Automation Behavior with Buttons

I have a 5 button Lutron Caseta Pico remote. I am trying to automate lights with it. If I have a behavior triggered by a condition when pressing the button, and I happen to press the button multiple times, does the instance of the automation trigger multiple times or is it one instance of the automation that is triggered?

Conditions don’t trigger automations. Triggers do.

In answer to your question:

The default (if no mode is specified) is mode: single.

So if you have not specified a mode for your automations only one instance runs at a time and a warning is written to the log if the trigger reoccurs while the automation is running.