Is there a setting that needs to be enabled to keep transaction history going back as many years as there are uploaded records? Or does it delete at certain point?

Hi @kitcooper21-gmai,

Whenever you connect an online bank account to your QuickBooks Self-Employed (QBSE) company, it automatically downloads your recent transactions.

Please be advised, some banks download a year's worth of transactions, while others download a month or so of transactions. It's the financial institution (FI) involved that decides the date range for this automatic download process. That said, QuickBooks doesn't have any control in this process, as we only receive what your FI shares with us.

What you can do in this situation is to upload the bank transactions that weren't downloaded via the process stated above. See this article for the steps: Add older transactions to QuickBooks Self-Employed.  

In case you bump into a situation where you have duplicate bank transactions, you can refer to this article: Handle duplicate transactions in QuickBooks Self-Employed. It's an article that walks you through how you can review your bank register so you can locate and remove duplicate transactions.

Don't hesitate to leave a comment if you have other questions about online banking in QBSE. I'll be around to help you out.