Massachusetts Gambling Losses doesn't recognize amount entered under Gambling Winnings

Make sure your gambling are properly reported on your Federal return. This should flow properly to your state tax return.

To enter your gambling winnings in TurboTax Desktop, you will do as follows:

1. Select "Wages & Income"
2. Click on "I'll Choose What I Work On?"
3. Scroll down to "Less Common Income"
4. Click "Start" by "Prizes, Awards and Gambling Winnings"
5. Follow through the screens and answer all questions related to your gambling winnings.

To enter your gambling winnings in TurboTax Online you will do as follows:

1. Click on "Wages & Income"
2. Scroll down the page to "Less Common Income"
3. Click the (down-facing) caret next to "Less Common Income"
4. Click on "Start" next to "Gambling Winnings"

When you enter your gambling winnings in TurboTax, the interview will also ask you questions regarding gambling losses, after you input your gambling winnings. Your gambling losses will flow to your state return. Your state may have different rules for gambling losses.

It will look like this in TurboTax Desktop:

 It will look like this in TurboTax Online:

Click here for additional information on gambling losses and what documentation is required.

Click here for additional information on itemized deductions.

Click here for additional information on entering W-2G.

Yes, In my federal I list my 2 W-2Gs totaling $2000.  Then I have $2,000 listed in the "Let us know if you had any gambling losses in 2024" page. 

That is all correct and flows, like I said previously, into Mass state.  If I Show Relevant Form it shows on Sch X that 2000 is entered.  When entering Gambling Losses Deduction, it lets you enter the amount and continue through but when the State Checkup is done, it comes back with the error "Schedule Y: Sch Y, Gambling Losses should not be entered unless there are Gambling winnings on Schedule X. and it highlights the "certain gambling losses" field. Subsequently going back to the Gambling Losses Deduction page shows a popup "Sch Y, Gambling Losses should not be entered unless there are Gambling winnings on Schedule X.

You need to go back through your Massachusetts return and make sure that you enter the gambling losses in the correct spot.  There are two places in the return where the program asks for gambling information.  

The fist one asks about specific Massachusetts lottery winnings, you should not enter anything there.  Then there is a question about Massachusetts, select "Had gambling losses incurred at certain licensed establishments."  In the next question enter the losses. 

See the images below for your reference:

@ronhaha108 

Yes, as I stated in my original post, I did that.  Doesn't matter, I just let it think there's an error, I verified the forms and they were correct so I filed with it.