I've been dealing with RSU wash sales for several years and want to add a perspective that might help simplify your decision-making process. The complexity you're describing - tracking which specific shares have adjusted basis, coordinating with trading windows, managing quarterly vestings - is exactly why many tax professionals recommend against aggressive tax loss harvesting with employer stock that has these restrictions. Here's a practical framework I use: Calculate the potential tax benefit of harvesting the $2,000 loss (your marginal tax rate times $2,000) and compare that to the time value and mental energy you're spending on tracking and managing these wash sale rules. For most people in this situation, the juice isn't worth the squeeze. Instead, consider this approach: 1. Set a "no company stock loss sales" rule for 35 days before each vesting date 2. Focus your tax loss harvesting on index funds or other securities without trading restrictions 3. Hold your RSUs for long-term capital gains treatment when possible The wash sale rules are designed to prevent exactly the kind of optimization you're attempting, and when combined with trading window restrictions, they often make it more trouble than it's worth. Sometimes the best tax strategy is the one you can actually execute consistently without creating administrative nightmares. Your $2,000 loss will eventually be recoverable when you sell those adjusted-basis shares, so you're not permanently losing the tax benefit - just deferring it to a time when you can manage it more cleanly.

I've been lurking in this community for a while dealing with similar RSU complications, and this thread has been incredibly enlightening! As someone relatively new to equity compensation, I had no idea how complex the interaction between wash sale rules and automatic sell-to-cover transactions could be. What strikes me most from reading everyone's experiences is how the "perfect" tax optimization strategy often becomes impractical when you layer in real-world constraints like trading windows, quarterly vesting schedules, and the administrative burden of tracking everything. I'm particularly grateful for the practical solutions people have shared - the 35-day buffer rule, requesting detailed wash sale reports from brokers, and the cost-benefit framework for deciding whether the tax savings justify the complexity. These are the kinds of actionable insights you just don't find in generic tax guides. For anyone else new to this situation: it seems like the consensus is that simplification often beats optimization when dealing with employer stock subject to trading restrictions. Focus your tax loss harvesting efforts on investments without these complications, and don't stress too much about perfectly optimizing every RSU transaction. Thanks to everyone who shared their hard-earned experience - this community is an amazing resource for navigating these complex situations!

I just wanted to add my experience since I had this exact same issue with my W2 showing VIS and DEN codes in Box 14. After going through this confusion myself last year, I learned that these codes are incredibly common and nothing to worry about. Your employer is simply reporting the amounts you paid for vision and dental insurance through payroll deductions. Since these were almost certainly taken out pre-tax (which reduces your taxable income), you should categorize both VIS and DEN as "Health Insurance Premiums" in TurboTax. The key thing to remember is that this won't affect your refund amount since the tax benefit already happened when your paychecks were calculated throughout the year. TurboTax just needs to know what these entries represent for proper documentation. You're so close to being done - don't let this one dropdown derail you! Select "Health Insurance Premiums" for both codes and submit with confidence. The IRS processes millions of returns with these same codes every year without any issues.

I can definitely help clear this up! VIS and DEN in Box 14 are standard employer codes for vision and dental insurance premiums. Since these were likely deducted from your paychecks on a pre-tax basis (which is typical for employer-sponsored vision and dental plans), you should select "Health Insurance Premiums" for both codes in TurboTax. The good news is that this categorization won't affect your refund amount since the tax savings already happened when your employer calculated your taxable wages throughout the year. TurboTax just needs to know what these codes represent for proper documentation and to ensure everything matches up with IRS records. Don't stress about this being the last step - you're making the right choice by taking the time to categorize them correctly rather than picking something random. Select "Health Insurance Premiums" for both VIS and DEN, and you'll be all set to submit your return!

I've been through this process twice with NY state and can share some practical tips that might help ease your anxiety. The 2-week timeframe they mention is pretty accurate - I received my letters on day 9 and day 12 respectively. Here's what I learned from my experiences: **Most common requests:** - Form DTF-172 (Identity Verification) - requires SSN, DOB, prior year AGI, and sometimes a photo ID - W-2 copies (even if you e-filed, they sometimes want the actual forms) - Bank account verification if you're getting direct deposit - Supporting docs for any large deductions or credits you claimed **Pro tips:** - Don't wait for the letter to start gathering documents - get your W-2s and prior year return ready now - The online response portal is much faster than mail (usually 7-10 business days vs 3-4 weeks) - Keep the reference number from your letter - you'll need it for everything - Make copies of everything you submit **Timeline expectations:** - Letter arrival: 7-14 days from status change - Document submission: Same day you receive letter (if you're prepared) - Processing after submission: 10-21 business days - Refund issued: Usually within a week of approval The good news is that 95% of these are routine verification requests, not actual problems with your return. NY has just gotten really strict about fraud prevention. Your federal refund is completely separate, so no worries there. Stay positive - you'll likely have your money within 4-6 weeks total!

