Quick answer summary (what to confirm with HR)

• When you’ll receive your final paycheck (and whether your state requires it sooner than the normal payday).

• What’s included in final pay: last hours/overtime, differentials, unused PTO/vacation (if applicable), commissions/bonuses due, and expense reimbursements.

• What’s being deducted: benefit premiums, 401(k) loans, wage garnishments, or authorized deductions—and get it itemized on a final pay statement.

• When benefits end (medical/dental/vision/life), and your COBRA options, deadlines, and costs.

• If you’re 65+ (or turning 65 soon): Medicare timing—your Part B Special Enrollment Period is time-limited, and COBRA doesn’t extend it.

• Retirement plan next steps: vesting, match timing, rollover options (direct vs. check-to-you), and tax withholding rules.

Why this checklist matters more than most people think

When you retire, you’re juggling a lot at once—your last week of work, handoffs, goodbyes, maybe even a move or travel plans. That’s exactly when small payroll/benefits details slip through cracks.

Real-life example: a long-time employee assumes health coverage runs 30 days after the last day. HR meant coverage ends on the last day of the month. That single misunderstanding can create a gap—or an unexpectedly huge bill—if you schedule a procedure in the wrong window.

Your goal: leave with clean numbers, clean coverage, and clean paperwork.

1) Final paycheck rules: what’s “normal” vs. what’s required

Here’s the blunt truth: federal law doesn’t require employers to hand you your final paycheck immediately. Many states, however, set specific deadlines (sometimes “same day” for terminations).

What to ask HR (timing + delivery)

• What is the final paycheck date (exact day)?

• Will it be paid by direct deposit or a paper check?

• If paid by check: where/when can I pick it up, or will it be mailed?

• Will I receive a final pay statement showing all earnings and deductions?

Pro tip I recommend: Ask HR to email the final pay date and what will be included. It’s not “being difficult”—it’s being smart.

2) What should be included in your final pay

Think of final pay as a bucket. You want HR to confirm what’s in (and what’s not) before your last day.

Earnings to confirm

• Final regular hours + any overtime

• Shift differentials, on-call pay, hazard pay (if you have them)

• Unused PTO/vacation payout (if your policy/state treats it as payable at separation)

• Commissions earned (and the company’s commission “earned vs. paid” rule)

• Bonus eligibility (especially if it’s tied to being employed on a certain date)

• Expense reimbursements (mileage, supplies, travel, per diem)

PTO/vacation: don’t assume

Many employees are shocked to learn that paid vacation/PTO isn’t required by federal law—it’s generally governed by company policy and/or state rules.
So your job is to get a direct answer: “Will my accrued unused PTO be paid out? If yes, at what rate and on what paycheck?”

3) The 10-minute final pay stub audit (do this even if you “trust payroll”)

On your last pay statement, quickly check:

Pay accuracy checklist

• Hours worked match your records (including any approved late timesheets)

• Pay rate is correct (especially if you recently changed roles or went part-time)

• Overtime rate and hours are correct (if applicable)

• PTO payout hours/rate are correct (if applicable)

• Bonuses/commissions match the written plan or HR confirmation

Deduction checklist (common surprise zone)

• Health/dental/vision premiums: were you charged the correct final amount?

• 401(k) loan repayment: did payroll take an extra amount?

• Any “one-off” deduction: ask what it is and why it’s authorized

If anything looks wrong: flag it immediately in writing. Payroll fixes are fastest when you catch them the same week.

4) Benefits: confirm end dates, COBRA, and retirement health transitions

A) Confirm your benefits end date (don’t guess)

Ask HR:

• What is the last day of coverage for medical, dental, vision?

• Does coverage end on my last day, end of that week, or end of the month?

• When does my HSA stop receiving employer contributions (if applicable)?

B) COBRA: the basics you need before you leave

COBRA can let you continue employer-sponsored health coverage, but you may pay up to 102% of the plan cost.
Also, you generally have an election window (commonly at least 60 days) and coverage can be retroactive to avoid gaps if you elect within the allowed timeframe.

What to ask HR

• When will I receive the COBRA election notice and from whom (HR vs. COBRA administrator)?

• What is the monthly premium for my coverage tier (self, self+spouse, family)?

• When is the deadline to elect?

• How do I pay the first premium, and when is it due?

C) Medicare warning for retirees (this one is huge)

If you’re working past 65 and covered under employer insurance, you typically get an 8-month Special Enrollment Period to sign up for Medicare Part B once you stop working (or lose employer coverage—whichever comes first). Importantly, COBRA doesn’t extend that Medicare SEP.

In plain English: If you delay Part B because you chose COBRA, you can accidentally create penalties and a coverage gap. This is one of the most expensive “simple misunderstandings” retirees make.

5) Retirement plan money: 401(k)/403(b)/457 and pension questions for HR

Retirement often triggers account decisions—rollover, leave it, or cash out (usually not ideal).

What to confirm about your workplace plan

• Are all employer matching contributions fully posted?

• What is my vesting percentage (if not fully vested)?

• How do I access distribution/rollover forms after my employment ends?

• Do you have my correct email and mailing address for future plan notices?

