Workflow Rule is not trigging in entirety

Hello

I've set up a "test" workflow to learn how to make them work and experiment with what I need. This very simple example should:

Add a tag under Condition 1
Send two emails under Condition 2

The first email (Did Not Book Private 1) has been received but the second email (TEST EMAIL 2) has not been received. See the attached screenshots for the workflow.

This has been the case in all the similar worksflows I have set up: First emails are sent and received, second, and third are not sent.

What am I missing?

Thanks

Dennis

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