Emails getting "stuck" in Outbox

Double-tap the home button to bring up the task bar. Find the mail app and swipe upwards to force closed the mail app. Remove the mail account and do a reset on the device. Hold the sleep/wake and home buttons together until you see the Apple logo. After the phone reboots, add the account back and see what happens.

Okay, that is a start. Does this happen on cellular data, Wi-Fi, or both? Is it always the same person that is not getting the mail, since you say you addressed a mail to two people and it only went to one?

I am getting the exact same problem on my iPad3.

Using it at home via wifi, and this morning I tried to send my first email since I upgraded it from iOS 7.x to 8.0.2 (12A405). I have checked the configuration of my mail account server and it does use SMTP Authentication, but does not appear to use encryption. In my email client (Claws-Mail under Linux) settings indicate that the system is using port 25 for SMTP and 110 for POP3.

iOS8 must have changed something in it's configuration settings with respect to sending emails. Is it possible that it now attempts to force use of encryption? If so, where would I look to see if that option can be disabled?

It is almost certain that this defect was introduced with iOS8 - nothing else on my iPad has changed apart from this upgrade.

SOLVED.

A little experimentation and I found the fix.

In your email settings, you have the option, on the SMTP settings, for including an email address and password. These have always been optional in earlier releases of iOS, but it would appear that with the release of iOS 8, they now have to be explicitly stated.

I simply included my mail address and account password in these fields, and all is fine...

Hope that helps...

They have always been marked as optional in iOS settings, however it isn't up to iOS as to whether you need them, it is your email client that does. Many email providers make changes in how they handle mobile mail and do not always tell their clients. Glad you got yours sorted.

I cannot talk about Gmail, since I do not use it. However with Exchange, there are no settings for SMTP. You just are logging into the Exchange server with the mail client and everything is handled on their end. Some users have said that changing their password on their Exchange account on the computer and then going into the mail client on the phone and changing it has straightened things out, but I find the action that you are describing more than strange. You might have to work with your Exchange administrator more and see where the disconnect is between your mobile client and the server.

This worked perfectly for me! Thank you! x🙂

I Did this pressed both buttons on my ipad2 together to reboot it and when it came back on

my emails in the outbox had all been sent thank you so much

Maureen