Message Stuck in the Outbox on an iPhoneby Todd Bowerman
Email messages sent from your iPhone first enter the iPhone’s outbox. Normally, a message only sits in the outbox long enough for it to be sent. However, connectivity problems or other issues could lead to the message being stuck in the outbox either until it is finally able to send or until you delete it manually. Some quick troubleshooting is usually enough to complete the sending process.
Kill the App
Sometimes all it takes to clear the outbox is a quick refresh of the iPhone’s Mail app. To close the app completely, press the iPhone home button two times. Swipe through the open apps until you see the Mail application and then swipe up to stop it from multi-tasking and close it. Return to the iPhone home screen and tap the Mail app icon to re-open it; stuck messages should send automatically.
Reset the Connection
Networking issues can lead to a reduced ability to send and receive messages. Force a quick reset of your iPhone’s connection to the Web by swiping up to open the quick access pane and touching the airplane icon to enable Airplane Mode, which shuts off all connections to the phone. Touch the airplane icon again to disable Airplane Mode and reestablish a connection. If the email was hung up due to internal connectivity strife, it may send once the phone reconnects.
Restart the Phone
Performing a quick restart of the iPhone closes all open apps and sometimes shakes out whatever bugs are preventing messages from sending. To restart your iPhone, press and hole the Sleep/Wake and Home buttons simultaneously. After a few seconds, the iPhone will automatically reboot. Wait for the phone to come back online and check to see if the stuck message is still present.
Delete the Message
As a last resort, it is possible to delete the stuck message from your Outbox. While pending messages do not allow for editing or deletion under normal circumstances, there is a simple workaround available for extreme circumstances. Swipe up to show the iPhone quick access pane and touch the airplane icon to enable Airplane Mode. Open the Mail app and scroll down to the outbox. Swipe left on the pending message to delete it. You can only delete pending messages if connectivity is disabled.