Outlook – unsent emails remaining in Outbox

Outlook has an intermittent problem in that it sometimes fails to send emails that are in the outbox. I’ve spent a fair bit of time googling* a fix, but cannot find one that reliable and definitive, so I’ve developed a quick workaround that enables easy spotting of the issue, plus first aid that works. Screenshots used here are from Outlook 2007, but I’ve struck a similar problem on Outlook 2003 recently where this advice applies.

This shows before and after Send/Receive (F9) when sending works normally.

Basically it boils down to a lack of timestamps. If an outgoing email appears in the Outbox with a timestamp beside it, it will successfully send on next Send/Receive sync. But if it’s timestamped “None” it just will not go, no matter how many times you hit F9 or Send/Receive. It’s a frustrating bug, as the email will stubbornly sit on your outbox, and if you don’t know or can’t see it, you may mistakenly think the email has gone, and be waiting a darned long time for the recipient to respond.

Before send – no timestamp (or timestamp is ‘None’)- after send there was no change – it didn’t go

First thing to try is edit the email in Outbox. Open the email, add a couple of spaces or a return at the top, save and send. If this activates a time stamp you win. But if not…….

Copy and paste into a new email. Clumsy yes, but in my experience the only reliable way. Don’t forget to copy all the address fields, the title, and the body. Send.

Top email will go as timestamp is ‘Today’ whilst bottom email will not be sent.

And here’s the final step – change your Favourite Folders so that you can spot repeat unsents. They will likely occur! Make an Outbox shortcut there by clicking and dragging Outbox from Mail Folders into Favourite Folders, then right click that new Outbox shortcut and select Properties, then Show Total Number Of Items. This creates a counter beside your outbox fave that can easily become a visual identifier of the problem – if it’s not zero (i.e. not present) then there is unsent mail in your outbox, and it just might be lacking a timestamp. So now you can assess it. But at least you know. And knowing is power. Isn’t that right? 😉

Click and drag ‘Outbox’ from Mail Folders to Favourites. NB this just creates a shortcut, and does not actually move your Outbox anywhere.

*Googling suggests AV plugins, Windows fix and disconnection from email server as amongst many various causes, some of which I’ve tried with no effect.

This workaround allows one thing – getting on with your email, so you can do what’s next after that.

JaunterCreekICT helping you, helping your gadgets.


Unable to display folder. Unknown error in Outlook iCloud Contacts

Perplexingly unable to open my iCloud contacts folder in Outlook 2007. Unknown error.

Google search and Apple & MS forums unhelpful.


Sorted by disconnecting Outlook and everything in iCloud Control Panel (with save) then reconnect.

1500+ contacts resurrected. Phew.


Update – if this fails, check and repair the PST file as per http://office.microsoft.com/en-us/outlook-help/scan-and-repair-corrupted-outl…


Update2 – if all this fails, uninstall (not repair – that doesn’t fix) iCloud and reinstall. Contacts tehn sync to Outlook from iCloud.