590 feeding issues

Did the problems start happening before or after the cleaning?

before. I bought this from a friend and the issue started when he 1st bought it. couldnt pass up the deal, so I am trying to fix it now.

Mine does this sometimes but seems to be only if I slowly rack it or rotate the gun while doing so. When I first got mine the Spring in the magazine tube was Fubar. I contacted Mossberg and they sent me a new one, this took some time because their was a drop in communication. So in the interim I fixed the original and it has worked fine. Now I have a backup spring.

So long story short I'd double check the spring.

mine will do it on a hard and fast rack sometimes. I have watched it in slow motion and still cant figure it out. I am almost ready to admit defeat and take it to a gunsmith. I really like doing my own work, but I think this is above my skill level.

You might want to start with replacing the spring then. I'd suggest one from Wolff springs, I have one in my 590 and it is awesome.

Well I don't know a whole lot about the internals of a shotgun but the bad spring idea does sound like it could be the problem, get another spring and if that doesnt fix it then take it to the smith.

Are you keeping the buttstock on your shoulder as you manipulate the slide or allowing it to drop? I've never had an issue with my 500 except when I just toss a shell in before loading.