Hi,
thank you all for contributing to this thread. I want to share a short update:
The new Outlook is not a version that we can fully support at this time and using the O365 integration with the new Outlook for Mac can result in known issues with email tracking.
The recommended workaround is to either switch back to the Legacy version of Outlook for Mac (Help > Revert to legacy Outlook) or to use Outlook on the Web.
Our product team is aware of this issue and is currently investigating. This feature request has already been submitted in our Ideas forum (thank you for sharing @tcross81!). Upvoting here will alert our Product Team to the popularity of this request. Doing so will also auto-notify you about updates from the product team & if/when this functionality becomes available within HubSpot. You can read more about how that review process works here.
Thank you for your understanding!
Mia, Community Team