Conversations Inbox with opted out contacts

We're just starting to use HubSpot Conversations for a few existing customers.  I saw this conversation today between a service rep and an active customer who had previously opted out of marketing email.

 

Rep can't send an email reply, doesn't understand it... uses Outlook (with the plugin) instead.  He includes this towards the end of his message:

 

Further, it looks like you've selected to disallow communication from [our support email address]. I had to jump through several hoops just to send you a response. Could you please allow communication from [our support email address] so we can continue to correspond?

 

Customer replies:

In regards to your email address,  I do not have it blocked or restricted, so I’m not sure why your emails aren’t coming through.  Our email client is Outlook.  I’ve checked Outlook and my gmail account and I can’t see that there are any restrictions in place on your email address.  If you have suggestions on how to address this issue, please let me know.  Until we can resolve this issue,  you can send your emails to [another colleague's email] and ask her to forward it to me.

 

Our rep replies with this crazy workaround:

 

I suspect that, at some point, you selected to unsubscribe from all acctivate email addresses, which would include [our support email address].  If you look at a past email in your inbox from an [our domain] email address, I expect you will see an option to "update your email preferences." Here, you should be able to re-subscribe, which should allow us to send you emails more easily.
 
PLEASE MAKE THIS EASIER/PROCESS BETTER.  Email conversations initiated by the opted out contact should be exempted from the opt-out, right?  Furthermore, many of these account-related messages for existing customers don't apply to CAN-SPAM.  In general, I would suspect that most Conversations Inbox messages should be exempt from the opt-out status for contacts.  Can we keep a contact opted out from email lists, but allow emails from service reps?