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I think you're probably right.  I was a programmer in my prior life and that caused me to go in to the first 1099-B and modify it so it was a "Wash" and magically all the 1099-B long term entries were listed.   Definitely an undocumented design "Feature" as we used to say. 

 

I'm going to try re-importing all 300 entries to see if it gets any better...I'm pretty sure it won't though. 

 

Thanks for your responses!