Hi there, @Mike29.

Let me help you auto-alert with a pop-up or email when the Gen Liability or Work Comp expiration is approaching in QuickBooks Desktop (QBDT). 

Before anything else, please know that the feature to track these items is only available in the Contractor and Accountant edition. If you switch to Contractor mode.

However, if you have a different edition, you can create a bill reminder and set it to notify before the due date. Here's how:

1. Open the bill.
2. Click Memorize, then choose Add to my Reminders List.
3. Choose how often you want to be reminded. Then, enter the date in the Next Date field.
4. Click OK.

On the other hand, in the upper right corner. Under the Company. You can set up any kind of reminder with a Date to show up. In the Preference, you can also set how many days in advance you want something to show up. Feel free to follow these steps: 

1. Go to Edit at the top menu bar, then Preferences.
2. Scroll down and click Reminders.
3. Choose the My Preferences tab.
4. Put a checkmark in the Show Reminders List when opening a Company file.
5. Go to the Company Preferences tab.
6. Select those reminders you need based on the one you've set up.
7. Click Ok

However, it was often left at 0, and you scheduled the reminder when you wanted it to show up. In the description, you can put something like XYZ's insurance expires next month or expires, etc. Also, you can look for a third-party app that can help you notify when a due date is near.

If you want to learn how to have automated payment reminders for invoices and statements, you can read this article: Create automated payment reminders for invoices and statements.

Click the reply button for additional questions about managing your transaction's due date reminders. I'll be willing to help. Keep safe and have a good one.