Can I still tax loss harvest before the end of 2018?

[The 585]

Good afternoon!

When looking at my wife and I's joint Vanguard taxable brokerage account, I've noticed that we have $4000 in unrealized losses between VTSAX and VTIAX, and probably will be even more after today's further decline.

However, we have dividends set to reinvest, so we received the 12/21 dividends of slightly over $500 for VTSAX and $500 for VTIAX. (Ack, and I also just remembered both of our Roth IRAs had dividends of less than $100 for both of these funds) Despite these recent dividends, can I still tax loss harvest to realize the losses? Would the wash sale of the dividends just lessen the amount which can be TLH'ed, or does it completely negate all benefit?

And if so, what would be good partners to buy for VTSAX and VTIAX? We both own these funds in our Roth IRAs, but have variants in our 401ks (Large/mid/small caps, VFWPX), so would we need to direct any new investments within the next 30 days to different funds in those accounts as well to avoid the wash sale?

Any guidance is appreciated, as I've never attempted a tax loss harvest but certainly want to take advantage of this opportunity if possible! Thanks in advance!

[seattlecyclone]

However many shares your recent dividend reinvestment purchased, let's call it N. The first N shares you sell for a loss would be a wash sale and not deductible from your income this year. However many shares you sell after that would not be a wash sale, and you could deduct the losses from those shares.

[The 585]

However many shares your recent dividend reinvestment purchased, let's call it N. The first N shares you sell for a loss would be a wash sale and not deductible from your income this year. However many shares you sell after that would not be a wash sale, and you could deduct the losses from those shares.

Wonderful explanation, that helps a lot! Thanks so much!

[The 585]

Just to follow up on few couple things to make sure I don't mess this up horribly:

1) If I sell ALL shares in my taxable account of VTSAX to buy VLCAX (a similar but different fund), would those recently purchased dividend shares no longer be considered a wash sale since they've been sold?

2) The recent ~$100 dividend reinvestment in VTSAX within the Roth IRA will definitely be considered a wash sale for that small amount. How is the disallowed amount due to wash sale calculated for the 1099-B? (Box 1g) Would Vanguard automatically calculate this for me, since our taxable brokerage AND Roth IRAs are both with Vanguard? I don't mind a wash sale negating a small amount of losses being claimed, but I certainly want to avoid all of my losses being negated!

3) After selling VTSAX to buy VLCAX, I just need to make sure we DON'T buy and more VTSAX within 30 days after? But buying VLCAX and any other funds would be ok?

Thanks again!