Don't forget to check if you need to issue 1099s to LLCs! This tripped me up. If an LLC is taxed as a sole proprietorship or partnership, you DO need to issue a 1099. If they're taxed as a corporation, you DON'T. That's why the W-9 is important - it should indicate their tax classification. If they checked "Individual/sole proprietor" or "LLC" (with no corporation selection), you need to issue the 1099. If they checked "C Corporation" or "S Corporation," you typically don't.

Great question! I went through this exact same process last year as a new business owner. Here are a few additional tips that helped me: 1) **Keep detailed records throughout the year** - Don't wait until tax season to organize your contractor payments. I created a simple spreadsheet tracking contractor names, total payments, and W-9 status as I went. 2) **Double-check your W-9s NOW** - Make sure the names on the W-9s match exactly how you'll report them on the 1099s. Any mismatches can cause headaches later. 3) **Consider your business growth** - If you think you'll have more contractors next year, investing in a system like the ones mentioned above might be worth it for the long term, even if the upfront cost seems high for just a few forms. 4) **State requirements vary** - Some states have their own 1099 filing requirements with different deadlines. Make sure to check your state's specific rules. The January 31st deadline comes up fast, so don't put this off! I learned that lesson the hard way when I almost missed the deadline my first year.

Has anyone successfully gotten an automatic revocation reversed? We missed 3 years of 990n filings because our treasurer had health issues, and now we're trying to get back in compliance. IRS website is confusing about the reinstatement process.

I went through this exact same situation last year when I suddenly became treasurer for our local theater group! The panic is real, but you're going to be fine. Here's what helped me the most: First, don't stress too much about being late - as others mentioned, you have a grace period before any serious consequences. The IRS is surprisingly understanding about transitions like yours. Before you start the filing process, gather these basics: - Your organization's EIN (should be on any previous tax documents) - The exact legal name of your nonprofit as registered with the IRS - Your current address and any address changes since the last filing - Gross receipts amount for the tax year you're filing One tip that saved me: when you get to the IRS portal, bookmark the exact page once you're logged in. The site times out frequently, and having the direct link makes it much faster to get back in if you get kicked out mid-process. Also, consider setting up a simple calendar reminder system for next year's filing (due May 15th annually). I use a recurring reminder starting in March to avoid this stress again! You've got this - taking responsibility and asking for help shows you're exactly the right person to handle this transition properly.

I went through this exact same situation last year! The "Where's My Refund" tool is notoriously unhelpful when it comes to rejected direct deposits - it often shows the refund as "sent" even when the bank has already returned it to the IRS. Here's what typically happens: When your bank rejects the deposit (which they definitely would for a closed account), they send the funds back to the IRS within 1-2 business days. The IRS then has to process the returned funds and issue a paper check, which usually takes 2-3 weeks from the date of the rejected deposit. Since your refund shows as deposited on February 15th, I'd expect your bank rejected it around February 16th-17th, meaning your paper check was likely issued around early March. You should be receiving it any day now if you haven't already! One thing to double-check: make sure the mailing address on your tax return is current. If you moved and used your new address on the return, you should be fine. If not, definitely set up mail forwarding with USPS just in case. Don't panic - your money isn't lost! The IRS is just slow to update their systems when these situations occur.

I went through something very similar two years ago and want to share what I learned! When the IRS website shows your refund was "deposited" but your account was already closed, it's showing the initial attempt, not the actual successful transaction. Here's the typical timeline: Your bank likely rejected the deposit within 24-48 hours of February 15th and returned the funds to the IRS. The IRS then needs 10-21 business days to process the returned payment and issue a paper check. Given that your deposit attempt was February 15th, you should expect your paper check to arrive sometime in mid-to-late March. I'd recommend calling your old bank first to confirm they rejected and returned the deposit - this gave me peace of mind that the money wasn't stuck somewhere. You can also check that your current mailing address matches what you put on your tax return. The good news is that this process is automatic once the bank returns the funds, so you don't need to do anything special to trigger the paper check. Just be patient - the IRS systems are notoriously slow to update, but your refund will come!

This has been such a valuable discussion! As a newcomer to options trading, I was completely overwhelmed by wash sale rules and honestly avoiding certain profitable setups because I wasn't sure about the tax implications. Reading through everyone's experiences, it's clear that the key insight is understanding what "substantially identical securities" actually means for options. The fact that different strike prices OR different expiration dates generally break this test gives so much more trading flexibility than I initially realized. I'm particularly impressed by the practical strategies shared here - the "strike ladder" approach for maintaining similar exposure while clearly avoiding wash sales is brilliant. And the emphasis on keeping detailed records resonates strongly, especially given how many people mentioned inaccuracies in Robinhood's reporting. One question for the group: for someone just starting to track trades manually, what's the minimum level of detail you'd recommend in a spreadsheet? I want to make sure I capture everything necessary without making it so complex that I won't keep up with it consistently. Thanks to everyone who shared real-world experiences rather than just theoretical tax advice. This thread has given me the confidence to approach options trading more strategically while staying compliant with wash sale rules!

This thread has been incredibly helpful! I'm new to options trading and was getting really anxious about wash sale rules after reading some conflicting information online. Your AMZN example is exactly the kind of situation I was worried about. Based on everyone's experiences shared here, it's reassuring to know that options with different strike prices OR different expiration dates are generally not considered "substantially identical securities." This gives me much more confidence to execute my trading strategies without being paralyzed by wash sale fears. I'm definitely going to start implementing the spreadsheet tracking system that multiple people have recommended. The fact that so many experienced traders have caught discrepancies in Robinhood's reporting makes it clear that keeping my own detailed records is essential, not just helpful. One thing I'm curious about - for someone who primarily trades weekly options on popular stocks like SPY, AAPL, and TSLA, how granular should I get with my record keeping? Should I track every single weekly contract separately, or is there a more efficient way to organize this data while still maintaining compliance? Thanks to everyone for sharing real-world experiences instead of just repeating generic tax advice. This discussion has been a game changer for my understanding of wash sale rules with options!

Reading the comments, I'm still confused about one thing. My son's 1098-T shows a big amount in Box 4 ($3270) but nothing in Box 1. If they adjusted a prior year payment, shouldn't that money show up somewhere on this year's form?

Based on what you've described, you're in a pretty straightforward situation. Since you didn't claim any education credits in 2021 and your scholarships exceeded your qualified expenses that year, the Box 4 adjustment of $2,016.12 likely won't require you to amend your previous return. Here's what I'd recommend: First, check your 2021 1098-T to see if that $2,016.12 was included in Box 1 (payments received) that year. If it was, and you didn't use it for education credits because your scholarships already covered everything, then removing it now doesn't change your 2021 tax situation. For your 2022 return, you only need to worry about the $1,425 in Box 5. Since you dropped the classes and presumably didn't have qualifying expenses to offset this scholarship amount, that $1,425 would be taxable income for 2022. The Box 4 adjustment is just the school's way of saying "we reported this payment in the wrong year previously" - but if you weren't getting tax benefits from it anyway, the correction doesn't hurt you.