2026 Roth IRA Conversions Explained: Smart Timing and Costly Mistakes

Roth conversions can be one of the most powerful tax planning tools in retirement, but they are not always beneficial. A Roth conversion involves moving money from a pre-tax account into a Roth account and paying taxes now to avoid taxes later. At Greenbush Financial Group, our analysis shows that Roth conversions are most effective when done strategically across multiple years, not as a one-time decision.

What Is a Roth Conversion and How Does It Work?

A Roth conversion moves funds from a Traditional IRA or 401(k) into a Roth IRA or 401(k).

Key Mechanics

• Converted amount is taxed as ordinary income

• No early withdrawal penalty if done correctly

• Future growth and withdrawals are tax-free

• No Required Minimum Distributions (RMDs) for Roth IRAs

Example

• Convert $50,000 from an IRA to a Roth IRA

• Pay taxes on $50,000 this year

• Future withdrawals are tax-free

At Greenbush Financial Group, we view Roth conversions as a way to “prepay taxes” at potentially lower rates.

When Roth Conversions Make Sense

There are specific scenarios where Roth conversions can significantly improve long-term outcomes.

1. Low-Income Years in Early Retirement

The period between retirement and starting Social Security or RMDs is often ideal.

• Lower taxable income

• Opportunity to fill lower tax brackets

• Reduce future tax burden

2. Before Required Minimum Distributions (RMDs)**

RMDs can force higher taxable income later in retirement.

• Converting early reduces future RMDs

• Helps avoid higher tax brackets in your 70s

3. Expecting Higher Future Tax Rates

If you believe your future tax rate will be higher:

• Paying taxes now may be beneficial

• Locks in current tax rates

4. Large Pre-Tax Account Balances

High IRA or 401(k) balances can create tax challenges later.

• Large RMDs

• Increased IRMAA surcharges

• Higher Social Security taxation

5. Leaving Assets to Heirs

Roth accounts can be more tax-efficient for beneficiaries.

• Tax-free withdrawals for heirs

• No lifetime RMDs for original owner

At Greenbush Financial Group, Roth conversions are often used as part of a broader estate and tax planning strategy.

When Roth Conversions May Not Make Sense

Roth conversions are not always the right move.

1. Already in a High Tax Bracket

If converting pushes you into a higher bracket:

• You may pay more tax than necessary

• Reduces the benefit of the conversion

2. Short Time Horizon

If you expect to use the money soon:

• Limited time for tax-free growth

• Less benefit from conversion

3. Paying Taxes From the Conversion Itself

Using IRA funds to pay taxes reduces the amount converted.

• Decreases long-term growth potential

• Less efficient overall

4. Expecting Lower Future Tax Rates

If your income will decrease later:

• You may pay more tax now than necessary

5. Impact on Medicare and Social Security

Conversions increase taxable income.

• May trigger IRMAA surcharges

• Can increase taxation of Social Security

At Greenbush Financial Group, we often see Roth conversions backfire when these factors are not considered.

The “Tax Bracket Filling” Strategy

One of the most effective ways to approach Roth conversions is by filling up lower tax brackets.

How It Works

• Identify your current tax bracket

• Convert just enough to stay within that bracket

• Avoid jumping into higher brackets

Example

• Top of 12% bracket = target income level

• Convert enough to reach that limit

• Stop before entering the 22% bracket

This strategy spreads conversions over multiple years, reducing overall tax impact.

Roth Conversions and IRMAA Considerations

Roth conversions increase your income for that year, which can affect Medicare premiums.

Key Impact

• Higher income can trigger IRMAA surcharges

• IRMAA is based on income from two years prior

Planning Tip

Balance Roth conversions with IRMAA thresholds to avoid unnecessary premium increases.

A Multi-Year Roth Conversion Strategy Example

Scenario

• Age 62, recently retired

• $800,000 in IRA

• Low income before Social Security

Strategy

• Convert $40,000–$60,000 annually

• Stay within a lower tax bracket

• Delay Social Security

Outcome

• Reduced future RMDs

• Lower lifetime taxes

• Increased tax-free income later

At Greenbush Financial Group, this type of phased approach is often more effective than a single large conversion.

Common Roth Conversion Mistakes

• Converting too much in one year

• Ignoring tax bracket thresholds

• Overlooking IRMAA impacts

• Not coordinating with Social Security timing

• Failing to plan conversions over multiple years

Final Thoughts

Roth conversions can be a powerful tool, but only when used strategically. The goal is not simply to convert assets, but to reduce lifetime taxes and create more flexibility in retirement income.

At Greenbush Financial Group, our analysis shows that the most successful strategies involve careful timing, tax bracket management, and long-term planning.

Rob Mangold

About Rob……...

Hi, I’m Rob Mangold. I’m the Chief Operating Officer at Greenbush Financial Group and a contributor to the Money Smart Board blog. We created the blog to provide strategies that will help our readers personally, professionally, and financially. Our blog is meant to be a resource. If there are questions that you need answered, please feel free to join in on the discussion or contact me directly.

1. Is it a bad idea to retire in a down market?
   Not necessarily, but it increases sequence of returns risk and requires careful planning.
2. How much cash and short-term fixed income should I have in retirement?
   Typically 1 to 3 years of living expenses.
3. Should I stop withdrawals during a downturn?
   Not entirely, but reducing withdrawals can improve long-term outcomes.
4. Can a market downturn ruin my retirement plan?
   It can if not managed properly, especially in the early years of retirement.
5. What is the best strategy during a market downturn?
   Maintain a cash reserve, adjust withdrawals, stay invested, and focus on long-term planning.

2026 Tax-Efficient Retirement Withdrawals: How to Keep More of Your Money

A tax-efficient retirement withdrawal strategy focuses on minimizing taxes while creating consistent income throughout retirement. The order in which you withdraw from taxable, tax-deferred, and Roth accounts can significantly impact how long your money lasts. At Greenbush Financial Group, our analysis shows that strategic withdrawals can reduce lifetime taxes and increase net retirement income.

