Tax loss harvesting

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Bubbagump
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Tax loss harvesting

Post by Bubbagump » Wed Aug 27, 2014 9:10 pm

I understand what tax loss harvesting is. What I don't understand is what the real benefit is for the trouble. So to make sure I have my theory correct... Say we have a down year on the domestic market. Before the end of the tax year, I would sell say a total stock market index and either sit on the cash for 31 days or perhaps buy into an S&P 500 fund (roughly equiv to the fund I sold) as a short term holding. Then after 31 days I can buy into the total stock fund again. So I assume this only happens on down years and likely once a year? Then I write off the loss at the point I sold the shares.

Then I have seen this $3000 limit thrown around. Is that the max deduction you can take? And if so, this seems like a lot of work for perhaps not a ton of return if you have a larger portfolio. Or am I missing something?

livesoft
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Re: Tax loss harvesting

Post by livesoft » Wed Aug 27, 2014 9:27 pm

1. If you believe 2 mouse clicks is a lot of work, then yes TLHing is a lot of work.
2. $3,000 is NOT the max deduction you can take.
3. If you can change the taxes on your future gains from 33% to 15%, would you do it? If you could get a risk-free return of 18%, would you do it?
4. Since most years in the stock market are up, one should not have much TLHing to do … perhaps a little bit every 3 years or so. However, 2008-2009 was special, as was 2000.
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Bubbagump
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Re: Tax loss harvesting

Post by Bubbagump » Wed Aug 27, 2014 9:52 pm

So it sounds like I mostly get it. The $3k is what is throwing me. What is that all about? I read the wiki like 5 times and still don't know what that is. It seems the sticking point is regular income. So am I to understand that you take a write off at a 15/20% rate, but the first $3k against standard income?

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villars
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Re: Tax loss harvesting

Post by villars » Wed Aug 27, 2014 10:01 pm

livesoft wrote: 4. Since most years in the stock market are up, one should not have much TLHing to do … perhaps a little bit every 3 years or so. However, 2008-2009 was special, as was 2000.
this is the biggest drawback to TLH that I have encountered since I learned about it 8 months ago. Occasionally I would buy total stock and the index would go down. But that only lasts a few days, and the losses are minuscule. The inconvenience of selling and then being locked out of contributing to the same fund for 3 months by Vanguard was just not worth it.

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Pocket Cruiser
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Re: Tax loss harvesting

Post by Pocket Cruiser » Wed Aug 27, 2014 10:01 pm

You can use capital losses to offset capital gains. If your losses exceed your gains for the tax year, you can deduct up to $3,000 from ordinary income, such as wages. If your capital loss is larger than $3,000, you can carry the balance forward indefinitely, which many are still doing from 08-09.

tomd37
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Re: Tax loss harvesting

Post by tomd37 » Wed Aug 27, 2014 10:27 pm

I have not seen it mentioned in any of the posts, but my understanding is that TLH only applies to taxable accounts and not IRAs and 401ks :?:
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CABob
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Re: Tax loss harvesting

Post by CABob » Wed Aug 27, 2014 10:33 pm

tomd37 wrote:I have not seen it mentioned in any of the posts, but my understanding is that TLH only applies to taxable accounts and not IRAs and 401ks :?:
Correct since tax advantaged accounts are not taxed immediately.
You should be aware, however, the 31 day waiting period would apply even if one of the buys or sells was in a tax advantaged account.
Bob

Sidney
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Re: Tax loss harvesting

Post by Sidney » Thu Aug 28, 2014 12:03 am

villars wrote:
livesoft wrote: 4. Since most years in the stock market are up, one should not have much TLHing to do … perhaps a little bit every 3 years or so. However, 2008-2009 was special, as was 2000.
this is the biggest drawback to TLH that I have encountered since I learned about it 8 months ago. Occasionally I would buy total stock and the index would go down. But that only lasts a few days, and the losses are minuscule. The inconvenience of selling and then being locked out of contributing to the same fund for 3 months by Vanguard was just not worth it.
My rule is that I don't TLH to an investment unless I am willing to hold that investment forever. Now days, with the variety of funds and ETFs with low cost and full diversification, that isn't hard.

You aren't locked out for 3 months. You are prevented from moving back via the web but you can move funds via mail.

