Using the free version(not sure if this is the issue), when you go to send a message later, it prompts you to create an application specific password. I did that and it schedules a message. This password doesn’t seem to get saved, so when you try to send another email, you must put the password in again. This doesn’t seem right.
Thank you for reaching out. This has nothing to do with being on a paid subscription or the free version, it sounds like it may be a bug. Does the message refer to an email that you’re trying to send with an iCloud account?
Yes, sending a message from the native apple mail app with mailbutler installed. when you try to send this in the future, it asks for the apple generated PW, but this never sticks.