Advanced automaions emails not sending

Hi there, Im trying to automate our bot ticketing proces but am running into an issue with email automations.

the use case is as follows: all customer conversations with our chatbot need an email transcript sent to the correct employee.

using advanced automations i can succesfully asign the chats to the right person.
i also have a protocol to send out an email to that person with an transcript. this email does not get sent.

to make sure my protocol was working correctly i added control messages to send after the email was sent. these control messages work.

on the first test i did recieve an email to the correct adress. however on all subsequent tests it fails to send. changing to a different email results in the same problem, the first test it works but on the second test no email gets sent.

the image shows the logic used in the protocol