How long do benefits last after leaving a job in Ontario?

It depends on the plan and how you left. Many plans end coverage on your last day of employment or at the end of that month. If you were terminated without cause, Ontario's Employment Standards Act requires the employer to continue benefit contributions during the statutory notice period, and a severance package may extend them further. Check your termination letter and ask HR for the exact end date in writing.

Can I keep my group health insurance after I quit?

Not the group plan itself. What you can do is apply for a conversion plan from the same or another insurer within 60 days of the group coverage ending, which guarantees acceptance without medical questions. Alternatively, you can apply for a regular individual health and dental plan, which usually costs less but may involve health questions.

Is it worth converting group life insurance when I leave a job?

Usually only if your health would make a new policy expensive or impossible. Conversion within 31 days guarantees an individual policy without medical evidence, but the premiums are typically much higher than a new term policy for a healthy applicant. Get a term life quote first, then decide whether to convert some or all of the group amount.

What happens to my disability insurance when I leave my job?

Group short- and long-term disability coverage ends when employment ends, and most group LTD plans have no conversion option. If your new employer offers LTD, you will be covered there, often after a waiting period. If you are going self-employed or contracting, you will need an individual disability policy, and applying while you are still healthy and employed is the best time.

Leaving Your Job? How to Replace Group Benefits

Group benefits end fast. On most plans, your health, dental, life and disability coverage stops on your last day of work or at the end of that month, and the paperwork to replace it comes with deadlines measured in days, not months.

The good news is that every piece of a group plan has a replacement, and some of them are guaranteed regardless of your health if you act in time. The less good news is that no single product replaces everything, and the guaranteed options are not always the cheapest. This guide walks through each benefit, what happens to it, and how to replace it, in the order you should deal with them.

It’s for anyone leaving an employer in Ontario: resigning, retiring early, being laid off, moving to contract or self-employed work, or waiting out the probation period at a new job before benefits start.

First, find out exactly when your coverage ends

Before anything else, get the end date in writing from HR. Plans differ: some end coverage at midnight on your last day, others at the end of the month. If you’re between jobs, that difference can matter for a prescription refill or a child’s dental appointment.

If you were terminated without cause, Ontario’s Employment Standards Act requires your employer to continue benefit plan contributions through the statutory notice period, whether you work that notice or receive pay in lieu. A negotiated severance package often extends benefits further, and the length of that extension is a legitimate thing to ask for. Insurers, however, do not always allow group coverage to continue beyond the notice period, so confirm what the employer has actually arranged rather than assuming.

If you resign, there is no notice-period continuation; coverage ends per the plan’s rules.

Also ask HR for a copy of your benefits booklet and a letter confirming the termination date of coverage. You’ll need the date to apply for a conversion plan, and the booklet tells you what you’re losing.

What happens to each benefit when you leave

Benefit	What happens at departure	Replacement options	Deadline
Extended health (drugs, paramedical, vision)	Ends with employment	Conversion plan (guaranteed), individual health plan (may be underwritten), spouse’s plan, new employer’s plan	60 days for conversion
Dental	Ends with employment	Same as health; usually bundled	60 days for conversion
Basic group life	Ends with employment	Convert to individual policy without medical, or apply for new term life	31 days for conversion
Optional group life	Ends with employment	Often convertible; same 31-day rule	31 days
Short-term disability	Ends with employment	EI sickness benefits as a partial backstop; individual DI	None (no conversion)
Long-term disability	Ends with employment	Individual disability policy; new employer’s LTD	None (no conversion on most plans)
Critical illness (if included)	Ends with employment	Some plans convert; otherwise apply for individual CI	Usually 31 days if convertible
Employee assistance program	Ends with employment	Community and virtual services; some individual plans include a version	None
Health spending account	Unused balance usually forfeited	Individual HSA if self-employed or incorporated	Submit outstanding claims promptly
Pension or group RRSP	Not insurance; separate transfer rules	Locked-in account or transfer	Per plan

The rest of this article takes each of the insurance pieces in turn.

Replacing health and dental coverage

You have three main routes, and they suit different people.

Route 1: a conversion (guaranteed-acceptance) plan

Most major group insurers offer a conversion plan for departing employees, and several insurers offer their own versions that accept anyone leaving any group plan. The defining feature is guaranteed acceptance with no medical questions, provided you apply within 60 days of your group coverage ending. Some insurers allow 90 days; do not rely on that.

That guarantee is valuable if you or a family member has an ongoing condition, takes expensive medication, or has a pre-existing condition that a regular plan would exclude. Because the insurer accepts everyone, though, the pricing reflects it. Conversion plans generally cost more than comparable individual plans and often carry lower drug and dental maximums than the group plan did. They are a safety net, not a bargain.