Understanding the Three Types of Retirement Accounts

Before building a withdrawal strategy, it is important to understand how different accounts are taxed.

1. Taxable Accounts (Brokerage Accounts)

• Capital gains taxes apply when investments are sold

• Long-term capital gains rates are often lower than income tax rates

• Dividends may also be taxed annually

2. Tax-Deferred Accounts (Traditional IRA, 401(k))

• Withdrawals are taxed as ordinary income

• Required Minimum Distributions (RMDs) apply starting in your 70s

3. Tax-Free Accounts (Roth IRA, Roth 401(k))

• Qualified withdrawals are tax-free

• No RMDs for Roth IRAs

• Provides flexibility for tax planning

At Greenbush Financial Group, we view these three “buckets” as the foundation of any tax-efficient withdrawal plan.

The Traditional Withdrawal Order Strategy

A common approach is to withdraw funds in a specific sequence to manage taxes over time.

Standard Withdrawal Order

1. Taxable accounts first

2. Tax-deferred accounts second

3. Roth accounts last

Why This Strategy Works

• Allows tax-deferred accounts to continue growing

• Delays ordinary income taxes

• Preserves Roth accounts for later years or legacy planning

However, this strategy is not always optimal in every situation.

Why a Blended Withdrawal Strategy May Be Better

Strictly following the traditional order can sometimes lead to higher taxes later in retirement.

The Problem

If you delay withdrawals from tax-deferred accounts too long:

• RMDs can become large

• You may be pushed into higher tax brackets

• Social Security may become more taxable

• Medicare premiums (IRMAA) may increase

A More Strategic Approach

At Greenbush Financial Group, we often recommend a blended withdrawal strategy:

• Withdraw from taxable accounts

• Supplement with partial IRA withdrawals

• Use Roth accounts strategically when needed

This helps smooth out taxable income over time rather than creating spikes later.

Roth Conversions: A Key Tax Planning Tool

One of the most powerful strategies in retirement is converting pre-tax money into Roth accounts.

How It Works

• Move funds from a Traditional IRA to a Roth IRA

• Pay taxes now at current rates

• Future growth and withdrawals are tax-free

When It Makes Sense

• Years with lower income (early retirement before Social Security)

• Before RMDs begin

• When tax rates are temporarily lower

Example

• Convert $50,000 from IRA to Roth

• Pay tax today at a lower rate

• Reduce future RMDs and taxes

At Greenbush Financial Group, Roth conversion strategies are often a cornerstone of long-term tax planning.

Managing Your Tax Bracket Each Year

Instead of focusing only on which account to withdraw from, it is often more effective to focus on your tax bracket.

Strategy

• Fill up lower tax brackets intentionally

• Avoid jumping into higher brackets

• Coordinate withdrawals with Social Security timing

Example

If the 12% tax bracket ends at a certain income level:

• Withdraw just enough from IRA to stay within that bracket

• Use Roth or taxable accounts for additional income needs

This approach allows for more control over lifetime taxes.

How Social Security Impacts Your Tax Strategy

Social Security income can change how your withdrawals are taxed.

Key Considerations

• Up to 85% of Social Security benefits can be taxable

• Additional income from IRA withdrawals can increase taxation

• Timing Social Security can impact your tax plan

Planning Insight

Delaying Social Security while using IRA withdrawals or Roth conversions early in retirement can sometimes lead to better long-term outcomes.

Avoiding Common Retirement Tax Mistakes

Many retirees unintentionally increase their tax burden.

Common Mistakes

• Waiting too long to withdraw from tax-deferred accounts

• Ignoring Roth conversion opportunities

• Triggering higher Medicare premiums (IRMAA)

• Not coordinating withdrawals with tax brackets

• Over-withdrawing in a single year

At Greenbush Financial Group, we often see that small adjustments can lead to significant tax savings over time.

A Simple Example of a Tax-Efficient Withdrawal Plan

Scenario

• Age 62, retired

• $1,000,000 in savings

  • $400,000 IRA

  • $300,000 Roth IRA

  • $300,000 brokerage

Strategy

• Withdraw from brokerage for living expenses

• Convert $30,000–$50,000 annually from IRA to Roth

• Delay Social Security until later years

• Use Roth funds strategically after RMD age

Result

• Lower lifetime taxes

• Reduced RMD impact

• Greater flexibility in retirement

Final Thoughts

A tax-efficient withdrawal strategy is not about following a fixed rule. It is about coordinating income sources, tax brackets, and long-term planning.

At Greenbush Financial Group, our analysis shows that retirees who proactively manage taxes throughout retirement often keep significantly more of their income and reduce the risk of large tax surprises later in life.

Rob Mangold

About Rob……...

Hi, I’m Rob Mangold. I’m the Chief Operating Officer at Greenbush Financial Group and a contributor to the Money Smart Board blog. We created the blog to provide strategies that will help our readers personally, professionally, and financially. Our blog is meant to be a resource. If there are questions that you need answered, please feel free to join in on the discussion or contact me directly.

1. What is the best order to withdraw retirement funds?
   Typically taxable accounts first, then tax-deferred, then Roth, but a blended strategy is often more effective.
2. Are Roth withdrawals always tax-free?
   Yes, if the account meets the qualified distribution rules.
3. What is a Roth conversion?
   It is when you move money from a pre-tax account to a Roth account and pay taxes now to avoid taxes later.
4. How can I reduce taxes on retirement income?
   By managing tax brackets, using Roth conversions, and coordinating withdrawals across account types.
5. Do Required Minimum Distributions increase taxes?
   Yes, RMDs are taxable and can push you into higher tax brackets if not planned for

Self-Employment Side Hustle? Benefits of a Solo 401(k) Plan

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

‍Today, more and more individuals have side hustles in addition to their main W-2 jobs. Others may be full-time business owners but only generate a modest amount of self-employment income. In both cases, one of the most powerful retirement and tax planning tools available is the Solo 401(k) plan.

