I went through almost the exact same situation with my single-member LLC formed in August 2021. The advice here about not being able to backdate before your LLC formation date is absolutely correct - I learned this the hard way when I initially tried to elect S-corp status from January 1, 2021. What really helped me was getting organized with all my documentation first. Make sure you have your Articles of Organization showing the exact formation date, copies of all your previous tax filings, and any correspondence from the IRS. When you file Form 2553 with the effective date of 3/23/2021, you'll also want to include a detailed reasonable cause statement explaining why you're filing late. One thing I wish someone had told me earlier - keep detailed records of when you submit everything to the IRS. They can take months to process late S-corp elections, and having your submission confirmation helps if you need to follow up. Good luck with getting this sorted out!

I'm dealing with a very similar situation right now - formed my single-member LLC in February 2021 but never filed the S-corp election on time. After reading through all these responses, I'm feeling much more confident about how to handle this. The key takeaways that have been most helpful: 1) You definitely can't backdate the election before your LLC existed (so March 23, 2021 is your earliest possible effective date), 2) Rev. Proc. 2013-30 relief seems like your best path forward since you've been filing consistently as an S-corp, and 3) You need to act quickly since that 3 year + 75 day window is approaching fast. I'm planning to use the approach mentioned by Margot Quinn - filing Form 2553 with my LLC formation date as the effective date and including a detailed reasonable cause statement referencing Rev. Proc. 2013-30. The fact that you've been consistently treating your business as an S-corp and filing accordingly should work in your favor. One question for anyone who's been through this - did the IRS require any additional documentation beyond Form 2553 and the reasonable cause statement, or was that sufficient for approval?

The Wisely early deposit feature is nothing compared to what traditional banks offer. Chase, BoA, and Wells Fargo all hold your money until the exact deposit date while Wisely releases it when they receive the notification. Last year my partner with a traditional bank got their refund on April 15th exactly while I had mine on Wisely April 13th. Your friend needs to check NOW though - the money is likely already there or will be within hours. This isn't some sketchy process - it's standard ACH handling.

I've been using Wisely for my refunds for the past two years and can share some real experience here. When SBTPG shows "funded," you're basically in the home stretch - usually means 1-2 business days max before it hits your Wisely card. Last year my refund came 3 days early, this year it was 2 days early. The key thing to remember is that Wisely doesn't actually control the timing - they just release the funds as soon as they receive the ACH notification from SBTPG. So while they advertise "up to 4 days early," it's really dependent on when the IRS sends the money and how quickly SBTPG processes it. Tell your friend to keep checking his Wisely app - if SBTPG shows funded today, there's a good chance it'll be there tomorrow or the next day. The process is pretty reliable once you understand the flow.

Dont forget about getting on a payment plan if you end up having to pay! The IRS fresh start program lets you set up monthly payments and sometimes they'll even reduce penalties. My brother owed like $7k and got on a plan for like $120/month. Just make sure to respond to the notice within the timeframe they give you or it gets worse.

I had a very similar situation in 2021 with an acquisition payout that got me a 1099-NEC. What really helped my case was getting a letter from the acquiring company's HR department that explicitly stated the payment was a "transaction bonus" related to the sale, not compensation for services I provided to them directly. The IRS initially wanted about $3,800 in self-employment tax from me, but after I submitted documentation showing: 1) The payment was outlined in my original employment contract as a potential acquisition bonus 2) I never performed any work directly for the acquiring company 3) The payment was made weeks after the sale closed and my employment ended 4) It was a one-time event tied to the transaction, not ongoing compensation They reversed their position and reclassified it as "other income" not subject to SE tax. The key was having clear documentation that separated this payment from regular compensation. Your "stakeholder bonus" language sounds promising - definitely get a copy of your employment agreement and any communications about how this payment was structured. Also, if you can get something in writing from either company clarifying the nature of the payment, that would be gold for your case. Don't just pay without fighting this - acquisition bonuses are frequently misclassified on 1099 forms because payroll departments aren't always sure how to handle them.

I'm confused about something slightly different but related. If my ISOs were underwater when I exercised them (like yours), but then I hold them and they go up in value later, does that somehow trigger AMT retroactively? Or is AMT only based on the value at the exact time of exercise?

You're absolutely right to be confused about this - the ISO/AMT rules are pretty complex! But the good news is that when your ISOs have a negative spread (exercise price higher than FMV), you don't need to worry about AMT at all for those specific exercises. The AMT adjustment for ISOs only applies when there's a positive "bargain element" - meaning you're getting shares worth more than what you paid. Since your shares were worth less than your exercise price when you exercised, there's no bargain element to report. You should definitely keep your Form 3921 for your records though, as you'll need it when you eventually sell the shares to calculate your capital gains/losses. Your cost basis will be whatever you actually paid (the exercise price), not the lower FMV at exercise time. So no Form 6251 needed for these underwater ISOs specifically, unless you have other AMT-triggering items in your tax situation!

Has anyone noticed if having tax fees taken out of your refund affects the timing? I'm wondering if that extra step with the tax preparer's bank might cause delays compared to people who paid their filing fees upfront.

I'm with Brinks too and have a 3/15 DDD - still waiting as of this morning. Based on what I'm seeing here, it sounds like Brinks is pretty reliable about hitting the exact date rather than depositing early like some other banks. @Amina Bah, thanks for confirming you got yours today with the same DDD! That gives me confidence mine should hit soon. I'm curious though - for those who've used Brinks for multiple tax seasons, have you noticed any pattern with what time of day the deposits typically show up? Some banks seem to process these overnight while others do it during business hours.