Outlook does not send Delayed Delivery Messages

Hello, 
I have a client that can set up a delayed delivery but it does not get sent out. The user opens a new message, adds some stuff, sets it to delay delivery until 8 AM the following morning, and then hits send. The message sits in the outbox until the following
morning. Meanwhile, the user opens the email back up periodically, adds some more information, and hit send again, throughout the day. But since moving to 2010 (and View – they were on Office XP and Citrix previously) the message never sends. Unless you open
it after the scheduled delivery date, and hit send again, then it goes out. I have checked the "Send/Receive Groups" and verified that the outbox is selected. Other users on the network have delayed delivery set and working correctly.
Any Ideas would be great, Thanks.
Tyler

Hi,
This behavior may occur if the following conditions are true:
Outlook is running in Cached Exchange Mode.
Outlook  is not running at the scheduled time of the deferred delivery.
When Outlook  is running in Cached Exchange Mode, it uses a local offline folder file (.ost). This file is periodically synchronized with the server.  When you enable the
Do not deliver before option to defer the delivery of a message, the message is deferred to the local Outbox, not to the server.  Therefore, the message will not be delivered from the local .ost file unless Outlook  is running when
the message is scheduled to be delivered.  This behavior does not occur in when Outlook is running in online mode.
To work around this behavior, enable the Do not deliver before option to defer delivery of the message when Outlook  is running in online mode.
Go to FILE -> Account Settings -> Account Settings -> Double click the account name, uncheck "Use Cached Exchange Mode", click "Next". You'll then need to restart Outlook to use Online Mode.
Regards,
Melon Chen
TechNet Community Support
Hi Melon,
Outlook is not running in cached mode because the clients are logging into a Vmware view environment. This is only happening when the user sets delayed delivery to overnight(a test at 45 minutes went through). Other users are able to send emails through without
fail under the same circumstances.
We believe it may be an issue with View when the user logs out and back in and gets a different desktop, but I'm not quite sure why.
Tyler

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