What's important to know is the cost "basis" for the shares you sell. You are taxed on your gain, which is the amount you sell for minus your basis.
If the shares were purchased in 2012 or later the fund/broker is required to track that for you and report it on a 1099-B in the year you sell. If so everything should just work. You import the 1099-B and TT figures everything out. (Make sure the 1099-B seems correct of course, like any imported document.) BTW this includes all subsequent purchases such as dividend reinvestment.
If the shares were purchased prior to 2012 the fund/broker might still have the basis info, but they are required to have it. If so import will still work the same, it's just a different checkbook will appear on a particular form and the fund/broker doesn't tell the IRS what the basis is. But they tell TT and TT will use it.
If the shares were purchased prior to 2012 and the fund/broker doesn't have the basis then the basis field will be blank and it will be up to you to figure out and type in the correct value.
Please feel free to ask follow-up questions.
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