Outlook Express's best feature was that EVERYTHING went into the outbox and stayed there until you hit send/receive. That way, you had a chance to think before the message was actually sent, and time to correct or delete it. How do I make Outlook do the same?
You can configure Outlook so that it does not Send Immediately, then it will work just like OE did.
Go to File, Options, Advanced and uncheck the option to Send immediately when connected (it's near the bottom of the page). With this unchecked, outgoing messages will be sent on the next scheduled send. (In older versions of Outlook, go to Tools, Options, Mail Setup.)
If you have Outlook configured to check for new mail automatically but only want to send when you hit Send and Receive, press Ctrl+Alt+S to open the Send and Receive Settings dialog. Either disable automatic send and receives or click Edit then select the account and uncheck Send mail items (shown in the last screenshot).
More Information
If you would rather use a rule to hold mail for a few minutes, see Tip 149: Deferred Delivery for more information.
Published May 20, 2014. Last updated on May 20, 2014.