Yes, in the last 8 months, you may not have had many significant opportunities. In 2008-09 it was like shooting fish in a barrel.
I always wanted to be a procrastinator.

kaneohe
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Re: Tax loss harvesting

Post by kaneohe » Thu Aug 28, 2014 12:10 am

If you have an ideal BH type portfolio of index funds that don't distribute LTCGs, then you are correct that you only get to use 3K of losses each yr. If you are in the 25% bracket, that's $750 in savings each yr which is not insignificant. If you harvest only during major downturns,that shouldn't be a lot of time spent doing it. If you have a less than ideal portfolio that spins off significant LTCGs, the TLH losses can be used to "neutralize" those gains in amounts limited only by those gains (or by your losses) and in addition you can have that 3K deduction against ordinary income if you have excess losses. If you sell your funds when you retire, you can use your TLH losses against
those gains. If nothing else, you get the benefit of the time value of money.......getting some early value from those losses.

A simple example: You invest 90K and the market crashes so your investments are worth 0. You TLH and get 90K in losses. If you have an ideal BH portfolio that doesn't generate any LTCGs, you get to use 3K of losses each yr. If you are in the 25% bracket, you benefit from $750 in tax benefits each yr which you reinvest. After 30 yrs you have used up your TLH losses and benefited from $22.5K in tax benefits as well as any investment gains from these reinvestments. As part of TLH, you also re-established your position in the same investment (or equivalent) at the bottom with basis of 0. The market recovers and after those 30 yr your investment is again worth 90K. If you sell, you have 90K of gains and if still in the 25% bracket must pay 13.5K in 15% LTCGtaxes Your net benefits are the investment gains generated by your 22.5K in tax benefits over those 30 yrs plus the 9K differential in tax rates (benefit from 25% ordinary rate on the TLH and pay 15% tax rate on the LTCG of 90K).

If you had never done the TLH, you would have bought at 90K, ridden the market down to 0 and back up to 90K. If you then sold, you would have no gains at all. Similarly if you had done the TLH and never reinvested the $750 in tax savings each year, you would have gained nothing in your investments............however you would have spent that $22.5K in tax savings on something....of permanent value or not depending on your choices . Having lowered your basis to 0, you would also be facing that 13.5K in taxes if you sold.

In addition to the time value of the re-invested TLH benefits, perhaps you never needed to sell your re-established position. Then you never needed to pay the tax on the 0 basis stocks and your heirs will get a stepped-up basis when they inherit and they never need to pay the LTCG tax either so there is additional gain of that 22.5K in addition.
Last edited by kaneohe on Thu Aug 28, 2014 10:22 am, edited 1 time in total.

Bubbagump
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Re: Tax loss harvesting

Post by Bubbagump » Thu Aug 28, 2014 9:31 am

villars wrote:
livesoft wrote: 4. Since most years in the stock market are up, one should not have much TLHing to do … perhaps a little bit every 3 years or so. However, 2008-2009 was special, as was 2000.
this is the biggest drawback to TLH that I have encountered since I learned about it 8 months ago. Occasionally I would buy total stock and the index would go down. But that only lasts a few days, and the losses are minuscule. The inconvenience of selling and then being locked out of contributing to the same fund for 3 months by Vanguard was just not worth it.
This was a bit of what I was meaning when I said it was a bother. I think after reading all of this the take away is, if it isn't obvious that it is time to TLH (see 2008) then I probably shouldn't do it. It just seems like something I could easily screw up. That said, this may seem harder now than it really is as the market has been up for the past few years and there are no real TLH opportunities in that period from what I can tell. Also, I think it maybe a bit harder for me in that I am in mutual funds rather than ETFs. ETFs I can see this being much easier to do TLH with. If you're in Scotrade or whoever, it is easy enough to dump VTI and get some Fidelity equivalent, pay your $14 in commissions or whatever, and be done. When you are in Vanguard proper via mutual finds, it's a bit more mental gymnastics.

livesoft
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Re: Tax loss harvesting

Post by livesoft » Thu Aug 28, 2014 9:40 am

kaneohe wrote:The market recovers and after those 30 yr your investment is again worth 90K. If you sell, you have 90K of gains and if still in the 25% bracket must pay 22.5K in taxes Your net benefits are the investment gains generated by your 22.5K in tax benefits over those 30 yrs..
The LT capital gains tax rate would be less than one's marginal 25% rate. Right now, it would be 15%, so the taxes on a $90K LTCG would be $13.5K and not $22.5K, so a further tax savings of $9K.
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livesoft
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Re: Tax loss harvesting

