One thing that might help you estimate your tax bill before selling is to gather all your wife's ESPP purchase records from 2015 onwards. You'll need the purchase dates, number of shares bought, actual purchase prices, and the fair market value on each purchase date. Since you mentioned you'll likely stay in the 15% tax bracket, here's some good news: for long-term capital gains (shares held over 1 year), taxpayers in the 10-15% ordinary income brackets often qualify for the 0% capital gains rate on at least a portion of their gains. This could significantly reduce your tax liability. For timing the sale, consider your total income for the year. If selling all at once would push you into the next tax bracket, it might be worth spreading the sales across tax years. You can use online tax calculators or consult with a tax professional to model different scenarios. Also, don't forget to check if your state has additional capital gains taxes - this varies widely by state and could affect your overall tax planning strategy.

Great question about the merger! Corporate mergers can definitely complicate ESPP tax calculations, but they're manageable with the right documentation. When a company merger occurs, the ESPP shares are typically converted based on the merger terms (exchange ratio, cash consideration, etc.). The key is that your original cost basis and purchase dates generally carry forward, but you'll need documentation showing: 1) Your original ESPP purchases before the merger 2) The merger exchange ratio or conversion terms 3) Any cash received in lieu of fractional shares 4) Your post-merger share holdings Since you're in California, you're right that state taxes will apply. California taxes capital gains as ordinary income, so you won't get the preferential federal rates at the state level. However, you may still benefit from the 0% federal long-term capital gains rate depending on your total income. For the merger documentation, check with both the old company's benefits department and the current company. They should have records of the ESPP conversion. You might also find this information in old account statements from around the merger date. The merger shouldn't change the fundamental tax treatment, but it does make the record-keeping more complex. Consider consulting with a tax professional who has experience with post-merger ESPP sales to ensure you're calculating everything correctly.

I'm dealing with a similar situation but with a 1099-MISC from Meta showing $1,850 when I only sold maybe $400 worth of old electronics and clothes. What's really frustrating is that I kept all my transactions in cash specifically to avoid any payment processing complications. Has anyone had success disputing these directly with the IRS instead of trying to get Meta to fix it? I've read that you can attach a statement to your return explaining the discrepancy, but I'm worried about triggering an audit. My tax preparer suggested just reporting the full amount and taking deductions for my cost basis, but that seems like I'm admitting to income I never actually received. Also, for those who got corrected forms - how long did the whole process take? I'm already cutting it close to the filing deadline and don't want to request an extension if I don't have to.

I went through this exact situation last year and want to share what worked for me. Meta reported $2,800 on a 1099-MISC when my actual Marketplace sales were around $650 in cash transactions for old furniture and household items. Here's what I learned from my experience: **First, don't panic about the audit risk.** The IRS is well aware that marketplace platforms have been having reporting issues since the new $600 threshold kicked in. As long as you document your actual sales in good faith, you're doing everything right. **Document everything you can remember.** I created a simple spreadsheet listing what I sold, approximate dates, and sale amounts. Even rough estimates are better than nothing. Include any Facebook messages, photos of items you sold, or even just notes in your phone about meetups. **You have two main paths forward:** 1. Try to get Meta to issue a corrected 1099 (worth attempting but don't count on it) 2. File your return with proper documentation explaining the discrepancy **For filing, I used Schedule D and Form 8949** to report the actual sales as capital transactions. Since these were personal items, most had a higher cost basis than sale price, resulting in little to no taxable gain. I attached a clear statement explaining that Meta's 1099 was incorrect and provided my documented actual sales. The IRS accepted my return without any issues. The key is being transparent and showing you made a good faith effort to report accurately. Don't let Meta's mistake cause you to overpay taxes on income you never received!

I've been having the same frustrating experience with the IRS website! After trying multiple browsers and different times of day without success, I discovered that using an older version of Internet Explorer (if you still have it) sometimes works when the modern browsers fail. I know IE is outdated, but the IRS website was apparently designed with older web standards in mind, and sometimes the legacy compatibility actually helps during their server overload periods. I was able to access and download my transcript using IE11 when Chrome, Firefox, and Edge all kept giving me error messages. If you don't have Internet Explorer, you can also try putting your browser into "compatibility mode" or using the "Internet Explorer mode" feature in Microsoft Edge. Go to Edge settings, click on "Default browser" in the left menu, then toggle on "Allow sites to be reloaded in Internet Explorer mode." It's ridiculous that we need to resort to using outdated browsers for a government website in 2025, but desperate times call for creative solutions! Worth a shot if the other suggestions in this thread haven't worked for you yet.

