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Education
It's not clear where $ 5545.75 is coming from, since 8601.75 - 5250 = only 3351.75.
Q. I entered the info from my 1098-T (with 8601.75 in box 1). I'm still supposed to enter this full value, correct?
A. Yes. But, for simplicity, it's OK to enter the net paid ($3352)and not deal with the rest of the complicated interview.
Q. I went to "Scholarships/Grants (for all schools)" > "Let us know if you got a scholarship, grant or any of these other types of aid" > I said YES for this. Correct?
A. No. It's not scholarship. You'll get a separate question/entry for employer assistance. Enter $5250.
Q. I'm not clear on whether the $5545.75 was technically "listed" on the W2 since it was lumped in with the rest of my income?
A. Yes, it is included/listed. It's always done that way (lumped in with your other wages).
Q. In the "Employer-Provided Assistance" box, is this where I put $5250? Or is is $5545.76?
A. $5250. Only the tax free part in entered there. For purpose of this section of TurboTax, the assistance that was taxed is not considered assistance. It's considered you taxed income.