I have recently been hit more and more by an issue that only occurs when I am on an unstable connection (i.e. when I’m working on the train between Copenhagen and Odense). If I lose my connection, my VPN client says it reconnects but it appears not always to be the case. However, Outlook thinks it’s connected, so it apparently sends any e-mails I have in my outbox. The problem is that I then believe they’ve been sent (!) but when I then look in my Inbox I see those annoying auto generated mails saying “Your message did not reach some or all of the intended recipients” and then lists every single recipient even though they are all valid… An example of the format is as below:

Your message did not reach some or all of the intended recipients.
Subject: RE: ES Office addresses incorrect
Sent: 28-06-2011 06:03

The following recipient(s) cannot be reached:
<Colleague name> on 28-06-2011 08:05
None of your e-mail accounts could send to this recipient.

In the above case, I sent an e-mail the minute after which went through OK. Do anyone out there know what’s going on? Any setting in Outlook that can be tweaked to say “double check connection before sending” or something?