I've been experiencing the exact same frustrating issue for the past week! What finally worked for me was a combination of several approaches mentioned in this thread. After trying Chrome, Firefox, and Edge without success, I followed the suggestion to try accessing the site at 5:30 AM EST on a Tuesday using Firefox with all cache/cookies cleared. I also disabled my VPN and went directly to the "Get Transcript Online" page rather than navigating through the main IRS dashboard. The key breakthrough was when I tried using my mobile phone's hotspot instead of my home WiFi - that network switching tip was genius! I think my ISP might have been having routing issues to the IRS servers during peak times. The transcript downloaded perfectly on the first try after days of error messages. For anyone still struggling, I'd recommend the early morning + different network + fresh browser combination. It's inconvenient to wake up early and use mobile data, but so worth it to finally access your transcript. Thanks to everyone who shared solutions - this thread has become the ultimate guide to beating IRS website technical issues! One additional tip: make sure you're logged out of all other IRS services before attempting the transcript download, as I found having multiple sessions sometimes caused conflicts.

I think you could also try entering $0 as your prior year AGI. I've heard that works for first-time filers, might work in your situation too? Worth a try before going through all the transcript hassle.

I went through this exact same nightmare last year! Here's what worked for me when I was completely stuck: If you have any financial institution that you bank with, check if they offer free tax transcript services. Many credit unions and some banks can help you get IRS transcripts through their secure portals. I found out my credit union had this service buried in their online banking under "Financial Tools" - got my transcript in about 10 minutes without having to deal with the IRS website at all. Also, if you remember which tax software you used last year (TurboTax, H&R Block, etc.), try logging into that account even if you don't think you saved anything. Most of these services keep your prior year data accessible for several years, and you might be surprised what's still there. I found my complete 2022 return in my old TurboTax account even though I thought I'd deleted everything. The paper filing route isn't the end of the world if these options don't work out, but definitely try the transcript services first. Way faster than waiting weeks for the IRS to process paper returns!

I've been using Free File Fillable Forms for the past 4 years and wanted to add my perspective since you're considering the switch from paper filing. For someone with a straightforward tax situation like yours, they're definitely worth trying. The biggest benefit is the speed - I consistently get my refunds in 2-3 weeks versus the 6+ weeks it took with paper filing. The built-in calculations also catch basic math errors that I used to make when doing everything by hand. However, there are some quirks you should know about: - The interface feels dated compared to modern tax software, but it gets the job done - You'll need to manually enter the same information on multiple forms (like your personal info on each schedule) - The system can be finicky about browser compatibility - I've had the best luck with Firefox - During peak season (March-April), the site can be painfully slow My advice would be to give them a try this year since your tax situation isn't complicated. If you find the process too cumbersome, you can always go back to paper filing next year. The time savings on getting your refund alone might make it worth the learning curve. Just remember to save frequently and maybe have a backup plan ready in case you run into technical issues close to the filing deadline!

I made the switch from paper to Free File Fillable Forms two years ago and it's been mostly positive for my situation. Like others have mentioned, the speed difference for refunds is huge - I went from waiting 8+ weeks to getting my refund in under 3 weeks. Since you mentioned your tax situation is straightforward with just a W-2 and basic deductions, you should be fine. The interface isn't the prettiest, but it does what it needs to do. A few things that helped me: - Set aside a solid 2-3 hour block when you won't be interrupted (the timeout issue is real) - Have all your documents scanned or organized before you start - I actually print out the forms first and fill them out by hand, then use that as a reference while entering online - prevents mistakes and makes it faster The biggest adjustment was getting used to not having any guidance on potential deductions or credits I might be missing. But honestly, for basic situations like ours, there usually isn't much we're missing anyway. My vote is to try it this year. Worst case, if you hate the experience, you can always go back to paper filing next year. But the faster refund alone made it worth it for me!