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This question already has an answer here:

Let's say that an aircraft owner is not a pilot and needs someone to fly an airplane for him. If the owner pays 100% of the costs for the flights but does not pay the pilot, does the pilot require a commercial certificate?

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marked as duplicate by Lnafziger, fooot, mins, Ralph J, SMS von der Tann Aug 9 '17 at 18:22

This question has been asked before and already has an answer. If those answers do not fully address your question, please ask a new question.

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    $\begingroup$ It's not completely clear what you are asking. Are "he" and "you" the same person? $\endgroup$ – bclarkreston Aug 9 '17 at 3:57
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    $\begingroup$ Try using "the owner" and "the pilot" instead of "him", "I", and "you". $\endgroup$ – Greg Hewgill Aug 9 '17 at 4:11
  • $\begingroup$ I reworded your question to what I think you're asking, but if I got it wrong please just rollback or edit again. $\endgroup$ – Pondlife Aug 9 '17 at 12:55
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This situation would be Illegal as the law stands. What it boils down to is that flight time is considered compensation. This answer covers it well and in your case, since you are not paying your pro-rata share and the owner is paying the full expenses you are in a way getting compensated in flight time.

This answer is somewhat related as well and its seems there needs to be some "common purpose" for everyone on board as well.

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  • $\begingroup$ I think there is an important distinction between "flight time is considered compensation" and "flight time may be considered compensation". Flight time is not automatically classified as compensation; but it can be, if it was a primary motivator for a flight. $\endgroup$ – abelenky Aug 9 '17 at 14:48
  • $\begingroup$ @abelenky I agree and was thinking while I was reading this that a better way to describe it would be that flight time generally provides a benefit to the pilot (particularly if they have a relatively low amount of flight time which needs to be built up in order to be competitive for a job). The FAA considers this benefit to be compensation if someone else pays for it (exact interpretation is in the linked question, which is really a duplicate). $\endgroup$ – Lnafziger Aug 9 '17 at 16:20

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