12 One thing nobody's mentioned - make sure you keep a complete copy of everything you send! I filed a paper return in 2023 and the IRS somehow lost parts of it. Having my own copies saved me a huge headache. Also take pictures of the signed forms before you mail them just to be extra safe.

Pro tip from someone who's been through this exact situation - when you do mail in your paper return, include Form 4506-T (Request for Transcript) along with it. This way you can get a transcript of your return once it's processed, which serves as official proof that the IRS received and processed your filing. Also, since you mentioned you're expecting a refund, be aware that paper returns are processed in the order they're received, and the IRS is still working through a backlog from previous years. Don't panic if it takes 12-16 weeks instead of the usual 6-8. The refund will come eventually, and like others mentioned, there's no penalty since you're getting money back rather than owing. One last thing - if your refund is over $1,500, consider having it direct deposited into your bank account rather than getting a paper check. Even with paper filing, you can still provide your banking info for direct deposit, and it's much faster and more secure than waiting for a check in the mail.

Is there any expiration on capital loss carryovers? I've been carrying some for almost 4 years now.

One thing I'd add to the great advice already shared - make sure you're applying your capital loss carryover in the correct order! The IRS requires you to use the oldest carryover losses first (FIFO - first in, first out). Since you had a $20,000 loss in 2022, that entire amount should be applied against your 2023 gains before you can use any losses from 2023 itself. This shouldn't affect your calculation (you'll still net $30,000), but it's important for record-keeping purposes. Also, double-check that you actually filed your 2022 return and properly reported that $20,000 loss. If for some reason it wasn't properly documented on your 2022 Schedule D, you might run into issues when the IRS processes your 2023 return. The carryover amount needs to have a paper trail from your previous filing.

Dont forget to check ur state return too! If u amend federal u usually gotta amend state also. I forgot this and got a nasty letter from my state tax ppl even tho IRS was fine with my amendment.

I amended my 2021 return last year for a similar situation - missed home office deduction as a contractor. The process was actually pretty straightforward and I didn't get audited. A few things that helped me: - Used Form 1040X and clearly explained each change in Part III - For home office, I measured my dedicated workspace (10x10 room = 100 sq ft) and used the simplified method ($5/sq ft = $500 deduction) - Included a floor plan sketch showing the office space - Made copies of everything before mailing The education credit from your 1099-T should be no problem at all - that's a very common amendment reason. Just make sure you're eligible for the American Opportunity Credit if you're claiming that one (only available for first 4 years of college). One heads up: you mentioned 2021, so double-check your deadline. You typically have 3 years from the original due date to amend, which would be April 2025 for most 2021 returns. Don't wait too long! Got my additional refund in about 16 weeks. Totally worth it for the peace of mind and extra money back.

Something nobody mentioned yet - since you have a regular W2 job, you could increase your withholding there to cover the taxes from your self-employment income. Just submit a new W-4 to your employer and put the additional amount you want withheld on line 4(c). This way you don't have to mess with quarterly estimated payments, and as long as you withhold enough through your W2 job, you won't face underpayment penalties. It's what I do with my teaching job to cover taxes for my tutoring side gig.

Great question about the W2/1099 combo! I went through this exact same situation a few years ago and learned some hard lessons. A couple additional points that might help: First, don't panic too much about the underpayment penalty - it's usually not as scary as it sounds. The IRS charges interest on what you owe, but if this is your first year with significant 1099 income, the penalty might be relatively small compared to the stress you're feeling about it. Second, make sure you're tracking ALL your business expenses throughout the year, not just the obvious ones. Things like mileage to client meetings, business meals (50% deductible), professional development courses, and even bank fees for your business account can add up. I use a simple spreadsheet to log everything monthly. Also, consider opening a separate checking account for your freelance income and expenses - it makes record keeping so much easier and looks more professional if you ever get audited. Even if it's just a free account, having that separation between personal and business finances will save you headaches later. One last tip: start putting 25-30% of each freelance payment into a separate savings account immediately when you get paid. That way you're not scrambling to find tax money later, and if you end up owing less than expected, it's like getting a bonus!

For anyone finding this thread later - if all else fails, you can just file a paper return! Yeah it's slower, but it works if you're up against the deadline and can't resolve the PIN issue. When I couldn't figure out my PIN issue last year, I just printed everything out and mailed it in. Got my refund in about 8 weeks. Not ideal, but better than not filing!

Just want to add another perspective here - if you're using TurboTax specifically, they have a feature called "Transfer Last Year's Data" that can sometimes help recover your Self-Select PIN. When you import your prior year return, it might pull in the PIN information automatically. Also, for future reference, I always write my Self-Select PIN on a sticky note and put it with my tax documents folder. Learned this lesson the hard way after going through the same panic as OP! The PIN is something you create, so there's no "official" record of it anywhere except what you or your software saved. One more thing - if you're still stuck and need to e-file today, try entering your prior year AGI as suggested above, but make sure you're using the exact amount from line 11 of your 2023 Form 1040. Don't round it or estimate - it has to match exactly what the IRS has on file.