maildrop in macOS mail broke since iOS 14

Strange one, it sounds like an account issue to me then, especially considering it doesn’t matter where it’s sent from, which device, file type, not receiving from different senders.

I have seen a mail message/draft jam up an account before because it’s stuck in limbo somewhere to where the account had to be repaired on the server side, (Of course Apple would need to do this).

Id probably give them a call, I don’t suppose you have another Apple ID you can use to sign in and test. No worries I’m usually up late too let me know how it goes!

Hey Franco Borgo!

Is there an error, or kick-back message?

If it is happening on all devices now, (even after an update), can you check how much iCloud storage you have available? Also, are they all trying to send through the same network? If so, will they send from another network, (If possible to test)? Most of the time I’ve seen this it’s either an account/iCloud storage issue or network related. Another thing that’s possible, (Although it’s happening on all your devices now, so most likely not), is your device’s local, available storage.

By the way, (maybe not related), but I have seen people try to “Mail drop”, but not through their Apple ID, but sending via their email provider, (Such as Google, Yahoo, Etc), and it fails because they have different sending restrictions than Apple. A good way to test is on the mail providers web site.

Ive seen an email send fine through Mail Drop, at iCloud.com, yet, you log into your email providers web site and send the same exact email, as in Gmail, (it may ask you to upgrade to Google Drive to be able to send).

For Apple here’s the Mail Drop limits:

https://support.apple.com/en-us/HT203093

Although the error message may shed some light if it’s so etching else, cheers!

Hey again, no worries.

I checked Apple’s server status’, all seems okay:

https://www.apple.com/support/systemstatus/

That was my second thought, now that we know all else is good. Can I ask what app you’re sending the mail from? And if the same happens using the web, or another app? Or another network, (Although I know the sender got the same result, worth a shot on your end, especially if the didn’t get an error message.

Did your friend get an error message?

Also, it’s worth checking if your iCloud mail is being forwarded to another email account.

To be sure you can check iCloud.com > Mail > Settings (On the bottom left, gear ⚙️) > Preferences > Forwarding), if so, the receiving email account may not be working as expected, (I’ve seen before, although unlikely if you’re not aware of it, possible).

Is your Apple ID one ending in iCloud.com Me.com or Mac.com? Or is it a standard email address? I ask to be sure it’s not trying to send from or to that actual address, but also I know some things have changed lately with being able to use Me.com or Mac.com etc.

Since the server appears to be okay, and of the same for you and senders, and the network doesn’t matter (If it is the same on multiple networks), and it’s not a storage issue, I’d assume it maybe an account issue, (Unless it’s an app specific, or device specific issue, although all yours appear to be Apple).

Either way let me know how it goes I’ll do what I can to help if possible. Those answers may help as well, thanks!

Oh good! Hope it stays working then!