The Medical Expires at Midnight and the Night Landings Are 96 Days Old
You are a CPL(A) holder employed as single-pilot commander of a Piper Chieftain (multi-engine piston, eight seats) on a night charter with six passengers and a 55-minute sector. Your licence, type rating and instrument rating are valid. Your Class 1 medical certificate expires at 23:59 local tonight. Your operator's approved recency scheme requires three take-offs and three landings in the preceding 90 days, at least one at night and all in the type, before carrying passengers at night. Your logbook shows your last three night landings were 96 days ago in a single-engine Cessna, and your last Chieftain landing was 40 days ago in daylight. Your operator proficiency check was 11 months ago and is valid for 12 months. The Certificate of Airworthiness and insurance are current. The MEL shows the left landing light unserviceable as a deferred item. The aircraft is 45 kg below MTOW with fuel for the sector plus 30 minutes. Departure is scheduled for 21:00 with return at 23:40, but the operator warns a 40-minute delay is likely. Weather is CAVOK.
1. Assess each item against the requirement and state whether the flight may depart as planned.
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Licence and ratings - valid, so the privileges exist; they are not the problem.
Medical. Valid until 23:59 tonight. Departure at 21:00 is lawful, but the planned return is 23:40 and a 40-minute delay puts you on the ground after 00:20 with an expired certificate. A licence and medical must be valid throughout the flight; you cannot depart on a plan that may breach it. That is a blocker unless the flight is guaranteed to land before 23:59 - which it cannot be.
Recency. Two separate failures against the approved scheme: the three night landings are 96 days old (outside 90) and they were in a Cessna, not in the Chieftain type. Your single Chieftain landing in the period was in daylight, so it satisfies neither the 'three' nor the 'at night' element. Carrying passengers at night is therefore not permitted. Note that the scheme may be more restrictive than the bare regulation - the approved scheme is what you must comply with.
Proficiency check - 11 of 12 months, valid; it does not substitute for recency.
Airworthiness, insurance, weight and balance - acceptable.
MEL - check the deferred item's own operating conditions. A landing light is not usually required equipment for night flight where runway lighting exists, but if the entry says night operations are prohibited, it becomes a third blocker.
Conclusion: two blockers. Do not depart as planned.
2. What lawful options do you have to complete the tasking, and what does each cost?
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Option 1 - swap the commander. Hand the flight to a pilot who meets night recency in type and whose medical is current. Fastest and cleanest; the cost is crew availability and the passengers may still be delayed.
Option 2 - regain recency first. Fly the three required night take-offs and landings in the Chieftain before the charter. They must be in the type and at night; they may be flown solo or with a safety pilot/instructor, subject to the operations manual and the MEL permitting night circuits with the landing light deferred. Cost: time, and the medical cut-off still bites - if the circuits run past 23:59 the problem simply moves.
Option 3 - move the flight. Depart earlier so the return is comfortably inside the medical validity, with the recency issue still needing Option 1 or 2 first. If the passengers can travel tomorrow, the medical can be renewed and the recency flown in daylight.
Option 4 - split the duty. You act as a non-PIC crew member only; but in a single-pilot-approved aircraft there may be no second seat function, so this usually collapses into Option 1.
What does not work: relying on the proficiency check, or on the fact that the regulation may be less restrictive than the scheme.
3. The client offers to sign a waiver accepting that the medical 'only expires after midnight', and asks whether it would be different if this were a private flight. Answer both points.
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On the waiver: it has no legal effect. Medical validity is a licensing condition attached to your privileges, not a contractual term between you and the passenger. A passenger cannot consent to you exercising privileges you do not hold. If the flight lands after expiry, you were flying without a valid medical: licence breach, likely insurance consequences for the operator, and an enforcement matter that follows you rather than the client. The same reasoning applies to pressure from the operator - the commander's signature on the flight record is what matters.
If it were a private flight: the medical requirement follows the flight, not its commercial nature, so the expiry problem remains identical. The recency requirement is different: recent experience requirements attach to carrying passengers, so a private flight with the same six passengers still fails, while a solo private flight generally does not. That distinction is worth knowing but it does not rescue this tasking.
Practical answer to the client: the flight either departs earlier and lands before 23:59 with a qualified, current crew, or it moves to tomorrow. Give the cut-off time explicitly so the decision is not made again at the aircraft.