Can I sell a bond to myself?

[vtMaps]

I have an inherited IRA (non-spousal) that has a thinly traded bond that matures in 2033. I am required to liquidate the inherited IRA before then. Therefore I will have to sell the bond or transfer it in kind (taxable event) to my brokerage account.

I do not want it in my taxable brokerage account, but I wouldn't mind having it in my traditional IRA.

Question: Can I sell it in my inherited IRA and buy it in my traditional IRA? If so, how? Both IRAs (inherited and traditional) are at Fidelity.

--vtMaps

[retired@50]

I have an inherited IRA (non-spousal) that has a thinly traded bond that matures in 2033. I am required to liquidate the inherited IRA before then. Therefore I will have to sell the bond or transfer it in kind (taxable event) to my brokerage account.

I do not want it in my taxable brokerage account, but I wouldn't mind having it in my traditional IRA.

Question: Can I sell it in my inherited IRA and buy it in my traditional IRA? If so, how? Both IRAs (inherited and traditional) are at Fidelity.

--vtMaps

An interesting question...
But, if the bond leaves the inherited IRA, in any way, shape or form, isn't that still a taxable event?

The answer might be different if there weren't two sets of IRS rules in place for these two IRA account types.

Regards,

[vtMaps]

But, if the bond leaves the inherited IRA, in any way, shape or form, isn't that still a taxable event?

No. I sell it for cash which remains in the inherited IRA. The buyer (me) buys it with cash in my traditional IRA. --vtMaps

[Longdog]

But, if the bond leaves the inherited IRA, in any way, shape or form, isn't that still a taxable event?

No. I sell it for cash which remains in the inherited IRA. The buyer (me) buys it with cash in my traditional IRA. --vtMaps

I suspect there will still be a broker markup to handle that transaction, so you probably won't buy it for exactly the same price that you sell it.

[LotsaGray]

But, if the bond leaves the inherited IRA, in any way, shape or form, isn't that still a taxable event?

No. I sell it for cash which remains in the inherited IRA. The buyer (me) buys it with cash in my traditional IRA. --vtMaps

Can’t do that. You MIGHT be able to buy for cash, but when the cash goes into inherited IRA, where does the bind go? It leaves the IRA and it cannot jump into your IRA. You can’t AFAIK roll assets between IRAs unless titled to same person. Inherited IRA is not titled same as you TIRA

Also remember the reason govt requires IRAs to be emptied in 10 yrs is so taxes are realized (well at least part of the reason. But after it is out of the inherited IRA you might be able to some way purchase in your Roth IRA. Not sure if this can be done much less how it would be but that seems to be only chance.

[vtMaps]

Can’t do that. You MIGHT be able to buy for cash, but when the cash goes into inherited IRA, where does the bind go? It leaves the IRA and it cannot jump into your IRA. You can’t AFAIK roll assets between IRAs unless titled to same person. Inherited IRA is not titled same as you TIRA

If it were a treasury bond, I would just sell it in the inherited IRA. In a separate transaction I would buy the same treasury bond in my traditional IRA. I could even buy the bond in my traditional IRA before I sold the bond in my inherited IRA. The problem here is that the bond is not a treasury bond and it is thinly traded. I can't just decide to buy it any time I wish.

--vtMaps

[alpenglow]

I would call the Bond Desk at Fidelity to see what they can do.

[LotsaGray]

Can’t do that. You MIGHT be able to buy for cash, but when the cash goes into inherited IRA, where does the bind go? It leaves the IRA and it cannot jump into your IRA. You can’t AFAIK roll assets between IRAs unless titled to same person. Inherited IRA is not titled same as you TIRA

If it were a treasury bond, I would just sell it in the inherited IRA. In a separate transaction I would buy the same treasury bond in my traditional IRA. I could even buy the bond in my traditional IRA before I sold the bond in my inherited IRA. The problem here is that the bond is not a treasury bond and it is thinly traded. I can't just decide to buy it any time I wish.

--vtMaps

Understand, but that is two separate and independent transactions.

Unless there is someway your IRA can directly purchase from inherited IRA, I don’t see how to do this. It seems there should be someway to do this.

[Weathering]

At the right time, based on inherited IRA rules, withdraw the bond in-kind from the inherited IRA to your brokerage account.
I am planning to do exactly this in 2031 (last year of an inherited IRA I have).

[Weathering]

If you really want to sel a bond to yourself, then use Fidelity. 1st put in a buy order for the bond. Then put in a sell order selecting your own purchase order as a fill-or-kill order.

