A while back, we added a UX enhancement that disabled sending the OOO message when an agent had replied to the conversation in the last 5 minutes. https://github.com/chatwoot/chatwoot/pull/11073 This would not send a "we will be back" message even if that reply was a private note. This would break for bots that posted private notes, and even for agents who need to just add a note and not actually reply to the email.