There's a limitation on the triggers, that if the Custom Fields changes in less than 30 seconds it won't trigger again (I think it's 30 seconds, I experienced this a long time ago).
Check with support and confirm, but if you're making the custom field change faster than every 30 seconds than it's likely that this is problem.
You could try using the 'sendFlow' method in the API, this could probably get the job done for you.
Also, if you're sending WhatsApp messages, you also have to consider the 24 hours. If the message is outside the 24 hours you need to send messages using Message Templates.
DM me if you need more help.
@Gustavo Boregio thanks so much for the answer! I'll try the sendFlow solution and I'll DM you if I have questions.
Off-topic: Another issue that I sometimes have is that everything is executed and I see the response in the Live Chat but WhatsApp doesn't show the response, even when I can see it in live chat. Have you experienced that as well?
@geekykidstuff I have not experienced this. I suggest you talk to support to see what may be going on there.