Emails hang in Outbox

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Outlook version
Outlook 2010 32 bit
Email Account
Changed from Outlook 2007 to 2010 and still have a problem with emails hanging in the outbox.
Thot it was caused by an Add-In from my VOIP vendor, since disabling the Add-In solves the issue. But it only happens in this one PC, now running Windows 7 32 bit, my other PC does not encounter this pblm.
The vendor, 8x8 has escalated the issue to second tier, recorded networking info for 24 hours, run a log on the issue, but nothing! No one else has this pblm, so they are pointing fingers back at me and some putative glitsch in my setup.
I'm not using Exchange.
Here's what happens, sporadically. I have not been able to find the trigger as it runs for days w no pblms, then rears its head like a cobra, and won't quit until I disable and renable the 8x8 add-in.
I hit send on a new email, it goes to the Outbox.
It fails to get bolded and italicized which should happen on msgs ready to be sent.
When I open the message and go to Options/Delay Sending, lo and behold it has a check next to "dont send bfr" and 5:00 pm is filled in with today's date.
Five pm rolls around and nothing happens. all msgs hang in the outbox.
If I uncheck the delay sending box, it automatically fills it in again.
If I fill in a different send time (either pre or post the present instant) it reverts to 5:00 pm. Seems like a little homunculus is lurking in the software riding a bug!
Enabling and disabling the 8x8 Add-in is the only solution I've found.
Any ideas what kind of quirk to look for on just this one PC and Outlook 2010?
The Delay sending checkbox is enabled when you click that button - if you open the options dialog using the expander button or direct replies to, it won't be checked. (Direct replies to will be filled in if you click its button.)

What antivirus do you use? Any other addins that are the on the affected computer and not the others? Does it send if you don't look in the outbox?
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