At the time I’m writing this post, this bug is still happening, so you should be able to reproduce it. I reproduced it using two iPhones running iOS 18.5 RC. As long as your audio message contains the phrase “Dave and Buster’s”, the recipient will only see the “dot dot dot” animation for several seconds, and it will then eventually disappear. They will never get the audio message.

MessagesBlastDoorService uses MBDXMLParserContext (via MBDHTMLToSuperParserContext) to parse XHTML for the audio message. Ampersands have special meaning in XML/HTML and must be escaped, so the correct way to represent the transcription in HTML would have been “Dave & Buster’s”. Apple’s transcription system is not doing that, causing the parser to attempt to detect a special code after the ampersand, and since there’s no valid special code nor semicolon terminating what it thinks is an HTML entity, it detects an error and stops parsing the content.

source: simon