[LotsaGray]

At the right time, based on inherited IRA rules, withdraw the bond in-kind from the inherited IRA to your brokerage account.
I am planning to do exactly this in 2031 (last year of an inherited IRA I have).

And pay taxes on the distribution plus it is now in op taxable account where he did not want it.

[gch]

I don’t know if there are any laws against this, but I don’t see why you couldn’t put an offer out for the bond in your inherited IRA and then lift that offer in your traditional IRA.

[jebmke]

I don’t know if there are any laws against this, but I don’t see why you couldn’t put an offer out for the bond in your inherited IRA and then lift that offer in your traditional IRA.

I don't know what the code actually says but this is what is written in IRS Pub 590 on prohibited transactions

The following are some examples of prohibited transactions
with a traditional IRA.
• Borrowing money from it.
• Selling property to it.
• Using it as security for a loan.
• Buying property for personal use (present or future)
with IRA funds.

[Watty]

If you really want to sel a bond to yourself, then use Fidelity. 1st put in a buy order for the bond. Then put in a sell order selecting your own purchase order as a fill-or-kill order.

I have never bought and sold individual bonds but wouldn't that risk that your buy order would be filled before you can enter your sell order? You might end up with the bond in both accounts for double the original amount.

Would it make sense to enter the sell order first and then if no one else buys it you could then enter the buy order to buy the bond from yourself? The worse case in that situation could be if someone else buys it then you would just have cash in both accounts with no bond.

[Longdog]

If you really want to sel a bond to yourself, then use Fidelity. 1st put in a buy order for the bond. Then put in a sell order selecting your own purchase order as a fill-or-kill order.

I have never bought and sold individual bonds but wouldn't that risk that your buy order would be filled before you can enter your sell order? You might end up with the bond in both accounts for double the original amount.

Would it make sense to enter the sell order first and then if no one else buys it you could then enter the buy order to buy the bond from yourself? The worse case in that situation could be if someone else buys it then you would just have cash in both accounts with no bond.

This is an interesting idea, but how would it ensure that the price sold/paid for the bond is the going fair market value of the bond? In the buy-before-sell scenario, what would prevent you from putting a buy order in for $0.01 and then on the sell side, put in the sell order for that amount? And in the sell-before-buy scenario, putting in a sell order for anything below market value would risk someone else recognizing the below-market ask price of the bond, and swooping in to snatch it up. Something just doesn't seem right about that - I think you need to have an intermediary bond broker to establish fair market value, and when that happens, you haven't gained any advantage of directly selling it to yourself since you've paid commissions on both sides, and the markup on the buy side.

[RyeBourbon]

It sounds like self-dealing which is prohibited in an IRA.

[vtMaps]

Would it make sense to enter the sell order first and then if no one else buys it you could then enter the buy order to buy the bond from yourself? The worse case in that situation could be if someone else buys it then you would just have cash in both accounts with no bond.

Yes, that is what I would do.
I would set the price high enough that I don't mind if someone else buys it. If I don't get the price I want, I can buy it myself.

--vtMaps

[gavinsiu]

Check if the broker if you can transfer in kind from your rmd. I recall this may be possible.

[vtMaps]

Check if the broker if you can transfer in kind from your rmd. I recall this may be possible.

I can definitely transfer it in kind to my brokerage account, and that would be a taxable event. Two problems with that:
1) I don't want it in my taxable account. I would like to have it in an IRA, but it can't stay in the inherited IRA.
2) I don't want to distribute it (taxable event) all in one year.

If I sell it for cash in my inherited IRA, then I can take cash distributions as I wish.

--vtMaps

[gavinsiu]

I can definitely transfer it in kind to my brokerage account, and that would be a taxable event. Two problems with that:
1) I don't want it in my taxable account. I would like to have it in an IRA, but it can't stay in the inherited IRA.
2) I don't want to distribute it (taxable event) all in one year.

If I sell it for cash in my inherited IRA, then I can take cash distributions as I wish.

--vtMaps

There is unfortunately no way to do a inkind transfer of asset from inherited Ira to an Ira that I know of hopefully others have suggestions.

[vtMaps]

There is unfortunately no way to do a inkind transfer of asset from inherited Ira to an Ira that I know of hopefully others have suggestions.

I agree. That's why I want to sell it within the inherited IRA for cash and use cash in the traditional IRA to buy it within the traditional IRA. --vtMaps

[SnowBog]

What do you mean by "thinly traded"?

Is they an actual marketplace where this transaction can occur? Do both accounts have access to this marketplace?