In this article, we’re going to walk through some of the tax strategies and wealth accumulation strategies we use with clients who have self-employment income and may benefit from a Solo 401(k). Specifically, we’ll cover:

• What a Solo 401(k) plan is

• How a Solo 401(k) can reduce tax liability

• How to use a Solo 401(k) to build a larger Roth bucket

• How to decide between pre-tax vs. Roth contributions

• What happens when the Solo 401(k) is terminated

What Is a Solo 401(k) Plan?

A Solo(k) plan, also called an Individual(k), is a retirement plan designed for owner-only businesses. This means the business cannot have any full-time employees working more than 1,000 hours per year, other than the owner and possibly their spouse.

Because these plans only cover the business owner, they are typically simple to administer, often have little to no administrative costs, and still provide the full benefits of a traditional 401(k) plan.

Solo 401(k) plans include:

• Pre-tax employee deferrals

• Roth employee deferrals

• Employer contributions

• Potential 401(k) loan provisions

Contribution Limits (2026)

Solo 401(k) plans allow for relatively high contribution limits. For 2026:

• Employee deferral limit: $24,500 (under age 50)

• Age 50+ catch-up: $32,500 total deferral

• Employer contribution: Up to 20% of net self-employment income (sole proprietor/partnership)

• S-Corp employer contribution: Up to 25% of W-2 wages

Example

Let’s say a sole proprietor generates $40,000 in net self-employment income and is under age 50.

They could contribute:

• $24,500 as an employee deferral

• $8,000 as an employer contribution (20% of $40,000)

That’s a total of $32,500 going into a retirement account from just $40,000 of side hustle income.

That’s a powerful savings and tax planning opportunity.

Reducing Tax Liability

One of the primary reasons business owners establish Solo 401(k) plans is to reduce their overall tax liability.

If someone has:

• W-2 income: $200,000

• Self-employment income: $40,000

That self-employment income gets stacked on top of their W-2 income and may be taxed at a high marginal tax rate.

However, if that business owner contributes $30,000 of that $40,000 into a Solo 401(k) using pre-tax contributions, they may only pay income tax on $10,000 instead of the full $40,000.

That can result in significant tax savings.

Solo(K) Plans Can Potentially Eliminate Federal & State Income Taxes

If a business owner has less than the annual employee deferral limit in net income, they may be able to defer 100% of their self-employment income into the Solo 401(k).

Example:

• Net self-employment income: $20,000

• Employee deferral limit: $24,500

Since the income is lower than the limit, they could defer the entire $20,000 pre-tax, avoiding federal and state income tax on that income.

Note: They still must pay self-employment tax, but they can avoid income tax on that portion.

Building a Larger Roth Bucket

Another major benefit of a Solo 401(k) is the ability to build Roth retirement assets, which can be extremely valuable long-term.

Roth contributions are made after-tax, but:

• The money grows tax-deferred

• Withdrawals after age 59½ are tax-free

One major advantage of a Roth Solo 401(k) is:

There are no income limits for Roth 401(k) contributions.

This is very important because many high-income earners are phased out of Roth IRA contributions, but they can still contribute to a Roth Solo 401(k).

Example

Imagine a 29-year-old business owner with a side hustle contributing $24,500 per year to a Roth Solo 401(k). The money grows tax-deferred for 30 years and then all of the earning in the account can be withdrawn tax free after age 59½.

We also see this strategy used for retirees who do consulting work. If someone is 65+ and earning self-employment income but doesn’t need the income, they can contribute to a Roth Solo 401(k) and move that money into a tax-free growth bucket instead of a taxable brokerage account.

This can be a powerful long-term tax strategy regardless of age of the business owner.

To Roth or Not to Roth?

Remember, there are two types of contributions to a Solo 401(k):

1. Employee Deferral → Can be Pre-Tax or Roth

2. Employer Contribution → Typically Pre-Tax

For sole proprietors and partnerships:

• Employer contribution = 20% of net earned income

For S-Corps:

• Employer contribution = 25% of W-2 wages

• Important: Only W-2 wages count — not S-Corp distributions

While SECURE Act 2.0 opened the door for Roth employer contributions, we are still waiting on full IRS guidance for this to be widely implemented in Solo 401(k) plans. So for now, employer contributions are generally still pre-tax, while employee deferrals can be Roth or pre-tax.

General Rule of Thumb

You might consider:

• Pre-tax contributions if you are in a high tax bracket today

• Roth contributions if you are in a lower tax bracket today or want tax-free income later

This is where tax planning and coordination with a financial advisor and CPA becomes very important.

What Happens When the Solo 401(k) Is Terminated?

Eventually, the self-employment income may stop. When that happens, the Solo 401(k) is typically terminated, and the assets are rolled into IRAs.

Typically:

• Pre-tax Solo 401(k) money → Traditional IRA

• Roth Solo 401(k) money → Roth IRA

The money can then continue growing in those IRA accounts, and the Solo 401(k) plan is closed.

Working With an Advisor Who Understands Solo 401(k) Plans

Solo 401(k) plans are extremely powerful, but there are important rules and nuances business owners must be aware of.

For example:

• If you hire employees, you may have to discontinue the plan

• Plan documents must be set up properly

• Once plan assets exceed $250,000, you must file Form 5500 annually

• There are coordination issues between your CPA and financial advisor

• You must choose between pre-tax vs. Roth strategies

• You must compare Solo 401(k) vs. SEP IRA vs. SIMPLE IRA

Because of these moving parts, it’s important to work with an advisor who understands how to design and manage Solo 401(k) plans properly as part of an overall financial and tax strategy.

Our firm offers free consultations for business owners and individuals with side hustle income who want to evaluate whether a Solo 401(k) plan makes sense for their situation. If you’d like help determining whether this strategy is right for you, we’d be happy to help you build a plan around your specific goals. Feel free to schedule your complementary consult via our website.

