If I sold a stock that was purchased at various times, do I need to break up each individual transaction?

[JamesG1]

You do not need to break the single transaction up into multiple transactions.  

But you do want to accurately record your purchase price (cost basis) and be able to explain how you constructed the cost basis should a tax authority have a question at a later time.

[fanfare]

"various times"

shares held one year or less must be reported on Form 8949 Page 1

shares held longer must be reported on Form 8949 Page 2.

This should be easily seen on your consolidated 1099-B.

For both cases you can enter one line with Date Acquired = VARIOUS

@DINUNZIO712