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Why You Should Convert to a Roth Right Now

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Ordinarily, when you have an important financial decision to make, you need a lot of time to consider all the factors and make an informed decision. But with one particularly valuable opportunity, there's no reason to wait -- and every incentive to act now, with nothing to lose.

Jumping on the Roth bandwagon
As we've highlighted this week, the benefits of Roth IRAs are now available to any investor who has a retirement account. Thanks to the lifting of income restrictions on conversions between traditional and Roth IRAs, many who had been denied access under previous laws can now take advantage of provisions that others have used for years.

Converting to a Roth can bring you a number of benefits. But those benefits come at a price: You have to include every penny you convert as taxable income, which will likely cost you a substantial amount in increased taxes. As a result, you may be reluctant to make a quick decision so early in the year, before you know what the rest of your tax picture will look like.

However, there's one incredibly useful facet of Roth conversions that most people don't focus on. It's potentially the most valuable thing about a Roth, and it amounts to a money-back guarantee.

Get a do-over
It sounds like a TV commercial: "If for any reason you're not satisfied, you can undo your Roth conversion absolutely free, with no further obligation." Yet that's exactly what the tax laws allow investors to do. With what's called a recharacterization, you can undo your Roth conversion in three easy steps:

  • Tell the financial institution that's acting as the trustee of your Roth IRA that you want to recharacterize the conversion, and get it to prepare the necessary documentation for the IRS.
  • Calculate the amount you'll need to return to your traditional IRA. That includes not only the original amount you converted, but also any earnings on the converted money.
  • Work with your financial institution to return that amount to your traditional IRA account.

As it turns out, that opens up a wealth of potential money-saving opportunities. And best of all, if you convert now, you have until Oct. 15, 2011 to give the IRS your final answer.

Don't wait and see
With the recharacterization in your arsenal, you can act now without any fear about the consequences. If things don't go the way you want, you can always recharacterize and make things exactly like they would've been if you had never converted.

Moreover, the earlier you act, the better off you'll often be. Consider that over time, stocks have risen more than they've fallen. All other things being equal, converting earlier means that the dollar amount of your conversion will be lower, thereby costing you less in taxes.

Say your IRA had 100 shares each of these four stocks in 2009:

Stock

Value of 100 shares on Jan. 2

Value of 100 shares on Dec. 31

Coca-Cola (NYSE: KO  )

$4,590

$5,700

Sears Holdings (Nasdaq: SHLD  )

$4,149

$8,345

DuPont (NYSE: DD  )

$2,618

$3,367

IBM (NYSE: IBM  )

$8,737

$13,090

Source: Yahoo! Finance.

If you converted right away when the year began, the total amount converted would be just more than $20,000. Yet if you did what many people would naturally do, and waited until the end of the year to think about your taxes, the value of your IRA would have risen to more than $30,000 -- and you'd have a tax bill that was 50% larger.

Conversely, though, say you had invested in losing stocks like Apollo Group (Nasdaq: APOL  ) , Citigroup (NYSE: C  ) , and Sunoco (NYSE: SUN  ) . You could then recharacterize, wait 30 days, and then reconvert. The recharacterization would save you a bundle in taxes, because the total value of your account would have fallen.

Get going
With a free do-over in your pocket, there's one more reason why you shouldn't wait to do a Roth conversion. But converting isn't an all-or-nothing proposition. How much of your traditional IRA should you convert to a Roth right now? We'll address that question tomorrow.

Stay tuned the rest of this week as Dan looks into the benefits of the new Roth conversion. Up next: deciding the right amount to convert.

Fool contributor Dan Caplinger doesn't usually fall for those late-night TV ads, although fellow Fool Eric Bleeker was kind enough to give him a Snuggie. He doesn't own shares of the companies mentioned in this article. Apollo Group, Coca-Cola, and Sears Holdings are Motley Fool Inside Value selections. Coca-Cola is a Motley Fool Income Investor pick. Try any of our Foolish newsletters today, free for 30 days. The Fool's disclosure policy is the best deal you'll find.


Read/Post Comments (38) | Recommend This Article (87)

Comments from our Foolish Readers

Help us keep this a respectfully Foolish area! This is a place for our readers to discuss, debate, and learn more about the Foolish investing topic you read about above. Help us keep it clean and safe. If you believe a comment is abusive or otherwise violates our Fool's Rules, please report it via the Report this Comment Report this Comment icon found on every comment.

