Listen, the IRS site is notoriously glitchy on mobile. Been that way for yrs. Most ppl don't realize their system runs on ancient tech that barely works w/ modern browsers. Quick fixes that work for most: - Try incognito/private browsing mode - Desktop comp > phone ALWAYS - Clear cookies/cache before trying - Try diff browser (Firefox tends to work better) - Log in super early AM or late PM If none of that works, just call the transcript req line (800-908-9946). Takes 5-10 days but way less hassle than fighting w/ their garbage website. Trust me, I've been down this rabbit hole many times.

I've been dealing with this same frustrating issue! What worked for me was switching to a different network entirely - I was on my home WiFi when having problems, but when I tried using my phone's cellular data instead, it worked perfectly. Sometimes the issue isn't just the browser or device, but the network connection itself. The IRS authentication system can be really finicky about certain internet providers or network configurations. If you have access to a different WiFi network (maybe at a library, coffee shop, or friend's house), give that a try. Also, make sure your phone's date and time are set correctly - I know it sounds weird, but security certificates can fail if your device clock is off by more than a few minutes. This happened to me with a different government site last month. Hope this helps! The transcript system really shouldn't be this difficult to use in 2025.

Has anyone here successfully claimed wigs as a medical expense? My oncologist wrote me a prescription for a "cranial prosthesis" (medical term for wig) after my chemo caused hair loss. I spent $2,400 on two decent wigs last year but not sure if I can include that with my other cancer-related expenses.

I'm so sorry to hear about your diagnosis, Olivia. I hope your treatment is going well and you're getting the support you need. I went through a similar situation with my father's cancer treatment that spanned 2023-2024. The key thing to remember is that medical expenses are deductible in the year you actually pay them, not when the services were rendered. So your $3,400 from 2024 can be claimed on your 2024 return (due this year), and all the expenses you're paying in 2025 would go on your 2025 return. One thing that helped us tremendously was keeping a dedicated folder for ALL medical receipts - not just the obvious ones like surgery and chemo, but also parking fees at the hospital, mileage logs for every trip to appointments, prescription receipts, and even things like special foods recommended by his oncologist. You'd be surprised how much these "smaller" expenses add up. Also, make sure you're tracking any insurance reimbursements carefully. You can only deduct what you actually pay out-of-pocket after insurance coverage. If you get reimbursed later, you might need to adjust future returns. The 7.5% AGI threshold can be tough to meet in normal years, but unfortunately cancer treatment costs often push people over that limit. Keep meticulous records - the IRS can be very particular about medical expense documentation. Wishing you strength through your treatment journey!

I tried the W4 adjustment thing last year and it sorta backfired. My company has a "blackout period" for W4 changes right before bonus payouts specifically because so many people were doing this. Check your company's payroll policies before assuming you can make last-minute changes!

This is such a timely discussion! I'm a tax preparer and see the aftermath of this strategy every filing season. While it's not illegal, there are some critical points to consider: First, the timing issue others mentioned is real - many companies now have blackout periods specifically because of this practice. You need to check your company's policy immediately. Second, bonuses are typically subject to the 22% flat supplemental withholding rate, but this might actually be LOWER than your regular withholding rate if you're in a higher tax bracket. In that case, adjusting your W4 could backfire. Third, the "safe harbor" rules are crucial. You need to pay either 90% of current year's tax or 100% of last year's tax (110% if your AGI was over $150k). If you're already meeting this through regular withholding, temporary W4 changes are less risky. My advice: Use the IRS withholding calculator first to see if you're already on track to meet safe harbor. If you are, and your company allows W4 changes, you could potentially adjust temporarily. But set multiple reminders to change it back - I've seen too many people get hit with huge tax bills because they forgot. The key is being strategic rather than "going crazy" with exemptions. Small adjustments based on your actual tax situation are much safer than dramatic changes.

Has anyone used TurboTax for reporting settlement income? I'm wondering if the regular version handles this or if I need to upgrade to their premium or self-employed version.

This is a really important question to get right! I went through something similar with a workplace discrimination settlement a couple years back. The key things I learned: 1) Yes, discrimination settlements are generally taxable as ordinary income, 2) You can deduct attorney fees "above the line" so you're only taxed on what you actually received, and 3) Set aside about 25-30% for taxes depending on your bracket. One thing I'd add that others haven't mentioned - make sure you get a proper 1099 form from whoever paid the settlement. Sometimes there are delays or errors with these, and you want to make sure the amount reported matches your records. Also, if any part of your settlement was specifically for medical expenses related to physical symptoms, that portion might be excludable from income, but you'd need clear documentation showing that allocation. I'd definitely recommend talking to a tax professional or even calling the IRS directly about your specific situation. Settlement taxation can be tricky and the stakes are high enough that it's worth getting professional guidance.

One tip about filing these old returns - don't e-file! The IRS only accepts electronic filing for the current tax year and 2 years prior. For anything older than that, you have to mail paper returns. Also, be sure to mail each tax year in a separate envelope. If you send multiple years together, it increases the chances of processing errors.

Just wanted to add something that might help with your peace of mind - even though you can't recover that 2017 overpayment, filing both returns will at least give you a complete picture of your tax situation from those years. I was in a similar boat with unfiled returns and kept putting it off because I was overwhelmed by all the unknowns. Once I finally bit the bullet and filed everything, it was honestly such a relief to have it done and know exactly where I stood with the IRS. One thing that helped me was creating a simple spreadsheet tracking what I owed for each year including estimated penalties, so I could budget for the payments. The uncertainty was actually worse than the reality of what I ended up owing. Good luck getting everything sorted out - you're already taking the right steps by researching this and planning to file!