Email not sending on iPhone

Same thing happened to me. After sending, I was unwittingly tapping Undo Send at bottom of screen by accidentally touching or swiping up to exit before mail had a chance to send. Undo Send option is on by default. There is a minimum 10 second delay to mail actually being sent, even after you hear the whoosh. Go to Mail preferences, scroll down to very bottom > Send > Undo Send Delay > Turn Off or choose 10/20/30 Seconds.

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’m copying in the advice that helped me below….it was because of the Undo Send we got in the 16.1.1 update. I haven’t had any problems since I turned it off…

Hope this helps:

Turn off Undo Send Delay in the mail app settings, or don’t close the mail app immediately after sending an email. It appears that if the app is closed during the undo send window, the email will disappear. This fixed the issue for me.

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.

Hi Lawrence, tried on both Wi-Fi and cellular data, reset network settings, nothing worked, then I simply put my user name and password in at the “outgoing” settings (even though it said they were optional) and ..... it works like a charm! Thanks for your help, and apologies to have taken up your time with this but sometimes we just can't see what's staring us in the face can we (least not me, anyways, duh)?

That means the password or other settings for outgoing (SMTP) mail server are missing or wrong. This can happen if you change your mail password but don’t change it in 2 places, for both incoming and outgoing. There’s an easy way and a hard way to fix an SMTP issue. The easy way is to go to settings/Mail/Accounts, tap on the account and delete it. Then restart your phone. Then go to settings/Mail/Accounts again and add it back.

The hard way is to go to settings/Mail/Accounts, tap on the account, tap on account again, tap on SMTP, tap on primary server, then enter all the correct settings. The hard way will not work for iCloud or Microsoft email accounts, for those only the easy way will work.

Turn off Undo Send Delay in the mail app settings, or don’t close the mail app immediately after sending an email. It appears that if the app is closed during the undo send window, the email will disappear. This fixed the issue for me.

I figured out the problem. It’s the time setting for “unsend email”. 10 and 20 seconds work. 30 seconds does not.

Change to 10 or 10 seconds and fixed. 30 seconds conflict with my Gmail main setting of 30 seconds for unsend so emails disappear to la la land.

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.

飞263 wrote:

I'm having the same issue in iphone, but in PC, it is working fine.

You probably have either no password or the wrong password in your outgoing mail settings on your phone. Every email account actually connects to 2 servers, one for incoming and a frequently different server for outgoing. If you change an email password you need to change it in both places.

Usually the easiest way to fix the problem is to delete the email account in Settings/Mail/Accounts, restart your phone, and add the account back in Settings/Mail/Accounts. This will set up both incoming and outgoing.

Let me describe what happen to me. Last Friday, I could use iCloud mail to send or receive emails without any issue in my iPhone. But when I tried to send on Saturday, the email went to outbox and stuck there. An alert popup - outgoing server P210-SMTP.mail.icloud.com.cn cannot be connected. I didn't do any changes on the settings to my iPhone. Looks like the incoming server was working fine while the outgoing server disconnected. Then I logged in the email account on PC web. It was working fine, sending or receiving, no problem. I tried my iPad with the same ID, the same thing happened, outgoing server cannot be connected.

Today, I logged out apple ID in my iPhone and logged in again, restarted it, still cannot connected to outgoing server. Then I went to the SMTP server settings, added a new server "smtp.mail.me.com", Miracle happened, the mail in outbox gone, sending successfully. I turned off the iCloud SMTP server, just leave the new server on, the mail stuck again. Crazy..., I turned off the new added SMTP server and turned on the default iCloud SMTP server again, the mail sending or receiving became normal. Now I can send or receive mails normally as before. No setting changes at all. Just changed the SMTP server and changed back. It sounds like program bug.

I just want to share my experience here to someone that has the same issue.

@Lawrence Finch, you're not being helpful. Please advise folks coming to this thread with this problem to simply switch off "Delay Sending" in the Mail Settings. That fixes it.

You suggest, "...either no password or the wrong password in your outgoing mail settings ...Usually the easiest way to fix the problem is to delete the email account ... restart your phone...add the account back". I'm concerned for the poor folks doing this, and simply re-installing the default "Delay Sending" and thus not solving their problem.

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).

You may be drawing on Microsoft experience, where apps often leave processes running after an orderly or disorderly close, sometimes requiring a re-boot or even manual identification, detection, and killing of the process (and a gaping hole for hackers). This is extremely rare in Apple-World (and thus inherently much more secure).

Folks, if your Apple Mails on iPhone are not sending, go to Settings, Mail etc and switch off "Delay Sending". Simple. Done.

It is not the same problem: The problems in this thread specifically say that the message is not saved in the Outbox or Drafts. Yours is saved in the Outbox, it just isn’t sending.

Do you have VPN installed on your phone? If so, try deleting the VPN profile and app.

I turned off the “Undo Send” in the Mail settings and it fixed the issue for me. Hope this helps.