When a DPE shows up to do an initial commercial pilot practical test, one of the things that they have to verify the applicant did was fly a qualifying long cross-country flight.
This is one of those requirements where the details count, and if the details weren’t carefully considered, it just might end up being a hard discussion with the applicant and/or their instructor if it wasn’t done correctly.
So, let’s talk about one of those scenarios that could leave the DPE, the applicant, and the CFI on the edge for just a little bit.
Let’s start with what the actual regulation says.
It indicates that a pilot seeking an intial commercial pilot certificate must complete the following requirement:

Note the requirement in this that there must be a point of landing that is at least 250 nautical miles from the original point of departure.
Ok, so, I have seen this go wrong a few ways. One was when the applicant and their instructor had their flight planning app software set to STATUTE miles instead of NAUTICAL miles because they had their flight planning in MPH because the aircraft POH listed speeds in MPH. Ugg. That meant their long-cross-country flight didn’t get far enough. So, watch for that.
But in this case, let’s look at a different scenario.
Here is the flight.

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