Retirement

Planning for Retirement: Benefits Impact & Transition Overview

This guide provides general information on how your benefits may change as you approach and enter retirement. It is not intended as tax, legal, or financial advice. Ryan Specialty does not offer retiree medical or insurance benefits. Coverage availability may vary based on age, plan elections, and applicable regulations.

 

401(k): Contributions & Distribution Options

 

Catch-Up Contributions

Employees may be eligible to increase retirement savings based on age:

  • Ages 50–59 and 64+: Eligible to contribute up to $8,000 in catch-up contributions (2026)
  • Ages 60–63: Eligible for Super Catch-Up contributions up to $11,250 (2026)
  • Employees earning $150,000+ in 2025 FICA wages must make catch-up contributions on a Roth (post-tax) basis

401(k): Distribution Overview – IRS Resource Guide

Age at Retirement What This Means for You
Under 59½ You may be eligible for penalty-free withdrawals under the Rule of 55 if you leave your job in or after the year you turn 55. This applies only to your current employer’s 401(k), and income taxes still apply.
59½ – 62 You can begin taking Roth 401(k) distributions without early withdrawal penalties if qualified distribution requirements are met. The Rule of 55 may also apply if you retired earlier and meet eligibility requirements.
62 – 64 You reach early retirement age (62) under the plan (after completing one year of service). If still employed, you become 100% vested in your 401(k), if not already vested.
65+ You reach normal retirement age (65) and are fully vested in your 401(k), if not already vested.


401k Distribution Key Rules & Considerations

Rule of 55 (Early Access Before 59½)

You may be able to withdraw funds from your 401(k) without a 10% early withdrawal penalty if:

  • You leave your job in or after the year you turn 55
  • The funds remain in your current employer’s 401(k) plan
  • Your plan allows withdrawals

Important limitations:

  • Applies only to the 401(k) from the employer you most recently left
  • Does not apply to IRAs or prior employer plans (unless rolled into your current plan before separation)
  • You will still owe income taxes on withdrawals


Roth 401(k): Qualified Distributions & 5-Year Rule

A qualified distribution from your Roth 401(k) is one that is completely tax-free, including investment earnings.

To be considered qualified, both of the following must be met:

  1. You meet one of these conditions:
    • You are age 59½ or older, or
    • The distribution is made due to death or disability
  1. You meet the 5-Year Participation Rule:
    • The 5-year period begins January 1 of the year you make your first Roth 401(k) contribution or Roth rollover
    • The period ends on December 31 of the fifth consecutive year
    • This 5-year rule determines when your investment earnings can be withdrawn tax-free

Deferred Compensation Plan

To be eligible for a retirement distribution, you must be age 65 or within 10 years of retirement age at the time you separate from service.

You may elect to receive your distribution as:

  • A lump-sum payment (within 90 days following retirement), or
  • Annual installment payments over 2 to 10 years

Retirement distributions are generally available to participants age 55 or older.

 

Health Savings Account (HSA)

 

Age at Retirement What This Means for You
Under 65 Your HSA is portable, meaning you keep the account after leaving the company. Funds can be used tax-free for qualified medical expenses.
65+ You can continue to use your HSA; however, once enrolled in Medicare, you can no longer contribute. Contributions must stop up to 6 months before Medicare enrollment due to retroactive coverage rules.

 

Flexible Spending Account (FSA)

  • Any unused FSA funds are forfeited as of your retirement date, regardless of age
  • Eligible expenses must be incurred before your retirement date to be reimbursed
  • Retirees cannot enroll in a new FSA, as it is a salary-deferral benefit

 

Ryan Specialty Benefits Coverage

  • Employees working 30+ hours per week are eligible for benefits
  • Coverage remains active through the end of the month in which you retire

At Retirement Age:

  • You may choose to maintain Ryan Specialty coverage as your primary plan
  • You may defer COBRA enrollment

Medicare (if eligible) may be used as secondary coverage

 

COBRA Coverage

 

Age at Retirement What This Means for You
Under 65 You have 60 days to elect COBRA after losing coverage. COBRA can last up to 18 months or until age 65 (whichever comes first). Coverage can be canceled at any time but cannot be reinstated.
65+ COBRA is typically more expensive than Medicare, and Medicare may be a more cost-effective option. The company offers a benefit through Allsup to assist employees in transitioning to Medicare.

Medicare

 

Age at Retirement What This Means for You
Under 65 Medicare is not available.
62 – 64 You can enroll in Medicare starting 3 months before your 65th birthday.
65+ You are eligible for Medicare. Consider how it coordinates with COBRA or existing coverage. The company offers a benefit through Allsup to assist employees in transitioning to Medicare.