How to file tax for the sale of stocks from form 1099B?
You report each position separately. You do this on form 8949. 7 positions is nothing, it will take you 5 minutes. There's a tip on form 8949 that says this, though: For Part I (short term transactions):  Note. You may aggregate all short-term transactions reported on   Form(s) 1099-B showing basis was reported to the IRS and for which no   adjustments or codes are required. Enter the total directly on   Schedule D, line 1a; you are not required to report these transactions   on Form 8949 (see instructions). For Part II (long term transactions): Note. You may aggregate all long-term transactions reported on Form(s)   1099-B showing basis was reported to the IRS and for which no   adjustments or codes are required. Enter the total directly on   Schedule D, line 8a; you are not required to report these transactions   on Form 8949 (see instructions). If the 1099B in your case shows basis for each transaction as reported to the IRS - you're in luck, and don't have to type them all in separately. "You can group your like-kind (same symbol, ST/LT) stock positions, just be sure that your totals match the total dollar amounts on the 1099.  An inconsistency will possibly result in a letter from IRS to clarify. So, if you sold the 100 shares, and they came from 7 different buys, list it once.  The sell price and date is known, and for the buy price, add all the buys and put ""Various"" for the date. If you have both long term and short term groups as part of those 7 buys, split them into two groups and list them separately."
"If you file the long-form Form 2210 in which you have to figure out  exactly how much you should have had withheld (or paid via quarterly payments of estimated tax), you might be able to reduce the underpayment penalty somewhat, or possibly eliminate it entirely.  This often happens because some of your income comes late in the year (e.g. dividend and capital gain distributions from stock mutual funds) and possibly because some of your itemized deductions come early (e.g. real estate tax bills due April 1, charitable deductions early in the year because of New Year resolutions to be more philanthropic) etc.  It takes a fair amount of effort to gather up the information you need for this (money management programs help), and it is easy to make mistakes while filling out the form. I strongly recommend use of a ""deluxe"" or ""premier"" version of a tax program - basic versions might not include Form 2210 or have only the short version of it. I also seem to remember something to the effect that the long form 2210 must be filed with the tax return and cannot be filed as part of an amended return, and if so, the above advice would be applicable to future years only. But you might be able to fill out the form and appeal to the IRS that you owe a reduced  penalty, or don't owe a penalty at all, and that your only mistake was not filing the long form 2210 with your tax return and so please can you be forgiven this once? In any case, I strongly recommend paying the underpayment   penalty ASAP because it is increasing day by day due to   interest being charged.  If the IRS agrees to your eloquent   appeal, they will refund the overpayment." "If you are a permanent resident (and it wasn't taken away or abandoned), then you are a resident alien for U.S. tax purposes. (One of the two tests for being a resident alien is the ""green card test"".) Being a resident alien means all your worldwide income is subject to U.S. taxes, regardless of where you live or work. That doesn't necessarily mean you need to actually pay taxes on your income again if you've already paid it -- you may be able to use the Foreign Tax Credit to reduce your taxes by the amount already paid to a foreign government -- but you need to report it on U.S. tax forms just like income from the U.S., and you can then apply any tax credits that you may qualify for. As a resident alien, you file taxes using Form 1040. You are required to file taxes if your income for a particular year is above a certain threshold. This threshold is described in the first few pages of the 1040 instructions for each year. For 2013, for Single filing status under 65, it is $10000. The only way you can legally not file is if your income the whole year was below this amount. You should go back and file taxes if you were required to but failed to. Having filed taxes when required is very important if you want to naturalize later on. It is also one component of demonstrating you're maintaining residency in the U.S., which you're required to do as a permanent resident being outside the U.S. for a long time, or else you'll lose your permanent residency. (Even filing taxes might not be enough, as your description of your presence in the U.S. shows you only go there for brief periods each year, not really living there. You're lucky you haven't lost your green card already; any time you go there you run a great risk of them noticing and taking it away.)" As @littleadv's comment on your question said, it is unlikely that you and your husband paid a total of $5K in income tax on $185K of wages in 2013. More likely, your 2013 tax return (assumed to be a Married Filing Jointly tax return) showed that you had not arranged to have  enough tax withheld from your salaries and thus you still owed $5K  to the IRS for 2013 taxes. Most likely, that $5K sum included not just the unpaid amount of tax but also  penalties for not paying enough income tax during 2013 and interest on the amounts not paid on time.  