  • Report this Comment On January 06, 2010, at 2:32 PM, funfundvierzig wrote:

    Investors should not be fooled by the short-term bounce in the shares of the much shrunken, ill-managed DuPont Company. For the ten year period ending November 30, 2009, the Average Annual Total Return was MINUS 1.80%! Repeat MINUS 1.80%, and that reflects dividends received. That sick performance hardly creates financial retirement security. ...funfun..

  • Report this Comment On January 06, 2010, at 3:56 PM, bookie0 wrote:

    Dan-- you may want to note that if you have been contributing to a nondeductable IRA, the entire conversion amount is not taxed, only the investment gain (particularly relevant since you refer to those who have been denied Roth conversion because of income restrictions).

    Regards.

  • Report this Comment On January 06, 2010, at 5:16 PM, jcurran516 wrote:

    I've heard this (conversions) being pushed lately but I may be missing one thing (or more). Currently at six figures, 6 years from retirement and completely debt free and I find it hard to believe that the total tax burden from the earnings on my traditional IRA will cost me more in retirement than the tax rate I'm at now..I'm thinking unless I draw out six figures during retirement (and I lead a much simpler life style than that) I'm better off staying traditional.

  • Report this Comment On January 06, 2010, at 5:21 PM, Fool wrote:

    There may be an alternative. If you are an independent contractor or similar situation, such as a realtor like my wife and I, and your expenses substantially exceed your income (sadly the case here), your CPA can do a pro forma 2009 tax calculation now to determine about how much you are short in income.

    Say it's $80,000 (you spent $80,000 more in deductible business expenses than your income). I believe you can then withdraw $80,000 from your convential IRA (withdrawals from conventional IRA's are taxed as ordinary income), to equal your expenses, and if my theory is correct, pay no taxes on the $80,000 IRA withdrawal. Comments?

  • Report this Comment On January 06, 2010, at 5:24 PM, nin4086 wrote:

    Agree with jcurran516...

    Yes, if you are going to convert it is a good idea to convert before the investments appreciate enough to put you in a higher tax bracket. And that point is well taken.

    But why do these articles assume that conversion is a good idea to begin with? It all depends on your tax rate when you retire. Most likely the tax rate will be lower because you won't have income from a job.

  • Report this Comment On January 06, 2010, at 5:25 PM, maccdw wrote:

    When you convert (part of, or all of) a Trad IRA into a Roth IRA, the portion that is taxed is the non-taxed value of your Trad IRA, as a share of the value at the previous year-end. Yes, that's a mouthful. However, it's easy to understand and to compute. Example: Your Trad IRA is worth $100,000 on 12/31/2009. Years ago, when you contributed pre-tax dollars to it, you put in $20,000 pre-tax and the rest (say, $50,000 with the balance being earnings). Today, in 2010, you decide to convert $40,000 into your Roth IRA. You will pay taxes on 80% of the $40,000 you convert. IOW, $32,000 will be taxed at your regular tax rate.

    Next year, if you convert more from the same Trad IRA, you'll take the same $20,000 away from the value as of 12/31/10, and you be taxed on that share of the amount you convert. Example: Your Trad IRA is worth $60,000 on 12/31/10 (you converted $40,000 of it in 2010, and you have earned a bunch in 2010). So, if you convert another $30,000 in 2011 into your Roth, you'll pay taxes on $20,000 which is 2/3 (of your $60,000 Trad IRA, $40,000 has never been taxed) of the $30,000 you're converting.

    Sounds complex in writing, but it is very simple. It is not explained accurately by Mr. Caplinger in this Foolish article.

  • Report this Comment On January 06, 2010, at 5:31 PM, maccdw wrote:

    Oops. I should not have said "...and you earned a bunch in 2010..."

    If, in my example, your Trad IRA had earned a bunch in 2010, it would be worth more than $60,000 a/o 12/31/10.

    The math stays the same: Say your 12/31/10 balance is $75,000 (your Trad IRA earned $15,000 during 2010). $20,000 is 27% of $75,000, so if you convert $30,000 in 2011 to your Roth, you'll pay taxes on 73% of the $30,000.

