It seems there are more "concrete" parachutes than golden ones handed out to retiring workers in the Cayman Islands these days. About 2,000 employers are in default on staff pensions and health insurance, the minister responsible said last month. A 67-year-old who gave the banking industry two decades expects her pension to run dry next year. And the body that speaks for older persons has just told Parliament that the over-65 population has nearly doubled in 11 years.

So, if ever there was a time for working folk, Caymanians and work permit holders alike, to huddle with family for a business talk, or to consult their pension administrator or an accountant about pending retirement, it is now.

For those nearing the end of their careers, several interlaced dilemmas, looming conundrums if you will, are steadily creeping up. Each signals a worrying lack of means to sustain beneficiaries in their golden years.

Take that 67-year-old. One of several siblings who entered the inchoate financial industry in the 1970s, she worked for about two decades in major banking organisations, then in another private sector agency, before retiring in 2022. The industry was built on these largely unsung administrative staff, a small, trusted band of men and women who were there when the cast was made for this pillar of our economy.

Today, still healthy and active, her net pension benefit of almost CI$1,400 a month is on the edge in Cayman's economy, and she expects the account to be depleted five years in: 2027.

This is in spite of raising her family, keeping a modest home and being wise with her funds. She said she withdrew no cash even when faced with major storm damage, illness and surgery. Back then she could afford her company's health policy. Today she is exposed, subsisting under the basic Standard Health Insurance Contract (SHIC) plan, and must swallow her pride and apply to be deemed "indigent" to receive some government subsidy.

"I do have US$25,000 in a private fixed-rate fund, from which I can choose to withdraw the interest, or the cash, when it matures," the grandmother told The Caymanian Journal. "However, I may also decide to leave it to my estate beneficiaries, eventually."

Her siblings, who helped bring to life the "golden era" of Cayman's history, are in similar straits, and work together to find common remedies, or to commiserate.

She is not an outlier. Many first-generation payees are finding that their limited contributions, over relatively short terms since pensions have only been mandatory since 1998, are now leaving them underwater, fiscally speaking. Add the sticker-shock of modern expenses against often-diminished savings. Some pension funds have not performed as anticipated. Some people's low salaries, and therefore paltry monthly contributions, make retirement prohibitive. Others withdrew funds, lawfully, to cover a health crisis, education or other emergencies; or after COVID and hurricanes; or to pay down property or mortgages, homes they can now hardly afford to keep up. The scale is not small: the employment ministry's own annual report, as reported by Cayman News Service on 3 October, shows about CI$6.5 million taken out of private pensions in 129 property-related withdrawals in the first half of 2025 alone, on top of the far larger COVID-era raid.

Then there is the employer who deducts a staff member's pension contribution from monthly pay but never deposits it, or the matching contribution, into the person's plan. Sometimes for years. Just last month, on Radio Cayman, Minister for Caymanian Employment and Immigration Michael Myles said about 2,000 local businesses are in default on staff pension and health insurance payments, and that work permits and trade and business licences will be refused until the accounts are cleared.

"No longer are they just cheating on their trade and business licence; they're also cheating on their work permits; they're cheating on health insurance; they're cheating on labour laws; they're cheating on everything," he said, adding that government now has to find the resources to enforce the law because of past policy mistakes. In March he had put the arrears at more than CI$14 million owed by at least 2,100 companies.

Here, vigilance is required of the staff member, to ensure the monthly injection appears on their statements. Administrators are legally mandated to monitor employer compliance and act on outstanding balances. If an employer falls behind, the administrator must submit a delinquent list to the Department of Labour and Pensions (DLP), which is shared with the Department of Commerce and Investment and WORC. Unconscionably, some businesses also neglect their staff's legally mandated health benefits.

Senior officials are acutely aware of the dilemma. After all, government often picks up the bill when older constituents face a life-altering crisis. To get a handle on it, the Ministry of Caymanian Employment and Immigration held stakeholder consultation meetings in September and October on proposed pensions and labour reforms. On pensions, the subjects were enrolment requirements and possible exemptions, and contribution eligibility and waiting periods for non-Caymanian employees.

