Thanks for getting back here in the thread, @simeonshigg. I'm here to provide more information about choosing a closing date to update transactions in QuickBooks Online (QBO).

Yes, you're right. If you continue your current settings, which is having your closing date cover at least three months' worth of transactions, you won't receive the same prompt again. But if you decide to expand your closing date to four months' worth of transactions or more, QuickBooks may have a hard time updating them.

In addition, I've got you this article to help you wrap up this years' payroll: Year-end checklist for QuickBooks Online Payroll.

Also, you can visit this page in case you'd like to add more details to your reports in QBO: Customize reports in QuickBooks Online.

As always, our door is open 24/7 in case you have any additional QuickBooks-related concerns. Don't hesitate to click the Reply button below. I'll be here, ready to respond. Stay safe!