  • Report this Comment On January 06, 2010, at 5:33 PM, shelli2 wrote:

    I'm thinking if I pay the gov't off now and convert to a roth, it may be cheaper in the fuiture when I withdraw my traditional IRA at a probably higher tax rate than the tax rate is now for a traditional IRA withdrawal. Unless of-course the gov't does the un-believable and lowers taxes by then. HA!

  • Report this Comment On January 06, 2010, at 5:39 PM, Wradical wrote:

    Whether or not you convert in the first place can depend on a lot of things, including what your plans for your IRA are.

    If your IRA is a place to accumulate funds to pass on to your heirs, and you never want to spend it, converting to a Roth is probably a good idea from an estate planning view. It eliminates the RMD rules when you hit 70½, which allows for more accumulations, and gets the estate tax, if any, out of the estate.

    But if you're going to use your IRA to provide for living expenses in your retirement years, WHOA! You really have to do some serious analysis. For retirees, things like medical expenses and property taxes can be big budget items, as well as deductions. And IRA distributions used to pay for them are therefore sheltered. So you may never have to pay a lot of tax on funds coming out of a traditional IRA used to pay for things like that. And paying a big percentage up front now, while still working, for the privilege of calling it a Roth, can get a big malpractice claim for the advisor who recommended the conversion.

  • Report this Comment On January 06, 2010, at 5:42 PM, DMalarkey wrote:

    The reason for converting any IRA to a Roth IRA is to avoid taxes when you start withdrawing funds from the Roth IRA. The CURRENT tax law allows you to do that. But, do you believe that Congress will allow the tax-free withdrawal when it needs additional funds to cover its outlays? Remember all the promises that the funds that you withdraw from Social Security would be withdrawn tax-free? These are funds on which you have already paid income tax. Now, the funds are taxed again. I will never convert any of my IRA funds to Roth IRA because I do not trust the Congress to live up to the agreement that Roth IRA funds will never be taxed in the future.

  • Report this Comment On January 06, 2010, at 5:44 PM, howlieb wrote:

    some clarification, please.

    as far as we know,

    will be able to transfer a selected amount from traditional to roth?

    will that be available for many years or is there a time limit?

    if we transfer to the roth today can we recharacterize

    a portion in transfering back to the traditional?

    would a recharacterization limit any future transfers to a roth?

    thanx for any clarification.

  • Report this Comment On January 06, 2010, at 6:20 PM, foolishlew wrote:

    It sounds to me like many of you think the Roth conversion decision is a simple process. It isn't so - unless you don't care if you fall into one of the many traps in the system. For instance, if your IRA is made up of several types of contributions like combined IRAs from several employers, taxed and pretaxed contributions, inherited IRAs, conversions of 401K accounts -- or many others, your 'do-over' may be prohibited or limited - your future withdrawals may be governed by some proportioning - your tax rates may be affected - the list goes on and on. It will pay dearly to have an expert in Roth conversions by your side. There aren't many that REALLY know all the details regardless of their 'professional title' Also, as far as future tax rates being lower on annual distributions than on the larger conversion -- you might want to think again. There are already hefty increases in income tax rates in the works and the effect of the out of control spending of the current government administration will have only one result -- considerably higher tax rates. The income tax rate today is about the lowest it has been in our lifetime - It will only go up.

  • Report this Comment On January 06, 2010, at 6:40 PM, noneyet wrote:

    In a recent round table(Barron's, I believe) a case was made that the goverment, ravenous for enormously more tax revenue in the not to diatant future, has 9 ways to effectively tax the distributions from a "tax free" Roth distributions. 33% of indivuals over 55 years of age have saved less than $ 10,000 for retirement!....SS won't cut it for them (or me for that matter)......the political pressure to "do something" will lead for those of us that have planned to "share our good fortune." If you do convert....do only a small %. Emmigration anyone?

  • Report this Comment On January 06, 2010, at 7:26 PM, rd80 wrote:

    "And best of all, if you convert now, you have until Oct. 15, 2011 to give the IRS your final answer."

    Except that by Oct 15, 2011 very few of us will know the most important piece of information needed to make the decision. How does my marginal tax rate today compare with my tax rate after retirement?

