Why do some emails sent in Outlook 2010 get stuck in Outbox with date set to "None"?

I'm using Outlook 2010 against Exchange 2007. Emails I compose sometimes get stuck in the Outbox with date "None" as shown below. These emails never leave the outbox unless I delete them and recompose. Sometimes the problem happens again until I restart the client.

Additionally, if I open a good (one with today's date) email from the outbox and then send it, it too gets dated "None" and never gets sent.

When I've seen this issue it's been because the 'delay delivery' option has been set to 5pm that day (even though the user has not set this option). You can't clear it (it re-applies) so the short term fix I've been using is to set it to 1 minutes time then the email is sent! Still looking for a proper cause/fix though...

I've read several places say this relates to anti-spam/anti-virus.

It happens to me if I compose a message offline and then go to the outbox to see what's there or edit the message before sending.

Rather than deleting the message, a simpler workaround for me has been to drag the message to my drafts folder, open it, and hit send

I found a free tool called ReliefJet Essentials which does this. See the "Unstuck Outbox Messages" section of http://www.reliefjet.com/Product/Features/OutlookTweaks.

1.) If you have Anti virus set to scan emails, turn it off, see if this problem stops.

2.) Go into the Outlook Options, then the Advanced option and under SEND AND RECEIVE is an option that says SEND IMMEDIATELY WHEN CONNECTED. Check the box to activate this option.

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It doesn't happen too often but when a message is stuck in the Outbox it can be a real pain. Below you'll find three methods to get the message out of the Outbox.

Method 1 Open the message from the Outbox and close it again. Now select the message and press DELETE

Method 2 Put Outlook in offline mode. To do this go to File-> Work Offline. Now restart Outlook and see if you can delete it (you can try this in combination with method 1). Don't forget to put Outlook back On-line again.

Method 3 Create a new pst-file; File-> New-> Outlook Data File... Set this pst-file as your default delivery location in your Account settings; Tools-> E-mail Accounts-> button Next When you now restart Outlook your original pst-file will show up as the secondary set of folders where should easily be able to remove the file from or even the complete Outbox folder Set the original pst-file as the default delivery location again and restart Outlook; the Outbox folder will be recreated and will be empty.

Method 4 Use the Microsoft MDBVU32.EXE tool to forcefully clear the Outbox. The instructions for this are the same for when removing a stuck read receipt but instead of choosing "MDB-> Open Root Folder" choose "MDB-> Open IPM Outbox".

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