What do you see in the app when you try to use the speakers? What prompts you to reconnect them each time? 
And have you tried turning the speakers and the router off at the wall, then (after two mins) turn the router back on, then the speakers one at a time once the router is back online?

What does “reconnect” mean to you?

No idea. I’ve not ever had to re-add my speakers to the system in this way. Is the app saying it has found speakers, reconnect them? Is the app saying can’t find the system? Without anything specific, it’s hard to advise.

But please do feel free to help the OP rather than fixate on my question.

Ok, when I turn my system on, the speakers show on the app. Some times they show not connected. Some times they show connected. I get no sound either way until I go to each speaker and hold down the play button for 5 seconds. This happens every time I turn on my Sonos. It does not matter if I'm listening to a playlist or the radio. I have a 4 speaker setup, only one speaker will play until I go to each satellite speaker and manually hold the play button down. This issue just started with the last update.