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With the Trump tax cuts expiring in 2025, would it be wise to start taking distributions now at a lower tax rate even if the funds are unneeded. (obviously not applicable to Roths)...opinions?
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With the Trump tax cuts expiring in 2025, would it be wise to start taking distributions now at a lower tax rate even if the funds are unneeded. (obviously not applicable to Roths)...opinions?

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If the money is not needed and you are OK with paying the tax at today's rate, then a Roth Conversion would be better than taking a straight distribution. That is what I have been doing each of the past ten years or so.
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If the money is not needed and you are OK with paying the tax at today's rate, then a Roth Conversion would be better than taking a straight distribution. That is what I have been doing each of the past ten years or so.

Thanks, I didn't even think of that...duh!
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But rather than Roth conversion now considering possibly higher tax rates later, Roth conversion in the midst of a major stock market correction can be more economical.

Biden keeps telling us only those making over $400K will pay more taxes. That would seem to provide lots of leeway for most of us.
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Roth conversion in the midst of a major stock market correction can be more economical. - paueckler

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How would that work? If you want convert $50K (pay the tax from separate funds) then you sell 500 shares of BHM Enterprises at $100/share, convert the $50K, then buy back $500 shares at $100/share.

How is the result any different in a down market if I have to sell 1,000 shares at $50 to raise the $50K to convert then buy back 1,000 shares at $50.

Either way, I end up with the same number of shares in the Roth that I started with in the TIRA.

I paid taxes on the same $50,000 in each case.

Where is the economical advantage?
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It depends on whether the 2025 Congress allows the Fed tax rules to revert to what they were prior to 2018 or the TCJA is modified to keep certain of the changes.

I assume you're retired and referring to $$ remaining in your former employer retirement plan and/or your Traditional IRA (TIRA).

If so and you think bracket rates will revert from 12% to 15%, 22% to 25%/28% (most retirees reading this will not be in the 32%/35% and 37%/39.6% I'd imagine), then you may want to do a Roth conversion to the top of your current bracket.

To get an idea how to calculate this, assuming you were retired for all of 2020 and you expect 2021 income and deductions to be about the same, look at your 2020 1040SR line 15. Next subtract from this number the amounts shown in lines 3a and 7 (assuming 7 is a positive number). This calculated number is your taxable ordinary income. If this value is less than $40,400 (single) or $80,800 (married filing jointly, MFJ), then you are in the 12% bracket and if you convert an amount equal to the difference between them, it will be taxed at 12%. But if you have amounts in line 3a and/or line 7, it gets a bit more complicated.

Example: A couple are MFJ and their 2020 1040SR line 15 = $60,000 and lines 3a + 7 = $10,000, this gives the couple $80,800 - $50,000 ($60,000 - $10,000) = $30,800 of 'headroom' in the 12% bracket. So if they convert $30,800 of their TIRA (one or both of them) to a Roth, that $30,800 will be taxed at 12%. However, with the adding of $30,800 of ordinary income in this example, the sum of lines 3a + 7 will be 'lifted' up above the top of the 12% bracket and will be taxed at 15% from their former tax rate of 0%. Thus their tax on this Roth conversion will actually be 12% X $30,800 PLUS 15% X 10,000 = $5,196 or $5,196/$30,800 = 16.9% instead of a flat 12%, for Federal tax (any state tax will be in addition to this). So for those with 'headroom' in their 12% bracket will get a more favorable tax treatment for a Roth conversion if they have little or no amounts in lines 3a or 7.

'Headroom' in the 22% bracket would be calculated the same way, except that the sum of lines 3a + 7 will continue to be taxed at the 15% rate so the calculation is a bit easier as only the Roth conversion amount is taxed at 22%.

Here are the tops of the ordinary taxable income tax brackets for 2021 for reference

MFJ Tax Bracket Rates
10% $19,900
12% $81,050
22% $172,750
24% $329,850
32% $418,850
35% $628,300
37% $638,300

Single Tax Bracket Rates
10% $9,950
12% $40,525
22% $86,375
24% $164,925
32% $209,425
35% $523,600
37% $523,600


FYI

BruceM
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The advantage is that you’re converting more shares for the same dollar amount. So your tax per share is lower. If your account balance pre-crash was $100,000, it would take you 2 years at $50,000 per year to convert. If post-crash, your account balance dropped to $50,000, you could convert the entire thing in one year.

