Here is a tip from the Outlook blog on the Microsoft Site about getting a message stuck on your outbox on it’s way:
“What do you mean you didn’t receive it? I sent it last night!” At least you thought you did. Now you’re red-faced in a meeting that was set up to review the PowerPoint presentation that never made it to your recipients.
You check your Outbox and there it is. If you ever find yourself in this situation, here are some reasons why and some steps you can take.
First try clicking Send All on the Send/Receive tab in Outlook.
Check your Outbox to see if the message is gone.
A message can get stuck if it includes an attachment that’s too large for some email servers to handle. For example, your workplace might limit the size of email messages you can send or receive. That slide deck with lots of pretty pie charts might be the culprit.
If re-sending the message didn’t work, try reducing the size of the attachments and send it again.
To do that, you might first try to either delete or open the message in the Outbox. But that might not work. Here’s why. Outlook is really responsive and keeps trying to send any message in the Outbox. You can’t open or delete a message if it’s doing that. Instead, you’ll probably see this message:
To stop Outlook’s wheels from turning, you can go offline. On the Send/Receive tab, click Work Offline.
Once offline, it’s easy to fix the problem: you can open the message, remove the attachment, reduce its size, and re-send it. Or you can delete the message and start from scratch-if of course you have a copy of the attachment.
Sometimes Outlook can’t send your messages because your email server is offline–whether an email server at work or online. If that’s the case, keep working! As soon as it comes online, Outlook will send all the messages in your Outbox in a second or two.
You’ll know your server is offline if you see “Disconnected” in the Status bar.
When you’re up and running, it will say “Connected.”
You should be good to go now. For pointers on trimming down attachments before sending, see Reduce the size of pictures and attachments.”
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