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At tax time, I rely quite heavily on exporting my trades into Turbo Tax, especially since I don't trust myself at keeping track of cost basis (especially with dividend reinvestments) and wash sales. I like the idea of transferring assets to Merrill Edge for the bonus, but would that mean I'd lose track of my trading history? Or does that somehow transfer as well?

For securities that you have purchased since brokerages were required to track the basis (tax year 2011 for most securities), the basis is required to be passed on. For securities that you may have purchased prior to that, or securities that basis tracking is not required (some types of debt securities, for instance) the basis may or may not be passed on.

That said, it's always best to track your own basis, because brokerages have been known to make mistakes in tracking basis, and there are some things (step ups in basis, for instance) that they may not know about. That's why there is a column on the form 8949 to adjust the basis reported to the IRS, and a whole list of codes in the form 8949 instructions to document the reason those adjustments were made.

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