Soft Landing · Chapter 6 · Required for everyone

The Deadline Tracker

A benefits deadline doesn't care that the notice was buried. Put every benefits and leaving clock on one page before a default date makes the decision for you.

Output: One dated tracker containing the trigger, controlling source, owner, deadline, and proof for every applicable route.

Routes0/5 conditional routes resolved

Rows0/4 applicable rows complete

Hard dates0 active red dates

Conflicts0 source conflicts flagged

Earliest unresolved dated actionNo unresolved dated action.

Tracker statusTracker incomplete: a baseline, route decision, row field, source conflict, or critical reminder remains unresolved.

Next: enter the separation or coverage-loss date.

1. Date the tracker and resolve applicability

Enter a calendar date only after identifying the trigger. Skipping an irrelevant route does not leave the tracker incomplete.

Separation or coverage-loss dateWhat the date represents

If You Have an FSARoute status

If You Have Life InsuranceRoute status

If You Have Equity or OptionsRoute status

If You Need Replacement Health CoverageRoute status

If You Have a Retirement Plan, Loan, or HSARoute status

Default route

2. Everyone

4 actions required for every reader

amberContact the state unemployment programAs soon as possible after becoming unemployedIncomplete · missing trigger event

Clock starts:
Becoming unemployed

Verify with:
State agency

If missed:
Delay, different payable week, or missing certification can affect benefits

Trigger eventCalendar deadlineResponsible ownerControlling document or current government sourceProof of submission, payment, or written confirmationUrgency markEarly reminder or professional reviewFinal reminder

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

blueInventory benefit documentsFirst weekIncomplete · missing trigger event

Clock starts:
Separation

Verify with:
Termination packet and plan contacts

If missed:
Hidden clocks remain unknown

Follow-up row: reminders are available but optional.

Two sources conflict. Flag the conflict instead of averaging the dates.

amberConfirm health-coverage end dateFirst weekIncomplete · missing trigger event

Clock starts:
Separation or plan notice

Verify with:
Plan or carrier

If missed:
Wrong date corrupts every replacement-coverage comparison

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

blueEnter every applicable route belowFirst weekIncomplete · missing trigger event

Clock starts:
Separation

Verify with:
This tracker

If missed:
Conditional deadlines remain unowned

Follow-up row: reminders are available but optional.

Two sources conflict. Flag the conflict instead of averaging the dates.

Conditional route

If You Have an FSA

3 applicable actions

redConfirm final eligible-incurrence dateBefore plan coverage endsIncomplete · missing trigger event

Clock starts:
Plan coverage ending

Verify with:
FSA plan and administrator

If missed:
Later expenses may be ineligible

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

redSubmit eligible claimsPlan runout deadlineIncomplete · missing trigger event

Clock starts:
Plan runout

Verify with:
FSA plan

If missed:
Valid earlier expenses may go unreimbursed

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

redEvaluate carryover, grace period, or continuationBefore the plan's election deadlineIncomplete · missing trigger event

Clock starts:
Plan election opportunity

Verify with:
FSA plan

If missed:
Optional access may expire

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

Conditional route

If You Have Equity or Options

3 applicable actions

blueInventory each grantAt separationIncomplete · missing trigger event

Clock starts:
Separation

Verify with:
Award agreement and portal

If missed:
Vested value and clocks remain unknown

Follow-up row: reminders are available but optional.