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

Frequently Asked Questions About Solo 401(k) Plans

1. Who qualifies for a Solo 401(k)?
   Business owners with no full-time employees working more than 1,000 hours per year.
2. Can I have a W-2 job and a Solo 401(k)?
   Yes. As long as you have self-employment income, you can open a Solo 401(k) for that income.
3. How much can I contribute to a Solo 401(k)?
   In 2026, employee deferrals are $24,500 (under 50), plus employer contributions up to 20% of income (or 25% of W-2 wages for S-Corps).
4. Can I contribute 100% of my side hustle income?
   Yes, if your income is below the employee deferral limit, you may be able to defer the entire amount.
5. Do Solo 401(k) contributions reduce taxes?
   Yes, pre-tax contributions reduce your taxable income.
6. Can I make Roth contributions to a Solo 401(k)?
   Yes, employee deferrals can be Roth, with no income limits.
7. What happens when I stop my side hustle?
   The Solo 401(k) is typically rolled into a Traditional IRA and/or Roth IRA.
8. Is a Solo 401(k) better than a SEP IRA?
   In many cases, yes, because it allows Roth contributions and higher contributions at lower income levels.
9. Do I have to file anything for a Solo 401(k)?
   Once the account exceeds $250,000, you must file Form 5500 annually.
10. Can I take a loan from a Solo 401(k)?
    Some Solo 401(k) plans allow participant loans, similar to traditional employer 401(k) plans.

The Hidden Tax Problem in the FIRE Movement (and How to Fix It)

The Financial Independence, Retire Early (FIRE) movement has inspired countless professionals to save aggressively, invest efficiently, and exit the workforce decades ahead of schedule. But there’s one tax mistake many FIRE followers don’t recognize until it’s too late: overloading their savings in tax-deferred accounts.

By focusing too heavily on 401(k)s and traditional IRAs, early retirees often create a tax trap that limits flexibility before age 59½ and exposes them to higher tax bills later in life. Here’s what that mistake looks like—and how strategic balance can prevent it.

How the FIRE Tax Trap Happens

The FIRE community is built on discipline: save 50–70% of income, invest consistently, and let compounding do the rest. The problem is where those savings go. Many early retirees direct most of their contributions into pre-tax accounts to minimize taxes today—but that strategy can backfire once they stop working.

Here’s why:

• Withdrawals from traditional 401(k)s and IRAs are fully taxable as ordinary income.

• You generally can’t access these funds before age 59½ without penalties (unless you use special exceptions).

• After reaching age 73, you must start taking required minimum distributions (RMDs), which can trigger higher brackets and Medicare surcharges later.

As a result, someone retiring at 45 may find most of their wealth locked inside accounts they can’t touch for 15 years—unless they want to pay a 10% early withdrawal penalty.

At Greenbush Financial Group, we have seen FIRE followers realize this only after leaving the workforce—when their living expenses suddenly need to come from taxable or penalty-free sources they don’t have.

The Hidden Cost of Being “Too Tax-Deferred”

In the early accumulation years, it feels great to lower your tax bill with pre-tax contributions. But down the road, the strategy flips. You may have built a seven-figure retirement account, yet each withdrawal comes out as taxable income.

Example:
Imagine a 45-year-old who retires with $1.5 million, all in a traditional 401(k). They need $60,000 per year to live on. Every dollar they withdraw is taxed as ordinary income. Even at a modest 22% bracket, that’s over $13,000 in annual federal taxes—without counting state taxes or future rate increases.

The bigger the pre-tax balance, the larger the future tax burden becomes. What feels like “saving on taxes” during the accumulation phase often becomes deferring a much larger tax bill into your 50s, 60s, and 70s.

What You Should Do Instead

The key is diversification—not just by asset class, but by tax treatment.

Here’s how FIRE investors can fix or prevent the mistake:

1. Build a Roth bucket early.
   Contribute to Roth IRAs or make Roth 401(k) contributions if your income allows. Qualified Roth withdrawals are tax-free in retirement.

2. Create a taxable bridge account.
   Invest in a regular brokerage account for flexibility. Long-term capital gains and qualified dividends are taxed at lower rates—and you can access this money anytime.

3. Plan Roth conversions strategically.
   After leaving work but before Social Security or RMDs begin, your income may temporarily drop. That’s an ideal time to convert pre-tax assets to Roth at lower brackets.

4. Use the 72(t) rule cautiously.
   The IRS allows early withdrawals from IRAs using Substantially Equal Periodic Payments (SEPPs), but they’re inflexible and complex. We usually recommend using this only as a last resort.

5. Think long-term tax balance.
   The goal is to retire with assets spread across three types of accounts—pre-tax, Roth, and taxable—so you can manage your income (and taxes) in any given year.

Our analysis at Greenbush Financial Group shows that households with this “three-bucket” approach could save hundreds of thousands in lifetime taxes compared to those with all assets tied up in pre-tax accounts.

What to Watch Out For

Even within the FIRE community, not all withdrawal strategies are equal. Watch for these pitfalls:

• Underestimating future tax brackets – Low brackets today don’t guarantee low brackets later. Once RMDs and Social Security start, taxable income can spike.

• Neglecting ACA subsidies – For those buying health insurance through the Affordable Care Act, high pre-tax withdrawals can disqualify you from premium tax credits.

• Ignoring Roth conversion windows – The best time to convert is usually the first few years after leaving work, before other income streams begin.

The Bottom Line

Reaching financial independence takes planning, discipline, and sacrifice—but staying financially independent requires thoughtful tax strategy. The biggest mistake FIRE followers make is deferring too much for too long, only to face tax inflexibility later.

By intentionally building a mix of pre-tax, Roth, and taxable assets, you can control when and how you pay taxes, keeping more of your hard-earned savings over a lifetime of early retirement.

If you’re pursuing financial independence or considering an early retirement, our advisors at Greenbush Financial Group can help you run detailed tax projections and withdrawal strategies to help your FIRE plan burn bright without burning through your savings.

Rob Mangold

About Rob……...