Of course, the big question is when will the next crash happen. If you can accurately predict that, then you’re a much savvier prognosticator than I am.

Regards,
-Chuck
Home Fool
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The advantage is that you’re converting more shares for the same dollar amount. - TMFBigfrog

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So? In essence, it's like a stock split, twice as many shares but at one-half the price. There is no gain or loss. Neutral.

True, if you convert 100% of your account, the tax on $50K will be less than on $100K but you had to experience a 50% drop in account value to score this "benefit".

I must be missing something but it wouldn't be the first time.
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I must be missing something but it wouldn't be the first time.

What I think you might be missing on this one is "the long game". There is a big "gotcha" embedded in Traditional retirement accounts that Roth IRAs do not have. That "gotcha" is the RMD -- required minimum distribution.

Once you're subject to RMDs, you must withdraw a certain percentage of your account balance every year (unless you donate the money to charity via a qualified charitable distribution). That percentage escalates over time, and that RMD money must be withdrawn from your retirement accounts entirely; it cannot be rolled from into a Roth.

The issue with RMDs is that they can drive the following:
* Higher income taxes on your withdrawals (since withdrawals from traditional accounts are generally taxable income)
* Forcing more of your Social Security to be subject to income taxes or your Social Security to be taxed at a higher rate (since your Social Security benefit is taxable based on your "combined income" that includes traditional retirement plan withdrawals)
* Raising your Medicare Part B premiums (since your Medicare Part B premiums are based on your income level)
* Putting your other investment income at risk of the Net Investment Income Tax

Since RMDs are based on your account balance, not your spending needs, they can drive your "tax and mandatory costs" higher simply based on a regulation, not based on what's best for you and/or your family.

Say you retire at 60 with a respectable $1,000,000 in your 401(k). If you don't need that money and let it grow until you're 72, at 10% per year, that will grow to around $3.1 million. If this table is accurate: https://www.irs.gov/pub/irs-tege/uniform_rmd_wksht.pdf , the RMD at 72 is about 3.9%, so you'd have an RMD of just above $121,000.

At that income level, something like 85% of your Social Security benefit would be taxable and according to this table: https://www.medicare.gov/your-medicare-costs/part-b-costs , if you're single, your Medicare Part B premium would be about double the standard level.

Assuming your balance continued to grow by about 5% per year after that (since you're losing frictional costs to the RMDs), your balance would be around $4.6 million by the time you reach age 80. At that point, your RMD would be just over 5.3%. That RMD would be around $246,000 per year, which would not only keep 85% of your Social Security taxable, but it would make your Medicare Part B costs about triple the standard level and put you at risk for the net investment income tax on any income from investments outside your retirement accounts ( https://www.kitces.com/blog/how-ira-withdrawals-in-the-cross... ).

A key reason to do Roth IRA conversions is to minimize the long term pain from RMDs, since under current rules, all the future growth in the account for the lifetime of the original account owner will be Tax Free and not subject to RMDs once the money is converted into the Roth IRA.

Take that same 60 year old retiree who, instead of letting the money compound in the traditional account, converted about 5% of the account per year to a Roth IRA and let the rest continue to compound. At age 72, instead of around $3.1 million, the account balance would be closer to $1.8 million, and the RMD would be closer to $56,000 . That's below the threshold for escalating Medicare Part B premiums, as well as generating a lower total taxable income...

Since tax rates and other cost triggers are typically based on absolute dollar amounts and Roth conversions are typically taxable income, people doing Roth IRA conversions typically look to convert a certain dollar amount per year or "up to a certain income level". As a result, a down market allows a higher percentage of the account to be converted in a given year to still allow you to be within that threshold. The higher a percentage of your assets you can convert early, the lower a percentage (and presumably, total dollar amount) are subject to RMDs and all the "gotchas" they entail, later in life.

