Funds Transfer Across Fiscal Years & QB Files

Record both sides of the transfer on the same day, as one transaction. The day it clears is irrelevant.

Even so, why two files?  There's usually no reason to create a new file with the new year.

It doesn't allow reconciliation that way.

I'm not sure what you mean?

You can reconcile both sides of a transfer transaction, or a check or deposit transaction used to record  the transfer. There's no need for two transactions to do so.

PP account for Jan '24 is already reconciled. If the transfer is shown as normal in '24, the CK account reconciles fine of course, but there is now an unreconciled $240 in PP.

I don't understand what you're describing.

It sounds like you're saying that when you record a transfer and then reconcile one side of it, in your bank account, that the other side - in the other account - is not reconciled.  If so, that is correct and normal: You have to reconcile the other account for that part of the transaction to be reconciled.

The issue is that on the PP statement for '24, there is no transfer for $240 because it was sent out on 12/31/23. So, when PP is reconciled, there is no record of a transfer. If I then add the transfer on 1/3/24 when it posts to CK, CK will reconcile perfectly, but now there is an unaccounted for $240 missing from PP that isn't on the statement. Thus, PP will not reconcile correctly.

Should I just change the starting balance of PP $240 higher even though it doesn't match the statement? Or is there a ledger adjustment I can make to add the $240 to the PP account so it then reconciles correctly? If the ledger adjustment is the correct method, how does that get entered?

This all sounds like complications that are a result of creating a new file from scratch and - effectively - not using the same starting point for both of the accounts.

But yes, if you want to reconcile an account, then all of the transactions that appear on the statement must be represented in the account's register.  To avoid creating an unwanted transaction in the checking account, record the transaction in the "PP" (?) account using an Equity account, or perhaps the same account you used in the checking account for the transfer.

Generally when starting a new file, the opening balance in an account that you reconcile should be dated on the starting date for the first month you'll reconcile and should be for the opening balance of that statement. And the account register should have all of the uncleared transactions entered in it.  The transactions from a prior period - before that start date - should be dated when they happened, and can use an equity account, such as Opening Balance Equity, or perhaps just an income or expense account.

The starting dates are the same for the file and both accounts, Jan. 1, 2024. 

What do I need to enter to show the debit from CK without effecting the PP account?

 Write a check & Opening Balance Equity as the account? If so, what do I put in the vendor area?