Hi, I’m Rob Mangold. I’m the Chief Operating Officer at Greenbush Financial Group and a contributor to the Money Smart Board blog. We created the blog to provide strategies that will help our readers personally, professionally, and financially. Our blog is meant to be a resource. If there are questions that you need answered, please feel free to join in on the discussion or contact me directly.

FAQs: FIRE Movement Tax Planning

1. Why is relying only on a traditional 401(k) risky for early retirees?
   Because you can't access most of those funds without penalties until 59 1/2, and every withdrawal is taxable as income.
2. How can I access retirement savings early without penalty?
   Use taxable brokerage accounts, Roth contributions (not earnings), or the 72(t) rule for limited access.
3. Are Roth IRAs better for early retirement (pre-59 1/2)?
   Yes. Withdrawals are tax-free, and contributions can be withdrawn anytime, offering flexibility.
4. What's a good account mix for FIRE planning?
   A balanced approach-roughly one-third pre-tax, one-third Roth, one-third taxable-provides strong tax diversification.
5. Can Roth conversions help early retirees?
   Absolutely. Converting pre-tax funds during low-income years can reduce lifetime taxes and future RMDs.

Tax Rules for Selling Your House to a Family Member

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

This article was inspired by a conversation with a client who is considering selling their primary residence to their child. One of the biggest challenges in today’s housing market is affordability for first-time homebuyers. With housing prices and interest rates rising dramatically over the past five years, many parents who were already planning to downsize, relocate, or move into a more retirement-friendly home are now considering selling their home directly to their children to help them afford their first house.

While this can be a great strategy, there are a number of tax rules, gift rules, and financing considerations that need to be understood before entering into an intrafamily real estate transaction. In this article, we’re going to walk through the key areas families should consider before moving forward.

Discounting the Price of the House

One of the most common questions we get from clients is whether they should sell the house to their child at full market value or discount the price.

For example, if a house is worth $600,000, can you sell it to your child for $400,000?

The answer is yes, you can sell your house for whatever price you want. However, if you sell the home significantly below fair market value, the difference between the market value and the sale price may be considered a gift.

So if:

• Market value = $600,000

• Sale price = $400,000

• Difference = $200,000

That $200,000 could be treated as a gift to the child.

For most families, this does not mean you will owe gift tax. However, you may need to file a gift tax return because the gift exceeds the annual gift exclusion. The amount above the annual exclusion simply reduces your lifetime gift exemption, which is currently $15 million per person at the federal level.

Why Selling at Fair Market Value May Be Better

From a tax standpoint, it may actually make more sense to sell the home at full market value rather than at a discount, because of the primary residence capital gain exclusion.

• Single filer: Can exclude $250,000 of gain

• Married filing jointly: Can exclude $500,000 of gain

Example

• Purchase price: $200,000

• Current value: $600,000

• Gain: $400,000

If the parents are married, the $400,000 gain is below the $500,000 exclusion, meaning they would owe no capital gains tax even if they sell the home for full market value.

But the bigger planning opportunity is actually for the child’s future taxes.

If the child buys the home for $600,000, that becomes their cost basis. If they later sell the home for $1,000,000, their gain is $400,000, which may be fully covered by the primary residence exclusion.

However, if the parents sold the home for $400,000, the child’s cost basis is $400,000. If they later sell for $1,000,000, the gain is $600,000, and $100,000 could become taxable.

So in many situations, a better strategy may be:

Sell the home at fair market value and gift money for the down payment, instead of discounting the purchase price.

This can create a better long-term tax outcome.

Do the Parents Hold the Mortgage?

The next big question is how the child will finance the purchase. There are two main options:

Option 1: Traditional Mortgage

The child gets a mortgage through a bank, and the parents receive cash from the sale.

Option 2: Parents Hold the Mortgage (Seller Financing)

If the parents do not need the cash from the sale, they can hold the mortgage and essentially act as the bank. The child makes mortgage payments directly to the parents.

This is commonly called seller financing or an intrafamily mortgage.

Minimum Interest Rate (AFR)

If parents hold the mortgage, they must charge a minimum interest rate called the Applicable Federal Rate (AFR) to satisfy IRS rules. For a long-term loan such as a mortgage, the long-term AFR applies.

As of March 2026, the long-term AFR is approximately 4.6%.

So the process typically looks like this:

• Determine purchase price

• Determine down payment

• Remaining balance becomes the mortgage

• Mortgage must charge at least the AFR rate

• Child makes monthly payments to the parents

Tax Treatment of Payments

As the child makes mortgage payments:

• The Principal portion is not taxable to the parents

• The Interest portion of each payment is taxable income to the parents

Forgiving the Mortgage

Another question that comes up with intrafamily mortgages is:

“Can we forgive payments or forgive the loan later?”

The answer is yes, but this brings us back to the gift rules.

Forgiving Monthly Payments

Let’s say the child’s mortgage payment is $3,000 per month and the parents decide to waive the payments for a year.

That would equal:

• $3,000 × 12 = $36,000 per year

If the parents are married, they can gift up to the annual gift exclusion amount each year without filing a gift tax return (for example, $38,000 combined in 2026). If the forgiven amount is below the annual exclusion, no gift tax return is required.

If the forgiven amount exceeds the annual exclusion, then a gift tax return must be filed, but again, no gift tax is owed unless the parents exceed their lifetime exemption.

Forgiving the Entire Mortgage

If the parents decide at some point to forgive the remaining balance of the mortgage, that is considered a gift of the remaining loan balance, and a gift tax return would need to be filed for that year.

This shows that there is actually a lot of flexibility when families use intrafamily mortgages. Payments can be structured, forgiven, or adjusted over time, but the gift rules must be tracked.

Summary

If parents are in the fortunate position where they can sell their home to their child, we are seeing this strategy more and more due to the challenges first-time homebuyers face in today’s housing market.

However, it’s important to understand the key planning areas:

• Should you sell at fair market value or discount the price?