Two sources conflict. Flag the conflict instead of averaging the dates.

redConfirm contractual exercise deadlinePlan-definedIncomplete · missing trigger event

Clock starts:
Plan or award event

Verify with:
Issuer or administrator

If missed:
Unexercised awards may expire under plan terms

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

amberReview ISO or NSO tax treatmentBefore exercise or extensionIncomplete · missing trigger event

Clock starts:
Exercise or extension decision

Verify with:
Tax adviser and issuer records

If missed:
Contractual time and tax status may diverge

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

Conditional route

If You Need Replacement Health Coverage

5 applicable actions

redCompare spouse or other employer planPlan-defined special enrollment periodIncomplete · missing trigger event

Clock starts:
Loss of eligibility

Verify with:
Other plan

If missed:
Special enrollment opportunity may expire

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

redCompare Marketplace or state-exchange plansUsually within the loss-of-coverage SEPIncomplete · missing trigger event

Clock starts:
Loss of qualifying coverage

Verify with:
Marketplace

If missed:
Enrollment route can become unavailable until another event or open enrollment

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

redElect COBRA if selectedElection-notice deadlineIncomplete · missing trigger event

Clock starts:
Later of coverage loss or notice under the federal baseline

Verify with:
Election notice

If missed:
Continuation option can expire

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

redPay COBRA initial premiumNotice and federal payment ruleIncomplete · missing trigger event

Clock starts:
Election and notice

Verify with:
Election notice

If missed:
Election can be lost for nonpayment

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

blueCheck Medicaid, CHIP, or MedicareHousehold-specificIncomplete · missing trigger event

Clock starts:
Household eligibility facts

Verify with:
Government program

If missed:
A lower-cost or required coordination route may be missed

Follow-up row: reminders are available but optional.

Two sources conflict. Flag the conflict instead of averaging the dates.

Conditional route

If You Have a Retirement Plan, Loan, or HSA

3 applicable actions

amberConfirm plan-loan treatmentPlan-defined eventIncomplete · missing trigger event

Clock starts:
Separation and plan terms

Verify with:
Recordkeeper

If missed:
Offset, default, or rollover planning may be delayed

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

redEvaluate age-55 exception before rolloverBefore moving the accountIncomplete · missing trigger event

Clock starts:
Account-movement decision

Verify with:
Plan and adviser

If missed:
IRA rollover can change access to the employer-plan exception

Critical row: both reminders are required.

Two sources conflict. Flag the conflict instead of averaging the dates.

amberConfirm HSA custodian and eligibilityAfter separationIncomplete · missing trigger event

Clock starts:
Separation and coverage change

Verify with:
Custodian and current tax guidance

If missed:
Fees, investment choices, or excess contributions may result

Follow-up row: reminders are available but optional.

Two sources conflict. Flag the conflict instead of averaging the dates.

Urgency marks

Red

A deadline that can terminate an option

Amber

A delay that raises cost or creates a coverage gap

Blue

A follow-up without a hard cutoff

The colors describe urgency, not legal merit.

Source conflicts and reminders

When two sources conflict, flag the conflict instead of averaging them. Ask which document controls, request the answer in writing, and record the time zone and delivery method when receipt matters.

Set two reminders for each critical date. Use the earlier reminder for professional review when tax, legal, coverage, or medical facts remain unresolved.

Keep the digital copy as the working file because it can hold links, uploads, and confirmation numbers. Print it when paper helps you pay attention. Paper is excellent at sitting on a desk and terrible at holding a confirmation link.

Common mistakes

Starting every clock on the termination date
Treating a common 31-day or 90-day period as the actual plan deadline
Assuming COBRA's retroactive feature provides free coverage
Confusing an FSA claims runout with permission to incur new expenses
Treating a contractual option extension as preservation of ISO tax treatment
Entering gross estimates where the decision requires an actual quote
Relying on an oral answer without recording the representative and confirmation
Marking an item complete before payment, documents, or election acceptance are confirmed

Completion test

Every conditional route is marked applicable or skipped. Every applicable row has one calendar date, the trigger event, the controlling source, an owner, and proof of submission, payment, or written confirmation. Critical rows also have two reminders.

This tracker organizes dates and proof. It does not determine eligibility, extend a deadline, interpret a plan, or replace current guidance from the controlling administrator, agency, carrier, or qualified adviser.

Monday Move

Enter the separation or coverage-loss date, resolve each conditional route, and complete the first Everyone row with the actual state-agency source and confirmation.

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