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Here's what I'm thinking - if I bought shares, and then sold them for $1k loss, and THEN buy the same # of shares back, and sell only a fraction of this lot (ie: 1 share), I would have answered "yes" to that question - because it asked if I sold *SOME* or all of shares in this sale.. "some" being key word. And this is where TurboTax would recognize $1k as a loss fully (because answering yes makes TT say it's not a "wash sale").

Your scenario describes two sales, not one, and would have been two separate TT inputs, not one. Your description doesn't offer enough facts to be able to predict what the Schedule D would look like. If you'd like to play around with some scenarios, create a dummy return and have at it. I have a friend who worked for a time at Microsoft trying to break software. I've always thought I'd be good at that.

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