Thanks for the reply. We do not post invoices until the end of the month so that's not causing the issue and emailing from historical won't help in this case because we prefer invoices be sent right after creation. Is there anything else that may be causing this issue? It's been going on since the Adagio specialist installed the Invoices module a couple years ago. I'm thinking it has something more to do with either closing the Invoices app and reopening the following day or perhaps trying to send the email from the queue on a different day than when it was put into the queue. Is there perhaps a setting that would remind us before closing the app that there are unsent emails in the queue to keep this from happening?