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If I sold to cover on the vesting date and the stock loses value between then and selling the rest of the stock from that  date, can I deduct the capital loss against ordinary income?

Meaning, lets say 1000 RSUs was worth $10, and on the vesting date I sold 300 shares and paid $3k taxes, and the stock drops to $5 by the time I sell, do I now have a capital loss of $5/share on the remaining 700, or -$3500?

Depends on how long you held them. The 1 year capital gains clock starts when the shares vest, and your tax basis is the closing price on the day they vested. 

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So if I only held them for a couple months due to an intervening quiet period, that’s a short term capital loss based on the cost basis the day of vesting?

It’s a short term loss but you can’t count it against ordinary income. Only against other capitol gains. 

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