Regards,
-Chuck
Home Fool
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>>I must be missing something but it wouldn't be the first time.<<

What I think you might be missing on this one is "the long game". There is a big "gotcha" embedded in Traditional retirement accounts that Roth IRAs do not have. That "gotcha" is the RMD -- required minimum distribution. - TMFBigFroh


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Believe me, I understand the implications of RMD's on taxability of social security, IRMAA, etc.

All the things you list are the benefits of doing Roth Conversions in general. I didn't see anything that supports the premise that coverting a specified dollar amount in a down market offers any advantage over doing that same dollar conversion in a not down market.

I concede if you suffer a big plunge in your TIRA account then it will not take as many years to drain the account. But that is not a reason to wait for a down year to make a conversion because of the "benefits". Each year you don't make a conversion is an opportunity lost forever. I wish I had started sooner.

Sorry if I am being obtuse.
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Sorry if I am being obtuse.

You're not. That's why I ended my original post in this thread with Of course, the big question is when will the next crash happen. If you can accurately predict that, then you’re a much savvier prognosticator than I am.

I completely agree with you that it generally doesn't make sense to wait for a down market, but rather to take advantage of one if it happens at the "right" time...

Regards,
-Chuck
Home Fool
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How is the result any different in a down market

If you convert 100 shares at $10/share, you pay taxes on $1000.

If you convert 100 shares at $5/share, you pay taxes on $500.

Either way you move 100 shares to your Roth.
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Thanks everyone for the replies. I'm much more prepared to make a decision based on your help.
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>>How is the result any different in a down market<<

If you convert 100 shares at $10/share, you pay taxes on $1000.

If you convert 100 shares at $5/share, you pay taxes on $500.

Either way you move 100 shares to your Roth. - pauleckler


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What you say is clear and easy enough to follow, but I think most people conceptualize and manage their affairs in terms of dollars. In your example,you have converted $1,000 dollars to your Roth in the first scenario but only moved $500 in the second so of course you have less tax to pay.

If you goal is to move $500 to your Roth you could accomplish that by moving 50 shares at $10 in a high market or 100 shares at $5 in a down market.

Your taxes will be the same and based solely on the dollar value converted, not the share count moved, so I still don't see any financial improvement from the conversion itself when done in a down market.

Later, if your $500 worth of converted stock goes up 10%, you have made a $50 tax free gain in the Roth. In the high market case that would be your 50 shares moving from $10 to $11 per share. In the down market case, that would be your 100 shares moving from $5 to $5.50 per share.
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so I still don't see any financial improvement from the conversion itself when done in a down market.

If the Roth conversion amount is the objective, whether the conversion is in cash or the number of shares transferred in-kind that is required to equal that dollar amount, then it doesn't matter....the tax will be the same. The value of doing this in a 'down market' is the presumed appreciation of the non-cash investments will be happening in the Roth IRA rather than the TIRA.

But this is kind of a moot point. Because we cannot see the future, we don't know when a 'down market' has happened. Take Monday as an example. With the S&P 500 dropping about 1.6%, is that a down market? If at the end of a week the S&P 500 drops 10%, is that a down market? We simply don't know. For all we know, that 10% drop in the index may represent the high point for the next year...or the lowest point. 'Down Markets can only be defined in retrospect. I wish now that I had done a large Roth conversion the 3rd week of March 2020, but at the time, I did not know where the market was going.

We used to tell our clients to not try to time the market, as it is a fools errand. We used to say that the worst thing that could happen in market timing is the person doing the timing hits it right, cause at that point, this person will think they are smart and make a much larger buy (or sell) the next time. It is how casino's make money.

BruceM
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I swear by Bob Brinker's 'The Market Timer' newsletter.

So far,I haven't had a reason to swear at it.
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Believe me, I understand the implications of RMD's on taxability of social security, IRMAA, etc.

All the things you list are the benefits of doing Roth Conversions in general. I didn't see anything that supports the premise that coverting a specified dollar amount in a down market offers any advantage over doing that same dollar conversion in a not down market.