I'm dealing with a similar situation right now and this thread has been a lifesaver! Just wanted to add that you can also check if your local library has free tax help services - some of the volunteer tax preparers there have experience with NY state verification letters and might be able to give you guidance while you wait. Also, if you haven't already, make sure you have access to your prior year tax return (especially the AGI amount) since that seems to be one of the most commonly requested pieces of info for identity verification. I learned this the hard way when I couldn't find my 2022 return and had to request a transcript from the IRS first. One last thing - don't panic if the letter takes the full 2 weeks to arrive. The postal service has been slower lately, and NY tax department customer service told me they send these letters via regular mail, not priority. I've been checking my informed delivery every morning to see if it's coming that day. The anticipation is brutal but at least we're all in this together! 😅

I've been fighting Error 6001 for over 2 years now and this thread is like finding a treasure map after wandering in the desert! The level of specific, actionable solutions here is incredible compared to the endless "have you tried restarting your browser" responses I've gotten from official support. What really resonates with me is how everyone describes the exact same finger-pointing pattern between IRS and ID.me. I've literally been told by IRS: "We don't handle ID.me technical issues, contact them directly" and then ID.me responds with "The IRS portal is blocking your authentication, we can't resolve that." It's like they have matching scripts to avoid responsibility! Reading through all these experiences, I'm realizing I probably have multiple data conflicts stacking up: - Moved 4 times since creating my ID.me account in 2019 - Sometimes file with my full legal name "Alexander Joseph Mitchell" and sometimes just "Alex Mitchell" - Had a brief period where I used my middle name professionally, so some documents have different variations The historical data mismatch theory from @PrinceJoe makes so much sense - these systems are probably trying to authenticate against old addresses and name variations that are still flagged in some database somewhere. I'm going to start with checking the exact name formatting between my ID.me profile and my most recent tax return (thanks @Jade Lopez for that insight!), then work through the Taxpayer Advocate Service route. Having all these specific phone numbers and department names is game-changing - finally feels like I have a real strategy instead of just calling the main lines over and over. This community knowledge is worth more than gold! Thank you everyone for sharing your battles and victories - gives me actual hope after 2+ years of pure frustration! 🙏

I've been stuck in Error 6001 hell for about 8 months now and this thread is absolutely incredible - finally found people who actually understand this specific nightmare! The detailed solutions and phone numbers everyone's sharing here are more helpful than literally dozens of calls to both IRS and ID.me support. The pattern everyone's describing is EXACTLY what I've experienced - both agencies acting like they've never heard of Error 6001, then immediately blaming the other system. I've gotten the classic "that's an ID.me authentication issue, contact them" from IRS and "the IRS portal is rejecting you, we can't fix that" from ID.me. It's like they have a playbook for passing the buck! Reading through all these experiences, I'm starting to piece together what might be causing my issues. I've had 2 address changes since setting up my ID.me account, plus I sometimes use my full name "Christopher David Martinez" on tax forms and sometimes just "Chris Martinez" depending on the document. That inconsistency could totally be creating authentication chaos between the systems. I'm taking detailed notes on all the specific approaches mentioned: - Taxpayer Advocate Service (1-877-777-4778) - Identity Protection Specialized Unit (800-908-4490) - Requesting "IAL2 authentication status refresh" - Checking exact name/address formatting between ID.me and tax returns - Form 8822 to force system refreshes Going to start with the simple name formatting check that @Jade Lopez suggested - seems like such a small thing but these government systems are apparently incredibly picky about exact matches. Then I'll escalate through the specialized departments if needed. This community knowledge is pure gold! Thank you everyone for sharing your specific solutions and victories - finally gives me hope after 8 months of bureaucratic purgatory! 🙏

I went through this exact situation two years ago when our rental property's kitchen was damaged by a burst pipe. The confusion is totally understandable because it involves multiple tax concepts that don't always work intuitively together. Your option 3 is definitely the correct approach - don't report the insurance payout as income, and only deduct repair expenses that exceeded what insurance covered. This is the standard treatment for casualty losses on rental properties. Here's what I learned the hard way: keep meticulous records separating what insurance classified as "repairs" versus what you might have upgraded during the process. Insurance companies sometimes pay for "like-kind replacement" but if you chose to upgrade fixtures or materials, those improvement costs need different tax treatment. Also, be careful about depreciation recapture if any of the damaged items were previously depreciated (like appliances or flooring). When insurance reimburses you for depreciated items, there can be tax implications. One thing that saved me a lot of headache was creating a spreadsheet tracking: 1) Insurance payout amount, 2) Actual repair costs, 3) Any improvement costs, 4) Out-of-pocket expenses. This made it crystal clear what I could deduct in the current year versus what needed to be capitalized. The peace of mind of handling it correctly is worth the extra documentation effort!

I'm dealing with a similar situation right now after storm damage to my rental property's roof and interior. Reading through all these responses has been incredibly helpful - especially the clarification that insurance payouts for property damage aren't taxable income. One thing I wanted to add for anyone else going through this: make sure to get a detailed breakdown from your insurance company showing exactly what they're covering. My adjuster initially lumped everything together as "water damage repair," but when I asked for itemization, it turned out they were covering some items at replacement cost and others at actual cash value (which factors in depreciation). This distinction matters for tax purposes because if insurance pays you actual cash value for a previously depreciated item (like flooring or fixtures), you might need to account for depreciation recapture on the difference between what you originally paid and what insurance reimbursed. Also, don't forget to factor in any insurance deductible you paid - that's typically deductible as a repair expense since it's your out-of-pocket cost for restoring the property. The key takeaway I'm getting from everyone's advice is: document everything, separate repairs from improvements, and only deduct what you actually paid beyond insurance coverage. Thanks to everyone who shared their experiences - this community is so valuable for navigating these complex situations!