I log paper check payments to “undeposited funds” and then when I view transactions, I match those payments to the deposit. Should I also be entering the lump sum deposit

It is your choice. You would have to manually createtge deposit in QB prior to matching. Once you have matched to the bank feed as you are now there are no longer items for this deposit to create it again.

What you do now enters the correct deposit with correct payments but if you had a large batch over several days it might save you time to "make" the deposit in QB contemporaneously with making the deposit at the bank.

While I can see the benefits and have used bank feeds I am still a firm believer in doing the work first - then the matching is just checking up

Thanks for dropping by here in the Community, @68stratford.

In addition to what @john-pero mentioned above, I would like to provide further insights. The way you enter the deposit depends on how it shows on your actual bank statement.

If the payments are showing as a lump sum on your bank, you need to record the same way in QuickBooks. This way, your transactions will match correctly during the reconciliation in QuickBooks.

Here's how:

1. Click the + New button in the upper-right corner.
2. Below Other, select Bank deposit.
3. Under Select the payments included in this deposit, put a check mark on the payments. 
4. Hit Save and close.

Additionally, I recommend the following resource which has video tutorials to help a user learn about making deposits, and how to manage them: Record and make Bank Deposits in QuickBooks Online.

Let me know in the comment section below if you have any other questions or concerns. I'll be here to help. Have a great day ahead.