Unable to get 2 workflows to work together

I am using Bookings and CRM, and am trying get the scheduling of a meeting to result in the sending of an email from a template associated with the Contacts module.

I've created 2 workflows for this.

#1 is executed when a meeting is created with the condition that the title of the meeting contains the word "Introductory", and has the instant action of changing the custom field "Contact Type" to "Prospect".

#2 is executed when a contact is executed when the Contact Type field is modified to "Prospect" for all contacts, and has the instant action of sending the email to the contact that scheduled the meeting and just changed to the "Prospect" Contact Type.

When I test the workflows by scheduling a meeting, #1 says it fails in view usage. The reason for the failure is "Related record not found to update." However, when I go to the contact I can see the Contact Type did in fact change to "Prospect". I further tested it by setting it to a different Contact Type and it worked, but still gave the error.

Then #2 never executes, at least not automatically. If I change the Contact Type to "Prospect" manually, then #2 does execute and the email sends.

What could I be doing wrong here?

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