I concede if you suffer a big plunge in your TIRA account then it will not take as many years to drain the account. But that is not a reason to wait for a down year to make a conversion because of the "benefits". Each year you don't make a conversion is an opportunity lost forever. I wish I had started sooner.

Sorry if I am being obtuse.


Only thing I can think of is that you're better off suffering the market collapse and then doing the conversion, than doing the conversion and then suffering the market collapse. Better off by the amount that doing the conversion at the lower valuation will save you in taxes.
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Only thing I can think of is that you're better off suffering the market collapse and then doing the conversion, than doing the conversion and then suffering the market collapse. Better off by the amount that doing the conversion at the lower valuation will save you in taxes. - warrl

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I can see that if, big if, that you think in terms of, "I'm gonna convert x number of shares to my Roth."

However I, and I think most people and including the IRS, think in terms of the number of dollars being converted to a Roth." When I plan a Roth Conversion, I first assess my expected tax situation by the end of the tax year, then I arrive at a dollar amount I want to convert taking into account impact on current year taxes as well as impact of tax on Social Security and IRMAA and remaining TIRA balance that will left to convert in future years.

After arriving at a dollar conversion target, I then assess what assets in my TIRA I want to sell to raise the dollar amount necessary for conversion. I tend to sell the ones I expect the most appreciation on or the ones throwing off the most dividends since those items lose their favorable treatment within my TIRA. I usually convert 90% of my target early in the tax year in order get the tax free returns going sooner rather than later. Then near year end, I revisit my calculation to true up the year end estimates and convert a final amount to get my toes right up to the tax line I am aiming for.

Anyway, it is a dollar denominated decision process and I see no benefit to thinking simply, the market is down so its a good time to convert some number of shares regardless of the dollar amount those shares represent.

I am not saying people who think that way are wrong, I just approach it differently. Namaste.
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Only thing I can think of is that you're better off suffering the market collapse and then doing the conversion, than doing the conversion and then suffering the market collapse. Better off by the amount that doing the conversion at the lower valuation will save you in taxes. - warrl

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I can see that if, big if, that you think in terms of, "I'm gonna convert x number of shares to my Roth."


Ah, no.

Let's say you have a $100K IRA and are in a 20% marginal tax bracket.

Scenario 1:

You convert $50K to the Roth IRA and pay $10K in taxes. The next year, you do it again. Then, the market collapses - down by half.

You now have a $50K Roth Ira, and paid $20K in taxes on the conversion.

Scenario 2:

The market collapses - down by half. Then you convert your remaining $50K IRA to Roth, paying $10K in taxes.

You now have a $50K Roth Ira, but paid only $10K in taxes on the conversion. You're ahead $10K.

CATCH IS... you don't know what is going to happen in the future.
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You now have a $50K Roth Ira, but paid only $10K in taxes on the conversion. You're ahead $10K.

CATCH IS... you don't know what is going to happen in the future. - warrl


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Thanks warrl. I can finally see the "benefit" of converting in a down market. It seems the step I was overlooking was the invocation of clairvoyance in order to obtain it.
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With the Trump tax cuts expiring in 2025, would it be wise to start taking distributions now at a lower tax rate even if the funds are unneeded. (obviously not applicable to Roths)...opinions?

I'm converting some regular IRA money into a Roth each year to fill up the 22% tax bracket, and even make use of some of the 24% bracket. The rationale is:
1. I think the tax rates will not get lower, and may get higher
2. Even if my marginal bracket stays the same, when I start taking Social Security, it may be untaxed, 50% of it may be taxed, or up to 85% of it might be taxed at my marginal rate. What drives the 0/50/85 taxation is the Provisional Income, which is your taxable income + tax free income + half of your SS. By drawing from a Roth, I found that I will pay $4000 less in taxes on my SS than if drawing from a regular (taxable) IRA.

If tax rates go up, or if the tax brackets shrink (or just fail to go up with inflation), then the recharacterization decision will look even better.

