Originally Posted by MidnightLight

I haven't seen this mentioned yet, so let me put out a warning that apparently the two free checked bags benefit does not fully apply if your itinerary has an additional stopover.

On my recent travel (SFO->HKG (main destination)->SIN (additional stopover)->CTU->SFO), I was charged a checked baggage fee for my final return journey from SIN, despite having paid for the reservation entirely with my Chase United Club credit card.

When I contacted United customer service, their agent informed me that the free bag benefit only applies twice per reservation, i.e. for one outbound journey and one return journey. If you have an additional stopover, this means you have to check in your bags a third time (at SIN, in my case)--and you are subject to checked baggage fees for all such additional check-ins beyond the first two. So I was out of luck here.

Just FYI to all other folks who might potentially run into the same situation in the future. And most likely the same policy also applies to the Explorer card's one free checked bag.