>carrying a WDF challenge coin at all
You know how sometimes you'll dig out a coat you haven't worn in ages and find money in it? (I love when that happens.) I suspect the challenge coin was like that - it happened to be in one of the pockets of that flight jacket, which he hadn't worn in quite some time.
You're right that jetting around in a jacket with a WDF Flight Test patch on it is an unlikely thing to have been doing in the Exile, but on the other hand, he did a lot of dumb things back then. :)
Anyway, it most probably was sometime in the early 2380s; I briefly had the vague notion that it could also have been during his stint on Earth in the early '50s, but that was before Aegis Florea and so cannot be the case.
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