I've been following this thread with interest since I had a similar issue recently. What really helped me was understanding that the IRS designed IP PINs to be temporary by nature - they're not meant to be retrieved later, which is why the phone representatives can't help you get old ones. After reading through everyone's suggestions here, I'd recommend a two-pronged approach: First, definitely request those account transcripts for 2020 and 2021 through the IRS website. As others mentioned, these will show if your returns processed normally without identity verification issues, which is likely what you need to prove rather than the actual PIN numbers. Second, while you're waiting for the transcripts, do check any old tax software accounts you might have used those years. I was surprised to find my 2020 PIN buried in my FreeTaxUSA account history - apparently they save more detailed filing information than I realized. The frustrating phone experience you described is unfortunately typical, but the good news is that the transcript route doesn't require talking to anyone and gives you the verification most people actually need when they think they need old PINs.

I went through this exact same issue about six months ago and can confirm what others have said - there's no way to retrieve expired IP PINs from previous years. The IRS treats them as single-use security codes that expire after each tax year. What worked for me was requesting account transcripts for the years I needed through irs.gov/account/view-your-account-information. You can get them online instantly if you can verify your identity, or mail in Form 4506-T if you prefer. The transcripts will show if your returns were processed normally, which is usually what you actually need to prove rather than having the specific PIN numbers. I also found it helpful to search through my emails for "IP PIN" or "identity protection" - the IRS has been sending email reminders in recent years, and sometimes those contain reference numbers or confirmation that your PIN was issued. It's not the PIN itself, but it can be useful documentation. For the future, I now take a photo of my IP PIN letter as soon as it arrives in December and save it in multiple places. Learned that lesson the hard way after going through the same frustrating phone experience you described!

I've given up trying to do this correctly in TurboTax and just hire a CPA every year. With RSUs, ESPP, and now some ISO and NSO options too, it's just too complicated. Last year I tried doing it myself and ended up with a CP2000 notice from the IRS saying I underreported my stock sales. Paid more in penalties than what a good accountant would have cost. Learn from my mistake!

I went through this exact same nightmare last tax season with my Fidelity RSU and ESPP sales! Here's what I learned after making several mistakes: The key insight is that your Tax Reporting Statement (1099-B) is what you'll enter into TurboTax, but you MUST use the Supplemental Information to correct the cost basis, especially for RSUs. The 1099-B often shows incorrect cost basis that doesn't account for the income you already paid taxes on when the RSUs vested. My process now: 1) Enter each transaction from the 1099-B exactly as shown, 2) When TurboTax asks for cost basis, use the adjusted numbers from your Supplemental Information instead of what's on the 1099-B, 3) Double-check that any ESPP sales are properly categorized as qualifying vs disqualifying dispositions. The supplemental statement is your friend - it contains the real cost basis calculations that prevent double taxation. Without using it, you'll likely overpay taxes significantly. I almost made a $2,000+ mistake before catching this! One more tip: Keep detailed records of both statements. If you ever get an IRS notice, having both documents makes it much easier to explain the discrepancies between what's reported on the 1099-B vs what you actually filed.

I'm still a bit confused about loan interest deductions. For example, if I use part of this personal loan to make improvements to my home office (I'm self-employed), would that portion of the interest be deductible as a business expense?

Great thread with lots of helpful information! I just wanted to add one more perspective as someone who recently went through this exact situation with a personal loan. The key thing that helped me was keeping detailed records from day one. Even though personal loan proceeds aren't taxable income (as others have correctly explained), I created a simple spreadsheet tracking: - Original loan amount and date received - Monthly payment amounts and dates - How I used the funds (categories like debt consolidation, home repairs, etc.) This documentation became invaluable later when I needed to reference it for tax purposes, especially when some of the loan went toward my small business expenses. One thing I learned the hard way: if you think there's ANY chance you might use even a small portion of the loan for business or investment purposes, track those expenses separately from day one. It's much harder to reconstruct that information later when tax time comes around. Also, regarding the earlier discussion about IRS resources - IRS Publication 535 (Business Expenses) has a good section on borrowed funds used for business purposes if that applies to your situation.

I learned this lesson the hard way last year. I hadn't been taking depreciation on my rental because I thought it would "save me" on taxes later when I sold. When I finally sold the property, my accountant informed me the IRS would reduce my basis regardless - so I had essentially given up thousands in tax deductions over the years while still getting hit with the same tax bill at sale. The worst part? You can only go back and amend returns for 3 years. I lost 7 years worth of depreciation deductions I could have taken. Don't make my mistake - ALWAYS take the depreciation you're entitled to.

This thread perfectly illustrates why depreciation is one of the most misunderstood aspects of rental property ownership. I've been managing rental properties for over 15 years and I still see experienced investors making this mistake. The key point everyone's hitting on is absolutely correct - the IRS uses "allowed or allowable" depreciation when calculating your adjusted basis at sale. This means whether you claim it or not, you're going to face the same tax consequences when you sell. The only difference is whether you got the benefit of reduced taxes during the years you owned the property. I always tell new landlords to think of depreciation as a mandatory tax strategy, not an optional one. The IRS has essentially decided you WILL get taxed on depreciation recapture regardless, so you might as well take the annual deductions that come with it. One additional point - if you're planning to hold rental properties long-term, you can also look into 1031 exchanges when you sell. This allows you to defer the depreciation recapture (and capital gains) by rolling the proceeds into another investment property. It's another reason why taking maximum depreciation now makes sense - you can potentially defer those tax consequences indefinitely through strategic property exchanges.

One thing nobody has mentioned yet is that Section 117(d)(5) has been on shaky ground in recent years. During the 2017 tax reform discussions, there was talk of eliminating this exclusion entirely, which would have made all graduate tuition waivers taxable income. While it survived that round, it's always possible future tax legislation could modify or remove this benefit. Make sure whatever documentation you rely on is current. The IRS Publication 970 (Tax Benefits for Education) gets updated annually and contains official guidance on these educational tax benefits. Always worth checking the most recent version!

Just to add another perspective - I work in university payroll and see these situations frequently. The distinction everyone's discussing between 117(d)(5) and Section 127 benefits is crucial, but there's one more wrinkle to consider. If you're classified as more than a half-time employee (typically 20+ hours per week), some universities will automatically categorize ALL your tuition benefits under Section 127 rather than 117(d)(5), even if you're also teaching. This is because they view your primary relationship with the university as "employee" rather than "student." I'd strongly recommend getting written clarification from both your graduate school AND your HR department about how they're classifying your benefits. Don't assume that teaching one class automatically qualifies you for 117(d)(5) treatment if you're primarily employed in administration. The IRS looks at the substance of the relationship, not just the presence of teaching duties. Also, if your university is treating this inconsistently or you're getting conflicting information, document everything. You may need to make your own determination based on the facts and circumstances of your situation.