    The reset button is pretty useless if I won' t have the info needed to use it intelligently before it expires.

  • Report this Comment On January 06, 2010, at 8:01 PM, Camacam wrote:

    I have questions about the recharacterization:

    If I convert 1000 shares of XYZ @ $100/share (ie $100,000) and it subsequently drops to $50/share (on the date I choose to recharacterize) but I sold it earlier at $70/share how much do I get to recharacterize?

    Do I convert each position in my traditional IRA to a separate Roth IRA so I can track them individually and then cherry pick the positions that decline to recharacterize thus minimizing the taxable income?

    I do not anticipate having to draw on my IRA (I'm blessed) so would like to leave a much as possible to my children and/or grandchildren for their lifetimes.

  • Report this Comment On January 06, 2010, at 8:02 PM, TMFGalagan wrote:

    @bookie0 -

    You're absolutely right: if you have a nondeductible contribution to a regular IRA, you don't have to pay taxes on that portion when you convert.

    best,

    dan (TMF Galagan)

  • Report this Comment On January 06, 2010, at 8:05 PM, TMFGalagan wrote:

    @bookie0 -

    Very good point. You're absolutely right that if you've been making nondeductible IRA contributions, you don't get taxed on them again if you convert.

    best,

    dan (TMF Galagan)

  • Report this Comment On January 06, 2010, at 8:09 PM, TMFGalagan wrote:

    @jcurran516 -

    If you're at your peak earnings, then you definitely might be better off not converting right now. The main question is where your income will come from when you retire. If it's coming from taxable distributions from traditional IRAs and your spending stays constant or goes up, then it's possible your tax bracket will stay the same or even go up. But for many, taxable income will go down in retirement, and it'll make sense to wait until then to convert or just stick with a regular IRA.

    If you're not at peak earnings right now -- either because you've already retired or you're early in your career -- then converting more often makes sense.

    best,

    dan (TMF Galagan)

  • Report this Comment On January 06, 2010, at 8:17 PM, TMFGalagan wrote:

    @howlieb - Taking your questions one by one:

    You can select the exact amount you want to convert.

    There's no way to guess what future tax law will allow you to do.

    I believe you can choose to recharacterize all or only a portion of what you originally convert. It limits further conversions in that you're not allowed to reconvert in the same year or within 30 days after you recharacterize.

    These rules get incredibly complicated, so it's best to check with your tax professional to go through your own particular situation.

    best,

    dan (TMF Galagan)

  • Report this Comment On January 06, 2010, at 8:17 PM, shtmtlman wrote:

    adding to nin4086...

    true you may not have the income from a job, but taxes will most likely be higher when you retire since they are at historically low levels now.

  • Report this Comment On January 06, 2010, at 8:19 PM, TMFGalagan wrote:

    @camacan -

    I've seen some experts recommend converting each piece to a separate Roth for exactly the strategy you suggest: cherry-picking gains and losses.

    I suspect that once enough people start getting fancy with it, the IRS will get Congress to put a stop to it. For now, though, it appears to be fair game.

    And I believe that it's your actual results that define the recharacterization amount, not the theoretical drop in the stock after you sold.

    best,

    dan (TMF Galagan)

  • Report this Comment On January 06, 2010, at 8:25 PM, Fool wrote:

    woodye, Congress has heard proposals from libral economic professors about creating a government "401K" and possibly a compulsory one. Some think it could include compulsory conversions of established IRA's for retirees.

    (1) Is this still under discussion in Congress and the White House

    (2) If you have converted to Roth and already paid your taxes, is it possible that would have a better chance to be converted as well.

    Having retireed from a rather viscous temporarily bankrupt company, lost 70% of a funded defined benefit program payment whose surplus went into the general PBGC fund, I am more than a little concerned it could happen again.

    Thanks for any opinion or input.

  • Report this Comment On January 06, 2010, at 8:45 PM, soycapital wrote:

    Many of the large brokerage firms have a calculator that you can figure a Roth vs a traditional IRA. I would strongly suggest that you run the numbers before making the jump. I'm sure the calculators are available other places also. Sorry if someone has already mentioned this.

  • Report this Comment On January 06, 2010, at 8:50 PM, xetn wrote:

    If I remember correctly, Social Security income was supposed to be, and was, non taxable. Since 1983 it is. What makes anyone think the same thing cannot/will not happen to Roth?

