot them are undelivered (purple icon). I realised that many of them (unfortunately not all, but I want to solve this case by now) are answers to previous emails, which has no answer from CRM. I mean client send an email, it is tracked, but he forgot to add some information, so after few minutes he answer/replies to his first email. The second one is undelivered and that's the problem. Tracking by token is on (some of mailboxes must track only answers to emails send from dynamics). I turn on smart matching, it worked for few tests, but then I got info, that other emails ain't matching again :c
This issue often happens because the second (reply) email isn’t correctly linked to the original CRM email activity, causing it to show as undelivered.
Common causes & fixes:
Smart Matching not fully reliable—it uses subject lines, conversation IDs, and tracking tokens, but replies can break matching if clients change subjects or reply formatting.
Ensure tracking tokens are included in all outbound emails so replies can be matched.
Check that email headers (like In-Reply-To and References) are preserved in replies—some email clients strip them.
You might need to increase smart matching timeout or adjust mailbox settings.
Consider manually linking emails or creating custom workflows to handle unmatched replies.
This is a common challenge with server-side tracking. If needed, I can help you review mailbox or tracking configurations.
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