Post by livesoft » Thu Aug 28, 2014 9:42 am

Bubbagump wrote:That said, this may seem harder now than it really is as the market has been up for the past few years and there are no real TLH opportunities in that period from what I can tell. Also, I think it maybe a bit harder for me in that I am in mutual funds rather than ETFs. ETFs I can see this being much easier to do TLH with.
It turns out that TLH is easier with Vanguard mutual funds than with ETFs. For instance, my last TLH with Vanguard funds was a simple exchange of shares of Total Stock Market Index fund into Large-cap Index fund. Can I ask you if you have exchanged funds at Vanguard before? How hard was it?
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Leif
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Re: Tax loss harvesting

Post by Leif » Thu Aug 28, 2014 9:47 am

Sydney wrote: My rule is that I don't TLH to an investment unless I am willing to hold that investment forever.
Very true. It happened to me. I sold my fund in taxable and purchased another fund in March of 2009. My plan was to reverse that out in 31 days. However that never happened. The market starting going back up and never looked back. It may not have been the fund I wanted long term, but it is still a very good low cost tax efficient fund.
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kaneohe
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Re: Tax loss harvesting

Post by kaneohe » Thu Aug 28, 2014 10:13 am

livesoft wrote:
kaneohe wrote:The market recovers and after those 30 yr your investment is again worth 90K. If you sell, you have 90K of gains and if still in the 25% bracket must pay 22.5K in taxes Your net benefits are the investment gains generated by your 22.5K in tax benefits over those 30 yrs..
The LT capital gains tax rate would be less than one's marginal 25% rate. Right now, it would be 15%, so the taxes on a $90K LTCG would be $13.5K and not $22.5K, so a further tax savings of $9K.
Good catch, livesoft! Thanks for wading thru all that verbiage. I'll see if I can edit it and you can pick out any remaining junk.
Will have to eat breakfast first next time.

Bubbagump
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Re: Tax loss harvesting

Post by Bubbagump » Thu Aug 28, 2014 10:28 am

livesoft wrote: It turns out that TLH is easier with Vanguard mutual funds than with ETFs. For instance, my last TLH with Vanguard funds was a simple exchange of shares of Total Stock Market Index fund into Large-cap Index fund. Can I ask you if you have exchanged funds at Vanguard before? How hard was it?
Not difficult. My larger point is that there is not a direct equivalent when staying in Vanguard. So while maybe you transfer from VTSAX to say VFIAX for your 31 days, they are not identical. Perhaps not a big deal for 31 days as you will capture most of the upside if there is any.

but I am not wrong in saying there has been little opportunity for TLH in recent years? I guess what I really don't understand is when it is worth doing. Much like rebalancing every 30 days makes no sense, is there a band concept or similar with TLH?

livesoft
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Re: Tax loss harvesting

Post by livesoft » Thu Aug 28, 2014 10:33 am

Bubbagump wrote:but I am not wrong in saying there has been little opportunity for TLH in recent years? I guess what I really don't understand is when it is worth doing. Much like rebalancing every 30 days makes no sense, is there a band concept or similar with TLH?
You are not wrong in saying there has been little opportuity for TLH in recent years. That's because the market has been going up for a number of years.

Here are my TLH tips:
http://www.bogleheads.org/forum/viewtop ... 15#p191615
http://www.bogleheads.org/forum/viewtop ... 4#p1556634
http://www.bogleheads.org/forum/viewtop ... 33#p747133
and so on.
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jebmke
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Re: Tax loss harvesting

Post by jebmke » Thu Aug 28, 2014 10:41 am

Bubbagump wrote:Not difficult. My larger point is that there is not a direct equivalent when staying in Vanguard. So while maybe you transfer from VTSAX to say VFIAX for your 31 days, they are not identical. Perhaps not a big deal for 31 days as you will capture most of the upside if there is any.
Even over a few months the tracking error will be of negligible importance. If you are still accumulating you can balance out with extended market for new purchases (or even something like SCV). When I was recirculating investments I used a 75% S&P500 and 25% extended holding as a surrogate for TSM. By chance, when the wheel stopped, I ended up with TSM but I would have been perfectly happy with the 75%/25% two-fund surrogate.
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Re: Tax loss harvesting

Post by Crow Hunter » Thu Aug 28, 2014 10:42 am

So what if a person TLH Total Stock Market in their taxable account and invested into Total International, then converted Total International held in IRA's to Total Stock Market to keep the same Asset Allocation?

Would this trigger wash sale rules?

