Hi all,

I experienced the problem described below for quite some time already.
Recently, I had the "opportunity" to re-install my PC :-(
The problem didn't disappear, so let me submit it.

Short problem description:
My Outlook contains a POP3 as well as a Exchange account.


In case I'm not connected to the Exchange account, I can't send any mail from my POP3 account through SMTP to a mail address that was not used before.
Message: "Outlook must be online or connected to complete the action"

I tried in some more detail to log my installation and to reproduce the issue.
Here my conclusions...
Software versions:

• Windows 7 x64 SP1
• Office 2010 Pro SP1

Step 1:
Configure a normal POP3 connection to a POP3 server on the internet. Sending through SMTP. All default settings.
This works fine, as expected.
Import an existing PST file (containing contacts, mails, agenda items from a previous installation).
Step 2:
Add an Exchange connection to an Exchange 2007 server. All default settings.

• This gives the expected warning that Exchange now takes its own delivery location. Just press Ok on this warning.
• Still in the account creation dialog, I select the POP3 account to be the default account (iso the newly created Exchange account).
• Then I start Outlook. Effectively, the delivery location is on the Exchange, showing the Exchange calender etc in the home page. Since I don't want that, I immediately change the delivery location to the POP3's PST file (through File | Account Settings | Data stores)
• Then I restart Outlook
• Everything seems fine: send/receive mails through POP3 and/or Exchange, just as expected

Step 3:

• Make sure you cannot connect to the Exchange server anymore (e.g. by going home, leaving the office network... that's what I did).
  Outlook now shows a yellow triangle, indicating that there is no connection to Exchange. Fine.
• Click on the Inbox of the POP3 account and create a new mail.
  Send a mail to a well-known mail address (I mean, one to which you have sent before)
  This works fine.
• Do the same, but now to an address that you've never used before.
  Outlook shows a message (pop-up from the system tray: "The connection with Microsoft Exchange is not available. Outlook must be online or there must be a connection to finish this action.".
• It then refuses to send that mail. Other mails can still be sent.

I have the feeling it tries to add the "newly discovered" email address to the Exchange's contact list and fails to do so (disconnected) and as a consequence refuses to send the mail.

Any help would be appreciated,
Johan