I didn't know that was an option! Most of the ones I looked at wanted the full payment upfront before even starting. Do you have specific ones you'd recommend that let you pay just for the filing part? I've already filled out all my forms so I'm really just looking for the electronic submission part.

FreeTaxUSA is pretty good for this approach. You can complete your federal return for free, then it's just $15 for the state portion. Some others like TaxAct and TaxSlayer have similar options where the federal basic filing is free and you just pay for state. If you've literally already completed the physical forms with a pen, then using the IRS Free File Fillable Forms mentioned above is your best bet. You'll just need to transfer the information from your paper forms to the electronic versions. There's a bit of duplicate work, but it's free and gives you the e-file benefits.

Certified mail with return receipt is essential too. It's a few extra dollars at the post office but gives you proof of when they received it. I file on paper every year and always use certified mail after having a return "lost" in 2018.

Not at all! Those quarterly estimated tax payments will be credited toward their total tax liability on the joint return. When they file the amended return, they'll include those payments on the appropriate line. The IRS keeps track of all payments made under both SSNs tied to a joint return.

That was actually one of my biggest concerns! Thanks for asking this. I was worried her quarterly payments would just disappear into the void or something since I didn't include her business on our return. Relieved to hear we can still use those payments toward what we owe.

What software did you use to track your wash sales? I've been trying to use Excel but it's getting really complicated with hundreds of trades.

I ended up using a combination of TaxAct Premier (which has a decent stock transaction import feature) and a custom spreadsheet. The key is to sort all transactions by stock symbol and then by date, which makes it easier to identify the 30-day windows. If you have more than a hundred transactions though, I'd strongly consider using a specialized tool like the one mentioned above or hiring a tax pro who specializes in investment taxes. I spent nearly 40 hours reconstructing everything manually and still wasn't 100% confident in my calculations. It's worth paying for help with this many transactions - especially with an audit on the line.

Yes! This is exactly right. CP2000 notices are handled by a different department than actual audits. When I called (using that phone service mentioned above), the agent confirmed that these notices are super common for the 2021 tax year because of all the trading platform issues.

Do you use any specific apps for tracking expenses? I've been just using my phone's camera for receipts but it's getting disorganized fast.

I personally use QuickBooks Self-Employed which automatically categorizes most expenses when connected to your bank account/credit card. It also has a receipt scanner in the app that can match receipts to transactions. There are also free options like Wave that work well for basic tracking. The important thing is having a system - any system - rather than trying to remember everything at tax time. Just make sure you're consistent with it and do a quick review weekly so things don't pile up.

I use 28% as my set-aside percentage and it's worked perfectly for the last three years. Also remember you'll need to make quarterly estimated payments if you expect to owe more than $1000 at tax time. The due dates are April 15, June 15, Sept 15, and Jan 15 of the following year.

You can still claim eligible education expenses even if they're not listed on the 1098-T! Just make sure you have receipts or statements from the university showing they were required fees for enrollment. I had to do this last year for some lab fees that weren't on my 1098-T.

Yikes, 4 months is a long wait! Is there any way to expedite the ITIN process? We're already in February and I'm worried about getting everything done before the filing deadline.

Unfortunately, there's no official expedite process for ITINs. However, you can use a Certified Acceptance Agent (CAA) instead of mailing in original documents, which can speed things up. Some CAAs can verify your documents on the spot and submit certified copies with your application. Also, you can still file on time even if the ITIN isn't processed yet. Just submit your return with the W-7 by the deadline, and you won't face late filing penalties. Your refund will be held until the ITIN is issued, but at least you'll be in compliance with the filing deadline.