To start PlayIt Live when you log into Windows you will need to drop a shortcut to PlayIt Live into the Startup folder. First, copy the shortcut you can find on the desktop after installing PlayIt Live:

Then press Windows+R to bring up the Run window and type shell:startup and click OK. Then paste the shortcut into the Startup folder.

This will start PlayIt Live when you log into Windows. On PlayIt Live, to start automation when PlayIt Live starts, go to Manage > Scheduled Events, and click Add New. Name the event Automation and select Trigger On Startup. Add an action, Change Playout Mode and select Automation ON (or Auto in previous versions). Click OK to save the changes.

When you log into Windows, PlayIt Live will start and automation will start.