If so, can people get into trouble if they have dividends automatically reinvested in their tax-advantaged accounts?

What if the taxable account is a joint account? Do the wash sale rules apply to both owners in their individual accounts as well?

Is a S&P500 fund "substantially different" from a Total Stock Market fund being that 75% of the TSM is the S&P 500?

jebmke
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Re: Tax loss harvesting

Post by jebmke » Thu Aug 28, 2014 10:43 am

Yes, it would be a wash sale if the identical fund were swapped between taxable and tax-deferred.
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Bubbagump
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Re: Tax loss harvesting

Post by Bubbagump » Thu Aug 28, 2014 10:48 am

Interesting. You are pretty adamant about NOT letting things become a long term loss. So to make that work, I assume one would have to change their cost basis method? More specifically to SpecID to be sure you are TLH based on the "newest" shares in the pool?

livesoft
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Re: Tax loss harvesting

Post by livesoft » Thu Aug 28, 2014 10:50 am

Yes, ALWAYS use Spec ID. I am pretty adamant about that, too. Besides, it's easier.
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jebmke
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Re: Tax loss harvesting

Post by jebmke » Thu Aug 28, 2014 10:53 am

I always use Spec ID (except for some short term muni funds which aren't volatile).

One of the side-effects of the great TLH of '09 was that we were able to consolidate almost all our equity slices into one lot. Not that it matters.
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Re: Tax loss harvesting

Post by technovelist » Thu Aug 28, 2014 10:58 am

kaneohe wrote: A simple example: You invest 90K and the market crashes so your investments are worth 0. You TLH and get 90K in losses. If you have an ideal BH portfolio that doesn't generate any LTCGs, you get to use 3K of losses each yr. If you are in the 25% bracket, you benefit from $750 in tax benefits each yr which you reinvest. After 30 yrs you have used up your TLH losses and benefited from $22.5K in tax benefits as well as any investment gains from these reinvestments. As part of TLH, you also re-established your position in the same investment (or equivalent) at the bottom with basis of 0. The market recovers and after those 30 yr your investment is again worth 90K.
That would be an amazing recovery from 0 to 90K! What is the compound annual rate for that over a 30 year period? :confused
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Bubbagump
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Re: Tax loss harvesting

Post by Bubbagump » Thu Aug 28, 2014 11:03 am

Wow, this has turned out to be an incredibly helpful thread. Perhaps a wiki update with some of these points is in order?

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Re: Tax loss harvesting

Post by iceport » Thu Aug 28, 2014 6:11 pm

livesoft wrote:It turns out that TLH is easier with Vanguard mutual funds than with ETFs.
Thank you, finally, for that concession. (Practically everything is easier with mutual funds. 8-) )

--Peter
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Re: Tax loss harvesting

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livesoft
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Re: Tax loss harvesting

Post by livesoft » Thu Aug 28, 2014 9:02 pm

petrico wrote:
livesoft wrote:It turns out that TLH is easier with Vanguard mutual funds than with ETFs.
Thank you, finally, for that concession. (Practically everything is easier with mutual funds. 8-) )

--Peter
It took a change in the law so that Vanguard was forced to keep track of individual tax lots for one's mutual funds. It was certainly not easier before the change in the law. So I have to pass your thanks on to the IRS.
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walletless
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Re: Tax loss harvesting

Post by walletless » Fri Aug 29, 2014 4:33 am

My general thinking is that I contribute to all my funds once a quarter (3/1,6/1,9/1,12/1). Due to wash sale rules, I cannot do any TLH one month before and after these dates. That essentially leaves one month each quarter where I can do TLH.

During that one month, if I see loses of over $1000 (tweak that limit based on your tax bracket and whether you think it is worth the effort. for folks in 25% federal bracket, you are essentially getting $250 for few clicks and some tracking due-diligence) in any of my stock funds, I sell and buy the rough equivalent. Then I sell and re-buy my original stock at the quarter start dates.

Few things you need to be careful about with TLH:
1) Make sure you have not bought or sold another fund tracking the same index in ANY of your accounts (Roth, IRA, 401K, etc) in that 1-month buffer time.
2) Do not do automatic dividend re-investment - makes it harder to track whether you have bought or sold in that 1-month buffer period.

Hope this helps....

