Email not sending on iPhone

A lot of my emails just straight don’t send. Like I press send and then some of them get sent to their destination and some don’t. coin toss. And if they don’t get sent, they’re just lost forever. Not in outgoing, not in sent, not in drafts. Just gone. VERY frustrating. Sure, unsend is cool but maybe just be careful before you hit send so it doesn’t duck up email sending all told!!

I’m having the same issue. I suspect it’s because “undo send” is too close to the swipe up feature. I’m starting to realize that when I immediately close the email app after sending an email I might be also accidentally hit “undo send”. It’s a design flaw. Can’t believe that Apple didn’t catch this during the UAT phase of development.

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.

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 ????

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...

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.

1945R1946 wrote:

Shame on Apple. After every update to correct a problem there's another two or three created and it's never their fault. So sad, time for an android.

Ah, someone else who didn’t bother to read the thread before posting. So sad.

But you should always get the product that best meets your needs. I’m sure that whatever Android device you buy, it will be absolutely perfect, and you will never have any complaints about it.

I am having a similar problem, but my emails are never visible. The recipient is not receiving them as well. It always happens when I close the email app just after sending the message. It is really frustrating, especially considering how much you have to pay for Apple's stuff and yet not be able to send a simple email without any issues.

I've just read your "article". You should really give up on giving advice on technology, as you are obviously lost. Let's just agree that you have never stated that "you should NEVER force quit any app unless it isn’t working". For your sake only.

People like you are the reason others hate the Apple community.

juliangallow wrote:

Regarding "force quit" (on iPhone I guess you mean swipe-up a running app, whereas on OSX it's an actual command) it seems as if you assume that Apple does a poor job of cleaning up all the bits-and-pieces required to run an app. I actually assume the opposite: Apple does a good job of cleaning up loose ends when an app is closed, cancelled, or quit (forced or otherwise).

When you swipe up a running app it is EXACTLY the same as choosing Force Quit on a Mac. iOS (or Mac OS) sends a Unix SIGKILL (kill -9) to the app, which terminates it immediately without giving it a chance to save its current state. The purpose, in both cases, is to stop an app that has stopped playing nice with cooperative multitasking. From: https://en.wikipedia.org/wiki/Signal_(IPC)

SIGKILL

"Signal kill"

The SIGKILL signal is sent to a process to cause it to terminate immediately (kill). In contrast to SIGTERM and SIGINT, this signal cannot be caught or ignored, and the receiving process cannot perform any clean-up upon receiving this signal.

This is the ONLY way to force quit an app that isn’t working in iOS (there are several ways in Mac OS). Apple included it to stop runaway processes; they never expected users to use it to stop an already suspended app that isn’t using any system resources.