"Our goal is to ensure that reforms protect workers, support Caymanian employment opportunities and remain practical for businesses. Stakeholder feedback is an important part of getting that balance right," Myles said in a Ministry statement issued on 12 October.

That waiting period is an aberration worth fixing. Every Caymanian or permanent resident worker is pensionable immediately on hiring. Work permit holders are only pensionable after nine months of employment in the Cayman Islands, which leaves seasonal hires, especially in the lucrative tourism high season, outside the pension net.

And while work permit holders do contribute, the overall outlook is deflated each time their personal pension funds leave our locally administered plans: transferred to approved plans in their home jurisdictions once they have been off-island for two years, or refunded in cash where the balance is small.

Another deficit is self-imposed. Only annual income up to CI$87,000 is subject to mandatory pension contributions, though contributions above that are allowed. (The cap was raised from CI$60,000 under the 2016 amendments to the Act.) So wealthier professionals keep a significant portion of their salaries free of pension deductions, and those higher contributions are missed in the wider investment pool.

The preceding fiscal soup is enough to send an actuary's calculator into hyper-drive, and its history is worth noting. Private sector pensions were only introduced by the National Pensions Act, passed in 1996 and in force from 1998, which set the mandatory contribution at 10% of salary, a minimum of 5% each from employer and employee. A 2007 Mercer review for government said 10% was not enough and recommended 12%; the industry and policy-makers now see 12% as required going forward. Workers who monitor their accounts are more often than not surprised by declines in the accrued funds.

The common maxim that a pension should merely supplement other income, like investments and savings, is overshadowed by Cayman's elevated cost of living, which usually negates the ability to save very much while working. For these and other reasons, the lower-paid sector will likely have insufficient pensions to see them through their first decade of retirement.

Closely related is a primary expense for most retirees: healthcare. Almost incredibly, most private sector workers lose company health insurance on retirement day, unless the employee or company extends payments for a few more months. Even so, insurers often refuse to reinsure the retiree, or premiums are prohibitive, even with no significant health episodes beforehand: the infamous "pre-existing conditions". Insufficient cover then depletes the pension further, especially with a chronic prognosis.

Socially speaking, the traditional extended family support network has all but dissolved. Ageing parents are often alone in big, empty-nest homes, still with significant bills for utilities, upkeep and big-ticket items like hurricane insurance. Even downsizing is usually prohibitive, given the escalated value of smaller properties, and the strata fees.

All the above relates to the private sector. Government, the largest single employer, is a different case. For decades its pensions were a Defined Benefit plan, with lifetime benefits once eligible. A Defined Contribution scheme became the norm for new entrants from 1 January 2000, the same type offered to private sector workers.

The civil service is now where the retirement-age debate is being had. A Private Member's Bill, the Public Service Management (Amendment) Bill, 2026, put forward by Chris Saunders, MP for Bodden Town West and an accountant, proposes that the normal retirement age in the civil service rise from 65 to 70. There is no mandatory retirement age here, in either public or private sector; a generally accepted, though flexible, age is the norm. Saunders is no parliamentary novice: in recent years he served as Deputy Premier and Minister for Finance and Economic Development.

The wider labour force gives that proposal its context. Though the population has grown, the Caymanian share of it is shrinking, as incoming work permit grants rise and the local population falls through lower birth rates, deaths and emigration. Possible solutions range from shifting the accepted retirement age to raising the contribution ceiling.

This month, Older Persons Month, brought a second submission. The Older Persons Council has called for enhanced national support for Cayman's ageing population in its first comprehensive report since the Council was established. Tabled in Parliament on 2 October by Minister for Social Development and Innovation Isaac Rankine, and presented to him on 16 July by former Chairperson Lucille Seymour and former Deputy Chairperson Sarah Alice Mae Coe, it notes the population aged 65 and over has risen by 98% over the past 11 years, and that most older persons live independently in their communities and need more support as they age.

Regardless, for a small Caymanian population with many citizens now wading into dire straits, propelled into a global fiscal situation, a solution must soon be found. And, like the approach that founded the successes of the Cayman Islands, it must be a straightforward one. One that is reasonable, yet equitable, and honouring to the deserving beneficiaries.