TLH time!

I don't have margin enabled and I've done it without settled cash.

I think it has something to do with me exchanging from and to Vanguard funds.

🤷
Correct, Vanguard allows me to use unsettled cash from an ETF sale to buy a different ETF two minutes later.
Apparently they have something similar for mutual funds but I have no personal experience with that.

Ok, I see the replies on the Exchange option for Vanguard mutual funds. I generally sell/buy whole shares of ETFs so that's why I wasn't aware...
 
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I've never done tax loss harvesting before. I invested in a total stock market index fund in my taxable account earlier this year, and it is is now in the red, so maybe this is a good time to explore the possibility.



I did that last week, but that may have been a mistake? I was converting shares in a total stock market fund. Does that mean I have to wait for thirty days until after I did that to sell for a loss in my taxable account?

Can anyone point me to some reliable information about how to go about tax loss harvesting and what I must do - or not do - in order to accomplish that?
The bogleheads link above is more complicated than necessary.
I don't understand what you did last week, so explain further.

Best way to TLH is to find a similar fund that you would be happy with. For a TSM fund, an S&P 500 fund is similar enough.
Then sell/buy or exchange the TSM shares with loss into S&P 500 shares. That's basically it.
There are more details to be aware of but you'll figure them out with time if you pay attention...
 
I don't have margin enabled and I've done it without settled cash.

I think it has something to do with me exchanging from and to Vanguard funds.

🤷
Yup, this is it.

Same thing with Fido. I can exchange mutual funds without ever being out of the market, as long as they're both Fido funds.

Which is why I prefer MFs to ETFs for tax loss harvesting.
 
I have a modest STL in EFT VGT (Technology) and would like ti swap it for the VITAX mutual fund.

Are they far enough apart to NOT have a wash sale problem?
 
I don't understand what you did last week, so explain further.
I had total stock market shares in my tIRA. I converted them to my Roth IRA last week. I didn't go through the process of buying or selling, but I wonder if converting counts. I don't know if that means that I can't sell total stock market shares in my brokerage account at a loss this week and benefit from that with my taxes.
 
Yup, this is it.

Same thing with Fido. I can exchange mutual funds without ever being out of the market, as long as they're both Fido funds.

Which is why I prefer MFs to ETFs for tax loss harvesting.
The exchange just has to be in the same family of funds. I exchange AQR funds for example.
 
The bogleheads link above is more complicated than necessary.
I don't understand what you did last week, so explain further.

Best way to TLH is to find a similar fund that you would be happy with. For a TSM fund, an S&P 500 fund is similar enough.
Then sell/buy or exchange the TSM shares with loss into S&P 500 shares. That's basically it.
There are more details to be aware of but you'll figure them out with time if you pay attention...
I think he’s concerned about wash sale rules.
 
Can anyone point me to some reliable information about how to go about tax loss harvesting and what I must do - or not do - in order to accomplish that?
You can’t buy essentially the same investment 30 days prior or 30 days after taking the loss, a 61 day window, TLH is for taxable accounts, but the rules apply across account types so you can’t rebuy in an IRA within the window.
If disallowed, the loss is added to the basis of the repurchased security.
The key though is to take the loss and as soon as possible put the funds back into a non identical investment. So if you take a loss in SPY, you can’t buy another S&P fund, but you can buy QQQ for example.
 
You can’t buy essentially the same investment 30 days prior or 30 days after taking the loss, a 61 day window, TLH is for taxable accounts, but the rules apply across account types so you can’t rebuy in an IRA within the window.
I am aware of that rule. What I don't know is whether converting shares counts as selling/buying the investment. Can I convert VTI from tIRA to Roth one week and then sell VTI at a loss in my taxable account the following week and still get the tax benefits?
 
When I saw TLH, I thought it meant the TLH Treasury Bond ETF. :)

My days of tax loss harvesting have been long over. My taxable accounts are small compared to my tax deferred and Roth accounts, and have had no inflow in years. Because I don't do much trade in the taxable accounts, the holdings were bought long ago and all show gains.
 
Does the Roth conversion involve buying VTI?
It was VTI already when it was in my tIRA. I converted it from my tIRA to my Roth where it is still VTI. I just want to make sure it doesn't count as a sell in my tIRA and buy in my Roth.
 
It was VTI already when it was in my tIRA. I converted it from my tIRA to my Roth where it is still VTI. I just want to make sure it doesn't count as a sell in my tIRA and buy in my Roth.
I think you are going to have to ask Vanguard. If they were able to do the conversion in kind with no sale and then buy you are probably safe.
 
It was VTI already when it was in my tIRA. I converted it from my tIRA to my Roth where it is still VTI. I just want to make sure it doesn't count as a sell in my tIRA and buy in my Roth.

That is an in-kind transfer, and is neither a buy nor a sell, and does not impact wash sales.
 
It was VTI already when it was in my tIRA. I converted it from my tIRA to my Roth where it is still VTI. I just want to make sure it doesn't count as a sell in my tIRA and buy in my Roth.
Be sure to turn off dividend reinvestment for VTI in all your accounts. There should be a distribution in a few days.
 
I have some, but only because I sold a bunch of individual preferreds and reinvested the proceeds into some preferred stock funds that have gone south about 4.5%. But even then it is only 3.5% of our taxable account and taxable account is only 24% of the total.
Only 24%? There are many on this forum that would kill to have that in their retirement mix.

Many here have posted about not having any taxable assets worth discussing. Consider our single friends here that can't take advantage of a $3K reduction on income because they have no taxable losses. That particularly stings as single filers get the SAME $3K reduction that MFJ get. And if that puts them into another IRMAA bracket ... ouch.

