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Just wanted to add that when you do respond to the CP2000, make sure you respond to EVERY item they're questioning, even if you agree with some parts and disagree with others. I made the mistake of only addressing the items I disagreed with, and it caused more confusion and delays. Also, if you're requesting an extension, do it as early as possible! The closer you get to your deadline, the more stressful it becomes.
This is really helpful! When I respond, should I send copies of all my documentation or just the specific records related to the discrepancies they found?
Only send copies of the specific documentation that directly addresses the discrepancies mentioned in your CP2000. Sending too many unrelated documents can actually confuse the review process and potentially delay resolution. Make sure each document you send clearly relates to a specific item they're questioning. I like to use a cover letter that lists each discrepancy and exactly which supporting documents address each one. This makes it easier for the IRS agent reviewing your case to connect your evidence to their questions.
Has anyone here ever had their extension request denied? I'm in a similar situation with a CP2000 notice, and I'm worried about what happens if they say no to giving me more time.
I've never heard of an extension request being denied if you ask before the deadline. The IRS is generally reasonable about giving people time to gather documentation. The problem comes when people ignore the notice entirely or wait until after the deadline to ask for more time.
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Levi Parker
Pro tip from someone who handles RSUs regularly: Always keep documentation from each vesting event, especially the fair market value on vesting date. This is your cost basis, and you need it to avoid exactly this situation. I create a spreadsheet each year with columns for: - Vesting date - Number of shares - FMV at vesting - Total value (reported as income on W-2) - Sale date - Sale price - Gain/loss since vesting (this is what goes on Schedule D) This makes tax time so much easier and helps prevent these IRS notices.
Libby Hassan
•Is there any software that does this tracking automatically? Seems like a lot of manual work if you have monthly or quarterly vestings.
Levi Parker
•There are several options for automatic tracking. Most of the major brokerages (Schwab, Fidelity, E*Trade) have reporting features that attempt to track this, but honestly they're often inaccurate for RSUs specifically. I've found that dedicated equity compensation tools like Carta, StockOpter, or even some features in tools like Personal Capital can help with tracking. There are also some newer fintech apps specifically for equity compensation, but I still recommend maintaining your own spreadsheet as a backup. Once you set it up initially, it only takes a few minutes to update each vesting period.
Something else to consider - check if your employer offered a "sell-to-cover" option where they automatically sold some shares to cover the tax withholding at vesting. If so, your W-2 already includes the income from the RSUs, and you only need to report any additional gain or loss that occurred between vesting and when you sold the remaining shares. When I had my IRS notice for unreported stock sales, I found out my company had only withheld at 22% for federal taxes, but I was in the 32% bracket, which created additional confusion.
Sofia Peña
•This is such an important point! My company does withholding at vesting but only at 22%, and I got hit with a huge tax bill my first year with RSUs because I didn't realize I needed to make estimated tax payments on the difference. The whole RSU taxation system is unnecessarily complicated.
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Here's a simple way to think about it - when you select "0" allowances, you're basically telling your employer "take out extra tax just to be safe." Each allowance you claim reduces the amount withheld. Most single people with one job should claim at least 1 allowance to account for the standard deduction (which is $13,850 for 2023). If you claim 0, you're likely overwithholding. But honestly, it depends on your comfort level with tax time. Some people prefer the "forced savings" of overwithholding to get a big refund. Others want their money throughout the year.
Sean Kelly
•Would it be bad to change it to 1 halfway through the year? I've been at 0 since January.
Not bad at all! You can change your withholding at any time during the year. If you switch from 0 to 1 allowance now, you'll just start having less tax withheld from your remaining paychecks this year. The withholding system is designed to adjust throughout the year. Your employer calculates the withholding for each individual paycheck based on your current W-4 information, not based on what you submitted in January. So making the change now just affects your future paychecks - it doesn't retroactively change anything.
Zara Mirza
Are you getting paid a lot more at this new job compared to your campus jobs? Because tax withholding is based on your projected annual income. If you were making like $15/hr part-time before and now you're making $25/hr full-time, you're in a higher tax bracket so they take out more.
Luca Russo
•This is the most likely answer. I remember the shock when I went from my $12/hr campus job to my first salaried position. Suddenly I was seeing hundreds in taxes instead of like $30-40 per check. Welcome to adult life lol
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Are you sure you're not actually in a partnership already? The IRS might consider you in a partnership if you're splitting profits regardless of whose name the money comes in under. If that's the case, you should be filing Form 1065 and issuing K-1s, not 1099s.
Diego Flores
•This! I got audited because my gaming channel had a similar setup where my friend and I split everything 50/50 but all revenue came to me. IRS determined we were a partnership and we had to refile 3 years of taxes. Better to get it right from the start!
Oh wow, that's concerning. How do I know if we qualify as a partnership vs me just having a contractor? We don't have any formal business structure set up - just Venmo him his half when I get paid.
Don't forget to consider quarterly estimated tax payments! If you're splitting $38k, each making $19k from the content creation, you both likely need to be making quarterly payments to avoid underpayment penalties. This bit me hard my first year!
Thanks for the reminder! Do you know what the threshold is for when quarterly payments are required? And how do I calculate how much to pay each quarter?
Generally, you need to make quarterly estimated payments if you expect to owe $1,000 or more in taxes when you file your return. For self-employment income like content creation, that threshold is pretty easy to hit. For calculating the amount, you have two options: pay 100% of last year's tax liability (110% if your income was over $150,000), or pay 90% of what you'll owe this year. Most people go with the first option since it's easier to calculate. The IRS Form 1040-ES has worksheets to help, or most tax software can calculate this for you. Payments are due April 15, June 15, September 15, and January 15 (of the following year).
Jacob Lewis
My dad always uses TaxAct and says there's a specific section for US Treasury interest that will automatically make it state tax exempt. I think most software has this but you gotta make sure you enter it in the right spot and don't just lump it in with regular interest.
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Amelia Martinez
•Does TaxAct have a cheaper option if you're just reporting W-2 and some 1099-INT forms? I've been using TurboTax but their prices keep going up every year.
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Jacob Lewis
•Yeah, TaxAct definitely has cheaper options than TurboTax! Their basic version handles W-2s and 1099-INTs just fine and costs a lot less. My dad switched from TurboTax about 3 years ago and says it's just as good for his needs. They have a specific section for savings bonds and treasury interest that makes sure it's handled right for state tax purposes. I think most of the tax software options (FreeTaxUSA, H&R Block, etc.) are getting better at guiding you through reporting I-Bond interest correctly, but you do need to pay attention to where you enter it.
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Ethan Clark
Just want to share that I made a mistake with this exact thing last year - entered my I-Bond interest in Box 1 of my state return and ended up paying state tax on it when I shouldn't have!!! Found out later that Treasury interest is state tax exempt. Called my state tax dept and had to file an amended return to get that money back. Don't make my mistake!!
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Mila Walker
•How much work was it to file the amended return? I think I might have made the same mistake last year but not sure if it's worth the hassle to fix.
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