Email not sending on iPhone

I clicked mee too on this thread, but I don’t get an error message of any kind. I have sent two emails that just don’t show up in sent mail (and no outgoing mailbox pops up). This never happened before the update and only happens when I send certain email with my phone.

I am having a lot of emails labeled “unsent” and going to outbox. When I go in the sent it says sent, so I don’t know if it sent or not. I have sometimes hit resend and it goes back to outbox like it didn’t send. Other times it works. This all started after the IOS16 upgrade.

The Mail app on iOS 16 is a royal mess. Random emails get stuck in Outbox with no intimation whatsoever which at times causes embarrassing situations. Many have reported this in my organization. It was all good on iOS 15.7.

I'm having the same issue since some time late fall last year. I type an email (sometimes lengthy), hit send, hear the swoosh, and then later go back to find that the email is not in my sent email or drafts. Super annoying as I have to go back and re-type the entire email. And it's random, doesn't seem to be entirely tied to closing the app before checking to see if the email is in sent.

Is turning off the delay the only option or is apple looking at fixing this so we can still have the delay on?

Still an issue in 16.2. Replied to an email, heard the swoosh sound. Found out later the person never received the email. There is no trace of it in my sent mail or drafts. The fact that the phone can't "schedule" and send it in the background after the delay seems like some really half-baked software design.

I’m having the same issue with my Mac.com email- and appreciate seeing your post as I thought I was experiencing some sort of dementia ! - I compose the email, hit send, hear the “swoosh” and the next day there’s nothing in my sent or draft files

similar problem on my iPad Apple Mail in last 2 weeks, 16.3 ; NO swoosh - nothing - the mail just disappears; not in outbox or sent folder either; my Gmail app works perfectly to send same messages to all the same addresses that Mail kills ????

Disabling undo-send does not rectify the issue. It persists. You might just not close Mail while it's still sending and hence notice is sooner.

Send e-mail with an exchange server (Office 365). Get an error that the message failed to send. But then go into the outbox and resend the message and it sends perfectly.

This started about a month ago and is just ridiculous. Happening on iPhone, and iPad. My older iPhone on 15.x does not exhibit this awful behaviour.

I tested what you said, closing app immediately after swoosh, but email was sent and found... think the problem is unwittingly touching the "undo send" at bottom of inbox list... it may occur simultaneously when swiping up to close the app...

Metro287 wrote:

This is definitely a iOS 16 problem.

No it is definitely an email account that wasn’t set up correctly. An email account accesses 2 servers, one for incoming email and a different one for outgoing email. Each requires a user ID and password to be set up for each email account that you use. Usually the easiest way to fix this problem is to go to Settings/Mail/Accounts, tap on and delete the account with the problem, then restart your phone, and go back to the same setting and add it back. When you add an email this way iOS will ask the server what the correct settings are, and set up both incoming and outgoing.

Any time you change your email password you have to change it in two places, for incoming and for outgoing (SMTP). Or, just delete the account, restart, and add it back.

1945R1946 wrote:

I disagree. I've been having the problem before the recent update, it's an Apple issue.

If you really believe that you will never solve the problem; the real problem is the email account is not set up correctly, and the easiest way to fix it is to delete the account, restart the phone, and add the account back. I have 7 email accounts of various types, (gmail, iCloud mail, 2 MS Exchange accounts, 2 IMAP accounts, 2 POP accounts) and all of the work perfectly all the time.

I’m having the exact same issue. It has persisted for months now even after multiple Apple updates and bug fixes. Had to pull my work email off of Apple Mail because too often, yet randomly, emails just weren’t being sent. Nothing in the outbox, no draft left behind, it’s as if I’d never responded—not a good look. And that I cannot retrieve even a draft leaves me needing to redo my work.

How very fortunate for you that this issue it seems has not impacted your account. I too have multiple email accounts and all worked perfectly for years before iOS 16. Further it’s not I the user who installed the accounts on my phone, rather it’s the Tech Team at my University, who tend to know what they are doing. I’m willing to try your suggestion to wipe out the account and reload it as a potential fix for the issue, but please refrain from making claims about a problem you’re not experiencing on behalf of those of us who are. I’d like to hear from Apple on this. Give that reports appear to go back to Fall of 2022, I’m curious why no fix nor any response acknowledging this real problem has been provided.

If you are in the habit of swiping up in the quick launch screen to close the mail app then you are causing the problem by closing mail before the send delay. When you kill an app it kills any transactions in progress.

So your philosophy is that you should never take advice from a doctor who hasn’t had the same symptoms that you have.

As I just posted, there is another explanation. Many people believe that it is a good idea to kill apps when you exit them by going to the quick launch screen and swiping up on the app screen image, on the mistaken belief that it will save battery life. In general, this is a very bad idea, but in the case of texts and mail if you swipe up before a message has been sent it will be lost forever, because when you swipe up the app is instantly terminated, before it can save in-progress work to storage. And this is aggravated by the new mail feature that delays sending mail so it can be recalled.