• Should the child get a traditional mortgage or should the parents hold the mortgage?

• What are the Applicable Federal Rate (AFR) rules?

• How do the gift tax rules apply if you discount the house or forgive payments?

• How does this affect the child’s future cost basis?

• How does this fit into the parents’ estate plan?

These transactions involve tax planning, estate planning, and financial planning, so we strongly recommend working with a tax professional and financial advisor when considering an intrafamily real estate transaction.

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

Frequently Asked Questions

1. Can I sell my house to my child for less than market value?
   Yes, but the difference may be considered a gift.
2. Do I have to pay gift tax if I sell the house at a discount?
   Usually no, but you may need to file a gift tax return.
3. Do I pay capital gains tax if I sell to my child?
   You may qualify for the primary residence capital gain exclusion.
4. Is it better to sell at market value and gift the down payment?
   In many cases, yes, for long-term tax planning reasons.
5. Can I be the bank for my child’s mortgage?
   Yes, this is called seller financing.
6. What interest rate do I have to charge?
   At least the IRS Applicable Federal Rate (AFR).
7. Is the interest my child pays me taxable?
   Yes, interest is taxable income to the parents.
8. Can I forgive mortgage payments?
   Yes, but the forgiven amount may be considered a gift.
9. What happens if I forgive the entire loan?
   It is treated as a gift of the remaining balance.
10. Should we work with a professional for this type of transaction?
    Yes, you should coordinate with a CPA, financial advisor, and real estate attorney.

In Retirement, What Healthcare Costs Can Be Paid from an HSA Account?

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

As people approach retirement, or enter retirement, healthcare costs often become one of the largest expenses in a financial plan. The good news is that Health Savings Accounts (HSAs) can be a powerful tool to help cover many of these costs using tax-free dollars. However, not every healthcare expense qualifies, so it’s important to understand both what can and cannot be paid from an HSA in retirement.

In this article, we’ll cover:

• Which Medicare premiums are HSA-eligible

• Whether COBRA premiums qualify

• Dental, vision, and hearing expenses

• Out-of-pocket medical costs

• Medical equipment and prescriptions

• Expenses that are not HSA-eligible

• HSA withdrawal rules before and after age 65

• Frequently asked HSA questions in retirement

Medicare Premiums

One of the most common uses for HSA funds in retirement is paying for Medicare premiums. HSA distributions can be used tax-free for:

• Medicare Part B premiums

• Medicare Part D premiums

• Medicare Advantage (Part C) premiums

However, Medigap (Medicare Supplement) premiums are not considered a qualified HSA expense, even though Medicare Advantage plans are. This is a commonly misunderstood rule and an important one for retirees to be aware of when planning healthcare costs.

COBRA Coverage

If you retire before age 65 or leave an employer and elect COBRA coverage, those health insurance premiums can be paid from an HSA. This can be especially helpful for early retirees who need to bridge the gap before Medicare begins.

Dental, Vision, and Hearing Expenses

Dental, vision, and hearing costs are some of the most common out-of-pocket healthcare expenses in retirement — especially since many retirees no longer have employer coverage for these services.

HSA-eligible expenses include:

• Dental cleanings, fillings, crowns, dentures, braces, and X-rays

• Vision exams, eyeglasses, contact lenses, and LASIK surgery

• Hearing aids and hearing aid batteries

Hearing aids alone can cost several thousand dollars, making the HSA a valuable tax-free resource for these expenses.

Out-of-Pocket Medical Expenses

Many routine healthcare costs in retirement are HSA-eligible, including:

• Doctor visits

• Specialist visits

• Hospital services

• Co-pays

• Deductibles

• Coinsurance

• Surgery costs

• Lab work and imaging

These are often the “everyday” medical expenses retirees experience each year.

Medical Equipment

If medical equipment is needed later in retirement, many of these expenses qualify for HSA distributions, including:

• Walkers

• Wheelchairs

• Blood pressure monitors

• Crutches

• CPAP machines

• Glucose monitors

Prescription Medications

Prescription drugs that are prescribed by a doctor are qualified HSA expenses.

However, over-the-counter medications typically do NOT qualify unless they are prescribed by a physician.

Expenses That Are NOT HSA-Eligible

Some healthcare-related expenses are not considered qualified medical expenses. These typically include:

• Gym memberships

• Nutritional supplements

• Cosmetic procedures

• Teeth whitening

• General health items not prescribed by a doctor

Even though these may improve health, they are not considered qualified medical expenses under HSA rules.

Why HSAs Are So Powerful for Retirement

HSAs are one of the most tax-advantaged accounts available because they offer:

• Tax-deductible contributions

• Tax-free growth

• Tax-free withdrawals for qualified medical expenses

Because healthcare costs are often highest in retirement, many individuals choose to pay for medical expenses out-of-pocket during their working years and allow their HSA to grow, using it later in retirement when healthcare costs increase.

HSA Withdrawal Rules: Before and After Age 65

It’s also important to understand the rules around HSA withdrawals:

• Before age 65

  • Non-qualified withdrawals = taxable income + 20% penalty

• After age 65

  • Non-qualified withdrawals = taxable income only (no penalty)

  • Works similar to a Traditional IRA if not used for healthcare

This provides additional flexibility later in retirement.

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

Frequently Asked Questions (FAQs)

1. Can HSA funds be used for Medicare premiums?
   Yes, for Medicare Part B, Part D, and Medicare Advantage premiums.
2. Can HSA funds be used for Medigap premiums?
   No, Medigap premiums are not considered a qualified expense.
3. Can I use my HSA for dental expenses in retirement?
   Yes, most dental expenses qualify.
4. Are vision expenses HSA-eligible?
   Yes, including exams, glasses, contacts, and LASIK.
5. Are hearing aids covered by an HSA?
   Yes, including hearing aid batteries.
6. Can I use my HSA for COBRA premiums?
   Yes, COBRA premiums are a qualified expense.
7. Are prescription drugs HSA-eligible?
   Yes, if prescribed by a doctor.
8. Are over-the-counter medications HSA-eligible?
   Typically no, unless prescribed by a physician.
9. What happens if I use HSA money for non-medical expenses before 65?
   You will owe income tax and a 20% penalty.
10. What happens if I use HSA money for non-medical expenses after 65?
    You will owe income tax, but no penalty.

