If Send Files are not being delivered to your intended destination, then there are a few things to check. First, let's check your internet connection. Make sure you can access the internet whether it be via Wi-Fi or Cellular connection. This can be done by opening Safari and confirming you can pull up a website successfully. Next, since Send Files are sent using the built in Email app on the iPad or iPhone, we will need to access the email app to troubleshoot the issue. Follow the steps below to access and re-send the messages stuck in the outbox.
- Open the Mail App on the iPad
- At the top left corner, tap on "< Mailboxes"
- Tap on "Outbox" from the menu on the left side
- Select the message on the left
- Tap anywhere inside the message to bring up the send option
- Press Send in the upper right to re-send the message.
The message should now disappear for the outbox and be sent to your desired recipient.
More information on troubleshooting Send Files can be found here: