This is incredibly helpful - thank you for sharing! I've been struggling to reach the IRS about a 1099-R issue from my 401k rollover and kept getting the "high call volume" disconnect. One thing I'd add for anyone trying this: make sure you have a pen and paper ready when they call back. The agent I spoke with (using a similar method) gave me a lot of important information quickly, and I almost missed some key details about reporting requirements. Also, for those worried about wait times - I've found that if you miss their callback, they don't automatically reschedule you. You have to start the whole process over, so definitely keep your phone close and answer unknown numbers during your callback window! Has anyone had success using this method for questions about estimated tax payments? That's my next hurdle to tackle.

This is exactly what I needed to see! I've been putting off calling about my backdoor Roth IRA conversion reporting because I was dreading the phone maze. A few questions for anyone who's used this method recently: 1. Do they ask what your call is about when you first get connected, or do they wait until the callback? 2. If I have multiple tax years to discuss (2022 and 2023), should I mention that upfront or focus on one issue at a time? 3. Has anyone tried this for questions about Form 8606 specifically? I want to make sure I don't get transferred around between departments. I'm planning to try first thing Monday morning (7:05am sharp based on everyone's advice). Really appreciate this community for sharing these practical tips - the IRS website is basically useless for actually getting help!

Don't overlook the marketplace facilitator laws! If you decide to expand beyond your website to sell on platforms like Amazon, Etsy, or eBay, those platforms handle the sales tax collection and remittance in most states now. This might be a way to expand your business without increasing your sales tax burden, especially for those occasional sales in states where you're not registered.

I understand your frustration completely - I went through the exact same confusion when I started my dropshipping business two years ago. Here's what I learned that might help simplify things: First, don't panic about registering in every possible state from day one. Most states have economic nexus thresholds (usually $100k in sales or 200 transactions annually) that you likely won't hit initially. Focus on your home state first, which you've already done correctly. For the supplier issue, try this approach: Ask your supplier if they'll accept a multi-jurisdiction resale certificate along with documentation showing you're registered in your home state. Many suppliers will accept this as reasonable good faith effort, especially for smaller businesses. Another practical tip: Keep detailed records of where your sales actually go. You might find that 80% of your orders come from just a few states, making your compliance much more manageable than you think. The reality is that perfect compliance from day one is nearly impossible for small businesses, but good faith effort and proper documentation go a long way. As your business grows and you can afford professional help, you can tighten up your compliance. Don't let analysis paralysis stop you from growing your business!

I'm going through the EXACT same thing right now but with DraftKings. Is anyone using TurboTax to handle this? I can't figure out where to enter my gambling wins and losses, and it doesn't seem to have a specific spot to reconcile the 1099-K amounts that aren't income. I'm so confused!!

I went through this exact situation last year with my Hard Rock account and PayPal 1099-K. The key thing that helped me was creating a detailed spreadsheet that matched up my PayPal transactions with my Hard Rock win/loss statement by date. What I found was that the 1099-K included not just my deposits, but also some withdrawals that got processed back to PayPal, which made the total even more confusing. The actual taxable amount was way less than what the 1099-K showed. One thing to watch out for - make sure your Hard Rock win/loss statement covers the exact same tax year as your 1099-K. Sometimes there's a day or two difference in how they calculate the reporting period, and those end-of-year transactions can throw everything off. I ended up using the gambling reconciliation worksheet that comes with the tax software to show the IRS exactly why my reported income was different from the 1099-K amount. Keep all your documentation - the win/loss statement, the 1099-K, and any records of your actual deposits/withdrawals. The IRS is seeing a lot of these cases this year so they're pretty familiar with the situation.

word of advice: DONT CALL!! been on hold for 3 hours today and got hung up on twice. just do the online thing

I just went through this process last month! The online verification at idverify.irs.gov is definitely the way to go - took me about 20 minutes total. You'll need your Social Security card, driver's license, and either your prior year tax return OR a bank statement/utility bill. They ask you some questions about your credit history too. After I verified, I got my refund in about 5 weeks, which was faster than I expected. Pro tip: do it during off-peak hours if possible to avoid the site being slow!

Has anyone had to deal with this for previous tax years? I just realized I over-contributed to my 401k in 2022 when I had two jobs, but I already filed and received my refund for that year. Is it too late to fix? Would I need to file an amended return?

Just went through this exact same situation last month! I over-contributed by about $2,800 when I switched jobs mid-year. Here's what worked for me: 1. Called my current 401k provider (not the old one) and explained I exceeded the annual limit due to job change 2. They handled everything - calculated the excess plus earnings and processed the corrective distribution 3. Got my 1099-R about 10 days later 4. Filed my taxes normally, reporting the excess distribution as income for 2024 The key thing that surprised me was that the earnings on the excess contribution get taxed in the year you receive the distribution (2024), not 2023. So make sure you understand that when you get your 1099-R. Don't stress too much - this is super common and the 401k providers deal with it all the time. Just make sure you get it handled before April 15th to avoid the double taxation issue that @Haley Bennett mentioned for previous years.