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Buy nowThanks for joining the thread, @P Austin.
I'll share some guidelines that could help you achieve your goal.
You can set a to-do reminder to set up vendor transaction reminders on or before a specific due date. In this case, a pop-up message will remind you to pre-pay your vendor's insurance.
You can utilize this article, which provides an overview of how to track your vendor's activity: Accounts Payable Workflows in QuickBooks Desktop.
Feel free to post here again if you have more questions. Have a great day!