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Tax Benefits Of In-Plan Conversions Of After-Tax 401(K) Contributions, #304

Retire With Ryan

Release Date: 05/05/2026

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More Episodes

On this episode, I’m digging into the ins and outs of in-plan Roth conversions. You'll learn what it means to convert pre-tax 401(k) dollars to a Roth 401(k), who is eligible, and why it might make sense for your retirement strategy. I cover the practical steps for making these conversions, and highlight the benefits and drawbacks. I also share a real-life example of how a client navigated her options to maximize her retirement savings. 

You will want to hear this episode if you are interested in...

  • [00:00] In-plan Roth conversions
  • [01:51] What is an in-plan Roth conversion?
  • [02:38] Eligibility for in-plan Roth conversions
  • [04:48] Real-life story of after-tax contributions in a client’s 401(k)
  • [06:07] Convert after-tax contributions plus gains within the 401(k) plan to Roth 401(k)
  • [08:38] Rolling over after-tax contributions and gains to IRAs outside 401(k)
  • [10:21] Preventing funds from sitting in a money market account

 

The In-Plan Roth Conversion

An in-plan Roth conversion allows participants to transfer funds from the traditional, pre-tax portion of their 401(k) into the after-tax Roth component of the same plan. This means you’re taking money that has not yet been taxed and converting it into money that—after the conversion taxes are paid—will grow and can be withdrawn tax-free in retirement.

This strategy is different from Roth IRA conversions, which involve moving money from a traditional IRA into a Roth IRA, often at the same financial institution. In-plan conversions, on the other hand, streamline the process by keeping all assets within your employer-sponsored 401(k), offering simplicity and potentially access to preferred investment options.

 

Who Should Consider an In-Plan Roth Conversion?

In-plan Roth conversions can be especially valuable if you anticipate being in a lower tax bracket this year compared to future years, or if you want to build a tax-free income stream for retirement. Additionally, if you already have after-tax contributions in your 401(k), converting those funds can optimize your tax efficiency by ensuring that all future gains are tax-free.

 

Real-Life Example: Amy’s Roth Conversion Journey

Let’s look at the example of “Amy,” who worked with me to create a financial plan. Amy had been contributing after-tax money to her General Motors 401(k), accumulating $63,000 in after-tax contributions and $40,000 in gains. 

Here’s how her options played out:

In-Plan Roth Conversion:

Amy could have converted both her after-tax contributions and the gains to the Roth 401(k). However, the $40,000 in gains would be taxable in the year of conversion, amounting to roughly $10,500 in taxes, or 26%. This would put her on track for approximately $200,000 in Roth assets in 10 years, assuming market growth.

Rollover to IRAs:

Alternatively, Amy chose to roll her after-tax contributions to a Roth IRA and the gains to a traditional IRA. This strategy avoided immediate taxation on the $40,000 in gains. The after-tax funds would grow tax-free in the Roth IRA, and future conversions of the traditional IRA can be planned according to her tax situation.

Amy's example highlights the importance of reviewing your plan’s rules, weighing tax implications, and considering your long-term retirement goals.

 

Conversion Best Practices

If you have after-tax contributions in your 401(k), now is the time to develop a plan. Consider converting these funds sooner rather than later to maximize the potential for tax-free compounding growth. Some plans allow automated conversions, but others require regular follow-ups with your provider.

In-plan Roth conversions can be a powerful tool to improve your retirement outlook. By understanding your plan’s rules, analyzing your current and future tax situations, and executing a smart conversion strategy, you can unlock significant tax advantages and peace of mind for your golden years.



Resources Mentioned

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