If so, I don't understand the question... Presumably you'd just put in a "sell" order. If it's not sold and you put on your "buy" order on the other side, then seems like you get your desired result. If someone else buys it - do you care?

If there isn't a marketplace for this transaction - then I'm at a loss, as it sounds like you are trying to do a private party transaction - which I've never heard of (not that that means anything) in an IRA...

[crefwatch]

Look, it's perfectly reasonable to WANT to avoid the bid-ask spread and the bond dealers' profit. But that doesn't mean there is a legal way to do it. Let go of your feelings of failure, and put the bond in your taxable account. That will preserve some "feeling" of being a "winner" on the deal. (Psychological investing, I mean.)

Is the bond simply thinly-traded, or is it so obscure that there could be a fee to collect the eventual redemption?

[vtMaps]

Is the bond simply thinly-traded, or is it so obscure that there could be a fee to collect the eventual redemption?

It is thinly traded. If I want to sell it, Fidelity puts it out for bids and then presents me with the results. I can take the best offer, or not sell it.

The cusip is 452151LF8. It's not a bond I would ever buy, but I inherited it. Coupon is 5.1% and it matures in 2033. 5.1% for a 9 year bond seems OK to me. I do need to sell it in the inherited IRA so that I can take required distributions. I do not need to buy it in my traditional IRA. If I can't get my asking price for the bond when I try to sell it in the inherited IRA, then I will match the best bid and buy it for myself in my traditional IRA.

--vtMaps

[LotsaGray]

Check if the broker if you can transfer in kind from your rmd. I recall this may be possible.

OP does not want the bond in taxable account. RMD from inherited can’t go into another IRA, in fact RMDS can’t go directly into any IRA. Would defeat the purpose of RMD. Plus the distribution would be a taxable event (so you would be paying tax and added basis to the IRA. )

So to meet OP needs, it can’t be any kind of distribution. It could be a rollover, but you can’t rollover from inherited IRA to your IRA. The only remaining option is to sell inside inherited Ira. But the bond is thinly traded, which implies large bid ask. OP solution is sell in inherited and buy in his IRA.

The problem is to avoid improper self dealing. Were OP to sell below market, he would be transferring value from inherited to IRA. Defers taxes past 10 yr window. If op were to do above market value, he is transferring value into inherited. If op is under 59.5, this allows no penalty access to IRA. This is why it seems difficult to accomplish.

[Longdog]

Is the bond simply thinly-traded, or is it so obscure that there could be a fee to collect the eventual redemption?

It is thinly traded. If I want to sell it, Fidelity puts it out for bids and then presents me with the results. I can take the best offer, or not sell it.

The cusip is 452151LF8. It's not a bond I would ever buy, but I inherited it. Coupon is 5.1% and it matures in 2033. 5.1% for a 9 year bond seems OK to me. I do need to sell it in the inherited IRA so that I can take required distributions. I do not need to buy it in my traditional IRA. If I can't get my asking price for the bond when I try to sell it in the inherited IRA, then I will match the best bid and buy it for myself in my traditional IRA.

--vtMaps

I think the emboldened statement should inform what you do. There is absolutely no reason you should attempt to get it into your traditional IRA - you would never buy it, so why would you continue to hold it? There is nothing so unique or special about it, other than the fact that you inherited it from a loved one. It may have nostalgic value to you, but nostalgia is not a great investing policy. Also, realize that you don't have to sell it all at once. You can sell it in $1000 increments, so you could spread out your withdrawals across multiple years if you felt that would save you on taxes. Otherwise, sell it before the 10 year period is up, withdraw the cash from your inherited IRA, and don't dwell on it.

[Geologist]

According to this site: https://www.municipalbonds.com/bonds/issue/452151LF8/ ,
this bond (apparently a taxable municipal) traded five times on Friday, twice to investors. Based on how Annette Thau describes municipal bonds in The Bond Book, this is not a particularly thinly traded bond (she describes many municipals as trading less than a dozen times a year).

[JoeNJ28]

Fidelity won’t help with this, sounds like a cross trade and would be busted I think.

