Anyone actually had a bad experience cashing out crypto winnings?

Used a bunch of different sites over the years and never really sweated much on cashouts, but a mate of mine had a weird one last week where his crypto withdrawal took almost two days. He was saying there was no error or anything flagged, just endless “processing” and then suddenly it landed. Made me realize I’ve always just trusted the process, but maybe that’s a bit naive given the volatility and all the off-chain drama lately.

Kind of curious if there’s any specific red flags or triggers I should be watching for, especially when the amount isn’t small. I always figure if the funds leave my balance, it’ll hit my wallet eventually, but maybe that’s not foolproof logic.