I am using Win 7, outook 2013 / Exchange.  For the last 3 days, when I try to send something, the email sits in my outbox and does not go anywhere.  Outlook says, everything is up to date (no errors), "All folder are up to date."  I have to manually go to my outbox and open each unsent email and click send.  Once doing so, the email sends immediately. I then open the next unsent email and click send and repeat the same process for all unsent emails sitting in the outbox.  Ever since an Exchange outage we had a few days ago, this problem now occurs.

So to send an email, I first draft it, then click send.  It is then placed in my outbox.  I then have to go into my outbox and open the email.  I click send, and it sends fine.  What is preventing the email from sending the first time I click send? 

I should also mention that under Advanced, I am set to "send immediately when connected" 

• Edited by swbst3 Monday, December 23, 2013 6:10 PM

Hi,

Please try to send emails on OWA to determine if it's Outlook Client specific, will the emails be stuck in Outbox?

If there's no issue on OWA, there are multiple causes for the issue.

We need to run Scanpst.exe to repair the .ost file if it is corrupted, please refer to the link below to find the detailed steps:

http://support.microsoft.com/kb/272227/en-us

Please also make sure your firewall and anti-virus program don't have a setting to block the email, disable them temporarily to check the result.

We can run Outlook in Safe Mode to determine if this issue is 3rd-party add-ins related:

Press Win + R and type outlook.exe /safe in the blank box, then press Enter.

If sending emails in Safe Mode works perfectly, disable the suspicious add-ins to verify which add-ins caused this issue.

I hope the information is helpful.

Regards,

Melon Chen
TechNet Community Support

• Marked as answer by Melon Chen CHNMicrosoft contingent staff, Moderator 20 hours 15 minutes ago

I was able to find a solution by removing add-ins from Outlook.  Although I am not sure which one was the culprit, it was either the Social Media add-in or the Apple Cloud add-in. 

After removing the add-in(s) and restarting outlook, I was able to send emails automatically without having to take the extra step of going in to my outbox, re-opening the email and then hitting send.

Thanks for the reply.  This is resolved for now. 

Hi,

Running Outlook in Safe Mode will disable all 3rd-party add-ins, you may try to disable add-ins one by one to verify which one caused this issue.

It's very nice to hear this issue has been resolved anyway.

Thanks,

Melon Chen

Forum Support