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I got it just before they raided out, but I was worried that I wouldn't.
The first time I checked on my progress, it looked like it was either stuck or had started late, because it was already close to 20 minutes after the stream began but the progress indicator said I'd been watching for less than half of the required time period of 15 minutes.
I think I refreshed the stream at that point, or maybe it was before that, because people in chat were saying that the drops weren't working.
I checked again at about 5 or 10 minutes after the hour-- that is, about 65 minutes or more into the stream-- and it said I'd been watching for about 90% or so of the required time period.
At that point, Gina got up to go message someone at Twitch (I think?), and I checked again when she came back a minute or so later, and it showed that I'd earned the drop and could claim it.
And then very shortly after that, they raided out.