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Wednesday, October 29, 2025

Rolling Over An Previous 401(okay)? Watch Out for These Gotchas.


Earlier this yr, a consumer rolled over an outdated 401(okay) into her IRAs at TD Ameritrade (the place we handle our purchasers’ investments). She obtained, appropriately, two checks from her 401(okay): one for her pre-tax 401(okay) account and one for her Roth 401(okay) account. She mailed each of these checks to TD Ameritrade…they usually had been each routinely dumped into her conventional IRA.

Not good. 

The after-tax/Roth cash ought to have been put into her Roth IRA. If it lives in her conventional IRA, then she loses a lot of the tax goodness of that after-tax cash. 

Fortunately, we caught the error shortly and had been capable of get the rollover cash correctly “located.” I then posted about it on social media, and a second consumer reached out saying that uh, she fears she might need simply performed that, too (rolling outdated 401(okay) into present 401(okay)).

It made me notice that there are most likely 1000 little (or not-so-little) ways in which rolling over your 401(okay) can go fallacious. So, as the most recent contribution to my casual, unnamed weblog sequence of “all of the bullshit you need to work out so as to handle your funds effectively on this nation,” I made a decision to write down up a bunch of ways in which rollovers can go fallacious.

I beforehand wrote an article about the fundamentals of rolling a 401(okay) to an IRA or to a different 401(okay). For right this moment’s article, I crowdsourced batshit/annoying/painful 401(okay) rollover errors from colleagues. (When you get pleasure from shows of exasperation and indignant resignation, simply ask monetary planners about how issues can go fallacious on this nation’s monetary infrastructure.)

I hope this listing helps you keep away from or repair errors when you roll over an outdated 401(okay).

[Sidebar: This is one of those times when I realize that half the value (not an exact measurement) of being a financial planner is simply that “we’ve seen a lot” and therefore know more of the stupid minutiae necessary to navigate the world of personal finance.]

Don’t Roll After-Tax or Roth Cash right into a Pre-Tax Account

That is the gotcha I discussed above. Ideally, the custodian (the monetary firm that hosts your 401(okay)) would do it correctly to start with, however clearly that doesn’t all the time occur!

You need to take note of this course of from starting to finish. Sorry.

  1. Affirm in case you have each pre-tax and after-tax/Roth cash in your outdated 401(okay).
    It is best to be capable to see this on the 401(okay) web site. I do know some web sites are simply Such Utter Sh*t that you could’t, wherein case, have a look at statements or name the 1-800 quantity.



  2. When you do have each varieties of cash, affirm along with your outdated 401(okay) custodian that you’re going to get two checks, one from every account.
    When you’re fortunate, the cash will likely be moved electronically, however I checks are, in some way (!!), nonetheless the norm.



  3. As soon as these checks are despatched to the brand new 401(okay) custodian, maintain monitor of them being deposited into the brand new 401(okay).
    Pre-tax cash into the pre-tax account. After-tax cash into the Roth account. 



  4. If you don’t see the best amount of cash going into the best account, name/chat/provider pigeon your new 401(okay) custodian and get it fastened ASAP!

Take into account Rolling After-Tax/Roth Cash into an IRA (Even If Pre-Tax Cash Goes into Your New 401(okay))

If you’re rolling your outdated 401(okay) into your new 401(okay), and you’ve got after-tax/Roth cash, however your new 401(okay) doesn’t have a Roth possibility (extremely unlikely in tech, however doable), then you possibly can all the time roll your pre-tax cash into the 401(okay) and the Roth cash right into a Roth IRA. Sure, you possibly can break up them up like this!

Even for those who can roll your Roth cash into your new 401(okay), you may not need to. Roth IRAs have some good options that Roth 401(okay)s do not, notably, you possibly can extra simply withdraw cash from a Roth IRA with out incurring taxes or penalties.

Don’t Ignore Communications from Your Previous Employer/401(okay) Plan

Monetary advisor Daniel Yerger tells this story:

A medical clinic shut down its 401(okay) plan in 2019. Notifications had been despatched out to all present and ex-employees with belongings within the plan, saying that they’d a 90-day interval to roll over their belongings; nobody may keep in as a result of the plan was being closed. 




The clinic began a brand new 401(okay) plan in 2022. The outdated plan’s TPA [Third Party Administrator, the company that manages day-to-day aspects of the 401(k) plan] contacted the clinic to say that they couldn’t do this as a result of the outdated plan, although now not reporting or energetic, nonetheless had 4 contributors with balances. 




As a result of the outdated 401(okay) plan hadn’t been compliant for over one plan yr, these belongings had been now non-qualified [i.e., they no longer had the tax protections of the 401(k)], and subsequently topic to tax and penalties. All 4 individuals had been ex-employees who ignored their notifications.

One worker subsequently ended up with a $40,000 taxable examine mailed to them just a few years after the outdated 401(okay) was shut down.

Ethical of the story? Don’t ignore communications about outdated accounts. 

Daniel’s story isn’t the one dangerous factor that might occur to you for those who do. Funding selections can change. Bills can change. Custodians can change. You need to know what’s occurring.

If You’ve Moved Lately, Don’t Overlook to Replace Your Mailing Deal with

[Added 7/18/2024] Each time I share this weblog publish on social media, I get one other horror story or warning, normally from a fellow advisor, based mostly on their expertise with purchasers. A colleague on Twitter (sure, Twitter, dammit!) warned, “for these on the transfer, make certain the sending recordkeeper has your appropriate mailing tackle earlier than you request a direct rollover examine.”