Rollover tip I strongly prefer (because it avoids nasty surprises)

When rolling over a workplace plan, a direct rollover is usually simplest because it helps avoid mandatory withholding that can happen when money is paid to you first. If you receive the distribution personally and later roll it over, withholding rules and the 60-day rollover timeline can create avoidable tax headaches.

6) HR documentation: what to collect before your access disappears

Before your last day, get copies (PDF is fine) of:

• Offer letter + any job change letters (title, pay, classification changes)

• Most recent benefits summary + plan contacts (especially COBRA administrator)

• Retirement plan contact info and your plan/account details

• Final pay confirmation email (date + what’s included)

• Any written agreements you signed (non-disclosure, non-solicit, etc.)

• Performance reviews or recognition letters (helpful for references later)

Also confirm:

• Where your tax forms will be mailed (W-2; and potentially 1099-R later if you take distributions)

• Who to contact after you leave (name + email/phone for HR/payroll)

A ready-to-send “Final Pay + Benefits Confirmation” email to HR

Subject: Final paycheck and benefits confirmation (retirement – last day [DATE])

Hello [HR Name],
As I prepare for my retirement and last day of work on [DATE], could you please confirm the following in writing?

1. Final paycheck date and delivery method (direct deposit or check)

2. Items included in final pay (final hours/overtime, PTO payout if applicable, commissions/bonus eligibility, reimbursements)

3. Any final deductions that will be taken and what they cover

4. End date of medical/dental/vision coverage and COBRA administrator contact + expected timeline for the COBRA election notice

5. Retirement plan next steps (how to request a rollover/distribution and whether any employer match will post after my last day)

Thank you for your help—this will ensure I transition smoothly.
Sincerely,
[Your Name]

Master checklist: final paycheck + last day of work

Use this as your “walk-out-the-door confident” list.

1–2 weeks before your last day

• ☐ Ask HR to confirm final paycheck date and delivery method

• ☐ Confirm PTO payout policy and your current balance

• ☐ Submit all timesheets, PTO requests, and expense reports

• ☐ Confirm commission/bonus rules and any final approvals needed

• ☐ Confirm benefit end dates + COBRA cost estimate

• ☐ If 65+, map Medicare steps (don’t let COBRA derail your timeline)

• ☐ Download pay stubs (at least last 2–3) and benefits summaries

Your last week

• ☐ Get HR/payroll confirmation in email (dates + what’s included)

• ☐ Ask who handles corrections if final pay is wrong

• ☐ Confirm where W-2/tax documents will be sent

• ☐ Gather retirement plan contacts + distribution/rollover instructions

• ☐ Return company property plan (laptop, badge, keys, credit card)

• ☐ Write down personal copies of important contacts (HR, manager, IT helpdesk)

Your last day

• ☐ Do a final “pay + benefits” verbal confirmation with HR

• ☐ Return property and get a receipt (email is fine)

• ☐ Verify any continuing obligations (confidentiality, non-solicit, etc.)

• ☐ Confirm how to access HR after separation (email/portal)

After your last day (when money starts moving)

• ☐ Review final pay stub using the 10-minute audit

• ☐ Track COBRA notice + decision deadline

• ☐ If rolling over a retirement plan, prioritize direct rollover steps

• ☐ Save all offboarding emails in one folder

Common FAQs

“What if my final paycheck doesn’t show up?”

Start with payroll/HR in writing. If the payday has passed and you still haven’t been paid, the U.S. Department of Labor notes you can contact the Wage and Hour Division or your state labor department.

“Does my employer have to pay out unused vacation/PTO?”

Not under federal law; it’s typically controlled by your employer’s policy and/or state rules.

“How expensive is COBRA?”

Qualified individuals may pay the full premium up to 102% of the plan cost.

“If I’m 65+, can I just use COBRA and sign up for Medicare later?”

Be careful: Medicare guidance warns that your Part B SEP is only 8 months after employment/coverage ends (whichever happens first), and COBRA doesn’t extend that window.

Final thoughts (my retirement opinion)

Treat your last day like a financial closing—because it is. When you walk out with final pay confirmed, benefits timelines clear, and retirement plan steps mapped, retirement feels lighter immediately. Your future self will thank you for doing the “boring” checks now—so you don’t spend your first month retired chasing HR emails.

Sources

• U.S. Department of Labor – last paycheck guidance

• Example of a state rule (Maryland) – final wages due by the day you would have been paid

• U.S. Department of Labor – vacation leave is not required by the FLSA

• U.S. Department of Labor + CMS – COBRA basics and premium up to 102%

• U.S. Department of Labor (EBSA) – COBRA FAQs (election period)

• Medicare.gov + SSA – working past 65, Medicare Part B SEP and COBRA not counting

• IRS – rollover rules and withholding considerations

Video section (helpful walk-throughs)

• COBRA Continuation Health Coverage (state labor department video)

• Medicare Special Enrollment Periods (plain-language overview)

• Medicare Open Enrollment – In The Flow (:15) (CMS official short)

• Direct vs. Indirect Rollovers (and the 60-day rule)

Disclaimer

This article provides general educational information and isn’t legal, tax, or benefits advice. State laws and employer policies vary—confirm details with HR, your plan administrator, or a qualified professional.