- Oct 8: purchased 1000 shares of VSMGX (Vanguard LifeStrategy Moderate Growth Index Fund)
- Nov 6: purchased 430 more shares
- Nov 12: purchased 130 more shares
- Dec 16: purchased 1200 more shares
- Dec 31: sold all shares of VSMGX

On my 1099, I see the following (rounded) listed for Dec 31:
- Nonqualified dividend: $1000
- Qualified dividend: $500
- ST capital gain: $95
- LT capital gain: $3700
So... the shares I purchased on Oct 8 were held for at least 61 days, but not the ones purchased in Nov or Dec. How do I figure out how much, if any, of the dividends need to be reclassified as unqualified dividends? Or is it possible that, my rounding notwithstanding, Vanguard actually correctly classified $500 as qualified dividends (from my Oct 8 shares) and the rest (from my shares purchased in Nov/Dec) as unqualified?If you hold shares for fewer than 61 days and receive qualified dividends from those shares, you cannot take them as qualified dividends, even though the fund company may state that they are qualified. Receiving dividends that are not qualified may outweigh the benefit of tax loss harvesting.
Also on the wiki, I find:
So I think I need to treat the $3500 LT capital gain that was distributed on 12/31 as a short-term gain instead. Is that correct?If you sell shares of a mutual fund at a loss, and you have held those shares for 6 months or less, special rules may alter the loss you claim. ... Second, if you held those shares while the fund distributed (long term) capital gains, you have to treat this loss as a long term loss up to the dollar amount of the distribution those shares produced.
Thanks in advance!