How long how much time it would keep on trying before it finally give up?
I need this to answer customer’s question of: “Do we need to restart the application services after Dynatrace Server down or unreachable for a long time?”
As far as I have experience - they don’t give up. I think they just increase the time between connection attempts. You should be more specific what is a long time for the customer (days? weeks? months?)
If your apps were instrumented and were running for a very long time (months) even before disconnection, you would probably have an outdated agent version anyway and restart is recommended.