Hey @ebunilink93 

Sorry for the delayed response!

You are correct that depending on the trigger you are using, a dynamic product block will only show the most recent “placed order” item. However, I have an idea that might work, but would take some energy to initially set this up.

• You would need to setup a post purchase flow for each product where the trigger is placed order and trigger filter of product equals XXX.
• Then create a time delay of 334 days
• Create first email with static product blocks so you can be very specific about the product that is ready for upgrade.
• Create the second time delay for 30 days
• Add email #2 

You can save some time by saving different blocks as universal content, which will allow you to plug and play different pieces of content easily between emails/flows.

My idea would allow you to trigger the flow on the day of the order based on the order details so we are capturing who purchased what items and then with the time delays send them the followups for upgrades. 

Please let me know what you think about this idea and we can keep workshopping this until you have what you need!