Just to be clear, note that the income tax you paid for 2013 during 2013 is the total of all income tax withheld from your wages by your employers (plus any estimated tax payments that you might have made for 2013). If your 2014 tax return (that you will be filing by April 15, 2015)  will likely show a similar amount due for 2014 taxes, you can avoid  the penalties and interest by increasing  your income tax withholding by a substantial amount for the remainder of 2014. If you are paid monthly and have two paychecks still to be received, then having $2500 extra withheld from each paycheck will cover the $5K shortfall that you expect to have for 2014 taxes. I assume that this is what your husband intended you to do, and to do  this, you need to fill out a new W-4 Form (asking that an addiitonal  $2500 be withheld from each paycheck) and give this form to your employer soon (i.e. well before Payroll processes your next paycheck which usually happens a few days before you get the paycheck).  If you do so, your take-home pay will be reduced by $2500 on each of the next two monthly paychecks because your employer will withhold this extra amount from your pay and include it in the amount sent to the IRS as income tax withheld from your paycheck. After your last paycheck for 2014 has been received, you should submit a new W-4 Form to your asking for only $417 in extra income tax to be withheld from each paycheck starting January 1, 2015, so that  the expected $5K shortfall for 2015 is paid in 12 equal monthly installments. If you neglect to do this, your employer will continue to withhold $2500 extra as income tax, and you will get $2500 less in take-home pay month after month in 2015. This money will not disappear forever; come 2016 when you file your income tax return for 2015, you will receive a substantial refund because you overpaid income tax by a lot during 2015. You will not, however, receive any interest on the amount that the IRS is returning to you unless the IRS delays in sending you the refund for some reason.  Alternatively, you can file a new W-4 asking for no additional tax to be withheld from 2015 paychecks, and a year from now, go through the same exercise as above: have $2500 extra withheld from the last two paychecks for 2015, right when the holidays are coming and people are shopping for gifts. There's no reason to keep the California LLC if you don't intend to do business in California.  If you'll have sales in California then you'll need to keep it and file taxes accordingly for those sales.  You can just as easily form a new LLC in Washington state and even keep the same name (if it's available in Washington, that is). Keeping the California LLC just creates paperwork for whatever regulatory filings California will require for no purpose at all.   As for your question about it looking suspicious that you just set up an LLC and then are shutting it down, nobody's going to care, to be honest.  As with your situation, plans change, so it isn't really all that unusual.  If you're concerned the government will say something, don't. "Yes, you can do that, but you have to have the stocks issued in your name (stocks that you're holding through your broker are issued in ""street name"" to your broker). If you have a physical stock certificate issued in your name - you just endorse it like you would endorse a check and transfer the ownership. If the stocks don't physically exist - you let the stock registrar know that the ownership has been transferred to someone else. As to the price - the company doesn't care much about the price of private sales, but the taxing agency will. In the US, for example, you report such a transaction as either a gift (IRS form 709), if the transaction was at a price significantly lower than the FMV (or significantly higher, on the other end), or a sale (IRS form 1040, schedule D) if the transaction was at FMV." This will work as intended, but there's another point to consider. In the US, the tax rate on proceeds from stock sales is higher for short term holdings, which are defined as held for less than one year. Both rates vary based on your income. Bracket numbers are for fiscal year 2014, filing as single. The difference between short and long term capital gains tax in the US is a minimum of ten percentage points, and works out to 15 percentage points on average. This is substantial. If you won't be reporting much income the year you move to the US (say because you only worked for a portion of the year) it is decidedly to your advantage to wait and sell the stocks in the US, to get that sweet 0% rate. At a minimum, you should hold the position for a year if you sell and rebuy, from a tax optimization perspective. Two caveats: Generally stock trades will require an additional Capital Gains and Losses form included with a 1040, known as Schedule D (summary) and Schedule D-1 (itemized).  That year I believe the maximum declarable Capital loss was $3000--the rest could carry over to future years. The purchase date/year only matters insofar as to rank the lot as short term or long term(a position held 365 days or longer), short term typically but depends on actual asset taxed then at 25%, long term 15%.  The year a position was closed(eg. sold) tells you which year's filing it belongs in. The tiny $16.08 interest earned probably goes into Schedule B, typically a short form. The IRS actually has a hotline 800-829-1040 (Individuals)  for quick questions such as advising which previous-year filing forms they'd expect from you.  Be sure to explain the custodial situation and that it all recently came to your awareness etc. Disclaimer: I am no specialist. You'd need to verify everything I wrote; it was just from personal experience with the IRS and taxes. I've talked to several very experienced accountants that deal with startup shares, stock 83(b)'s, etc. weekly (based in SF, CA) as this issue would have had a massive impact on me.  The most important part of filing an 83(b) is notifying the IRS within 30 days. The law requires the written notification within the 30 day window. Adding it to that years tax return is an IRS procedure. Forgetting to include a copy of that years tax return is apparently a common occurrence when no tax was owed (0 spread, you actually paid the FMV). And the accepted method to resolve this is to simply file a blank amendment for that years return and include the copy of the 83(b) election.