Has anyone actually looked at the Terms of Service for this company? I had a similar issue with another US retailer and found that buried in their terms was language about "all applicable taxes and fees may be charged based on internal company policies." Basically giving themselves wiggle room to charge whatever they want. It might not be legally enforceable, but they could argue you agreed to their terms which include potentially paying these fees. Might be worth checking if there's something like that in their terms.

This is a classic case of incorrect sales tax application on international orders. As someone who's dealt with similar issues, I can confirm that you should absolutely NOT be charged US sales tax as a UK resident receiving goods in the UK. The key principle here is that US sales tax is destination-based, not origin-based. Since your goods are being consumed in the UK (where you'll pay UK VAT and duties), they should qualify for the export exemption from US sales tax. The company's claim about collecting tax based on shipping "FROM" a US jurisdiction is completely backwards - that's not how sales tax works. My suggestion would be to escalate this beyond regular customer service. Ask to speak with their tax department or compliance team, and specifically mention the "export exemption" for goods shipped internationally. Reference IRC Section 4221(a)(2) if you need to cite specific tax code - it covers exemptions for exported articles. If they continue to refuse, consider filing a complaint with the attorney general's office in the state where they're located (Kentucky or New Jersey, based on your post). Companies sometimes change their tune quickly when they realize they might face regulatory scrutiny for improper tax collection. Don't let them keep money they have no legal right to collect!

If nothing else works, you can also file Form 4852 (Substitute for W-2) with your tax return. You'll need to estimate your wages and withholding as accurately as possible using your final paystub or other records.

I went through this exact situation two years ago and it was so stressful! My old employer kept giving me the runaround too. What finally worked for me was sending them a certified letter (not just calling) stating that I needed my W-2 by a specific date and mentioning the IRS penalties for non-compliance that others have mentioned here. In the meantime, I'd definitely recommend getting your wage transcript from the IRS as your backup plan. The online account setup is really straightforward and you get the info instantly. Don't risk filing an incomplete return - it's just not worth the potential headaches later. Also, if you're really pressed for time, remember you can always file for an extension. Better to file correctly with an extension than rush and file incorrectly by the deadline. The IRS cares more about accuracy than speed.

Has anyone considered the home office deduction angle instead of medical? If you have a legitimate home office where you do therapy or medical management for your family member, some security costs might be deductible that way too.

Thank you all for this incredibly helpful discussion! As someone new to navigating medical expense deductions, I'm dealing with a similar situation where my elderly father with Alzheimer's needs additional security measures to prevent wandering incidents. From what I'm gathering here, the key seems to be: 1. Getting proper medical documentation that establishes necessity (not just convenience) 2. Understanding the 7.5% AGI threshold requirement 3. Keeping detailed records of all medical-related components vs general security features 4. Being prepared for potential IRS questions with comprehensive documentation I'm particularly interested in the services mentioned like taxr.ai for getting initial guidance on whether expenses qualify, and Claimyr for actually speaking with IRS representatives when you need official clarification. Has anyone had experience using both services, or would you recommend one over the other for different situations? Also wondering - for those who successfully claimed these deductions, did you work with a tax professional or handle it yourself? I'm trying to decide if the complexity warrants professional help or if the documentation process is straightforward enough to manage independently.

Has anyone successfully carried forward capital losses from worthless securities to future tax years? I'm in a similar situation with about $20k in losses, but my income isn't high enough to use all the losses in one year with that $3,000 annual limit.

For anyone dealing with worthless securities, definitely check if your broker has any documentation available before going elsewhere. I had a similar situation with Schwab and they actually had a "Corporate Actions" section in my account history that showed when companies were delisted or went bankrupt. One thing to be really careful about - the IRS is pretty strict about the "worthlessness" year. It's not when the stock price hits zero, but when it becomes legally worthless (like through bankruptcy or delisting). Sometimes there's a gap between when a stock stops trading and when it's officially worthless for tax purposes. Also, if you're planning to amend multiple years, do them in order starting with the earliest year. The IRS processes amendments sequentially and it can get messy if they receive them out of order.

When I filled out my insolvency worksheet, I took pictures of all my furniture and household items and asked a local thrift store manager to give me a rough estimate of what they would price them at. The IRS accepted this documentation when they questioned my values.

I went through this exact same process about two years ago with a 2017 debt cancellation. The IRS audit was stressful, but here's what I learned that might help: For household goods, I used a simple rule: whatever I could reasonably expect to get at a garage sale. For thrift store items, I valued them at about 25-50% of what I originally paid. The IRS examiner told me they're looking for reasonable estimates, not exact appraisals. Regarding missing records - I was able to recreate some utility bills by calling the companies directly. Even though it was years later, most kept basic account history that showed my average monthly payments during that period. For medical bills, I contacted my insurance company for explanation of benefits statements that showed what I owed. One thing that really helped was creating a simple spreadsheet with three columns: Asset/Liability, Value/Amount, and Notes explaining my reasoning. The IRS examiner appreciated the organized format and clear explanations. For your land contract situation, definitely include it as a mortgage liability. I had something similar and the IRS considered it a legitimate debt obligation since I was contractually bound to make payments. Don't stress too much about perfect accuracy - they understand records get lost over time. Just be reasonable and document your thought process.