Hi @BK9999,
Thanks for sharing this with the community.
It doesn’t look like you’re doing anything wrong here.
Try cloning the flow message, and re-toggling smart sending on and off again for the cloned version. If that works, I recommend simply using the cloned version of the flow message.
If that does not remedy the situation, try saving the flow message as a template, deleting the flow message (keep in mind this will remove all data associated with this flow message) and re-adding it using the saved template.
I also recommend testing the flow message itself. You can achieve this by setting that flow email to manual mode and quick adding a profile that’s already recently received an email to the list that triggers the flow. When a flow message is set to manual, you will see all ready-to-review-and-send messages in the Needs Review section within the Analytics snapshot in the left-hand sidebar. By clicking View all Analytics, you will be taken to a report where you can manually dispatch the flow message. It could very well be that smart sending is still disabled in practice (despite the icon).
I hope that’s helpful.