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Don't forget that if you're trading frequently enough, you might want to make estimated quarterly tax payments to avoid underpayment penalties. This caught me by surprise my first year of serious trading. The IRS expects you to pay taxes as you earn income, not just at filing time.
What's the threshold for when you need to make these quarterly payments? Is there a specific dollar amount or percentage?
Generally, you need to make quarterly estimated payments if you expect to owe $1,000 or more in taxes when you file your return. The safe harbor rule is that you need to pay either 90% of the current year's tax liability OR 100% of last year's tax liability (110% if your prior year AGI was over $150,000) through withholding and estimated payments combined. Since you're making $25-35k from trading on top of your regular income, you're probably hitting that threshold. I learned this the hard way when I got hit with underpayment penalties even though I paid everything I owed when filing. The IRS wants their money throughout the year, not all at once in April. You can make estimated payments online through EFTPS or mail them in quarterly (due dates are typically Jan 15, April 15, June 15, and Sept 15). Just calculate roughly what you'll owe on your trading profits and divide by four.
One thing I haven't seen mentioned yet is the importance of keeping detailed records beyond just what your broker provides. I learned this lesson when I got audited two years ago on my trading activities. The IRS wanted to see not just my 1099-B forms, but also documentation of my trading strategy, research methods, time spent, and the business-like nature of my activities. I had to reconstruct months of trading decisions from memory because I wasn't keeping proper records. Now I maintain a simple trading journal with entry/exit reasoning, time spent on research, and any educational expenses (courses, books, software subscriptions). This documentation became crucial when establishing my trader status with the IRS. Also consider opening a separate checking account just for trading-related expenses and transfers. It makes tracking so much cleaner at tax time and shows the IRS you're treating this as a serious business activity rather than just casual investing. The paper trail is your friend if you ever face scrutiny.
Don't forget that even if you can justify the mileage deduction, you need to be keeping REALLY good records to survive an audit. The IRS is super picky about mileage logs. You need date, starting location, ending location, miles driven, and business purpose for EVERY trip. There are some good apps that can help track this automatically.
Any app recommendations? I've been trying to track my business mileage but I always forget to log it when I'm rushing between shoots.
I've been using MileIQ for the past year and it's been a lifesaver! It automatically tracks your trips using GPS and then you just swipe left or right to classify each trip as business or personal. Super easy when you're rushing between locations. QuickBooks Self-Employed is another good option that integrates with tax prep. It not only tracks mileage but also helps categorize expenses. Since you're dealing with both W-2 and 1099 income, having everything in one place really helps at tax time. The key is finding something that requires minimal effort to use consistently - because like you said, remembering to manually log every trip when you're busy is nearly impossible!
This is a really complex situation, but I think you're on the right track with your thinking. The key distinction here is that you're not just commuting to work - you're operating a legitimate equipment rental business that happens to serve the same client as your W-2 job. Since your vehicle serves as mobile storage and transport for rental equipment that generates 1099 income, you have a strong business purpose for those miles. The fact that you never report to a central office and are sent directly to different locations each day further supports this. I'd recommend keeping detailed logs that clearly document: 1. Equipment being transported each day 2. Business purpose of each trip (equipment delivery/pickup/transport) 3. How your vehicle storage is essential to your rental business operations 4. Any instances where you make separate trips solely for equipment purposes The IRS will likely want to see that your mileage deductions are reasonable and directly tied to your Schedule C business activities. Since you're receiving both equipment rental income AND a car stipend on 1099, you'll want to report all that income and then offset it with legitimate business expenses including the appropriate portion of your mileage. Consider consulting with a tax professional who has experience with mixed W-2/1099 situations like yours - the documentation and allocation methods you use now could save you major headaches if you ever get audited.
The 3-year vs 2-year rule is really important! I learned this the hard way. Had a huge overpayment from 2019 that I tried to claim in 2023, but the IRS rejected it because I was past the 3-year window by like 2 months. Over $3,000 just gone!
You might still have options! If the payment was made after the original due date, the 2-year rule might still apply. I'd request a tax transcript from the IRS and check the exact date the payment posted. If it was more than 3 years from the due date but less than 2 years from the payment date, you could appeal.