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Re: Tax loss harvesting

Post by inbox788 » Fri Aug 29, 2014 10:46 am

walletless wrote:My general thinking is that I contribute to all my funds once a quarter (3/1,6/1,9/1,12/1). Due to wash sale rules, I cannot do any TLH one month before and after these dates. That essentially leaves one month each quarter where I can do TLH.

During that one month, if I see loses of over $1000 (tweak that limit based on your tax bracket and whether you think it is worth the effort. for folks in 25% federal bracket, you are essentially getting $250 for few clicks and some tracking due-diligence) in any of my stock funds, I sell and buy the rough equivalent. Then I sell and re-buy my original stock at the quarter start dates.

Few things you need to be careful about with TLH:
1) Make sure you have not bought or sold another fund tracking the same index in ANY of your accounts (Roth, IRA, 401K, etc) in that 1-month buffer time.
2) Do not do automatic dividend re-investment - makes it harder to track whether you have bought or sold in that 1-month buffer period.

Hope this helps....
Yes, there is a benefit of TLH, but it isn't as great as it seems at first. You've cashed out $250 in losses which you can put to work that was tied up in cost basis, but you've also downwardly adjusted your cost basis, so when you regain the $1000 down the road and you sell it, you'll have to pay capital gain taxes on the $1000 gain, which you wouldn't have to if you didn't take the tax loss. Assuming tax rates don't change, that's a wash, so this benefit is like an interest-free loan. If you can reduce your tax liability, then that's a second win (or lose in situations where tax liabilities grow).

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Re: Tax loss harvesting

Post by Epsilon Delta » Fri Aug 29, 2014 11:26 am

livesoft wrote:
petrico wrote:
livesoft wrote:It turns out that TLH is easier with Vanguard mutual funds than with ETFs.
Thank you, finally, for that concession. (Practically everything is easier with mutual funds. 8-) )

--Peter
It took a change in the law so that Vanguard was forced to keep track of individual tax lots for one's mutual funds. It was certainly not easier before the change in the law. So I have to pass your thanks on to the IRS.
If you keep your own records specific id was always easier. The IRS did and does require you to keep your own records. I suppose it's always easier to just ignore the rules.

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Re: Tax loss harvesting

Post by kaneohe » Fri Aug 29, 2014 12:27 pm

inbox788 wrote:
Yes, there is a benefit of TLH, but it isn't as great as it seems at first. You've cashed out $250 in losses which you can put to work that was tied up in cost basis, but you've also downwardly adjusted your cost basis, so when you regain the $1000 down the road and you sell it, you'll have to pay capital gain taxes on the $1000 gain, which you wouldn't have to if you didn't take the tax loss. Assuming tax rates don't change, that's a wash, so this benefit is like an interest-free loan. If you can reduce your tax liability, then that's a second win (or lose in situations where tax liabilities grow).
it's not a wash since you took the TLH benefits at ordinary rates if you didn't have LTCGs and paid the taxes on the sale at LTCG rates so assuming there is a differential between the 2 rates as there is now , you gain on that delta.......and of course if you don't sell because you have sufficient other assets, you don't pay the tax and neither do your heirs.

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Re: Tax loss harvesting

Post by livesoft » Fri Aug 29, 2014 12:33 pm

inbox788 wrote:[…]
Assuming tax rates don't change, that's a wash, so this benefit is like an interest-free loan.
But, by definition, rates do change in practically all circumstances: One gets a tax-break at one's marginal income tax rate for the loss and eventually pays taxes at the lower LT capital gains tax rate. For me that's like going from a range of 25% to 33% marginal income tax rate to an eventual LT cap gains tax rate of 0% to 15%.

(PS: I wouldn't use the word "wash" in a thread on TLHing unless you mean wash sale. :) :) )
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Re: Tax loss harvesting

Post by grabiner » Fri Aug 29, 2014 5:27 pm

walletless wrote:My general thinking is that I contribute to all my funds once a quarter (3/1,6/1,9/1,12/1). Due to wash sale rules, I cannot do any TLH one month before and after these dates. That essentially leaves one month each quarter where I can do TLH.
You can TLH in the 30 days after your contribution without creating a wash sale; sell the shares you purchased in the last 30 days (for a small short-term capital gain or loss).
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Re: Tax loss harvesting

Post by Bubbagump » Mon Oct 13, 2014 7:45 pm

FWIW, I took the opportunity to exchange VTIAX for VFWAX and set a calendar reminder for Nov 15 to flip things back to VTIAX on a bunch of short term lots. It was post 9/23 dividend and about a $4k loss. I hope I did well here.

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