Health Savings Account Distribution Tax and Penalty Rules

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

Health Savings Accounts (HSAs) are one of the most tax-advantaged accounts available, but the tax treatment of distributions depends on how the money is used and the age of the account owner. There are essentially four different distribution scenarios that HSA owners can run into, and each scenario has different tax and penalty rules that are important to understand.

In this article, we’ll cover:

• The four HSA distribution scenarios

• Tax treatment before age 65

• Tax treatment after age 65

• Why HSAs are so valuable for retirement planning

• Advanced HSA distribution strategies

• Common HSA distribution mistakes to avoid

• Frequently asked questions about HSA distributions

Why HSA Accounts Are So Valuable

Health Savings Accounts are unique because they offer a rare triple tax advantage:

1. Contributions are made pre-tax

2. The account grows tax-deferred

3. Distributions are tax-free if used for qualified medical expenses

Very few accounts receive this type of tax treatment. Traditional retirement accounts are tax-deferred, and Roth accounts are tax-free on the way out, but HSAs can be tax-free on both the contribution and distribution side when used correctly.

Because of this, many financial planners recommend not spending HSA funds during working years if possible, and instead allowing the account to grow and using it later in retirement when healthcare costs are typically much higher.

The Four HSA Distribution Scenarios

There are four main distribution scenarios that determine whether you owe taxes and/or penalties on HSA withdrawals:

Let’s walk through each scenario.

Distributions Prior to Age 65 (Qualified Medical Expenses)

If you take a distribution from an HSA before age 65 and use the money for a qualified medical expense, the distribution is:

• Tax-free

• Penalty-free

This is the ideal use of an HSA. Qualified expenses can include:

• Doctor visits

• Deductibles and coinsurance

• Dental and vision care

• Hearing aids

• Prescription medications

• Medicare premiums (after age 65)

• Medical equipment

In these cases, the HSA functions exactly as intended — a tax-free healthcare account.

Distributions Prior to Age 65 (Non-Qualified Expenses)

If you take a distribution before age 65 and the expense is not qualified, the distribution is:

• Subject to ordinary income tax

• Subject to a 20% penalty

For example, if someone is in a 30% tax bracket and takes a non-qualified distribution:

• 30% tax

• 20% penalty

• Total loss = 50% of the distribution

This is why it is usually recommended to preserve HSA funds for medical expenses whenever possible.

Distributions Age 65 or Older (Qualified Medical Expenses)

This scenario works the same as before age 65.

If the distribution is used for qualified medical expenses, the withdrawal is:

• Tax-free

• Penalty-free

This is why HSAs are often used as a retirement healthcare fund.

Common qualified expenses in retirement include:

• Medicare Part B premiums

• Medicare Part D premiums

• Medicare Advantage premiums

• Out-of-pocket medical expenses

• Deductibles and coinsurance

• Dental and vision care

• Hearing aids

• Medical equipment

Distributions Age 65 or Older (Non-Qualified Expenses)

This is where the rules change.

After age 65, if you take money from an HSA for non-qualified expenses:

• You pay ordinary income tax

• No 20% penalty

At this point, the HSA starts to function similarly to a Traditional IRA. The money can be used for anything, but it becomes taxable income if not used for medical expenses.

This provides flexibility in retirement in case the funds are needed for non-medical expenses.

Important Rule: Reimbursed Expenses Do NOT Qualify

One important rule that retirees need to be aware of:

If a medical expense is reimbursed by insurance or a former employer, you cannot also take a tax-free HSA distribution for that same expense.

For example:

• Some retirees have employer retiree health plans that reimburse Medicare premiums.

• If the retiree is reimbursed for Medicare Part B or Part D, those expenses cannot also be reimbursed from the HSA tax-free.

This would be considered a non-qualified distribution, and taxes would apply.

Advanced HSA Distribution Strategies

There are several advanced strategies that can make HSAs even more powerful:

1. Save Receipts and Reimburse Yourself Later

There is no time limit on when you reimburse yourself from an HSA for a qualified expense, as long as:

• The expense occurred after the HSA was established

• You kept the receipt

This means someone could:

• Pay medical expenses out-of-pocket during working years

• Allow the HSA to grow

• Reimburse themselves years later tax-free

This effectively turns the HSA into a tax-free retirement account.

2. Use HSA for Medicare Premiums

HSA funds can be used tax-free for:

• Medicare Part B

• Medicare Part D

• Medicare Advantage

(This becomes a built-in retirement healthcare fund.)

3. Treat HSA Like a Backup Traditional IRA

After age 65, if needed, HSA funds can be withdrawn for non-medical expenses and simply taxed as income, with no penalty.

Common HSA Distribution Mistakes

Some of the most common mistakes include:

• Using HSA funds for non-qualified expenses before 65

• Losing receipts for reimbursement

• Using HSA funds for reimbursed expenses

• Spending HSA funds during working years instead of investing them

• Not investing HSA funds for long-term growth

• Forgetting that non-qualified withdrawals before 65 have a 20% penalty

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

Frequently Asked Questions (FAQs)

1. Do I pay taxes on HSA distributions?
   Only if the distribution is used for a non-qualified expense.
2. What is the penalty for non-qualified HSA withdrawals before age 65?
   A 20% penalty plus ordinary income tax.
3. What happens to the penalty after age 65?
   The 20% penalty goes away, but distributions are still taxable if not used for medical expenses.
4. Can I use my HSA for Medicare premiums?
   Yes, for Medicare Part B, Part D, and Medicare Advantage.
5. Can I reimburse myself years later from my HSA?
   Yes, as long as the expense occurred after the HSA was established and you kept the receipt.
6. Are HSA distributions reported on a tax return?
   Yes, distributions are reported on IRS Form 8889.
7. Can I use my HSA for my spouse's medical expenses?
   Yes, even if your spouse is not on your health insurance plan.
8. What happens to my HSA when I turn 65?
   You can still use it tax-free for medical expenses, and penalty-free for non-medical expenses (taxable).
9. Can I use my HSA for dental and vision expenses?
   Yes, most dental and vision expenses qualify.
10. Is an HSA better than a 401(k)?
    For medical expenses, an HSA can be more tax-efficient because it is tax-free on both contributions and qualified distributions.

