What exactly does this mean?
I noticed a flight scheduled even an hour past from the current time still shows the Actual/Estimated 14 minutes past the filed departure time. Before the flight has begun, shouldn’t those times match?
If it’s in italics, it’s an estimate. We’ll estimate departure times that may differ from the schedule or flight plan.
I already knew all of what you said, but still have the same question(s).
Maybe I don’t understand your question, but you said “What exactly does this mean” in the context of “Actual/Estimated”
The answer is that we’ll list a time in italics if it’s an estimate and not in italics if it’s actual. So, if we estimate a time to be 4:22 it’ll look like that – but if it’s actually happened, it’d be 4:22.
As far as, "I noticed a flight scheduled even an hour past from the current time still shows the Actual/Estimated 14 minutes past the filed departure time. " – I’ve re-read that several times and am not entirely sure what that means.
“Before the flight has begun, shouldn’t those times match?” in the context of “Actual/Estimated” – the answer is that if we estimate a different time, it’ll be different than the scheduled time.
If I’m missing the point, can you re-phrase the question and maybe link to an example?
I think maybe he is asking why your estimates are so off. As in…a flight was scheduled to take off an hour ago, but FA estimates its 14 mins late, when in reality, it’s over 60 minutes late.
Yes? No?
“What exactly does this mean?”
I know what it’s “supposed” to mean, but I meant what exactly does it mean. I guess instead I should have asked, how is it calculated?
“I noticed a flight scheduled even an hour past from the current time still shows the Actual/Estimated 14 minutes past the filed departure time. Before the flight has begun, shouldn’t those times match?”
Lets say it’s 12:00 noon. What I meant was, I noticed a flight that was filed to depart an hour from now, at 1:00 PM. Yet, FA was saying it was the “Actual/Estimated” departure time was 1:14 PM. Given that there’s still an hour until the filed departure time, why wouldn’t FA just estimate the departure time to be 1:00? Where does it come up with this estimate to add an extra 14 minutes? This was not at a busy airport. Do they know the pilots? 
Those times are usually from ETMS/TFMS which adds expected taxi out time/delays to to the scheduled departure time (which is usually gate departure time for the airlines).
The flights I’ve seen it on are not airlines.
You’ll have to provide more information (link) or we’re just guessing.
I don’t think it’s possible to explain every piece of decision making logic, but things like an inbound approach that’s expected to block an IFR departure, historical departure time trends, expected release times, etc.