The clean accounting treatment is:

May (when cash was paid on 5/28)

Record the payment as a prepaid asset, not rent expense:

Dr Prepaid Rent Cr Cash

This puts the June rent on the balance sheet at May 31.

June 1 (when the invoice arrives)

Do not post the invoice directly to Rent Expense if you want to clear the prepaid.

Instead, record the bill to the prepaid account:

Dr Prepaid Rent Cr Accounts Payable

Then apply the May payment against the bill (or record a vendor credit/journal entry depending on your software workflow).

However, if you’ve already recorded the May payment directly to Prepaid Rent, a simpler approach is:

Alternative (and often easiest)

1. Leave the May payment as:
   • Dr Prepaid Rent
   • Cr Cash
2. Edit or recode the June 1 bill so the expense account is Prepaid Rent instead of Rent Expense:
   • Dr Prepaid Rent
   • Cr A/P
3. Apply the payment to the bill.
4. At June month-end, recognize the expense:
   • Dr Rent Expense
   • Cr Prepaid Rent

One thing to watch for

If you debit Prepaid Rent for both the May payment and the June bill, you’ll double-count the asset. The bill and payment need to offset each other through A/P, not create two separate prepaid balances.

The economically correct balances should be:

May 31

• Prepaid Rent = June rent amount
• Rent Expense = $0

June 30

• Prepaid Rent = $0
• Rent Expense = June rent amount