Use Automator to send files via Messages App

Question

I've seen some older posts about this issue but no real fixes.

I"m using macOS 13.1 and I would like to use Automator to send my clients iMessage or SMS texts that include images. I am able to send actual "text" just fine.

When I try to send a file, I see the file in the Messages app but I get a failed to send error. I see the same behavior using SMS or iMessage.

My simple Code

    set image to POSIX file "/Path/To/File.ext"
    
    tell application "Messages"
        activate
        set iMessageService to 1st account whose service type = iMessage
        set client to participant "5551234567" of iMessageService
        send image to client
    end tell

Again, I can send texts to the same number but not a file. I am able to send the file to the number directly from the Messages app.

Google, Apple Developer, multiple phone numbers.