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Assuming I am interpreting the below FAR correctly, one must either be solo, or have an instructor present to complete the long cross country requirement. More specifically, it seems to me that you could meet the requirements with a passenger present if an instructor is on board.

§61.129 Aeronautical experience.

(4) Ten hours of solo flight time in a single engine airplane or 10 hours of flight time performing the duties of pilot in command in a single engine airplane with an authorized instructor on board (either of which may be credited towards the flight time requirement under paragraph (a)(2) of this section), on the areas of operation listed under §61.127(b)(1) that include—

(i) One cross-country flight of not less than 300 nautical miles total distance, with landings at a minimum of three points, one of which is a straight-line distance of at least 250 nautical miles from the original departure point.

I'm trying to understand what the purpose of the solo requirement is, and how it could be alternatively achieved without being solo, but only if an instructor is onboard.

It's clearly not for safety of the passenger, since, as a private pilot, its completely legal for me to make the very same flight with a passenger; I just can't use it to meet the commercial requirement quoted above. Why not? And how could adding an instructor to the plane make any difference?

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    $\begingroup$ They addressed this question at askacfi.com/5172/…. For insurance purposes, it is often not possible to solo in a twin or helicopter and for consistency, they extended it to single engine. It also allows you to count time working on your IFR toward the commercial. e.g. if your long IFR cross-country can count for your commercial as well. $\endgroup$ – JScarry Feb 26 '17 at 15:32
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    $\begingroup$ The askcfi link doesn't answer the question why the x-country must be done solo (except where they waive the requirement). What is the harm in allowing the long cross country occur with a passenger onboard for the purpose of this requirement? $\endgroup$ – Greg Taylor Feb 26 '17 at 22:15
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I got this answer to my question from a CFI...

The idea behind the solo requirement is to assure the pilot can accomplish the trip unassisted. Other passengers are permitted if an instructor is present because the instructor will assure that the passengers do not assist with the flight.

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    $\begingroup$ I'm not sure I buy this answer, but it's the best I've heard so far. $\endgroup$ – Greg Taylor Mar 1 '17 at 15:52
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I've always believed that the idea behind the solo requirement is to develop confidence as a pilot. When the flight is all up to you, the idea is that you will rise (pun intended) to the occasion, and realize that you are Pilot in Command, you are the only one in the airplane so it is really obvious that you are final authority and responsibility for the operation and safety of the flight.

From a legal perspective, I think the answer to your question might be found in this response from the FAA.

Because this flight time is a substitute for solo flight time, the pilot is not receiving instruction and therefore cannot log this time as dual instruction received. The pilot can log the time to meet the requirements of § 61. 129(a)(4) and log total flight time. Section 61.51 (e) prescribes the requirements for logging PIC time. The pilot could log PIC time under § 61.51(e)(l)(i) if the pilot has a private pilot certificate with the appropriate ratings for the aircraft. Otherwise, the pilot cannot log PIC time. None of the other § 61.51(e) logging provisions are applicable to your scenario. However, § 61. 129(a)(4) permits crediting of the time toward the 100 hours of PIC time required for the commercial pilot certificate under § 61.129(a)(2). The logbook entry should accurately reflect the provision under which the flight time is logged.

So the wording in 61.129 isn't really about being alone in the airplane, it looks like this is actually to clarify that that the commercial pilot student (in this case) needs to actually conduct the flight as PIC (with all the responsibilities therein - see below), and if the CFI goes with the CPL student, the CFI cannot log it as PIC time (as they normally would when acting as a CFI), and the time would not be logged as dual received for the Commercial Student, but just straight PIC time.

As a reminder PIC is defined in 14 CFR § 1.1:

Pilot in command means the person who:

  1. Has final authority and responsibility for the operation and safety of the flight;
  2. Has been designated as pilot in command before or during the flight; and
  3. Holds the appropriate category, class, and type rating, if appropriate, for the conduct of the flight.

As a final note, I think it gets confusing because 61.87(a) defines solo flight, but only for subpart 87, which is clearly talking about students who have not obtained their private pilot certificate yet:

The term “solo flight” as used in this subpart means that flight time during which a student pilot is the sole occupant of the aircraft...

The same definition does not exist in 61.129 (Aeronautical Experience for Commercial Pilot Applicants). Noticeably absent from the regulation, however, is the mention of any passengers, so I think the choices are a) the pilot is the sole occupant of the airplane, or b) the pilot is making the flight with their flight instructor, however, the flight instructor is essentially a passenger (unable to log PIC or dual-given time), and the pilot must log the flight as PIC.

I believe this idea that it must be either solo or with your CFI is further confirmed by this interpretation from 2016:

a pilot must choose to log all ten hours as solo flight time in a single engine airplane or, in the alternative, log all ten hours performing the duties of a pilot in command in a single engine airplane with an authorized instructor on board. A combination of hours is not permissible under the rule.

This means you must plan for the 10 hours in 61.129(4) to either all be solo, or all be with an authorized instructor (who is not acting as PIC).

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What they're really after here is can you flight plan a trip to a different region of a country or continent and successfully navigate it. This requires more through flight preparation to an unfamiliar airport or where the weather may be different or changing from you time of departure to your ETA. It also forces you to cope with changing conditions e.g. day into night, etc.

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