Sweepstakes Online Casinos and deductions

cowlthor
cowlthor Member Posts: 1 Newcomer
edited March 28 in Filing my taxes

Hello, please note I am going to start the post with assumptions being made to avoid the discussion of issues not at hand: Regardless of your personal or professional opinion, filing both as an amateur or professional gambler will allow deducting all wagers made versus the wins regardless of if it is a land based, normal online, illegal online, or sweepstakes casino.

Receiving a 1099 or W-2G will both report income but without a W-2G issues, the IRS will not assume that the amounts reported on 1099 are gambling related. On FreeTaxUSA, you are unable to enter deductions for gambling losses unless you report W-2G amounts. As such, the reporting of gambling winnings either must be reported twice (both in W-2G and 1099 reporting locations) which overstates income but allows deductions up to the W-2G amount or can be reported only on the 1099 income but will not allow any gambling deductions since deductions are limited to the amount listed under W-2G ($0 in this instance).
I am looking for a way to enter into a deduction not in the list provided by the software or attach the 1099 directly to the W-2G entry.

I am ONLY interested in how to get the deductions entered and do not want opinions on if this is allowed by the IRS. Thank you.

Comments

  • panickyfloppy
    panickyfloppy Member Posts: 10 Level 3

    I think you just have enter the gambling winnings in that section of Other Income instead of as a 1099 and then FreeTaxUSA will know there are gambling winnings and will have the option for losses in itemized deductions.