This is exactly the kind of situation where timing matters so much! Based on what you've described, you should be good until April 2025 since the 3-year rule from the original due date would apply (as Daniel explained well above). But here's something to keep in mind - make sure you actually file your 2021 return if you haven't already! The refund statute expiration gives you the deadline to CLAIM the refund, but you need to have filed the return first. If you only made payments but never filed the actual return, the IRS won't process any refund until they have your complete filing. Also, double-check your payment records to make sure that overpayment actually got credited to your 2021 tax year and not accidentally applied elsewhere. Sometimes the IRS applies payments to different years or types of taxes than intended, especially if there were any outstanding balances on your account. You can get a tax transcript online to verify exactly how your payments were applied. Don't wait until the last minute though - even if you have until 2025, get this sorted out soon so you can actually get your money back!
This is really helpful advice! I'm actually in a similar situation where I made a large payment in 2022 but I'm not 100% sure it got applied to the right tax year. How exactly do I get the tax transcript to check this? Can I get it online or do I need to request it by mail? Also, if the payment did get misapplied to a different year, is there a specific form I need to fill out to get it moved to the correct year, or do I just call the IRS about it?
Just wanted to add another perspective on the 1099-G issue. If you use TurboTax, there's a specific section when you enter the 1099-G info that will calculate how much of your state refund is taxable. It asks if you itemized last year and then does some calculations behind the scenes. Also, if you took the standard deduction last year (2020), then NONE of your state refund is taxable for 2021! The form is still issued, but you don't have to report it as income. This is because you didn't get any tax benefit from deducting state taxes.
Does this apply to H&R Block software too? I always use them and I'm honestly not sure if I itemized or took the standard deduction last year.
Yes, H&R Block software has a similar feature. When you enter your 1099-G information, it should ask whether you itemized deductions last year. If you're not sure whether you itemized, look at your 2020 return - check if you filed a Schedule A. If there's no Schedule A, you took the standard deduction and your state refund isn't taxable at all. Most tax software will walk you through this, but you need to know whether you itemized or not from the previous year to get the right answer. If you still have your 2020 return, look at line 12 on Form 1040 - if it shows the standard deduction amount for your filing status, you didn't itemize.
Omg this exact thing happened to me last year! I freaked out because I thought I had to pay taxes on the entire refund amount. My accountant explained that you only have to report it if you itemized, AND only the amount that actually benefited you. Pro tip: if you change your W-4 to have the right amount withheld by your employer, you can avoid getting large refunds in the first place. Then you don't have to deal with this 1099-G nonsense the following year!
How do you figure out the "right amount" to have withheld though? I always end up getting refunds no matter what I do with my W4.
The IRS has a withholding calculator on their website (irs.gov) that can help you figure out the right amount! You enter your income, filing status, dependents, etc. and it tells you exactly how to fill out your W-4. I used it last year after getting tired of big refunds and it worked perfectly - I ended up owing less than $100 instead of getting a huge refund. It's especially helpful if you have multiple income sources or your situation changed during the year.
Abby Marshall
According to IRS Publication 559 and Internal Revenue Manual 21.5.3.4.6.1, amended returns are processed by the Submission Processing Center and generally follow a different workflow than original returns. TaxSlayer's platform is fully compliant with current e-file requirements for Form 1040-X. However, there are limitations you should be aware of: 1. Per IRS guidelines, only amendments for tax years 2019 and later can be e-filed 2. Not all situations qualify for electronic filing of amendments 3. The IRS's current processing time for amended returns is approximately 16 weeks according to their operations status page If your amendment involves complex calculations or multiple supporting forms, you might consider consulting with a tax professional to ensure proper completion.
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Lucas Turner
I'm dealing with a similar situation - just received a corrected 1099-R myself and need to file an amendment. Reading through all these experiences is really helpful! It sounds like TaxSlayer can handle the job, but I'm taking notes on the common issues: file size limits for attachments, potential timeout problems during uploads, and the importance of keeping detailed records throughout the process. One question for those who've been through this - did you find it helpful to call the IRS after filing to confirm they received your amendment? I'm seeing mixed experiences here with processing times ranging from 12-20 weeks, and I'm wondering if there's a way to get some peace of mind that it's actually in their system. Also, @Atticus Domingo, have you checked if your specific 1099-R correction scenario is one that TaxSlayer handles well? Might be worth reaching out to their support before diving in.
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Fernanda Marquez
ā¢Thanks for pulling all this information together @Lucas Turner! As someone new to filing amendments, this thread has been incredibly valuable. I'm in a similar boat with needing to file a 1040-X, though mine is for unreported freelance income rather than a corrected 1099-R. Based on what everyone's shared, it sounds like the key is being really prepared before starting - having all documents ready, understanding the file size limits, and blocking out enough time to complete everything in one session. The 12-20 week processing timeline is definitely something to plan for! @Atticus Domingo, I'd be curious to hear how your amendment goes if you decide to use TaxSlayer.
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