Or someone that needs a new roof and only has a IRA and Roth account. So, instead of selling 10K of a large winner and offsetting it with 10K of LT losses - thus getting the 10K to pay for the roof without adding a dime to their taxes (or AGI) - they need to make the decision to add to AGI from taking the money from their IRA and pay the taxes or take it from their ROTH. However, if the only reason that they have a Roth (that cost them 22% in taxes) was because their heir is in a really high tax bracket ... that becomes quite the lose-lose situation.
 
I had total stock market shares in my tIRA. I converted them to my Roth IRA last week. I didn't go through the process of buying or selling, but I wonder if converting counts. I don't know if that means that I can't sell total stock market shares in my brokerage account at a loss this week and benefit from that with my taxes.
That's called an in-kind Roth conversion. I did one back in mid December.
If you're with Vanguard, you can go to your Roth IRA account in their app, then click on Cost Basis.
Scroll down to find that conversion/transfer and then see the Date Acquired for that transaction.
That will answer the question...
 
^^^ if you did an in-kind transfer of shares from tIRA to Roth that counts towards a wash sale. The in kind conversion is considered to be a sale in the tIRA at fair value and a purchase in the Roth at fair value even though it seems like neither a sale or a purchase but just a transfer.
 
Only 24%? There are many on this forum that would kill to have that in their retirement mix. ...
Yes, it is a nice problem to have. However, this taxable account is my inheritance from my parents that I gave earmarked in my mind for the next two generations ( our kids and grandkids) so the only benefit that I intend to get from that account is from tax loss harvesting. Our personal taxable accounts ran out of runway just as I started SS, as planned but generally just luck.
 
Only 24%? There are many on this forum that would kill to have that in their retirement mix.

Many here have posted about not having any taxable assets worth discussing. Consider our single friends here that can't take advantage of a $3K reduction on income because they have no taxable losses. That particularly stings as single filers get the SAME $3K reduction that MFJ get. And if that puts them into another IRMAA bracket ... ouch.

Or someone that needs a new roof and only has a IRA and Roth account. So, instead of selling 10K of a large winner and offsetting it with 10K of LT losses - thus getting the 10K to pay for the roof without adding a dime to their taxes (or AGI) - they need to make the decision to add to AGI from taking the money from their IRA and pay the taxes or take it from their ROTH. However, if the only reason that they have a Roth (that cost them 22% in taxes) was because their heir is in a really high tax bracket ... that becomes quite the lose-lose situation.

Count me among those who have only a small percentage of taxable accounts in their stash. I just added them all up, and the total is 5.6%, even though it still a few hundred Ks. I used to have a lot more in taxable, but the years of ER prior to 59-1/2 have drained them. Sometime, I thought it would be nice to have more taxable to enjoy the tax-free long-term capital gain for non-earned income up to more than $100K/year as I did back then in early ER. But then, I remember that my situation now is quite different.

I will face RMD soon and that along with SS which I can delay no longer will put me permanently into the 24% bracket. The only way out of it is if the market gets decimated, and I would not want that. So, might as well pay the tax now to do aggressive Roth conversion to get it over with. And having done that for a few years, we now have Roth accounts in the 7 figures, and that's still a fraction of the remaining IRA/401k to be converted.

And the tax-free Roth accounts allow me to take advantage of the market movements more freely without having to think about the tax ramifications. I remember in the long past, how often I was reluctant to book a stock gain even though I felt it was topping out, all because of the thought of the short-term cap gain tax liability cutting into the profit. And I held on, until there was no longer a gain but a loss.

No, my situation is now completely different. And I act accordingly. The return of my Roth has been greater than the gain in my tax-deferred accounts, which is higher than the gain in my taxable, because I have been paying more attention to the Roth while the taxable is buy-and-hold. And buy-and-hold over so many years mean no loss anywhere to do tax loss harvesting.
 
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Only 24%? There are many on this forum that would kill to have that in their retirement mix.

Many here have posted about not having any taxable assets worth discussing. Consider our single friends here that can't take advantage of a $3K reduction on income because they have no taxable losses. That particularly stings as single filers get the SAME $3K reduction that MFJ get. And if that puts them into another IRMAA bracket ... ouch.

Or someone that needs a new roof and only has a IRA and Roth account. So, instead of selling 10K of a large winner and offsetting it with 10K of LT losses - thus getting the 10K to pay for the roof without adding a dime to their taxes (or AGI) - they need to make the decision to add to AGI from taking the money from their IRA and pay the taxes or take it from their ROTH. However, if the only reason that they have a Roth (that cost them 22% in taxes) was because their heir is in a really high tax bracket ... that becomes quite the lose-lose situation.
I have about 35% of the portfolio in taxable and it really does provides a number of advantages for early retirement and thereafter.
 
^^^ if you did an in-kind transfer of shares from tIRA to Roth that counts towards a wash sale. The in kind conversion is considered to be a sale in the tIRA at fair value and a purchase in the Roth at fair value even though it seems like neither a sale or a purchase but just a transfer.
I wondered about that...
 
^^^ if you did an in-kind transfer of shares from tIRA to Roth that counts towards a wash sale. The in kind conversion is considered to be a sale in the tIRA at fair value and a purchase in the Roth at fair value even though it seems like neither a sale or a purchase but just a transfer.

I partially disagree.

For purposes of taxation, I agree that the FMV on the date of the conversion is included in ordinary income.

I disagree that an in-kind Roth conversion interacts with wash sale rules. However, I'm not aware of any IRS documents that say one way or the other. I asked Grok and it agreed with me, but as my Dad used to say, "That and a quarter will buy you a cup of coffee".

Perhaps @cathy63 would be willing to opine.
 
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