I’ve done it, but this was in Michigan and the system there was a little different perhaps?
This was about 6 years ago, but the way it worked in Michigan was that you enrolled in unemployment. Once accepted you had to call in to an automated phone system called “MARVIN” once a week to schedule an unemployment check. The way it worked in Michigan is that I got 8 months of unemployment checks, as long as I called in for them. If I didn’t call in one week I didn’t lose that check, I could call it in the following week essentially extending my unemployment time.
So, when I had wracked up 40 hours of freelance time I wouldn’t call in that week. I think they had it set up that way so that you could get the unemployment money if you needed it, but if you made more than your benefit in a given week you weren’t supposed to call it in. I declared everything and never had any tax / legal issues.
I guess it was legal?