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When a one-way trip is considered one or two segments (for upgrade purposes)

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Hello Flyertalkers!

I am attempting to route a long one-way flight the way I want, without separating the flight into two segments, and am quickly realizing that this may not be possible.

Details: I will fly DOH - HNL, and am hoping for an overnight layover in EWR. Ideally, the legs would be DOH-IAD, IAD-EWR, EWR-HNL in Y. And then I will upgrade the flight using miles+copay.

This works fine if I want to power through 35+ hours of flying, but I would prefer an overnight break(<24 hours) in EWR(family there). Any forcing of the layover splits the flights into 2 segments and doubles the miles+copay for the whole flight.

After speaking with the elite desk, they explained that the flight will only count as a single segment as long as they appear in the OW United search results (it doesn't).

Any tips or rule details will help, or am I chasing a dream here?

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