  • Report this Comment On January 06, 2010, at 9:33 PM, foolishlew wrote:

    jcurran and bookie

    Seriously -- this isn't the place to be getting Roth conversion answers. I see very naive comments and bad advice from some that make it sound like they speak from authority. I'm certainly not an expert but I've spent hours with those that are -- and I've seen examples of the pitfalls of uneducated conversions and also of not converting at all. If you are going to convert -- early - or later, consider this. You don't have to pay all the tax in the first year. Wisely invested, the growth of the Roth can offset the taxes you have to pay and in 2 years, the resulting Roth after taxes may be close to or larger than the IRA you started with. So - earlier may enable you to capture more of that offsetting growth.

    I cannot emphasize enough that if your IRAs are made up of a variety of components, know how each component is treated in a Roth and how they affect the other parts. Rules learned too late are unforgiving and penalties can be severe.

  • Report this Comment On January 06, 2010, at 10:59 PM, 0123Abc wrote:

    Some states do and some don't tax Social Security, I believe. AARP should have the info, if its .com is up to date.

  • Report this Comment On January 07, 2010, at 11:54 AM, szugyi wrote:

    Interesting to see other folks share my longstanding suspicion that Roths will not remain untaxed in the long run. I am young yet and don't trust what the taxation landscape will look like in 30 years.

    Nevertheless finally started a Roth after having only Traditional for the last 10 years. May convert some of the Trad over if I still have room left in our tax bracket.

    But I dont know the nuts and bolts. Feel free to tell me more about these severe penalties, foolishlew . . .

  • Report this Comment On January 07, 2010, at 1:04 PM, bzhayes wrote:

    To all of you roth withdrawal tax conspiracy theorists:

    Your SS analogy is not as valid as you may think. There is no comparable tax shelter to SS. The Roth has the traditional and vice versa. Future changes to IRA tax rules will have to take into account the differences between the two. They will not double tax the roth and leave in place the tax deferral for the traditional. What could very well change in the future is the marginal tax rate. So the assumption that you will have a lower tax rate when you retire is not necessarily valid.

  • Report this Comment On January 08, 2010, at 4:00 AM, galton wrote:

    Another risk that I don't think was mentioned:

    To get the ever-increasng taxes government needs from us, there is pressure building to add & increase value-added and sales taxes, as is done in Europe.

    Taxes on internet buys are inevitable. Thus gov. can keep its word to not take income tax from Roth withdrawls, but still steal an ever-increasing part of those withdrawls as you spend them.

  • Report this Comment On January 08, 2010, at 11:44 AM, MarlieP wrote:

    An additional factor no one has mentioned are state taxes or penalties. Even though the conversion may be allowed for federal purposes, all states do not currently allow the conversion -- I believe that Wisconsin does not yet, for example.

  • Report this Comment On January 09, 2010, at 10:13 PM, mpala007 wrote:

    I will keep my Roth IRA about 30% of my 457 Deferred Comp. When I need to withdraw an amount like $30k from my 457, I will pay the taxes with money from my Roth. This way I won't have to withdraw and pay taxes on $40k and have to pay tax on the extra $10k and I only will pay the taxes on the actual amount I need. This not only reduces the withdrawals on my 457 but essentially makes that money tax free and there isn't any taxes paid during any conversion.

  • Report this Comment On January 11, 2010, at 3:44 PM, howard1924 wrote:

    So many comments focus on tax rate now vs later. Who knows what rates will be? However we all know that if you pay the tax to convert, from the IRA account or otherwise, you will never be able to invest that money again. I think it is better long term to keep that money invested and hope for growth.

  • Report this Comment On January 13, 2010, at 5:27 PM, KingKev wrote:

    The conversion makes the most sense for those having a considerable amount of time prior to retirement and enough funds outside their retirement accts to pay the taxes(which can be spread over two years).

    I'll give an example(assumes a 8% rate of return on investments):

    John is 40 and has a 60,000 IRA rollover, will retire at 70. He is at a 28% tax rate currently and expects it to rise in the future.

