Complex situation, not sure how to file?

[Walexis25]

Hi there, 

Thank you all for taking the time to answer these questions! 

I have a bit of a complex situation. During 2021, I had quit a few major life changes.

• 1) I was on unemployment
• 2)I got off unemployment because I finally got a new full time job. However, this new job is in a different state from mine, so I have been working remotely. (I am in Maryland and my job is in Oregon) So I am not sure how to proceed with my taxes in that regard. I filled out Maryland tax forms for this job.
• I started a small business that has slowly progressed.
• This is the biggest change: I won a competition that paid my $100,000 dollars of my student loans. The money was not directly given to me. They were directly paid to my loan provider.  They also gave me a check for 20% of what they paid to contribute to the taxes.  1) How do I determine the taxes I owe for this competition if the money was not directly given to me? Do I report this as income? How do I report it? 2) Since they directly gave me a check for the money, am I supposed to report that and does that become taxed too? I have not received a 1099 from them. 

I am just wondering how do I go about all of these new changes when filing? 

Thank you

Alexis

[GeorgeM777]

It appears you do not have to pay taxes to Oregon.  The Oregon Department of Revenue, in their Payroll Tax Basics document, states the following on page 5:

"Oregon employers with nonresident employees working outside the state are not required to withhold Oregon taxes on these wages."

Thus, because you indicated that you are performing all of your services for which you are compensated in MD, and not in OR, it would appear that OR will not tax your wages.  Moreover, as noted above, while your employer is not obligated to withhold OR taxes from your paycheck, they may have done so, albeit inadvertently.  In that case, you will want to file a non-resident OR return to obtain all of the withholding that was paid to OR.  The link to the OR Payroll Tax Basics document is below.

The money you won in the competition is taxable income and must be included on your return.  Had you declined the money, the result might have been different; however, because you accepted the money from the competition, such money is taxable to you.  It doesn't matter if you receive a 1099-MISC or a W-2G reporting your winnings or not. You'll still need to report all income to the IRS. You just have to add your unreported winning amounts to the applicable lines on your tax return.

You don't need to know where to place each item of unreported income on your tax return. TurboTax can help by asking simple questions to make sure you're reporting all of your income and winnings that need to be reported.

Oregon Payroll Tax Basics

[Walexis25]

Thank you for your response!! This is helpful.