Driver's headlamp requires a "manual" push to come on...

[dghii]

A few years back I had a 98 Box that I picked up to sell. I pulled the headlights to wet sand and when I replaced them, the passenger side headlight wouldn't work. After some investigation, I found that the tray connector (on the vertical part of the tray at the back) was not seated completely due to a crack in the tray plastic. I finally pulled the wheel well cover and braced the tray with my hand while my son pushed the headlight assembly into the fender. All good after that.

[itsnotanova]

There's a yellow retaining clip that holds the headlight wire harness onto the back of the headlight tray. I'd check to see if it's still there.