The Long Island Retirement Checklist

Five years to one year

Five years out

These items need the most lead time, so they come first.

• Get your service credit in writing from your retirement system. Not an estimate you assembled yourself. Public pension formulas step at 20, 25, and 30 years, and being a few months short is permanent.
• Identify your tier and what it actually entitles you to. Tier 6 changed between 2022 and 2026: vesting at five years, a three-year final average salary, lower NYSLRS contributions from October 1, 2026 and, at NYSTRS only, an unreduced pension at 58 with 30 years.
• Find out where your salary stops counting. Tier 6 pensions are built on earnings up to the Governor’s salary, $250,000; members who joined from April 1, 1996 (NYSTRS: July 1, 1996) are capped at the federal limit, $360,000 for 2026; Tier 5 and 6 overtime is capped separately.
• Claim purchasable service credit. Prior public service and military service can carry you over a threshold. The cost rises with delay because interest compounds.
• Ask about reinstatement to an earlier membership date. Tier reinstatement restores a terminated membership, and with it an earlier membership date and possibly an earlier tier.
• Track down pensions from former employers, including companies that no longer exist. Search Form 5500 filings and the PBGC unclaimed pension database.
• Do not drop your employer medical coverage. Some employers require enrollment on your last active day, and some a run of consecutive years before it (six at Northwell for its enhanced plan), so a year without coverage can cost it.
• Open a Social Security account at ssa.gov and check your earnings record for errors. They are far easier to correct now, with old W-2s, than later.
• Find out whether your employer offers a 457(b) in addition to a 403(b) or 401(k). The limits are separate ($24,500 each in 2026, plus $8,000 at 50, or $11,250 in the years you are 60 through 63) and you can fund both.
• If you have a non-governmental 457(b) or a 409A deferred compensation plan, read the distribution election now. It is a promise by your employer, it cannot be rolled over, and the default schedule can put the whole balance into one tax year.

An avoidable mistake with a large cost

Retiring weeks short of a service credit milestone. Under NYSTRS and NYSLRS Tier 4, crossing 20 years re-rates every year of service you have, not just the twentieth. Reaching 30 years removes the age reduction entirely at 55. Special 20-year and 25-year plans pay a full benefit at the milestone and nothing comparable a month before it. Confirm your date with the system, in writing, before you commit to anything.

Two years out

• Request benefit estimates under several payment options and at more than one retirement date. Compare them side by side rather than reading them one at a time.
• Model the survivor decision jointly with your spouse. When one of you dies, the household keeps the larger Social Security benefit, not both. Two pensions in one household need two elections made together. Look at what the survivor actually lives on.
• Check the income on the tax return you are filing now. Medicare premiums use a two-year lookback, so this year’s income sets your premium later. The Medicare example further on puts a number on it.
• Map the final working year before you choose a retirement date. Severance, an unused leave payout, a deferred compensation distribution, a final bonus and a partial year of salary can all land in the same twelve months as the first pension payment. That year sets your Medicare premium two years later, and a conversion or a large sale in the same year adds to it. If you hold options or restricted stock, the exercise and sale schedule belongs on the same calendar as the retirement date.
• Map your income sources by tax treatment. New York exempts government pensions, Social Security, and Railroad Retirement entirely, and excludes up to $20,000 per person of other pension, annuity and IRA income from 59½.

One year out

• Confirm retiree health coverage eligibility in writing, including the age, service, and continuous-enrollment requirements.
• Note your Medicare Initial Enrollment Period if you turn 65 in this window. It starts three months before your birthday month, and the Part B late penalty is permanent.
• If you are still working past 65, confirm in writing that your coverage is based on current employment. Retiree coverage and COBRA do not protect you from the penalty.
• Stop HSA contributions before enrolling in any part of Medicare, including premium-free Part A, which can be applied retroactively.
• Review beneficiary designations on every account. They override your will, and an old form naming a former spouse can still pay the former spouse.
• Get a durable power of attorney and health care proxy in current New York form, if you do not have them.
• If your estate is within reach of the New York cliff, $7,350,000 in 2026 with the benefit lost entirely at 105% of it, the year before retirement is when a gift or a change of ownership still has time to work. New York adds gifts made within three years of death back to the estate, a rule now extended to deaths before 2032.
• Ask whether the first death would waste an exclusion. New York does not allow portability, so an exclusion left unused when the first spouse dies is gone. A married couple that leaves everything outright to the survivor can lose the first $7,350,000 of shelter and push the whole estate into the cliff at the second death. The remedy is a credit shelter provision in the will or trust, and New York lets the qualified terminable interest election be made on the New York return itself, so the state decision can be made on its own. This is drafting work with an attorney, and it takes months, not days.

What the milestones are worth: three worked examples

These use the systems’ published formulas and 2026 figures. They are illustrations of how the rules work, not projections, and your own numbers will differ.

One month short of 20 years, NYSLRS Tier 4

Final average earnings $185,000. At 19 years and 11 months the formula pays 1.66% for each year: 19.92 × 1.66% = 33.1%, or $61,200 a year. At 20 years the rate becomes 2% and applies to every year: 40%, or $74,000 a year. One month of service is worth $12,800 a year for life, before any cost-of-living adjustment. The special 20-year police plan under Section 384-d has the same shape in a starker form: 50% of final average earnings at 20 years, and no such benefit at 19 years and 11 months.

Retiring at 55 with 29 years and 10 months, NYSTRS Tier 4

Final average salary $245,000. With fewer than 30 years, retiring at 55 keeps 73% of the benefit: 29.83 years × 2% = 59.7%, reduced to 43.6%, or $106,700 a year. Two months later, at 30 years, there is no age reduction and the pension factor is 60%: $147,000 a year. The difference is $40,300 a year, permanently, for eight weeks of work. The same member working to 33 years at 60 reaches 64.5%, or $158,025.

A $100,000 Roth conversion, seen from Medicare two years later

A married couple with $300,000 of modified adjusted gross income pays the 2026 Part B premium of $405.80 a month each, plus a $37.50 Part D adjustment, because they sit in the $274,001 to $342,000 bracket. Convert $100,000 in the same year and the income becomes $400,000, which lands in the $342,001 to $410,000 bracket: $527.50 for Part B and $60.40 for Part D, each. The difference is $144.60 a month per person, $3,470 for the couple over the year, billed two years after the conversion. That is not a reason to skip the conversion; it is a cost to put on the same page as the tax it saves. Form SSA-44 removes a surcharge only for listed life-changing events, and a conversion is not one of them.