time sensitive messages GRRRR

I have been looking at all of the Time Sensitive options here in the community and cannot find any thing that helps, here is my problem, I keep getting this message when I send a message to a few people (not all together)

After sending the message I get a red line at the top of the screen left to right but it does not reach the right hand side, the message gets delivered but I then get a notice not delivered and a circle with a red ! in it (see pics)

I need some expert help with this one please, this is happening to a few of my contacts, some contacts do get though, I have a iPhone 11 max pro