How to deal with IRS response of no action to 83(b) election?
I think you should consult a professional with experience in 83(b) election and dealing with the problems associated with that. The cost of the mistake can be huge, and you better make sure everything is done properly. For starters, I would look at the copy of the letter you sent to verify that you didn't write the year wrong. I know you checked it twice, but check again. Tax advisers can call a dedicated IRS help line for practitioners where someone may be able to provide more information (with your power of attorney on file), and they can also request the copy of the original letter you've sent to verify it is correct. In any case, you must attach the copy of the letter you sent to your 2014 tax return (as this is a requirement for the election to be valid).
When I went on vacation to London a few years ago, I looked around at banks with ATM deals with UK banks. I found that B of A had a deal with a UK bank that you could use their ATMs to take out money from your US account for practically no fees. So the week or so before I left, I opened an account at B of A, put a bunch of money in it, and used the B of A debit card during my trip as much as possible. "tl;dr:  Prosecutors probably thing they can't meet the ""reasonable doubt"" standard, and the deck is heavily stacked against lawsuits.  The whole running the company into the ground part is legal.  It's stupid, but no different than any bad boss that pits employees against each other.  Just on a much grander scale.  The real estate thing is extremely shady.  However, when you're the boss of a company, It's not considered theft to do business with another company you own.  The truth is Sears is drowning in debt.  The CEO offered an easy out.  They sell the property, and only pay reduced rent.  It also means closing stores is easier, and Sears is on the decline.  So, on its own, it's shady, but not the worst way of getting quick cash.  The fact that the CEO is responsible for that decline is what pushes things into potential legal trouble.  It's essentially a complicated form of theft.  One where if Sears goes bankrupt too early (before 2020 or so), his real estate business can't handle it and burns.  However, these sorts of executive theft are almost never prosecuted.  The best chance would be a shareholder lawsuit, but it would have to be against the entire board for supporting him.  Then you run into the issue that, while the board is ""elected"", the laws governing it allow for tricks that make the Russian election look sterling in comparison.\*  Basically, if a CEO is backed up by the board, and not doing something blatantly illegal, they can probably get away with it.  Board elections tend to be rigged to the point that having a member that cares about the company, and all the minor shareholders is laughable.  \* In addition to how the candidates are chosen, votes are cast, etc..., etc... many companies have several types of shares.  Some of which have no voting power, and some of which count for many times the vote of a normal share." "The short answer is that the IRS knows this is an issue, so they are prepared to deal with the ""discrepancies.""  The filer does not need to something special to call it to their attention.  Keep good records and consistently report according to your accounting processes.   Exactly how the IRS resolves / flags this, I don't know.  Maybe someone else can answer, but you can imagine that if they track you for multiple years they should have some idea of how many dollars are rolling over and whether you might have ""forgotten"" to report something from a few years ago that happened at a year-end break." Now assume these shares are vested, held for at least 1 year, and are   then sold for $5 each. Everything I've read implies that the grantee   now owes long-term capital gains taxes on the difference, which would   be 10k * ($5 - $1). No. That's exactly what the SO is NQ for. Read more on the differences between ISO and NQSO here. Now assume these shares are vested, held for at least 1 year, and are   then sold for $5 each. Everything I've read implies that the grantee   now owes long-term capital gains taxes on the difference, which would   be 10k * ($5 - $1). At this point you no longer have NQSO, you have RSU. If you filed 83(b) when  you exercised, then you pay capital gains tax when they vest. If you didn't - its ordinary income to you. NQSO is a red herring here since once exercised they no longer exist. If you didn't file 83(b), then when the stock vests the difference between the FMV at vest and the money you spent on it when exercising (if any) is considered wages and taxed as ordinary income (+FICA etc). From that point the RSU becomes a regular stock investment and the capital gains clock starts ticking. They will not send a bill, though there's a chance they will eventually send an accusatory letter.  You must proactively pay your taxes. The simplest route is to send a check to each taxing authority with the respective full amounts due.  I wouldn't bother calling them.  You could also file amended returns with each containing the correct information.  As a general rule, tax advisors tend to counsel against giving bank account information to the IRS for payment purposes (as opposed to refund purposes), both to protect the timing of payment and to make it slightly more difficult for them to seize or lien your account. If you choose to send a check, you can use Form 1040-V and NY Form IT-201-V.  Please triple check your Social Security Number matches your tax return SSN, so they correctly credit you for payment.  You may include an explanation of the closed account if you are feeling either fearful or contrite, but if the amount due is paid in full, then neither taxing authority should really care about your error. "Depending on what you need to explain, you can submit your electronic return without the supplemental information and subsequently mail a Form 8453 with the additional information.  This is helpful for form 8489, for example, where you need to list every transaction reported by your stock broker on a 1099-B.  See https://www.irs.gov/pub/irs-pdf/f8453.pdf for more details on this form. If the information you need to submit an attachment for doesn't follow one of the options on that form, you will likely need to file a paper return or use a paid tax preparation service/application. Limitations of FreeFile are explained here, along with a list of forms that are available: https://www.irs.gov/uac/List-of-Available-Free-File-Fillable-Forms The ""Attaching Statements"" and ""Write-in information"" sections seem like they might apply to your situation. Attaching Statements - If you need to add statements and you can't use Form 8453, U.S. Individual Income Tax Transmittal for an IRS e-file Return, to mail that information, you will not be able to use this program to efile your return Identity Protection PIN's (IP PIN) - This program only supports the entry of a Primary taxpayer's IP PIN. If the spouse or dependents have an IP PIN, you cannot use this program to efile the return. Writing In Information - Your ability to ""write in"" additional information to explain an entry is generally limited to the 1040 forms and some of the more frequently submitted forms. If you need to write in additional information on a form, other than the 1040 series, you may not be able to use this program to efile your tax return. E-filing Forms - To efile forms, (except Form 4868) they must be attached to a 1040 series form (1040, 1040A or 1040EZ). Form Limitations - There may be Known Limitations of forms you plan to complete. Please review them. A form limitation may keep you from completing or e-filing your return." I'd be surprised if this ended in a materially-damaging final settlement. It may take more than 5 years to resolve, unless a smoking gun is produced. If PWC and outside counsel really issued written opinions, it could get a lot messier. Especially when we tip over into another recession, the IRS will come under intense Congressional pressure to cut a nominal deal. Note that folks may also be shopping for supplies for a nonprofit tax-exempt organization. I made such a purchase a few weeks ago. Whatever the legal basis of the exception,  you need to be able to prove to the store that you have it. If you can't,  they must collect the tax.