@jh73  "According to the IRS instructions for Form 8949, Code M means "You report multiple transactions on a single row as described in Exception 2..."   The word "transactions" here is referring to sales and has nothing to do with the "various" notation you're seeing on Form 8949.  You have, maybe by mistake, told the IRS "I'm just going to enter lump sums for a whole bunch of trades and I'll send in the detail - sale by sale listing - later."  One way or the other you do need to itemize every sale of a noncovered security to the IRS.  I'd advise deleting the 1099-B and starting over.   The IRS has, for a long, long time, allowed you to use "various" in the Date Acquired field when you've executed a trade where multiple lots are sold.  Your obligation here is to report the trade correctly which comes down to date of sale, proceeds, the "term" of the security sold (long or short) and the basis.  In this instance you don't provide support for the term or the cost basis you're reporting for the trade to the IRS.  ... View more

Sure you can.  If you sold 500 shares of a stock and some lots were long term and some lots were short term, simply break up that 500 share sale between the two terms and report them separately.  The IRS really isn't looking to see that "500 share" sale as a line item on your income tax return so reporting the 1 sale as 2 sales is perfectly OK, as long as you get your dollars correct. ... View more

This is a user to user forum and nobody here can see your income tax return nor your computer screen.  Accordingly, you need to provide some information before anybody can make a stab at answering your question.    What what exactly are you referring to by "type of stock investment" here?  TurboTax, very broadly, has an interview for stocks that aren't acquired via some sort of employee stock compensation program and some specialty interviews for stocks that were acquired through these programs.  Maybe that's what you're referring to?    But of course there are also interviews that deal with the "basis" of stock you're selling when you didn't simply buy the stock through a broker but instead it was gifted to you, you inherited it, and so forth.   Edit your message to provide some background information. ... View more

"...the difference between the option price and the fair market value on the grand date should be the compensation element, and the cost basis adjusted to reflect that."   Not necessarily.  With a qualifying disposition the compensation/basis adjustment is the lesser of: the discount allowed on your purchase, determined as of the "grant date" your profit from the shares (selling price minus what you paid for the stock) In my experience TurboTax does make these calculations correctly though I'll add that I haven't actually done a test entry into the 2019 program. ... View more

"Thanks. So I just received my 1099-B, but for some reason it only includes my RSU's sold as a gain/proceed (even though I sold same day)."   You need to understand how RSU's are reported on the 1099-B; the broker reports $0 basis even though that's wrong.  (The IRS changed the reporting rule for RSUs just a few years ago allowing this incorrect reporting, and the cynical me feels it was done so that taxpayers that didn't understand that $0 was the wrong basis would over-report their income.)  So you need to correct that incorrect reporting and ThomasM125 explains how to do that.  On a per-share basis your basis for the stock sold is exactly the same as the per share "fair market value" figure your employer used to calculate the compensation in the first place.   Compensation = GROSS number of shares vested x per share "fair market value" at vest date.   ... View more

Is this a matter that the broker doesn't provide downloads at all, or is it a situation where the 1099-B isn't available yet?  If the former, then manual entry will be necessary, if the latter then I'd suggest simply waiting.   I'm not sure what "four pages of RSU sales" really means.  Sometimes a broker will sell execute a trade of, let's say, 500 shares from one cost lot but the sale of the shares happens somewhat piecemeal, e.g., 50 shares are sold followed by 125 shares sold and then 100 shares are sold, etc., etc., until all 500 shares are gone, and then the broker lists each and every trade.  If that's your situation, you can "compress" all those sales into one sale of 500 shares and omit the detail.  Sometimes a broker will execute a trade of shares from different cost lots and then list out the one trade as several trades, breaking out the cost lot information.   In this situation, again, you can compress all that detail into one trade.   If you really have way too many individual trades that need to be reported the IRS allows, and TurboTax supports, reporting the trades in "summary" fashion but then mailing in the detail of the individual trades to the IRS - the 1099-B will typically cover that - along with Form 8453 is also an option.  The "On Demand" tax guidance will tell you what you need to do. ... View more

@Hspeed  Since you state that TurboTax is calculating compensation I know that you've used the RSU step by step interview, and I know that you've entered something incorrectly.   Understand that there's no real "income tax return reporting" reason to use that interview.  There really are only 2 legitimate reasons the use that interview: Somehow the compensation associated with the vesting wasn't reported on the W-2, or You don't have a clue as to what the proper basis for the stock is and need TurboTax's help to come up with a reasonable estimate. I take it that neither reason pertains to you.    What you're selling here is plain-vanilla "stock", really not a bit different than a stock you might have purchased through your broker, and that's the easier and less mistake-prone approach.  You enter the 1099-B exactly as it reads, wrong basis and all, and then correct the basis using TurboTax's correction mechanism to get the Form 8949 to reflect everything properly.   Accordingly, I generally recommend NOT using that interview because it can be confusing and people frequently make mistakes.  If you use the RSU interview TurboTax uses the exact same method that your employer uses to calculate the compensation - GROSS shares x a per share FMV figure - so you've overstated the gross number of shares vesting, probably because you've told TT about the same vesting twice, and TT isn't smart enough to figure that out.   I'd say delete the trade or trades you've entered using the RSU interview and simply report the trade as a regular stock sale, correcting the broker-reported incorrect basis. ... View more