It's time to admit dafeet?

[Xairbusdriver]

I've installed and deleted three different apps that claim to be able to "Send Later" an email.

• Mailbutler - It probably can but only if one purchases the "Preimium" package.
• Spark - It actually did, but it has a 50 addressee maximum and a horribly crippled message editor
• Airmail - Can get it to actually work, even with text "support". It's the least expensive app at ~$3/mon

There are some who have designed Automator/AppleScripts that may not now work. Apple is letting AS slowly die, probably for safety concerns.

I will probably return to Apple Mail and simply create drafts a few days ahead of time and a Calendar event to remind me of the day I need to send the messages (~85 addresses, 4 to 8 times/mo). Sending any email while using Comcast/Xfinity requires disabling the NVP which I seem to forget every other day...

[Paddy]

If you're sending to a list, have you considered something like Moosend? (I think it allows scheduled sending on the free plan - Mailchimp no longer does)

Or - you can do scheduled sending from Gmail using the webmail version -  which also allows you to send to up to 500 non-Gmail addresses at a time and up to 2000 Gmail addresses.

Interestingly - there is a third-party desktop app for Gmail: https://apps.apple.com/us/app/mail-for-gmail/id1216244845?mt=12

I'm assuming that you mean you have to disable your VPN to send email - not your "NVP" (an early form of VOIP)

[Xairbusdriver]

If you're sending to a list

It's a list, but the main person changes with each date. As impersonal as an email is, I like the "To:" to be the birthday person. Everyone else is in "Bcc:". I just copy two parts of the 'email' column in the spreadsheet and paste. I'm just stubborn and cheap!
I don't use Google, nor Gmail. I refuse to surrender!!

I'm assuming that you mean...VPN

True, my keyboard maid a miztake.

I just today got a note from MailButler asking if I needed more help with their app. I didn't bother suggesting that they put the "Send Later" function in the free option.

Still 'thinking' about Automator/AppleScript. The sending part is actually the easiest of the tasks. Coming up with something at least a bit personal for people, most of whom I haven't talked to for over 55 years, is more difficult. At least some of them have 'bio's' at the class web site. At our age we will probably not remember what the email said 365 days ago!