Import issue

You may have created a "Wash Sale'

The wash sale rule prohibits taxpayers from claiming a loss on the sale or other disposition of a stock or securities if, 

• within the 61-day period that begins 30 days before the sale (generally, the trade date) or other disposition, 
• Or they: Acquire the same or a “substantially identical” stock or securities.

To simplify this:

• If you buy and sell a stock at a loss, and buy it back again within 30 days, you cannot take the loss.  
• It will reduce the basis of the stock and be credited when you finally sell those shares.

Wrong assumption regarding wash sale since this is not the case. These were two independent sales and not a wash sale.  The stock were purchased at different dates and were sold on the same day.  So, what other issue could there be. 

I can't explain why one of your transactions did not import.  After verifying (compare the TurboTax transaction totals to the 1099-B totals) that the transaction is missing, just manually enter the missing transaction. It will be a lot easier than trying to determine why it did not import.