Your question sounds like it's pointing to "take money out of a regular IRA, pay taxes on it, and let it sit in a non-tax-advantaged account where one might get a tax break on capital gains." But, if you're going to pay taxes on it, you may as well recharacterize the IRA as a Roth because the tax rate on further gains in a Roth will be zero (under current law).

Also, you need to be older than 59.5 to withdraw money from an IRA without a 10% penalty, but that doesn't apply to a recharacterization.
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Roth conversion in the midst of a major stock market correction can be more economical.
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How is the result any different in a down market if I have to sell 1,000 shares at $50 to raise the $50K to convert then buy back 1,000 shares at $50.
Either way, I end up with the same number of shares in the Roth that I started with in the TIRA.


Let's say I converted a fund in April of 2020. The value at that time was $60,000, so when I did my 2020 taxes, I paid tax on $60,000 of extra income. Had I converted later in the year, I'd have paid taxes on $80,000. Of course, if I'd converted in March of 2020, I'd have paid taxes on even less than $60,000. And, like you say, the value of that fund is worth the same today regardless of how much taxes I had to pay or if I even converted at all. But how much tax is owed really does depend on the "when" of the conversion.
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...After arriving at a dollar conversion target, I then assess what assets in my TIRA I want to sell to raise the dollar amount necessary for conversion.

Just curious...why do you sell, transfer (convert) the cash created by the sell and then repurchase in the Roth? Why not just transfer, in-kind, the required number of shares that will equal the $$ conversion amount, to your Roth? The IRA custodian will calculate the dollar value of the transfer and this amount will go in box 1 and 2a of the form 1099-R you'll receive early the next year, assuming no other withdrawals or conversions that year. And I agree that transferring shares early in the year that pay qualified dividends would be a good choice. But by transferring shares, the asset allocation balance does not change. The only change is where the shares are located.

BruceM
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Just curious...why do you sell, transfer (convert) the cash created by the sell and then repurchase in the Roth? Why not just transfer, in-kind, the required number of shares that will equal the $$ conversion amount, to your Roth? The IRA custodian will calculate the dollar value of the transfer and this amount will go in box 1 and 2a of the form 1099-R you'll receive early the next year, assuming no other withdrawals or conversions that year. And I agree that transferring shares early in the year that pay qualified dividends would be a good choice. But by transferring shares, the asset allocation balance does not change. The only change is where the shares are located.

BruceM


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I usually use a mixture of in-kind transfers and re-balancing.

I do my planning and analysis in dollar terms only. Then I arrive at a separate decision of what to sell to achieve that dollar amount. What I sell in the TIRA and what I buy in the Roth are not always identical, some is, some isn't.

For example, when I decided I wanted to exit Vanguards Total International Fund, I sold all shares in the TIRA, and bought S&P500 Index in the Roth.

For a long while, I was paring down Wellington in my TIRA because of the lack of favorable treatment of Cap Gains and Divs in the TIRA. For a few years, I was buying back the same number of Wellington shares in the Roth, but in the finl conversion I bought some Dividend Appreciation Index Fund instead.

Now that the Wellington has been eliminated in my TIRA, I have been sourcing my conversion from the S&P Index. For a while, this was going into the Dividend Appreciation Index Fund in the Roth but when that balance built high enough to suit me, I switched and started buying the S&P Index in the Roth. My next conversion (in 2022) should allow me to eliminate the 500 Index in my TIRA, then I will start converting the Federal MM fund. I saved it for last since the income is so low, the unfavorable tax treatment hurts less than with the other stock funds.

As you can see mine is a two step process, determine a dollar based conversion target, then assess what I want to lighten up in the TIRA and what I am trying to build up in the Roth. So instead of straight in-kind transfers, there is a bit of re-balancing going on embedded in the conversion.
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As you can see mine is a two step process, determine a dollar based conversion target, then assess what I want to lighten up in the TIRA and what I am trying to build up in the Roth. So instead of straight in-kind transfers, there is a bit of re-balancing going on embedded in the conversion.

Rebalance at Roth conversion. Hmmm. Never thought of doing both together, but it certainly makes sense.