    Taxes Paid 2011 2012

    TradIRA 0 0

    Roth $8400 $8400

    Total Taxes paid Age 70(assuming a lump sum dist and a 28% tax rate)

    TradIRA $182577

    Roth $16800

    After Tax Value age 70

    TradIRA $469483

    Roth $652060

    I put the lump sum distribution in there to better illustrate the potential tax savings.

    The fact that you don't have to touch the money and it can be passed on tax-free to any heirs are major advantages to a Roth as well. But every case is different and speaking with a tax advisor is a must prior to any conversion thoughts.

  • Report this Comment On January 13, 2010, at 10:09 PM, boger1 wrote:

    KingKev sums it up best.

    T Rowe Price and others have calculators to help one assess the merits of conversion based on current tax bracket, retirement bracket, and time until retirement.

    Trying to guess future tax policy is akin to guessing the number of angels dancing on the head of a pin; however, it is safe to assume that rates for upper earners (28% bracket and above) will be higher in the future, perhaps significantly so. Also safe to assume that the government will not touch tax status of Roth funds already saved (any existing accounts will likely be grandfathered).

    Thus two of the primary benefits of conversion (estate planning/tax benefits to heirs, and the lack of required minimum distributions) may be enough to offset any concerns over the loss of current tax-deferred principal to invest (if one were to pay the tax out of the rollover funds).

    I for one plan to convert a substantial portion of rollover IRAs from my wife's previous employers in the current tax year, but hedge by not converting all of it. To our benefit this won't raise our marginal rate (can't get any worse)...except that it WILL go up to 39.6% in 2011 as the rate schedules return to default levels.

    So there is also the consideration of paying ALL the tax in 2010 tax year vs. spreading it out over 2 years.

    In order to preserve the tax-exempt compounding effect, we will be paying the taxes out of other (already taxed) funds.

    Boy, it seems like a flat tax would be a whole lot simpler.

  • Report this Comment On January 15, 2010, at 11:02 PM, kluttzy wrote:

    Is there a minimum amount of money that must be earned to convert to a Roth? I will probably earn less than $25k in 2010. Can I for example take $50k from a Trad and start a Roth?

  • Report this Comment On March 18, 2010, at 1:35 AM, wrkdiver wrote:

    I have a 457K (government employee) and the fund management swears I CANNOT convert to a Roth until AFTER I retire - because they won't give me a disbursement until after I retire. Maybe it's different with a 401K, or do I need to unleash the dogs of government (or lawyer up)?

    Also, it's my understanding that you cannot take a withdrawal from a Roth for 5 years.

    I further heard that there is an age limit - I'm 70 3/4 now.

  • Report this Comment On March 23, 2010, at 7:23 PM, familyonthego wrote:

    Am I missing something???

    We earn over $200,000 and have not been able to contribute to a ROTH IRA for years. We have only Roth IRAs and 401(k)s. No other retirement accounts. We are in our early 40's.

    I am planning to contribute $5000 to a traditional IRA for 2009 and another $5,000 for 2010. Before year end, I will convert it to a Roth IRA (as the money has only just been put in - there will be little growth upon which to pay taxes). Can I do this every year into the future, (ie... put $5000 in a traditional IRA in January, convert it to a Roth IRA in February)? Year after year. It seems a simple way around the Roth IRA income limitations.

    What am I missing and why isn't anyone promoting this as a way around the income limitations?

    I have read the IRS publications and looked all over the internet. I cannot find anything about holding periods prior to conversion or anything else to lead me to believe this is not a viable option.

    ANYONE???

  • Report this Comment On June 10, 2010, at 6:51 PM, mandyjune wrote:

    Couldn't agree more! Roth IRAs seem to convert much better! However, when do you think is a good age to start contributing to or starting Roth IRAs? I think that as soon as one can get a full time job(seemingly difficult at this moment), it's fair to say that some contributions should be made.

    PS: Here's an article you guys can check out on how to start up a Roth IRA, too. http://www.gobankingrates.com/easy-ways-to-set-up-roth-401-k...

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Dan Caplinger has been a contract writer for the Motley Fool since 2006. As the Fool's Director of Investment Planning, Dan oversees much of the personal-finance and investment-planning content published daily on Fool.com. With a background as an estate-planning attorney and independent financial consultant, Dan's articles are based on more than 20 years of experience from all angles of the financial world.

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