[Oregano]

As the above poster noted, this is a cross trade that is not allowed (not an IRA-specific issue). Bigger picture is that you're probably overly concerned if it ends up in a taxable account for a few years - a little bit of ordinary income isn't going to kill you. Anytime someone ends up with a bond they aren't familiar with, it's a good idea to try to find out the details. With munis, you can use the EMMA website. There, you can find a link to the offering document (https://emma.msrb.org/MS207901-MS183209-MD355299.pdf) which points out that this bond has a sinking fund redemption that started on June 1 of this year and will continue each year until 2033. It has a pro-rata redemption, so if you have a large block of the bond, perhaps a small slice of it was already called 2 months ago? In any case, some of your bonds should get redeemed well ahead of 2033, so I don't think you should take any action at this time. Just sit on the bonds and check in early June each year to see if some got redeemed. There is one potential catch if you own a very small number of these bonds, which is that different brokers have different methods for pro-rata allocations and they aren't always logical or fair. So it's hypothetically possible that if you had only say, 8 bonds, the broker's allocation method might just manage to pass over you every year. Or, even if their allocation method is fair, you might just have bad luck and not get many redeemed earlier. Nonetheless, my recommendation remains that you should just sit on these and let it play out.

[SnowBog]

As the above poster noted, this is a cross trade that is not allowed (not an IRA-specific issue).

Had to look up cross trade - hadn't heard that term before... https://www.investopedia.com/terms/c/crosstrade.asp

If I'm following, the issue seemed to be trying to do this "off book", or outside of the marketplace.

Is there anything preventing them from simply placing a sell order on the market, and if it's not selling at the price they offer, executing a buy order in their other account?

Doing so would go through the market, would be recording as a normal transaction on both sides, and presumably would not be a cross trade since it actually went through the marketplace. For clarity, I'm assuming the entire transaction takes place with a fair market value - not some extremely inflated market value...

Obviously they risk someone else buying the bond, but seems like they wouldn't care, the goal was to get cash in the IRA, and didn't sound like this was a bond they wanted to own anyway. So I'd think that would be a "win/win" if it happened.

[bd7]

The problem isn't that it is particularly thinly traded, but rather that it is OTC and Fidelity doesn't have an active market for it. The best you can do is to go through their process for selling it in the inherited IRA (request a bid from a dealer) and then see if the bond desk will buy it for you on the OTC market in your other account. Or perhaps you can enter a buy order manually, although I suspect it will reject your bid. There appears to be about a 1% or so bid/ask spread which is simply the cost of doing business. IDK what Fidelity's fixed income folks will charge you though, you should call and ask.

[vtMaps]

Nonetheless, my recommendation remains that you should just sit on these and let it play out.

I am happy enough sitting on the bonds for a few more years and collecting the 5.1% coupons, but the coupons do not throw off enough income for me to take the RMDs from the inherited IRA. Also, the inherited IRA must be liquidated before 2031 and the bond matures in 2033.

Obviously they risk someone else buying the bond, but seems like they wouldn't care, the goal was to get cash in the IRA, and didn't sound like this was a bond they wanted to own anyway. So I'd think that would be a "win/win" if it happened.

True enough, I don't really care if I buy it. There is no doubt I will sell it in 2025 (or sooner) because I need to take RMDs from the account.

If I sell it, the price I will get is less than its face value. The reason I think about buying it is because I will buy it at less than face value and my income will be the coupon plus the "capital gain" (difference between the price I pay now and the face value I receive at redemption). Of course, the "capital gain" in an IRA is taxed as ordinary income.

In the interest of simplicity I will just sell it. Thanks everyone for comments and advice.

--vtMaps

[Geologist]

First, you inherited this bond in the IRA, so I’m not sure why you care about its value compared to face value (you didn’t pay for it). Second, it is trading at a price very close to par (see https://emma.msrb.org/Security/Details/?id=452151LF8#): for example, a customer sold it on 8/15 at 99.495 (and another bought it at 100.015) so the capital element of the transaction is not large.

[SnowBog]

First, you inherited this bond in the IRA, so I’m not sure why you care about its value compared to face value (you didn’t pay for it). Second, it is trading at a price very close to par (see https://emma.msrb.org/Security/Details/?id=452151LF8#): for example, a customer sold it on 8/15 at 99.495 (and another bought it at 100.015) so the capital element of the transaction is not large.

Third, "face value" seems to be anchoring bias - bonds are only worth what someone is willing to pay for them. Granted, if you held to maturity, you'd get the face value back, but that didn't seem like an option within your IRA - so again its value is only whatever someone is willing to pay for it.

[vtMaps]

First, you inherited this bond in the IRA, so I’m not sure why you care about its value compared to face value (you didn’t pay for it). Second, it is trading at a price very close to par (see https://emma.msrb.org/Security/Details/?id=452151LF8#): for example, a customer sold it on 8/15 at 99.495 (and another bought it at 100.015) so the capital element of the transaction is not large.

