dmertz
Level 15

Retirement tax questions

That's based on the assumption that the stock valued at $2,756 now will appreciate by about 850%.  That whole portion of the discussion is probably moot, though, since the distribution can be made in-kind and any appreciation can still be realized.  As fanfare suggested, if distributed in-kind and subsequently held for more than a year, the $23,476 of appreciation would eventually be taxed as a long-term capital-gain instead of as ordinary income.  Paying tax on $23,476 of LTCG will likely save at least 10% over having it taxed as ordinary income.  Regardless of which way the $23,476 is realized, it will have the same effect on the cost of Medicare premiums and the taxability of Social Security.