Dynamics 2016 email tracking ignoring outgoing replies

Question

We have server-side synchronisation set up for our Dynamics 2016 on-premise instance, and it is correctly sending emails from a Case, and tracking replies from the customer. However, when an internal user replies using Outlook (without the CRM add in), their responses aren't being tracked. This means that the email conversation consists of an initial "outgoing" email, followed by only incoming responses.

The full scenario is:

1. Internal user sends an email from a CRM Case. Email tracked in CRM
2. Customer replies to email. Reply tracked in CRM and goes to internal user's Outlook
3. Internal user sends a reply from their Outlook. Reply is not tracked in CRM
4. Customer replies to email. Reply tracked in CRM and goes to internal user's Outlook

Is it possible to allow the Internal user's replies (point 3) to be tracked in CRM without installing the Outlook add in (i.e. so it also works from the Web/mobile versions of Outlook)?

Answer 1

I have heard back from our Microsoft Partner, and they say that this scenario isn't possible. By design, it'll only track incoming emails to CRM, or outgoing if sent from within CRM itself.