Does Cash App Taxes handle 1099-MISC forms? I did some freelance design work and got one of those, plus I have some investment stuff to report.

Yes, Cash App Taxes handles 1099-MISC forms without any issues. I've used it for freelance income alongside investment reporting for years now. The interface for entering 1099 information is actually pretty straightforward, and they support multiple 1099s if you had several clients. They also walk you through any deductible expenses related to your freelance work, which can significantly reduce your taxable income from those gigs.

Whats substituted cost basis mean? I have investments but im confused by all the tax language on my forms.

Did you report each transaction individually or did you consolidate them? I have hundreds of trades and wondering if I need to list every single one or if I can summarize somehow.

I reported each transaction individually because that's the technically correct way to do it. However, if you have hundreds of trades, there is an alternative. You can attach a separate statement to your return that includes all the required information (date acquired, date sold, proceeds, cost basis, gain/loss) and then enter the totals on Form 8949. On the Form 8949 itself, you would check Box C (not reported on Form 1099-B) and write "See attached statement" in the description column. Just make sure your statement has all the same information that would be required on the form itself, organized in a similar format.

Staking rewards are typically treated as ordinary income at the fair market value when you received them, not as capital gains. You'd report these on Schedule 1 as "Other Income." When you eventually sell the tokens received from staking, that would be a capital gain/loss transaction. Your cost basis would be the value at which you initially reported the income (when received).

This is so annoying though cause nobody tells you when they switch systems! My company did this last year and sent ONE email that went to my spam folder. Is there any requirement for them to notify us about where to find tax docs?

Companies should notify employees about where to find tax documents, but there's no specific legal requirement about the method of notification. They're only legally required to provide the documents by January 31st, either electronically or by mail. Sometimes these notifications end up in spam folders because they come from the third-party provider rather than your company's domain. I recommend checking with HR or the payroll department if you're unsure. Many companies also post this information on their intranet or employee portals during tax season.

That's actually smart. I always forget that paper forms are still an option. Did they give you any hassle about sending it by mail?

This is a great suggestion. Do you typically just call their main number and ask for accounts payable? I'm dealing with a medium-sized marketing agency if that helps.

For medium-sized agencies, I usually check their website first for direct contact info for their finance team. If that doesn't work, yes, calling the main number and asking for accounts payable or vendor management usually works. Marketing agencies tend to be more flexible than large corporations in my experience. Just be polite but firm that you're happy to provide your tax information but prefer to use the standard IRS form. I usually say something like "for consistency in my record-keeping" rather than making it sound like I don't trust their system.

I work in accounts payable and please don't do this. It creates a huge headache for us and will likely result in your documents being rejected or severely delayed. Most large companies have automated systems that flag modified forms for manual review, which puts your paperwork at the bottom of a very long queue.

Do you know if the Free File options mentioned above handle Michigan state taxes too? Or would I need to do that separately?

Some Free File options include state filing, but not all of them. FreeTaxUSA, which I mentioned, offers free federal filing but charges about $15 for state filing. The Michigan Department of Treasury actually has its own free filing options called MIFile that's completely free for qualifying residents. Check michigan.gov/taxes for details on eligibility. Most people with straightforward tax situations and lower incomes can use it.

FreeTaxUSA is my go-to. Handles all forms including Schedule C for 1099 income, and only charges for state filing. Their interface isn't as slick as TurboTax but it gets the job done for WAY cheaper.