I've been following this thread as someone who just started getting annuity payments myself, and there's so much helpful information here! One thing I'd add is to double-check whether your annuity qualifies for any special tax treatment. Some annuities have a portion that's considered "return of principal" (if you made after-tax contributions) which wouldn't be taxable. The pension administrator should be able to tell you what percentage of each payment is taxable vs. non-taxable. This can significantly affect how much you want withheld. Also, if you're over 59½, you don't have to worry about early withdrawal penalties, but if you're younger, make sure you understand if any penalties apply to your specific type of annuity. The 1099-R you receive will have codes that indicate the tax treatment, which is super helpful when filing. For what it's worth, I ended up using a combination of the advice here - filled out the W4P with minimal withholding since I have other income sources with withholding, and I'm planning to reassess after a few months once I see how it all balances out.

I just want to thank everyone who contributed to this thread! As someone who was completely overwhelmed by the W4P form and all the annuity paperwork, reading through all these responses has been incredibly helpful and reassuring. The key takeaways I'm getting are: 1. Yes, I do need to fill out the W4P form even for my small $319/month annuity 2. I'll receive a 1099-R (not a regular 1099) showing the payments and withholding 3. I can always adjust my withholding election later if needed 4. I should coordinate withholding between my annuity and part-time job income 5. I need to check if any portion of my payment might be "return of principal" and non-taxable I'm feeling much more confident about tackling this now. I think I'll start by calling my pension administrator to walk through the W4P form and ask about the tax treatment of my specific annuity, then use a conservative withholding approach initially and adjust as needed. The reminder that this doesn't have to be perfect right away really takes the pressure off! Thanks again to everyone, especially the tax professionals who shared their expertise. This community is such a valuable resource!

Hey Connor, I totally feel your frustration! I went through the exact same thing a few months ago and was ready to pull my hair out. After reading through all these great suggestions, I wanted to add one more trick that saved my sanity. If all the phone methods fail, try reaching out to the IRS through their online account system first at irs.gov. Sometimes you can get more detailed information about why your return is delayed, which makes your eventual phone call much more productive. Create an account if you don't have one - you can often see if there are specific issues flagging your return. Also, I noticed you filed in February and it's now April - that's actually not too unusual for processing times this year. The IRS has been running about 6-8 weeks behind on refunds that need manual review. Your $3,600 refund might have been flagged for additional verification simply due to the amount. One thing that really helped me was calling my state representative's office. I know it sounds dramatic, but they have staff who deal with IRS issues daily and can sometimes get answers when regular taxpayers can't. They don't charge anything for this service - it's part of what your taxes pay for! Just Google "[your area] congressional representative" and call their local office. Don't give up - between all these strategies, you'll definitely get through to someone. The early morning calling method combined with having all your documents ready seems to be the most reliable approach. Good luck with those car repairs!

Wow, this thread has been incredibly helpful! I've been dealing with a similar situation - filed my return in early March and still waiting on a $2,800 refund. I've tried calling the main IRS line probably 20 times with no luck, just like Connor described. I'm definitely going to try the early morning strategy combined with the incorrect SSN trick that Jamal mentioned. That's such a clever workaround! I never would have thought to intentionally enter wrong information to get routed to a human. One quick question for everyone who's successfully gotten through - how long should I expect the actual conversation with the agent to take once I'm connected? I want to make sure I block out enough time and don't have to rush through my questions. I've got my 2022 and 2023 returns ready, plus a list of specific questions about my refund status. Also, has anyone had success with the Taxpayer Advocate Service route? I'm wondering if I should try that first since my situation involves needing the refund for medical expenses (which definitely qualifies as hardship). Thanks everyone for sharing your experiences and actual solutions instead of just venting! This community is amazing when people really need help navigating these frustrating government systems.

This is a great discussion! I've been volunteering at a local literacy center for the past two years and was always unsure about the mileage deduction. Based on what everyone's shared here, it sounds like my situation definitely qualifies since I'm tutoring students (providing services) rather than just attending events. One thing I'd add from my experience: I keep a simple spreadsheet with columns for date, starting odometer reading, ending odometer reading, total miles, and purpose of trip. It takes literally 30 seconds to fill out each time, but having that documentation gives me confidence when tax time comes around. For anyone on the fence about tracking these miles - they really do add up! I drive about 12 miles round trip twice a week to volunteer, so that's roughly 1,200 miles per year. At 14¢/mile, that's about $168 in deductions I would have missed without proper tracking. The key insight from this thread is distinguishing between "providing services" vs "just donating items." That's a distinction I hadn't fully understood before. Thanks everyone for the clarification!

I've been volunteering at our local animal rescue for about six months now, and this thread has been incredibly helpful! I was always hesitant to claim the mileage because I wasn't 100% sure it was legitimate, but after reading everyone's experiences and the clarification about "providing services," I'm confident my situation qualifies. I do dog walking, help with adoption events, and assist with basic medical care - definitely providing services rather than just dropping off donations. The rescue is about 18 miles from my house, and I volunteer there twice a week, so that's going to be a significant deduction I've been missing out on. One question for those who've been tracking this longer: do you include miles for special trips, like if the rescue asks me to transport an animal to a vet appointment? That seems like it would definitely count as providing services, but I want to make sure I'm not overstepping. Also, Giovanni's point about the 14¢ rate being stuck since the 1990s is wild - with gas prices and car maintenance costs today, that rate seems pretty outdated compared to the business mileage rate!

Tell your dad to look into quarterly estimated tax payments going forward. Since Doordash doesn't withhold taxes, he should be making quarterly payments to avoid penalties. For 2023, the deadlines are April 18, June 15, Sept 15, and Jan 16, 2024. The IRS Form 1040-ES helps calculate how much to pay each quarter. Wish someone had told me this when I started with Instacart! Got hit with penalties my first year because I had no idea about the quarterly payment requirement.

Just wanted to add something important that I don't think anyone has mentioned yet - make sure your dad keeps detailed mileage logs! The IRS is really strict about mileage deductions for gig workers. He needs to track every mile driven for Doordash work, including the drive to the first pickup and drive home from the last delivery. I use a simple notebook in my car and write down the odometer reading at the start and end of each shift, plus note which app I was using. Some drivers use mileage tracking apps, but the IRS prefers written logs. With $19k in earnings, his mileage deduction could be substantial - potentially several thousand dollars in deductions if he drove a lot of miles. Also, since he's new to this, he might want to consider setting aside 25-30% of his Doordash earnings in a separate savings account for taxes. Self-employment tax plus regular income tax can be a shock if you're not prepared for it!

Has anyone considered that the interest rates might change? The IRS adjusts these quarterly. If the Federal short-term rate drops, so will the overpayment interest rate. So even if this crazy scheme worked (which others have pointed out it doesn't), you'd have no guarantee of keeping that 7% rate for long.

As someone who works in financial compliance, I wanted to add that the IRS also has sophisticated data analytics that can easily identify patterns inconsistent with normal taxpayer behavior. They cross-reference your payment patterns with income reported on W-2s, 1099s, and previous returns. If you suddenly start making massive estimated payments that don't align with your reported income or business activity, it will trigger automated flags in their system. They can then demand documentation justifying these payments, and if you can't provide legitimate business or income reasons, they'll process an immediate refund - often within days rather than the normal processing time. The system is specifically designed to prevent exactly what you're thinking of doing. Your best bet for earning decent returns is still traditional investment vehicles like I-Bonds, CDs, or high-yield savings accounts that are actually meant for storing money.