Emails sent via calls to MAPI sometimes hang in Outbox

We have a small API we've created that encapsulates calls to native MAPI operations, enabling us to send emails if a customer has Outlook installed (and they elect to do this in our system).
We're seeing the following:
1. Send email if Outlook 2013 (on Win 8.1) is running - works, emails get sent pretty much right away.
2. Send email if Outlook 2013 (on Win 8.1) not running - works, email is sent as soon as Outlook is eventually started.
3. Send email if Outlook 2010 (on Win 7) is running - works. emails get sent petty much right away.
4. Send email if Outlook 2010 (on Win 7) not running - fails, when Outlook is started emails are stuck in Outbox and remain there no matter what we try to get them sent.
I'm unsure if the behavior is specific to some version (e.g. 2010) of Outlook or if its some random thing and we need to code better for this.
Cap'n

If you look at the message in the Outbox folder, is it shown italicized?
Can it be sent if you open the message and click the Send button?
Dmitry Streblechenko (MVP)
http://www.dimastr.com/redemption
Redemption - what the Outlook
Object Model should have been
Version 5.5 is now available!

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