Bizarre Apple Mail behavior using "Send Again"

I’ve drafted an email that I want to modify slightly, depending on the recipient. To do this, I created the “base” email, saved it as a draft, then moved it to a “Templates” folder. I then select the message in Templates and call the Send Again feature, which normally lets you enter the recipient and modify the body as desired.

BUT, when I select Send Again, as soon as I enter the recipient and click the address that pops up from my address book, all the body text disappears!

If I type in an address that’s not in my address book, the body text doesn’t disappear. And after entering that one, if I enter one that IS in my address book, it doesn’t disappear.

So it appears that the body text disappears only when a recipient is in my address book and it’s the FIRST recipient in the To field. (No problem when you enter the first one in the cc field)

I selected the folder and rebuilt the mailbox, but it didn’t help. Any idea what’s going on?

Using an M1 MacBook Air with the latest Catalina.


Drafts folders are weird. I’d send the message to myself, then send again on the message in the sent folder.

That’s a good idea. I tried it and this doesn’t exhibit the problem I described.


This won’t help you solve the problem, but I’ve had something similar happen to me. I’ve only seen it when I have created the email by using the “action button” or “share sheet” (or whatever the heck Apple is calling it these days). I think it’s happened from both Safari and Finder, but I can’t be sure.

The email is created, the attachment and signature are there, but when I select the email address or finish the autocomplete, everything is erased. It’s beyond frustrating, but it doesn’t happen reliably.

So, you’re not alone!