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Wierd solo endorsement question

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§ 61.93 Solo cross-country flight requirements.
(a) General.
(1) Except as provided in paragraph (b) of this section, a student pilot must meet the requirements of this section before -
(i) Conducting a solo cross-country flight, or any flight greater than 25 nautical miles from the airport from where the flight originated.
(ii) Making a solo flight and landing at any location other than the airport of origination.

The "loophole" doesn't apply; the regulation doesn't just apply to cross country flights in excess of 25 nm, but in accordance with 14 CFR 61.91(a)(1)(ii), to making a solo flight with a landing at any point other than the point of departure.

(2) Except as provided in paragraph (b) of this section, a student pilot who seeks solo cross-country flight privileges must:
(i) Have received flight training from an instructor authorized to provide flight training on the maneuvers and procedures of this section that are appropriate to the make and model of aircraft for which solo cross-country privileges are sought;

I don't recall if you stated weather the student has a solo endorsement for cross country yet in the Cessna 150 (I believe you stated he has the solo endorsement, but didn't state weather he has a cross country solo endorsement in the same). If he doesn't have a cross country solo endorsement in the airplane, then you must give him that training and endorsement.

(ii) Have demonstrated cross-country proficiency on the appropriate maneuvers and procedures of this section to an authorized instructor;
(iii) Have satisfactorily accomplished the pre-solo flight maneuvers and procedures required by § 61.87 of this part in the make and model of aircraft or similar make and model of aircraft for which solo cross-country privileges are sought; and
(iv) Comply with any limitations included in the authorized instructor's endorsement that are required by paragraph (c) of this section.
(3) A student pilot who seeks solo cross-country flight privileges must have received ground and flight training from an authorized instructor on the cross-country maneuvers and procedures listed in this section that are appropriate to the aircraft to be flown.

Again, in order to endorse for the cross country in make and model, you must have provided instruction in make and model, both ground and flight, for the cross country maneuvers and proceedures appropriate to that aircraft.

(b) Authorization to perform certain solo flights and cross-country flights. A student pilot must obtain an endorsement from an authorized instructor to make solo flights from the airport where the student pilot normally receives training to another location. A student pilot who receives this endorsement must comply with the requirements of this paragraph.
(1) Solo flights may be made to another airport that is within 25 nautical miles from the airport where the student pilot normally receives training, provided -
(i) An authorized instructor has given the student pilot flight training at the other airport, and that training includes flight in both directions over the route, entering and exiting the traffic pattern, and takeoffs and landings at the other airport;
(ii) The authorized instructor who gave the training endorses the student pilot's logbook authorizing the flight;
(iii) The student pilot has current solo flight endorsements in accordance with § 61.87 of this part;
(iv) The authorized instructor has determined that the student pilot is proficient to make the flight; and
(v) The purpose of the flight is to practice takeoffs and landings at that other airport.

This applies more exactly to your question. You may provide the instruction at the field to be used within 25 nm, and that instruction is not aircraft specific. However, you may have little to fall back on if the student has a problem and you show that the instruction you gave was in an entirely dissimiliar aircraft (eg, Cessna 170 for training, vs. Cessna 150 for solo). This is especially true as the entire purpose of the regulation, and clearly stated in 61.93(b)(1)(v) is to perform practice takeoffs and landings. How are you going to defend yourself when you show that you gave an authorization to perform takeoffs and landings at the other field using an aircraft the pilot isn't qualified to operate? Legal, but juicy liability not in your favor.

(2) Repeated specific solo cross-country flights may be made to another airport that is within 50 nautical miles of the airport from which the flight originated, provided -
(i) The authorized instructor has given the student flight training in both directions over the route, including entering and exiting the traffic patterns, takeoffs, and landings at the airports to be used;
(ii) The authorized instructor who gave the training has endorsed the student's logbook certifying that the student is proficient to make such flights;
(iii) The student has current solo flight endorsements in accordance with § 61.87 of this part; and
(iv) The student has current solo cross-country flight endorsements in accordance with paragraph (c) of this section; however, for repeated solo cross-country flights to another airport within 50 nautical miles from which the flight originated, separate endorsements are not required to be made for each flight.

You may endorse a student pilot certificate for a cross country flight, but only after giving instruction in the specific make and model. Repeated trips over the same routing takes place by endorsing the student logbook, and is not aircraft specific.
 

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