Route 2: a regular individual health and dental plan

If your household is in reasonable health, a standard health and dental plan bought on the open market is usually the better value. You choose the tier, and premiums are lower than conversion plans. Some tiers are guaranteed-issue; higher-drug-coverage tiers may ask health questions and can exclude a pre-existing condition or decline. Waiting periods for major dental commonly apply, so the sooner it starts the better.

Indicatively, an individual in Ontario might pay roughly $60–$150 a month and a family roughly $150–$350 a month for a mid-range plan. These are illustrative ranges only; the tier, deductible and insurer change the number. Our guides on private health insurance cost in Ontario and health and dental insurance for the self-employed go deeper.

Route 3: a spouse’s plan, or wait for the new employer

If your spouse has group coverage, ask their HR about adding you as a dependant. Leaving a job is generally a “life event” that allows enrolment outside the usual window, but the request usually has to be made within a set period (often 31 days), so don’t delay.

If you’re starting a new job, find out when benefits begin. Probation periods of three months are common, and some plans apply a longer wait for certain benefits. A short-term individual plan, or a conversion plan for a few months, can bridge that gap. Compare the premium against the risk of being uninsured, remembering that OHIP still covers doctors and hospitals; the gap is drugs, dental and paramedical.

Which route is right for you

Ongoing health conditions or costly prescriptions: conversion plan within 60 days, and start there even if you later switch.
Healthy household, wanting value and choice: individual plan, applied for before the group coverage ends.
Spouse with a good plan: join theirs; consider a small individual plan only for anything it lacks.
Between jobs for a defined period: bridge with a conversion or individual plan, then cancel when the new plan starts.

Replacing group life insurance

Most group life plans in Canada include a conversion privilege: within 31 days of leaving, you can convert your group life amount (usually up to a stated maximum) into an individual permanent or term policy from the same insurer without medical evidence. It’s a valuable right if your health has changed since you were hired. If you’re diabetic, have had cancer, or have a heart condition, conversion may be the only way to keep that coverage, and you should use it.

If you’re healthy, the calculation flips. Converted policies are priced for a pool of people who often convert precisely because they can’t get coverage elsewhere, so the premiums are typically well above what a healthy applicant pays for a new term policy. Group life is also usually only one or two times salary, which is rarely enough on its own; our guide on how much life insurance you need explains why.

The practical sequence: get a term life insurance quote as soon as you know you’re leaving. If you qualify at standard rates, buy the new policy and let the group coverage lapse. If underwriting comes back with a rating or a decline, convert the group amount within the 31 days instead. A broker can run both in parallel so you’re not caught by the deadline. More on the trade-offs in group vs. individual life insurance.

Replacing disability insurance

This is the benefit people underestimate, and it is the hardest to replace.

Group long-term disability almost never converts to an individual policy. When you leave, it’s gone. If you’re moving to another employer with LTD, you’ll be covered under their plan, usually after the waiting period. If you’re going self-employed, contracting, or taking time off, you have no income protection unless you buy it.

An individual disability insurance policy replaces a portion of your income (typically in the range of 60–70%) if illness or injury stops you from working, with benefits that are tax-free when you pay the premiums yourself. Applying while you’re still employed makes it easier to document your income, and being healthy makes underwriting simpler. Self-employed Ontarians can also opt in to EI special benefits, which provide up to 26 weeks of sickness benefits at 55% of insurable earnings up to the annual cap; useful, but nowhere near a full replacement.

Our guide to disability insurance for the self-employed in Ontario covers how policies are structured and what they tend to cost.

Before your last day: a short checklist

Use the coverage while you have it.

Fill prescriptions for the maximum supply the plan allows.
Book dental cleanings and any outstanding work that fits within the annual maximum.
Use paramedical balances for physiotherapy, massage, psychology and vision.
Submit every outstanding claim before the deadline in your booklet; many plans allow claims for a period after termination, but only for services received while covered.
Request the coverage end letter and booklet from HR.
Apply for replacement health and dental coverage so it begins the day after group coverage ends.
Get a term life quote and note the 31-day conversion deadline as a fallback.
If you’ll be self-employed, apply for disability insurance while your income history is clean and your health is documented.

How Hayes can help

Replacing group benefits is not one decision; it’s four or five, each with its own deadline. As an independent brokerage in Ottawa, we compare individual health and dental plans, conversion plans, term life and disability coverage from 30+ Canadian insurers, and we’ll tell you honestly where a conversion plan is the right call and where it’s overpriced for your situation. Our advice costs you nothing.

Leaving a job in the next few weeks? Get a free quote and we’ll map out what to replace, in what order, before your coverage ends. Or contact us and we’ll walk through your benefits booklet with you.