BruceM
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Again thanks to all. I've begun the conversion now by sending TIRA dividends earned to my Roth. In December when I get a clearer picture of my income I will do a bulk transfer either cash or in kind to bring me to the top of my bracket. Thanks so much. A final question, are the taxes paid/withheld considered part of the transfer or just the net amount?
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Your IRA custodian will likely offer you, as part of the conversion process, the option of having a % of the withdrawn (converted) amount to be sent to the IRS as a tax withholding. Unfortunately, that % is considered part of the withdrawal. So, let's say you do a conversion worth $10,000 and you elect 10% to be withheld and sent to the IRS, your conversion amount will be $9,000 and $1,000 will be mailed by the custodian to the IRS. But the taxable amount will show up on your 1099-R as $10,000. Or, you can elect to pay the tax withholding for the full $10,000 conversion from a taxable account as part of your quarterly estimated tax payments to the IRS.

Interestingly, if you were paying for investment advice and it were charged to you as a % of assets under management, that fee can be paid for with dollars from the IRA and is NOT considered a taxable withdrawal to you.

BruceM
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Thank you Bruce
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I've come to learn that Medicare supplemental premiums are a factor in this so I've calculated a second "headroom" amount based on MAGA and the Medicare High income threshold to assure that I don't jack up my Medicare premiums doing this conversion.
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I've come to learn that Medicare supplemental premiums are a factor in this so I've calculated a second "headroom" amount based on MAGA and the Medicare High income threshold to assure that I don't jack up my Medicare premiums doing this conversion. - Johnski

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Good for you. I did not learn of the secondary IRMAA consideration until late in the game. This is one of the reasons I wished I had started my Roth conversions way earlier than I did.

And with the two year look back for IRMAA, I am going to be stuck with the next to the max medicare premiums for a few years which I could have been avoided if I had started conversions earlier.

I think my revised strategy will be to trickle out the remaining TIRA balance over ten years or so to reduce IRMAA impact. The problem with that is that RMD's will force me to pull money out of the TIRA that otherwise would have made it to the Roth. I need to run some spreadsheets to optimize all this but I haven't got around to it yet.
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Perhaps the tax savings will exceed the Medicare premium bump. I haven't checked into that but I need to while there is still time to adapt my strategy. All depends on the difference between taxable income vs MAGI since the Medicare threshold is slightly higher than the top of my marginal bracket.
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Perhaps the tax savings will exceed the Medicare premium bump. I haven't checked into that but I need to while there is still time to adapt my strategy. All depends on the difference between taxable income vs MAGI since the Medicare threshold is slightly higher than the top of my marginal bracket.

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Just make sure to factor in the two year lookback. The IRMAA penalty you pay in 2022 will be driven by your 2020 MAGI.
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I need to run some spreadsheets to optimize all this but I haven't got around to it yet.

I was about to recommend that.... :-)

I'm sure you know this, but for the benefit of others, remember the RMD comes out first before any conversions. The Roth conversion amount does not count as investment income, but it will increase the MAGI and so may indirectly increase the NIIT if your AGI gets up above $250K for MFJ.

My neighbor recently sold his Queen Anne large house in SW Portland they bought in the 1970s. Even with the %500K exclusion on gain of principal residence, he still has about $600K in capital gains along with about $200K in other income. They got a rude awakening to Fed Income tax, State (OR) income tax, the NIIT and IRMAA (although his increased part B and D premiums won't occur until 2023...I think). That gain on sale of a personal residence is subject to the NIIT. Cute. Really bummed him out.

BruceM
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The Roth conversion amount does not count as investment income, but it will increase the MAGI

So with this in mind I need consider these conversions into my "Medicare Headroom" calculation...to protect myself two years from now?
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So with this in mind I need consider these conversions into my "Medicare Headroom" calculation...to protect myself two years from now?

Yes.

Are you handy in Excel? It is the best way to do these calculations and get as close as possible

BruceM
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Are you handy in Excel? It is the best way to do these calculations and get as close as possible

I'm able to stumble through simple stuff. There are entirely too many functions for me to know the most efficient ways to do stuff. I have to record my macros and my VBA skills are all but non-existent.
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