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.

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).

Thanks for this perspective! I do keep pretty detailed records of material costs, time spent, etc. just for my own tracking. I haven't really marketed my stuff beyond the occasional craft fair, but I have been thinking about setting up an Etsy. Do I need a business license or anything formal to call it a business on my taxes? And would I still use Schedule C even for such a small operation?

You don't necessarily need a formal business license for tax purposes, though your local requirements might vary. For federal taxes, you can absolutely use Schedule C even for very small operations - there's no minimum income threshold. The detailed records you already keep are perfect - that's exactly what helps establish it as a business rather than a hobby. If you're thinking about Etsy, that's another indicator of profit motive. Other things that help: having business cards, a dedicated Instagram for your woodworking, participating in multiple craft fairs, reinvesting income into better equipment, and learning new techniques to improve your products. The IRS looks at your intent and behavior more than the actual profit.

This is super helpful - thanks! TurboTax has been confusing me with this exact issue. Does this also work if the amounts don't match exactly? My 1099-NEC is slightly different than my 1099-K total (like $50 difference) because of some timing issues with the payments.

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?

I've heard mixed things about Cash App Taxes - doesn't it have limitations on which forms it supports? I need to file some investment forms and I think I read somewhere that they don't support all of them. Have you used it with any complex investing situations?

You're right that it does have some limitations. It works for most common investment forms (1099-B, 1099-DIV, etc.), but doesn't support some of the more obscure forms. I have fairly standard investments and it worked fine for me. They don't support foreign income, multiple state filings, or K-1 forms for partnerships. If you need any of those, it wouldn't work for your situation. Their website has a complete list of supported forms that's worth checking against your specific needs before you invest time in entering all your data.

CalFile is great but they have income limits and other restrictions. Worth checking if you qualify first: https://www.ftb.ca.gov/file/ways-to-file/online/calfile/qualifications.html Not everyone will be eligible unfortunately!