In my 1099B it says "Type of Gain or Loss -Short Term" in front of Box 2.Does this mean I should check Box 2 Gain or loss is Ordinary when adding each sales in Turbotax?

[ssetayeshfar]

I also have a Stock Plan Transaction Supplements from Etrade in which it has a column named Adjustment Amount (Ordinary Income) that is listing the total amounts that my employer reported to E*TRADE as ordinary income from the acquisition and/or sale of the shares.

[DDollar]

No, you do not want to check Box 2 to indicate Ordinary Gain.

You need to make an adjustment to the cost basis on the 1099-B so that it includes the amount on your Supplemental statement.  That same amount should have been included on your Form W-2, Box 1 as ordinary income.   On the TurboTax entry page, just below the Box 2 Entry, is a box to enter the corrected cost basis.  That should be the amount reported on the 1099-B plus the amount on the supplemental statement.  You may want to click on the box on the previous screen for "Guide me step-by-step".