<prompt> Human: Theres both a legal and finance aspect to this but I will keep the discussion to the finance part of it. For the legal part I made a separate thread on rlegaladviceLong story short small transactions were made over the past year that I didnt notice because I use the service almost daily Uber so I thought nothing of the charges. Specially since I live relatively comfortably 85-95k so I didnt suspect a thing until the numbers didnt add up when I started getting my taxes together. The total amount this person used is basically 10,000 over the past year. But before I keep going with the details what kind of professional should I be talking to deal with this financial loss and additional professional advice? A CPA?I dont know if I need one but I do know my options are to either report it to my bank, write it off as a loss or sue. Are there more? I would rather not sue since its a relatively close friend, will probably not be able to pay me back and would prefer he not go to jail. I could pay less taxes by writing it off as a loss but is that wise? Also, this person was obviously not authorized to use it but if I report it to the bank I dont know if my bank Chase will see it as fraud and refuse to cover my losses because I know the person? Also dont know if reporting it to the bank will make Chase prosecute himI didnt originally know who it was until I split an Uber last weekend with said person and the charges appeared twice in my card statement. Thats how I started to find all this out. On the bright side, just in time for tax time! How lucky! sSince he earns a low income it feels like my best option is to report it as fraud to my bank and get my money back without a hassle. I know for a fact this person wont be able to pay me back in a timely manner so thats another reason why I dont want to sue.Whats option would benefit me the most financially speaking?Assistant: Write it off as a loss means what exactly? This is apparently a gift you gave someone. A gift is not a loss its an exercise of discretionary income, which confers no tax benefit. 10,000 over the course of what sounds like 100 transactions is not going to just be refunded by your bank. Thats well into the felony level and it will be investigated. Chase cant choose to prosecute someone, but they can certainly refer the matter to a prosecutor who can bring charges. It sounds like your only options are reporting your friend or eating the loss. 10,000 on a 85k salary sounds like an awful lot to me. Human: I cant write something off as a loss on my taxes when I never authorized those transactions? It wasnt a gift, it is technically theft  <response>: IRS Topic number 515 deals with this. Theft is deductible if you itemize, but I can guarantee deducting a 10,000 cash theft is going to be a huge audit flag at the IRS. and ifwhen you get audited, what proof do you plan to present of this theft? Youre going to show them your credit card statements that you dutifully paid every month over the course of 100 transactions to pay for a person you admit is a close friend? My usual rule is to say whatever you think is criminal tax fraud probably isnt but this sounds like a very strong case of tax fraud. Not because you are actually trying to defraud but because it looks absolutely terrible. Without a police report in hand it looks like you just paid for your friend and are trying to defraud the IRS.At the very best, youd be on the hook for civil fees. At worst, you could be be guilty of tax evasion. 