What will happen to my restricted units?
This should all be covered in your stock grant documentation, or the employee stock program of which your grant is a part.   Find those docs and it should specify how or when you can sale your shares, and how the money is paid to you.  Generally, vested shares are yours until you take action.  If instead you have options, then be aware these need to be exercised before they become shares.  There is generally a limited time period on how long you can wait to exercise.  In the US, 10 years is common. Unvested shares will almost certainly expire upon your departure of the company.  Whether your Merrill Lynch account will show this, or show them as never existing, I can't say.  But either way, there is nothing you can or should do.
"You mention ""early exercise"" in your title, but you seem to misunderstand what early exercise really means. Some companies offer stock options that vest over a number of years, but which can be exercised before they are vested. That is early exercise. You have vested stock options, so early exercise is not relevant. (It may or may not be the case that your stock options could have been early exercised before they vested, but regardless, you didn't exercise them, so the point is moot.) As littleadv said, 83(b) election is for restricted stocks, often from exercising unvested stock options. Your options are already vested, so they won't be restricted stock. So 83(b) election is not relevant for you. A taxable event happen when you exercise. The point of the 83(b) election is that exercising unvested stock options is not a taxable event, so 83(b) election allows you to force it to be a taxable event. But for you, with vested stock options, there is no need to do this. You mention that you want it not to be taxable upon exercise. But that's what Incentive Stock Options (ISOs) are for. ISOs were designed for the purpose of not being taxable for regular income tax purposes when you exercise (although it is still taxable upon exercise for AMT purposes), and it is only taxed when you sell. However, you have Non-qualified Stock Options. Were you given the option to get ISOs at the beginning? Why did your company give you NQSOs? I don't know the specifics of your situation, but since you mentioned ""early exercise"" and 83(b) elections, I have a hypothesis as to what might have happened. For people who early-exercise (for plans that allow early-exercise), there is a slight advantage to having NQSOs compared to ISOs. This is because if you early exercise immediately upon grant and do 83(b) election, you pay no taxes upon exercise (because the difference between strike price and FMV is 0), and there are no taxes upon vesting (for regular or AMT), and if you hold it for at least 1 year, upon sale it will be long-term capital gains. On the other hand, for ISOs, it's the same except that for long-term capital gains, you have to hold it 2 years after grant and 1 year after exercise, so the period for long-term capital gains is longer. So companies that allow early exercise will often offer employees either NQSOs or ISOs, where you would choose NQSO if you intend to early-exercise, or ISO otherwise. If (hypothetically) that's what happened, then you chose wrong because you got NQSOs and didn't early exercise." "I am but one man but here's my ""use-case"":  I setup my Alexa Dot in the kitchen/living room area and use it most for:  - Asking it to play whatever I feel like listening to without fumbling over my phone with chicken hands - Asking it to set a variety of timers for whatever might be baking/cooking etc. - Keeping track of my grocery list as I inevitably run out of something mid-meal prep. - I often ask it do do simple math I can't be bothered with, or unit conversions   Of course, there are most certainly other solutions to this but it just seemed like a simple one to some of my ""problems"". It's a nicety, of course not a necessity... I just like it.  *Disclaimer* I'm extremely lazy and MOST of the time if I have to pause what I'm doing/drop what I'm holding, to reach for my cellphone or a paper list, I just wont.  But like you said, to each their own!" "The issues of trading with unsettled funds are usually restricted to cash accounts.  With margin, I've never personally heard of a rule that will catch you in this scenario.  You won't be able to withdraw funds that are tied up in unsettled positions until the positions settle.  You should be able to trade those funds.  I've never heard of a broker charging margin interest on unsettled funds, but that doesn't mean there isn't a broker somewhere that does. Brokers are allowed to impose their own restrictions, however, since margin is basically offering you a line of credit.  You should check to see if your broker has more restrictive rules. I'd guess that you may have heard about restrictions that apply to cash accounts and think they may also apply to margin accounts.  If that's the case and you want to learn more about the rules generally, try searching for these terms: You should be able to find a lot of clear resources on those terms.  Here's one that's current and provides examples: https://www.fidelity.com/learning-center/trading-investing/trading/avoiding-cash-trading-violations On a margin account you avoid these issue because the margin (essentially a loan from your broker) provides a cushion / additional funds that avoid the issues.  