Attention Non-Spouse 10-Year Beneficiaries: 2030 Is Rapidly Approaching

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

If you inherited an IRA or other retirement account from a non-spouse after December 31, 2019, the clock is ticking—and for many families, the tax consequences are coming into sharper focus.

The SECURE Act, which went into effect in 2020, dramatically changed how non-spouse beneficiaries must handle inherited retirement accounts. While these rules may have seemed far off at the time, 2030 is now just around the corner for those who inherited accounts in the first year of the new law.

In this article, we’ll cover:

• How the SECURE Act’s 10-year rule works

• Why 2030 could trigger significant tax liabilities

• How market growth has quietly made the problem bigger

• Practical tax-planning strategies to consider now

• Why waiting until the last year can be costly

 A Quick Refresher: What Changed Under the SECURE Act?

Prior to 2020, most non-spouse beneficiaries could “stretch” distributions from an inherited IRA over their lifetime. This allowed smaller required distributions and, in many cases, never required the account to be fully depleted.

That all changed with the SECURE Act.

For most non-spouse beneficiaries:

• The inherited retirement account must be fully depleted within 10 years

• The rule applies to anyone who passed away after December 31, 2019

• All pre-tax dollars distributed during that period are taxable income

From the IRS’s perspective, this rule change was a revenue raiser—it ensures that inherited retirement assets become taxable within a defined window.

Why 2030 Is Such a Big Deal

For individuals who inherited a retirement account from someone who passed away in 2020, the 10-year clock runs out at the end of 2030.

That means:

• Only five tax years remain (2026–2030) before the final distribution year

• Any remaining balance must be distributed—and taxed—by the end of year 10

• Large balances could result in substantial one-year tax spikes

Many beneficiaries have only been taking small distributions or the minimum required amounts. While that may have felt prudent at the time, it can create a tax bombshell in the final year if the account balance is still large.

RMD Rules Add Another Layer of Complexity

Required Minimum Distribution (RMD) rules under the SECURE Act depend on whether the original account owner was already taking RMDs when they passed away.

• Some beneficiaries were required to take annual RMDs

• Others were not required to take annual distributions—but still must empty the account by year 10

Regardless of which category you fall into, the key issue remains the same:
Waiting too long often concentrates taxable income into fewer years.

Market Growth Has Made the Problem Bigger

Ironically, strong market performance over the past several years has amplified the issue.

For individual that have a large allocation to stocks within their inherited IRA, since the market returns have been so strong over the past few years, they may have seen the balance in their inherited IRA increase despite taking RMDs from the account each year.

This is great from a wealth-building perspective, but it also means:

• Larger balances remain late in the 10-year window

• Larger forced distributions

• Larger tax bills await

In short, investment success can unintentionally worsen the tax outcome if distributions aren’t coordinated with a broader tax plan.

Why Smoothing Income Often Makes Sense

For many non-spouse beneficiaries, the goal should be tax smoothing—intentionally spreading distributions over the remaining years to avoid one massive taxable event in year 10.

This often means:

• Taking more than the minimum each year

• Coordinating distributions with your current income level

• Evaluating how many years remain in your 10-year window

The sooner this planning happens, the more flexibility you typically have.

One Common Strategy: Offset Taxes With 401(K) Contributions

One tax-planning strategy we often explore with clients involves maximizing employer-sponsored retirement plan contributions.

Here’s a simplified example:

• A 50-year-old employee is contributing $15,000 to their 401(k)

• In 2026, they may be eligible to contribute up to $32,500

• That’s an additional $17,500 of potential pre-tax deferrals

A possible strategy:

1. Take a $17,500 distribution from the inherited IRA (taxable)

2. Increase payroll deferrals so more income flows into the 401(k) pre-tax

3. Use the inherited IRA distribution to supplement take-home pay

Result:
Taxable income from the inherited IRA distribution is fully offset by pre-tax retirement contributions, while also shifting assets into the inherited IRA owner's personal 401(k) account, which does not have a 10-year distribution restriction.

A Critical Caveat for 2026

High-income earners should be aware that starting in 2026, certain catch-up contributions for those over age 50 may be required to be made as Roth contributions. Roth deferrals do not provide an immediate tax deduction, which could limit the effectiveness of this strategy.

When Waiting Can Make Sense

Not every situation calls for accelerating distributions.

For individuals who plan to retire before the 10-year period ends, delaying distributions may be intentional and strategic. Once paychecks stop:

• Ordinary income may drop significantly

• Larger inherited IRA distributions could fall into lower tax brackets

This can be a very effective approach—but only when planned in advance. 

The Real Warning Sign to Watch For

This article isn’t about fear—it’s about awareness.

If you:

• Inherited a retirement account after 2019

• Have only been taking small distributions or RMDs

• Haven’t mapped out the remaining years of your 10-year window

There’s a real risk that a large, avoidable tax liability is waiting at the end of the road.

Final Thoughts

The SECURE Act permanently changed the landscape for non-spouse beneficiaries, and 2030 is approaching faster than many realize. Thoughtful, proactive tax planning—especially in the final years of the 10-year period—can make a meaningful difference in outcomes.

Now is the time to:

• Count the remaining years

• Project future tax exposure

• Coordinate investment, distribution, Medicare premium, and tax strategies

Advanced planning today can help turn a looming tax problem into a manageable—and sometimes even strategic—opportunity.

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.