Exchange / Outlook 2013 - Delay Delivery emails never send for some users
I have users trying to use the "Delay Delivery" option in Outlook.  When a message is sent using this is put's the message in the outbox, but never actually sends the message, even after the time allotted.  If I go into the message and even remove the Delay option, the message still never sends...  any ideas?
June 19th, 2015 12:57pm

There are some issues I've run across with when using the "Delay Delivery" and "Cached Mode". When Cached mode is enabled on the client, the "Delay Delivery" email sits in the Outbox in the Outlook client and it's not in the Outbox on the server. This apparently is by design, but means that the Outlook client needs to be running for the "Delivery Delay" to work correctly. If you uncheck Cached Exchange Mode, then the emails are saved to the Outbox on the server.

I usually instruct users that have to use the "Delivery Delay" option to not run their Outlook in Cached Mode. Even after removing the "Delivery Delay" option, you still need to click "send" to have the email sent or it will just sit in the Outbox.

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June 19th, 2015 1:20pm

When I tested and had the issue, I was not using cached mode.  The message is still sitting on my Outbox.  I did hit send when done editing the message, I've since removed the Delay option and tried to resend from the same message, and the message is still just sitting in the outbox.  I'll probably have to delete it and re-send, but then that means the Delay function is broke and unusable.
  • Edited by JoeFri Friday, June 19, 2015 4:41 PM
June 19th, 2015 3:35pm

what Outlook version are you using and does it have the latest patches applied to it? I've seen this type of behavior before but it was in earlier versions of Outlook 2010 and 2013.

If you were running in cached exchange mode then I would say it's a corrupted OST but you said you weren't running in cached.

If your Outlook is up to date, I would try to create a second outlook profile for testing and see if the behavior is the same.

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June 19th, 2015 6:09pm

what Outlook version are you using and does it have the latest patches applied to it? I've seen this type of behavior before but it was in earlier versions of Outlook 2010 and 2013.

If you were running in cached exchange mode then I would say it's a corrupted OST but you said you weren't running in cached.

If your Outlook is up to date, I would try to create a second outlook profile for testing and see if the behavior is the same.

June 19th, 2015 6:09pm

Outlook 2013 SP1, yes we patch on a monthly basis.
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June 22nd, 2015 8:22am

If your client antivirus solution has email scanning or "Outlook Integration" enabled, then that can prevent emails from being moved from your Outbox to your sent items.  Try unchecking any antivirus related add-on's in Outlook.
June 22nd, 2015 10:46am

We use Symantec Cloud Endpoint Protection, the only add-in that it loads is a "Norton AntiSpam Outlook Plugin" and I had that disabled when I ran my test's.
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June 22nd, 2015 3:13pm

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