It is possible that if you over-extend yourself that you'll get a ""margin call,"" but that seems to be different than what you're asking and maybe worth a new question if you want to know about that." To explain the capital gains part of the question, non qualified stock options (NSOs) are always treated like earned income and have payroll taxes withheld. It's advantageous for the company to issue these because they can deduct them as expenses just as they do your salary. Articles talking about capital gains would probably be referring to incentive stock options (ISOs) or possibly even restricted stock units (RSUs). If you were granted the option to buy the stock and/or hold it for a period of time, then the stock options could be treated as capital gains, short-term gains if you held them for less than a year, and long-term gains if you held them for more than a year. This payment for your NSOs is exactly like a cash bonus. The withholding follows the same guidelines. You may wish to look at what this will mean for your annual salary and adjust your W-4 withholding up or down as appropriate depending on whether the 25% federal withholding rate is more or less than what you think your final marginal rate will be with this bonus included in your annual salary. This slave rents from slumlords now.  They suck, but at least I was able to keep my dog.  The 10 years that it will take to rebuild my credit is daunting, but it's not okay to artificially inflate the price of something, only to drop it back down to half of the original price in the span of 2 years.  Nothing happened to that neighborhood.  It was and still is quiet and lovely.  But the schools there were abysmal, and I can't let my very gifted daughter think she's doing well when she's not working for the A that she gets. "I haven't dealt with this kind of thing in any way, but I found some quotes from IRS publications which I think are relevant and hopefully help. Your scenario sounds to me like a Qualified Tuition Reduction as described in Publication 970 Tax Benefits for Education. It appears the rules are different for graduate study as opposed to pre-graduate work, though I don't see anything about any dollar amount limit. There are various requirements and exceptions, so hopefully reading through that section of the publication can help you understand whether the benefit is supposed to be taxable. If taxable, it should show up on your W-2 like any other income: Any tuition reduction that is taxable should be included as wages on your Form W-2, box 1. Report the amount from Form W-2, box 1, on line 7 (Form 1040 or Form 1040A) or line 1 (Form 1040EZ).  It doesn't appear that there is any special designation or box for the tuition reduction as opposed to ""normal"" work, it just is income that's been earned like any other. If you need guidance on how much of the income is for ""normal"" work and how much is for the tuition reduction, you probably need to see if you can figure it out from her pay stubs, or contact the university's HR department. Well, looking through the credits I see in Publication 970, there appear to be two possible credits: The ""American opportunity credit"" section, under ""No double benefit allowed"", says things like (my emphasis added): You can't do any of the following.  ⋮ My understanding from reading through the section is that expenses are only excluded if they were tax-free, so that there can't be a double-dipping of benefits. If they're included as taxable income, I think they would count under your second interpretation, that the employer paid them like any other income, and your wife spent them as educational expenses just like other students, and they would qualify for educational credits. In fact, it explicitly states: Don't reduce qualified education expenses by amounts paid with funds the student receives as: Which sure sounds to me that anything that counts as W-2 Box 1 ""Wages"" would be payments received that then the expenses were logically paid separately from. The other credit, the ""Lifetime Learning Credit"", appears to use identical language (No double benefits; and don't reduce by wages). Obviously this is just from my looking through Publication 970; there may be more nuances here and for ""real"" advice you may want to speak more to the university HR department (who perhaps have dealt with this before) and/or a real tax advisor. You might also see if you can get any sort of a ""receipt"" or even a Form 1098-T from the university of what amount was paid on your wife's behalf, to help document it is truly that she was just paid more wages and spent them on classes as far as tax law is concerned." "Would my (new) landlord even be aware of the fact that I'm his   guarantor? Does that show up on a credit report or would there be   another indication of it somewhere? It may come up during background checks, and it may not come up. You're expected to disclose material information on the rental application, and withholding it may lead to voiding the rental contract and eviction. But the problem is slightly different. Can you afford paying two rents? By being the guarantor you take the responsibility of paying the rent ""in the case if..."". You need to treat it as a real liability that you will be expected to pay. With all the respect to your brother, if something unexpected happens - you will be on the hook. You have to account for that." Yes, all the house footage is treated the same. The use of home is a (suspected) audit trigger, so do consult with a tax professional if you want to take this deduction. From the statute (IRC Sec. 280A): The term dwelling unit includes a house, apartment, condominium,   mobile home, boat, or similar property, and all structures or other   property appurtenant to such dwelling unit.