Would this browser trick work with Edge too? I don't have Firefox installed and don't want to download another browser just for this if I don't have to.

I haven't personally tested Edge, but other users have reported success with it. The key seems to be avoiding Chrome, which has some weird compatibility issues with the Free File system's PDF handling. Edge should work better than Chrome since it uses a different rendering engine. The main thing is that some browsers handle the form submissions differently, especially with checkboxes and special characters. If you're getting the same rejection repeatedly in one browser, it's definitely worth trying a different one before giving up.

I actually tried that method last year with a different form (not 8863) and it failed because the Free File system requires certain forms to be filled electronically so their system can read the data. You can't just attach a scanned form as a PDF - the system needs the actual data in the fields.

Thanks for this advice! Would it help if I started paying a portion of the rent directly to the landlord instead of giving the money to my boyfriend? I'm worried that the Cash App transfers labeled "rent" might not be enough proof since the actual rent receipts are in his name.

That would definitely strengthen your case! If you can arrange to pay even a portion directly to the landlord, that creates a clearer paper trail. Ask the landlord if they can note your payment specifically in their records, even if the lease remains in your boyfriend's name. The Cash App transfers labeled "rent" are still useful evidence, especially if they show a consistent pattern that aligns with rent due dates. But direct payments to the landlord would be more compelling. Also, consider getting a simple written statement from your boyfriend acknowledging that your Cash App transfers are contributions toward household expenses - this adds another layer of documentation.

I used TurboTax last year with a similar HOH situation. It asks you the basic qualifying questions but doesn't really get into documentation issues. It'll let you file HOH if you say you meet the requirements, but doesn't help you prove it or explain the gray areas. You might want to consult with a tax pro if you're uncertain.

Thanks for sharing your experience. Did you have any issues after filing with TurboTax? Like did the IRS question your HOH status afterward or did everything go through okay?

17 Is there a minimum amount you have to make before reporting? I thought there was some threshold where you don't need to bother reporting small side income?

3 Technically, all income is supposed to be reported regardless of amount. However, if you make $400 or more in self-employment income, you're required to file taxes on it because that's the threshold for paying self-employment taxes. Some people talk about a $600 threshold, but that's actually just the limit where payment platforms or clients are required to send you a 1099 form. Even if you don't receive a 1099, you're still supposed to report the income. The IRS has been cracking down on unreported income from online platforms, so better safe than sorry!

13 Do you know if this applies if you're selling through platforms like Etsy or eBay? I thought they handled the sales tax stuff automatically?

I hadn't thought about the backdoor Roth approach. Would that still work if my tax liability is already zero? And would I still need to worry about the documentation of foreign expenses if I go that route?

The backdoor Roth works regardless of your tax liability because you're making non-deductible contributions to a traditional IRA first, which doesn't require you to have tax liability. You'd report these non-deductible contributions on Form 8606. No need to worry about foreign expense documentation for this approach. You can take the full standard deduction, apply your FTCs to reduce your tax to zero (carrying forward any excess), and still do the backdoor Roth. The only documentation you need is for the FTCs themselves (foreign tax statements or equivalent), not itemized expenses.

FTCs can only be carried forward, not backward. You can carry them forward for up to 10 years, but you can't apply them to prior year returns unfortunately.

Is there any repository or website where you can look up these specific state rules? Trying to figure out what counts as "payment" in Colorado.

You can usually find these rules in your state's tax code or administrative code, which should be available online through your state's legislative website or department of revenue site. Search for terms like "date of payment" or "timely payment" along with "tax." For Colorado specifically, I believe they follow what's known as the "timely mailed, timely filed" rule, which means the postmark date is considered the payment date if sent by U.S. mail. They also have specific provisions for electronic payments. You can find these details in the Colorado Revised Statutes and the Department of Revenue's tax regulations. Their taxpayer service division can also provide this information if you call them directly.

Electronic payments aren't always an option for everyone though. My small business has to make special estimated payments for a particular industry tax that our state still requires to be submitted by mail with a special voucher form. It's ridiculous but that's how they want it.

That's a fair point. I didn't consider that some specialized tax types might still require physical payments. In those cases, I'd probably still try to use my bank's bill pay service rather than writing personal checks, since the bank creates an electronic record of when the payment was sent out, which gives you an additional layer of documentation. It's frustrating that some tax departments haven't fully modernized their systems yet, especially for business-specific taxes. Hopefully more states move toward comprehensive electronic payment options soon, as it's clearly better for both the taxpayers and the tax departments in terms of record-keeping. Profile: 1