Do I enter 59 times for 1099B for 1 time stock sale in 1 company? Summary of Proceeds has 8 entries to check Code A on Form 8949, Code D has 50, and Code X has 1 entry.

posted

You can consolidate and make 3 entries ... one for each section code. Use the term VARIOUS for the data bought & 12/31/2019 for the date sold to make things simple.

From your description it sounds like the broker listed out each and every lot making up the sale in each sale category, which is not unusual, but @Critter has it right that all that "lot" information can be compressed into one dollar amount for the one sale in each sales category; it's simply not necessary to provide that cost basis detail in your income tax return. I'd use the actual sales date for each of the 3 entries.

Assuming that the "X" sales category transaction is "long term" (which it usually is) you will be reported as an "E" sales category transaction - "Long-term transactions reported on Form(s) 1099-B showing basis wasn’t reported to the IRS" - and have to provide the basis for that sale from your own records.