Customer deposits $14,000 in cash to their personal (individual) checking account and then writes a check from the same account to purchase a Cashier's Check for $14,000. How is the legacy CTR form completed, specifically, is this multiple transactions and would you check both Negotiable Instrument Purchased and Deposit/Withdrawal? Thanks.

Only the cash deposit would be reportable on the CTR. Deposit/Withdrawal only.

For the CTR, there is only one transaction -- the deposit of cash. The purchase of the cashier's check does not involve cash.

Note: If the cashier's check purchase had been for an amount between $3,000 and $10,000, inclusive, you'd have to treat it as a cash purchase of a monetary instrument for record keeping purposes even though the cash was actually deposited to the account.