Some Mail not sending in iOS 16

It was the Undo Send Delay option for me too. At the bottom of the Mail tab in Settings, turn Undo Send Delay OFF, reboot iPad (in my case), and I could finally send email again.

I’m logged into several accounts through the apple email app, both yahoo and gmail, and I couldn’t send mail from any of them. As others have said, I’d hit send, I’d hear the swoosh sound, but the email would be sitting in my outbox and no matter how long I waited, even hours and then overnight, it just sat there. I could try to resend from there, I could delete the message from there, but no matter what, everything I tried to send stalled in the outbox.

I tried deleting my primary email account and re-logging in through settings, nope, same problem, every email I try to send stalled in the outbox. I did also try turning off Undo Send Delay because of other people on this thread who mentioned it, but that didn’t work at first either. It wasn’t until I tried again this evening, turning off Undo Send Delay *and rebooting my iPad before I tried sending an email again and finally, for the first time in days, I can send an email from my iPad. So annoying!

I was hoping the restart helps but it didn’t.

Nobody got the « Sender address was invalid » ? Of course I’ve checked several times my login details, both IMAP and SMTP ones… But I can send emails if I disable iCloud Mail. It’s really getting on my nerves!

Same problem with mail just completely disappearing. Every indication is that it’s been sent but when you don’t have the expected reply, one way or another you discover that the email has simply vanished! Not in drafts or sent or outbox, just **** gone. This is a major issue!

I had to reset both my iPhone and iPad for this to work… Glad you’d needed just a simple restart ^^

Frustrates the f*** out of me that when you speak to Apple support they know nothing about it and come up with inane and hopeless suggestions on what to check etc instead of dealing with the software issue that they are not allowed to admit!

Apple has rapidly gone downhill over the past 3-4 years. My friend's Samsung knocks my iPhone into last century. Dictation is accurate, keyboard typing is accurate, spell check is helpful, not ridiculous "phailia" (WTF...??) and the camera on the Samsung just blows me away. It's stunning especially in low light/nighttime. Why do we persist with Apple phalias!

Not the same problem as this steam

I have exactly the same problem. I’ve had 3 emails just completely disappear since iOS 16.1.1 installed on my phone…no error message, not in drafts, not in any folders. Just disappeared in cyber-space somewhere.

I have tried emailing myself then hitting “undo send” but that makes the msg show again so it can be canceled, added to, etc. It does not make the msg disappear.

I am now checking every email to make sure it was sent. Help!

The problem I have is when using the Apple Mail app with iOS 16.1.1. My email account is a Gmail one. Since discovering this issue I’ve used the Gmail app on my iPhone rather than the Apple Mail app. I’ve had no problem while using the Gmail app. It’s possible the problem only occurs with “replies”. I’ve not created any “new” emails recently. They’ve all been replies.

No. If you've not sent any new emails and have only sent replies, how on earth did you deduce that it only happens with replies?

The problem is as previously described by so many in this stream.

W.court, if you’d read what I wrote instead of trying to appear smart, I said “it’s possible” it only occurs with replies. I was merely alluding to the possibility in case that information was of assistance to someone.

I read what you wrote, and it is 100% not possible that it is only with replies.

The fact that you didn't like my message doesn't require you to start badmouthing. And when it comes to smart, I'm sure you read this stream before you posted your message. You are definitely not smart

My wife has had some "sent" e-mails not sending since 16.1.1 was automatically installed. She has now gone into settings and there was a red notice to say that she needed to accept the terms and conditions. On accepting this the e-mails seem to be working and hopefully will continue to work.

I did accept the terms and conditions right away - before trying to send email and realizing some was disappearing. I have disabled the “undo send” feature and that appears to fix the issue. But I’m still double checking that each email I send is actually sent….

…some *were* disappearing….

I've installed the latest iOS 16.1.2 update that was released on November 30th, 2022 last Thursday 12/1/22 on the affected users iPhone that I had mentioned in a previous post. There weren't any specifics to the native iOS mail app at the time and I have yet to look for more release notes. I am hoping this fixes the experience my user was having:

"Cannot Send Mail - An error occurred while delivering this message"

Not seeing a Sent item within Sent mail, although the message was indeed sent; I was able to notice this when I saw duplicate sent items within the users Sent folder on their computer (vs iPhone).