I've had your product only a few weeks and went through

Hi. I've had your product only a few weeks and went through an update already, which is awesome. It tells me you are on top of your game keeping the plugins working well. But the reason I am asking help is that last time I have to go through having to delete the plugin then have to download the new one and re-install. What's hap with that? Will I need to do that everytime there is an update?
When I click on update, I get the window to click "update now" and next I get the warning that I have the latest version of the plugin but I don't.
I hope you can help.
Please advise.
Thank you
Esther