The last statement I looked at (before starting this thread) was July 1 and the value was $18,469.83 for a face value of $20,000. I was seeing the coupon rate of 5.1% plus a "capital gain" of over $1,500 if I could hold it to maturity in my non-inherited IRA.

I just checked online and the value today is higher, $18,846.87. Regardless of its value, I must either sell it or transfer it in kind to a taxable account. A transfer in kind means I am taking the full value as an IRA distribution. I will sell it (within the inherited IRA) and take distributions over the next 6 years. I'm done thinking about this, I think.

--vtMaps

[Oregano]

Regardless of its value, I must either sell it or transfer it in kind to a taxable account. A transfer in kind means I am taking the full value as an IRA distribution. I will sell it (within the inherited IRA) and take distributions over the next 6 years. I'm done thinking about this, I think.
--vtMaps

Ah, I think I see why you are making this out to be a bigger deal than it is. You do not need to distribute the full position at one time. For example, if your 2025 RMD is say $2,500, you can distribute just 3 of these bonds next year to cover the RMD and leave the other 17 in the Inherited IRA. Or you distribute 2 plus a bit of cash to get to the RMD amount. Again, that assumes that none of them are redeemed on June 1, which is not yet known.

Stop looking at this like a 2033 bullet bond and start looking at it more like a bond ladder, with anticipated (though unfortunately uncertain) redemptions along the way. Do you really want to give up 2+% on the bond market bid/ask spread when you don't need to?

[vtMaps]

You do not need to distribute the full position at one time. For example, if your 2025 RMD is say $2,500, you can distribute just 3 of these bonds next year to cover the RMD and leave the other 17 in the Inherited IRA. Or you distribute 2 plus a bit of cash to get to the RMD amount. Again, that assumes that none of them are redeemed on June 1, which is not yet known.

You are quite right, and I did briefly consider that.

In order for me to sell the bond at Fidelity, Fidelity will put the bond out for bid and a few hours later will tell me what the best offer is. Then I have to respond within a certain amount of time and let them know if I take it or leave it. That's not my investing style, I prefer to trade VTI or FZROX or whatever at market price. One click and I'm done.

So when I sell the inherited bond, I will do it once and be done.

Stop looking at this like a 2033 bullet bond and start looking at it more like a bond ladder, with anticipated (though unfortunately uncertain) redemptions along the way. Do you really want to give up 2+% on the bond market bid/ask spread when you don't need to?

The spread is why I originally considered selling the bond to myself.

Thinking (and posting here) about all the ways to deal with this inheritance has been a great intellectual exercise (may help stave off dementia??), but when it comes to actually taking action, simplicity will prevail.

--vtMaps

[Weathering]

In your case, I don't think you should sell that bond to yourself (just my opinion).
However, I'm posting because I just sold a bond to myself. It is a bond I purchased in a taxable account when bond prices were lower (Q2 of this year). I didn't have room to buy it in my tax-deferred account back then, but I do now. Since the bid/ask spread is relatively wide (~2%), I took the risk of selling the bond to myself. First, I put in the buy order to see if it would be filled. Then, I put in the sell order by selecting my own offer (the highest offer in the book). The order was fill-or-kill. It was nerve-wracking to hit that sell button because I wouldn't have been happy if someone else had somehow bought it from me at 1% below the lowest bid. Getting the bond into my tax-deferred account costs me $2 per $1000 of face value (and generates a capital gain this year in my taxable account). Still, my tax rate will be lower when I eventually withdraw the proceeds from my tax-deferred account.

All in all, I won't be doing that again. I was more nervous about hitting the sell button than I care to experience again.

[vtMaps]

First, I put in the buy order to see if it would be filled. Then, I put in the sell order by selecting my own offer (the highest offer in the book). The order was fill-or-kill.

I don't think I can do online what you did. When I look at the bond in the "positions" view at Fidelity, there is a "sell" button, but there is no "Buy" button. I guess it's too thinly traded. I presume I could buy it through the bond desk. Anyway, I won't be trying to buy it. I will sell it in 2025. I need cash in the account for RMD next year. With a little luck interest rates will come down and its value will be a bit higher.

--vtMaps

[nalor511]

First, I put in the buy order to see if it would be filled. Then, I put in the sell order by selecting my own offer (the highest offer in the book). The order was fill-or-kill.

