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TT is classifying all of the reinvested dividends from my inherited stocks/funds as long term, even though clearly they should be a mix of long and short term holding periods. I have tried contacting TurboTax support, with no luck. Anyone have any idea how to get TT to properly classify the sales of these reinvested dividends?

I don't specifically know about TT, but . . .

I sold some stock in 2009. I had one sale, but there were multiple purchase lots. I split it between LT and ST based on my records of when I bought it. When I went to put it into TaxWise, I used "various" for the purchase date of the LT because that was three different purchase lots and I only wanted to type one line. I expected to have to tell the program that it was long term, but it simply assumed as much.

The VITA site manager told me that "various" is always long term, and I was expected to have actual purchase dates for short term. Fortunately, I had only one purchase lot that was short term, so I didn't go nuts trying to figure out how to tell TaxWise that a "various" purchase was really short term.

If TT is making the same assumption about various dates that TaxWise did, you may need to put in the dividend dates as purchase dates for the short term part. If this results in needing to use a couple more lines of Schedule D or D-1 to report the sale, oh well. That's life.

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