Quicken: This was something I came up with years ago. I create a separate file called points (so it doesn't influence my financial statements). Each airline and/or hotel program becomes a "bank account" within the file (Example: American, Marriott, United, etc.). The account number is my account number for that program (makes it easy to look them up). The categories are my own (Flight Actual Miles, Flight Class of Service, Member Bonus, Hotel Points, etc.). When I check a web site (such as AA or Marriott) and I see the actual entry, I put in the exact amounts and mark the item as "Cleared" (just like they get marked when I download from the bank). Then, when I get the printed statement, it is just like a bank statement: I reconcile (which is why you create them as bank accounts instead of asset accounts or something else). The "missing" entries are obvious and I follow up. I have my history and my balances going back for years.