I don't think I can do online what you did. When I look at the bond in the "positions" view at Fidelity, there is a "sell" button, but there is no "Buy" button. I guess it's too thinly traded. I presume I could buy it through the bond desk. Anyway, I won't be trying to buy it. I will sell it in 2025. I need cash in the account for RMD next year. With a little luck interest rates will come down and its value will be a bit higher.

--vtMaps

Personally, I would just sell it now, and immediately reinvest into individual treasuries maturing when you want them to ($1k increments). In the event you should need the funds sooner, treasuries are very liquid and take 30 seconds to sell

Selling treasuries at fidelity is no harder than selling ETFs, except you can only do it on the website (not on the app)

[Weathering]

Earlier, I mentioned having successfully sold a bond to myself (from my taxable account into my tIRA). Today (quite a while after the trade), I received a message in my Fidelity account that the trade did not have a unique buyer and unique seller, which, therefore, violated some rules. I was asked in the message not to do any further trades like this. I will not be doing any more of these trades.

I'm now going to call Fidelity (both the retirement/IRA group and the bond desk) to ask if there is another way I can move bonds from my taxable account to my IRA. The reason I want to do this occasionally is because this year, there have been occurrences of high-quality corporate bonds with above (historically) average yields. I don't always have cash available in my retirement accounts to buy them, but I do in my taxable. So, I bought them in taxable but later wanted to move them into my IRA after freeing up cash in the IRA. I don't have an issue paying Fidelity a transaction fee (or two) to achieve this.

[Nate79]

Earlier, I mentioned having successfully sold a bond to myself (from my taxable account into my tIRA). Today (quite a while after the trade), I received a message in my Fidelity account that the trade did not have a unique buyer and unique seller, which, therefore, violated some rules. I was asked in the message not to do any further trades like this. I will not be doing any more of these trades.

I'm now going to call Fidelity (both the retirement/IRA group and the bond desk) to ask if there is another way I can move bonds from my taxable account to my IRA. The reason I want to do this occasionally is because this year, there have been occurrences of high-quality corporate bonds with above (historically) average yields. I don't always have cash available in my retirement accounts to buy them, but I do in my taxable. So, I bought them in taxable but later wanted to move them into my IRA after freeing up cash in the IRA. I don't have an issue paying Fidelity a transaction fee (or two) to achieve this.

You can only move cash from a taxable account to an IRA and it counts as a contribution.

[JoeNJ28]

Sounds like a cross which would be prohibited. We had a client do a sell of a large tech stock in their ira and a buy in their taxable. One order. It was busted because they were both sides of the trade which was amazing to begin with due to the volume but our firm clearly paired the orders off internally. To do this successfully you would need that bond to trade somewhere else in between your trades.

[20cm]

but when the cash goes into inherited IRA, where does the bond go?

The bond goes to the buyer, the same as when you sell anything in any account. The OP is simply asking if they can arrange to be the buyer of this specific bond so that they can narrow the bid/ask spread.

[LotsaGray]

but when the cash goes into inherited IRA, where does the bond go?

The bond goes to the buyer, the same as when you sell anything in any account. The OP is simply asking if they can arrange to be the buyer of this specific bond so that they can narrow the bid/ask spread.

You need to consider the whole series of questions asked. Ultimately, depending on how done, if not done at market, which is ultimately what OP is structuring, either value is extracted from tIRA that should be subject to 10% penalty or value of inherited IRA is shifted into tIRA thus improperly extending the required 10 withdrawal and taxation of the inherited IRA. But if OP enters both sides of trade at market, there is no guarantee both sides will be matched. That is op May receive less or pay more than he intended.

[vtMaps]

Thanks for the further comments. Rather than sell it all at once in 2025, I am thinking about Oregano's suggestion:

You do not need to distribute the full position at one time.

I could sell just enough each year to meet the RMD, or sell half in 2025 and the remainder a few years later, or I could sell it all in 2025 and be done with it. So annual small sales, two larger sales, or one sale and be done. I am not sure what I will do, but definitely not annual sales.

--vtMaps

[Oregano]

Thanks for the further comments. Rather than sell it all at once in 2025, I am thinking about Oregano's suggestion:

You do not need to distribute the full position at one time.

I could sell just enough each year to meet the RMD, or sell half in 2025 and the remainder a few years later, or I could sell it all in 2025 and be done with it. So annual small sales, two larger sales, or one sale and be done. I am not sure what I will do, but definitely not annual sales.

--vtMaps

To be clear, I don't think you should SELL any of them, and breaking the sales up into smaller lots is likely to get worse pricing. Wait until after June 1 to see if any of your bonds are redeemed, then re-read my recommendations.