I haven't filed a tax return in 10 years. I've been on disability and unable to work. I'd like to straighten it out with IRS. Should I? Where to begin?

You probably do not have a filing requirement, unless you need tax returns to prove your income.

Disability (SSDI or SSI) can be taxable if you have enough other income or if you are married, living with your spouse, and filing separately. To calculate if any of your disability income is taxable, use the combined formula. You take half of your disability income and add it to your other income. Then look at the taxable threshold for your filing status.

Income Taxes And Your Social Security Benefit

If you have taxable disability income, add the taxable portion of your disability to your other income. If that amount was more than $12,950 in 2022 and you are single, you had a filing requirement because your income was more than the standard deduction.

There are other situations that can mean you have a filing requirement if your income was less than the standard deduction - self-employment income of more than $400 per year, having health insurance subsidized through the marketplace, stuff like that.

It's usually a good idea to file a tax return if the total proceeds (including disallowed wash sales) for your capital gains transactions are more than the standard deduction, even if your actual net gain is very small. That's because IRS doesn't always get the cost basis information from brokerages. Or if you have a capital loss instead of capital gain, you might want to file so you can carry the loss forward to future years.

If you want to file tax returns you can try something like FreetaxUSA to prepare your federal return and see if you need to file. They have several prior years available, and you can include the capital gains income for free. You should also include your disability income from your SSA-1099, even if it's not taxable. You don't have to pay for federal returns with FreetaxUSA, but they do charge 17.99 for state returns.

Try doing 2020 through 2022 to see if you have any taxable income. If your taxable income on the Form 1040 is always zero, and you don't owe and won't get a refund, you probably don't need to file.

Another option is to wait until next tax season and go to your local AARP Tax-Aide. Their in-person locations are usually open Feb 1 through April 15, and most require appointments. They do have some drop-off locations, and they might start offering virtual tax preparation. One big caveat is that they do not do any returns with any crypto transactions, and I think they won't do tax returns for day traders with a lot of transactions. Here's the information from their website:

Documents You Need For Free Help From Tax-Aide

Check their site locator in late December / early January next year. Next year they should be able to file 2020 - 2023 for taxpayers who are behind.

Another free tax preparation program is VITA, but you'll need to check if your local program will do any capital gains transactions. Mine used to but doesn't any longer.

Free Tax Return Preparation for Qualifying Taxpayers