The very last thing you need (okay, there most likely belongings you need much less, but it surely’d nonetheless be an enormous PITA) is to request the rollover examine and have it despatched to an outdated tackle.I’ve by no means skilled this with my purchasers, however I can simply extrapolate simply how unbelievably troublesome this is likely to be to undo.

Don’t Overlook to Set Up Your Beneficiaries Once more within the New Account

I hope you’ve gotten your beneficiaries (i.e., who will get this cash for those who die?) designated on all of your 401(okay)s and IRAs (and life insurance coverage insurance policies, too, whereas I’m at it). It’s not necessary till It Actually Is And Now It’s Too Late. Which is to say, it’s essential. 

When you’ve got a 401(okay) with out beneficiaries set correctly, the fallacious individuals would possibly get your cash for those who die.

When you’ve got beneficiaries designated in your outdated 401(okay) and also you roll that cash into a brand new account, these beneficiary designations don’t switch with the cash. So, guarantee that that new account has beneficiaries arrange the best way you need.

(ht @ monetary advisor Brian Gawthrop for this contribution)

Don’t Do an Oblique Rollover

Whenever you roll over a 401(okay), it will possibly occur one in all two methods:

  • A direct rollover: the cash from the 401(okay) by no means touches any taxable account you personal—like a checking account or taxable funding account—and goes instantly out of your outdated 401(okay) into your new 401(okay) or an IRA. The examine is made out to one thing like “Constancy fbo [for benefit of] Meg Bartelt”

     




  • An oblique rollover: the cash does contact such a taxable account. The examine is made out to “Meg Bartelt.”

    To calm your anxieties (“OMG, am I going to by chance do an oblique rollover?”), let me simply say that, in my expertise, oblique rollovers are far much less frequent. I’ve in truth by no means seen this with our purchasers within the tech business.

Right here’s how an oblique rollover works:

  1. Let’s say your outdated 401(okay) is $100,000. 



  2. You do an oblique rollover, and the 401(okay) cash is distributed on to you.



  3. Your outdated employer routinely withholds 20% of the steadiness to pay earnings taxes, $20,000.



  4. You obtain a examine for $80,000 and put it in your IRA.



  5. When you don’t do anything, you now owe earnings taxes and a penalty on that $20,000, as a result of it has been deemed a withdrawal/distribution out of your 401(okay)…and you’ve got $20,000 much less in your retirement account than you used to. 



  6. To keep away from this, you need to provide you with $20,000 money from…someplace to additionally put into your IRA (for a complete of the unique quantity of $100,000), and you then’ll get the $20,000 withholding again at tax time.

Many individuals don’t simply have an additional $20,000 money (or no matter quantity) hanging round. And lots of different individuals don’t notice they’ll get taxed and penalized in the event that they don’t deposit it of their IRA.

Brian Gawthrop’s recommendation? “If the examine is made out to you, ship it again and don’t deposit it in your checking account.”

(ht @Andy Lindeman for this contribution)

Don’t Roll Your 401(okay) Over Too Rapidly

When you roll over your outdated 401(okay) within the first few weeks after leaving your job, it’s doable that you just’ll must request a second 401(okay) rollover shortly thereafter. Why? Two doable causes:

  1. As a result of for those who don’t wait to your ultimate paycheck—and the 401(okay) contribution that comes out of it—to completely course of earlier than doing a 401(okay) rollover, you then’ll have a bit extra money contributed to your 401(okay) after you’ve rolled a lot of the cash out. (ht @ monetary advisor Luis Guardia for this contribution. Advisor Jeff Bograd assures me that “A whole lot of plans are arrange so you possibly can’t request a distribution for a particular time period following termination of employment particularly to keep away from residual balances.” So, this gotcha most likely isn’t quite common.)
  2. Your organization does a 401(okay) match “true up” after the top of the fiscal yr. When you depart your job early within the yr and roll your cash out of your 401(okay) earlier than the true-up cash “lands” in it, you’ll obtain the true up into the now-empty 401(okay) account. (ht @ Andy Lindemann; I’m crowd-sourcing this mofo!)

Not the top of the world. Only a ache.

Don’t Depart It Too Lengthy

I normally describe rolling over an outdated 401(okay) as “necessary, however not pressing” as a result of, within the tech business, nearly all 401(okay)s have low prices and broadly diversified funding choices. Particularly in a world the place there normally are pressing monetary duties to maintain, I believe it’s necessary to tell apart pressing from not.

However for those who depart it for years, the psychological hurdle to Simply Doing It (finally) goes to get increased and better. Not less than, that’s what I’ve seen with our purchasers. [Added 7/18/2024] We had one consumer (God bless ‘im) who waited so lengthy to roll his outdated 401(okay) account over, and the one proof he had of it was a decade-old (by no means deposited) rollover examine, that we needed to play sleuth simply to determine the place the cash now lived. (Reply? The state’s unclaimed property division.) The jury continues to be out about how he’ll truly get the cash again

So, whereas, once more, it’s not mandatory to roll your 401(okay) over quickly after leaving your final job, in case you have a very good place to roll it to, you’re most likely higher off simply getting it performed performed DONE now as an alternative of getting to summon the motivation sooner or later.


I’m certain there are different gotchas. The financial-services business appears customized made to journey up even essentially the most diligent of us. However this can be a actually robust begin to the listing.

Bonne probability!

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Disclaimer: This text is offered for academic, basic info, and illustration functions solely. Nothing contained within the materials constitutes tax recommendation, a suggestion for buy or sale of any safety, or funding advisory providers. We encourage you to seek the advice of a monetary planner, accountant, and/or authorized counsel for recommendation particular to your scenario. Copy of this materials is prohibited with out written permission from Move Monetary Planning, LLC, and all rights are reserved. Learn the total Disclaimer.

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