Trigger not firing unless first "run" from Maestro

@Koltrasten, welcome to Keyboard Maestro (KM) and its Forum.
KM is one of the best Mac automation tools available, its Forum is one of the best and friendliest forums on the Internet. Whenever you reach a tough stumbling block trying to use KM, please feel free to post your question/problem here for help.

You will also find this helpful:
Tip: How Do I Get The Best Answer in the Shortest Time?

Actually, Keyboard Maestro (KM) is designed for those with no programming skills (but is also very useful to us programmers).

Like any language, or Mac app, you have to spend some time to learn how to use it.
With KM, a little bit of learning goes a long way.

The design of KM is much different from, and IMO much better than, QuicKeys.
You may find this KM Wiki article helpful: Transition From QuicKeys

As you have a little bit of time try to work your way though this:

Getting Started with Keyboard Maestro

For more help, see Getting Started with Keyboard Maestro and the Forum .

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