I had a really bizarre experience last night when I was waiting for my ORD-FNT flight operated by SkyWest. I was on AA3088, with an inbound aircraft coming from DTW as AA3059. I was sitting in the G-Concourse AC (They had sports on the TV, not news, in case anyone asks), and I decided to check on the inbound flight's status. I pull it up, and it's marked 45 minutes late and still on the ground at DTW (My flight is showing on time). I go over to the AAngel at the desk, and he tells me it's a maintenance delay.

At 8:53PM, the DTW-ORD flight's delay jumped to 1h55m, still on the ground at DTW, and my flight posts a delay to 11:05PM. I was keeping an eye on it, and at 9:10PM, my flight un-delayed itself, went back to its 10:10PM departure, and the DTW flight was marked as in the air for 50 minutes and almost arrived. I asked the AAngel how the heck that could happen, and he said SkyWest schedule updates aren't automated. Someone has to radio the flight status down so a person can update it manually, and it would seem nobody radioed telling them the flight had ever taken off.

The real weirdness was weirder, though. I got to the gate, saw all the passengers run off the plane to make connections, and suddenly the gate screen went from "Boarding Soon" to "Flight Closed." I refreshed the app, and it said we had taken off from ORD and landed in FNT within a span of 5 minutes. With no mention about this, and several confused passengers who had run up from other connections wondering if they'd missed the flight, the gate agent appeared and started boarding. I kept looking at the app throughout boarding, and all of the following happened:

• We departed and arrived 5 minutes later
• We departed and were en route to get there 14 minutes before we left (Delayed)
• We departed and arrived 14 minutes before we left (On Time)
• We departed and were en route to get there 14 minutes before we left (Delayed)
• We un-departed and were scheduled to depart and get there 14 minutes before we left (On Time)

By the time the door closed (About an hour late. The pilot said we needed to de-ice, but he was discussing an "f'd up repair" (their words, my censorship) with a maintenance guy in the galley), the schedule was solid about the fact that we had already left and arrived 14 minutes before we left, but were again delayed. At no time did the schedule actually show what happened until after we actually arrived.

TL;DR: So apparently SkyWest planes can't report their statuses automatically, which I didn't know, and the people responsible for updating the schedules really dropped the ball last night.