Advice for IRA's when trying to do tax loss harvesting

[slash12]

I have vanguard investments both inside IRA's, and outside of them. In my taxable account, i've setup my dividends to go directly into a bank account so that I can manually re-invest them in a way that does not disrupt tax loss harvesting. 

I'm not sure what to do about my investments in my IRA's, however.  I'm currently setup to make automatic contributions to my ROTH IRA, and I'm also re-investing my dividends.  I invest in the same funds within my IRA that I do outside of it.  This is complicating my attempts do tax loss harvesting, because both dividends, and automatic investment are coming at inopportune times.

What should I do about my IRA investments?  Even if I turn off automatic investments, I've still got the dividends to contend with.  What do you do with your IRA's, to enable you to do tax loss harvesting?

In a related note, I've also recently sold some shares for a loss (in an attempt to tax loss harvesting), only to realize in retrospect, that my IRA was setup to reinvest dividends on the exact same fund I just sold (within the 30 day window).  So will my 50$ dividend reinvestment in my IRA negate the ability for me to claim that $2,000 loss from my that loss from my taxable account?  I'm under the assumption that it will.  Will this be handled automatically by turbotax when I import my tax information from vanguard?  Or do I have to deal with this manually somehow?

Thanks in advance, for any advice.

[seattlecyclone]

For one thing, I allocate my investments across accounts based on Bogleheads' tax-efficient fund placement suggestions. This means there's ideally only one asset class where there's any overlap between the taxable account and the retirement accounts, though in practice it can be a bit more because of more limited 401(k) fund selection. For any funds where there is overlap, I turn off dividend reinvestment in the retirement account. Simply having a dividend doesn't make wash sales happen, it's the reinvestment part.

As to your specific question, the $50 reinvestment in the IRA won't wipe out the whole loss in the taxable account. There's a notion of "replacement shares" where if your reinvestment bought 10 shares but you sold 100 shares for a loss in the taxable account, the reinvestment only wipes out the loss for 10 shares and you can still claim the loss on the other 90.

[slash12]

Thanks for the response!  Your link was helpful.

I should have specified, but I'm 38, and entering retirement this year (although my wife is doing another 4 years).

My investments break down like this:

my 403(b) from TIAA-CREF - All stocks, shouldn't be hard to avoid wash sales, because the variable annuities don't produce dividends.
my wife's 403(b) - also all stock, and variable annuities, so dividends aren't a thing.
My 2 kids education investments (529 plan) - It's a lifecycle fund, so shouldn't conflict with my other investments for TLH
2x ROTH IRA through vanguard - Currently I do a Total stock market(VTIAX), and Total international stock (VTIAX)
Taxable investments - Here I also do Total International(VTIAX), and now FTSE All World (VFWAX).

I'm now thinking of moving my bond investments into my ROTH IRA's, and keeping the VTIAX only in my TAXABLE account.  This would help minimize taxes, and also eliminate the TLH conflict.

[PhysicianOnFIRE]

Yes, you will only have a partial wash sale on the $50. Vanguard may or may not report this, so it may be up to you.

I TLH'd about $40,000 in losses last year, thanks to the drops in Jan, Feb, and the Brexit.

To avoid wash sale issues, I keep TLH partners VTSAX and VFIAX in taxable, along with a total international fund (like you)

In tax deferred in Roth, I have REIT, emerging markets, bonds, and the US stocks are in non-substantially identical funds, including small and mid-cap funds. If you didn't want to tilt smaller, a large cap fund could do th trick.

Also, you can set dividends in taxable to go to a Vanguard MM fund, so they won't have to make a round trip to a bank.

Congrats on your upcoming Early Retirement!