Hey, I really like these low-charisma reactions from NPCs, but you guys should know that by re-initiating conversation with most of these lets you do the stuff they normally wouldn't let you do via. the first failed convo.
In the case of the Herald I was able to get a sending out simply by talking to her directly after the first failed convo, (won't do so again,) knew it was a new addition, so I wanted to let you know as I wasn't sure if it was a bug or not.
Yes, trying immediately after it fails will allow you to reroll. How long do you want us to wait between tries optimally?