How to forbid sending an email from the default account to some people in Outlook?

Question

I have to use multiple email accounts with Microsoft Outlook. I have a default account, but when sending emails to a few people, I should use the non-default one. In practice, I often forget to change the account before sending an email, and notice my mistake only when it's too late.

Is there a way, in Microsoft Outlook 2007, to either lock the Send button according to the email addresses in the "To" field if the "Account" field is wrong, or to adjust the "Account" field automatically?

Answer 1

You can't make the "Send" button's functionality locked or not based on the value of the "To" field. Furthermore, Outlook has no idea if the "Account" field is "wrong", as you say; if it is a valid account on the computer, Outlook will happily send from it.

However, you may be able to prevent accidental sends. There are a few ways to do this, some more elegant than others.

1. You could set the default account to a bad (empty) account (i.e. with a nonexistent server name etc). Then, you'd have to manually select a "from" account each time you sent an email. I'd suggest removing the erroneous account from send/receive groups so it doesn't generate errors there.
2. For a less intrusive version of the same reminder methodology, you could add a default mail signature to all of your accounts, reminding you to verify the "from" address before sending.
3. If the emails you need to send have a formulaic pattern (i.e. a "to" address in a particular format/range etc), you could consider making a custom action to nag you to verify the account when you send the email, add that custom action to an outbound rule that also defers delivery of the message for a few moments--long enough for the reminder to take effect and for you to correct the error if it occurs.
4. You could just install an outbound rule on all messages (or those matching certain criteria) with a delay, and count on your 20/20 hindsight to remind you that a message was sent to the wrong account. This works for me; I usually realize the mistake seconds after I hit "Send".
5. If the emails you need to send as the non-standard account are all replies to messages that have a specific (formulaic) content, you could make a rule to copy them to the "Inbox" folder of the account that they should be sent as. Then, when clicking "Reply", Outlook should automatically select that account as the outbound one. However, this may be Outlook-2010-only behavior; I think 2007 might lock you into the default account no matter what. But speaking of Outlook 2010...
6. You could upgrade to Outlook 2010. Not only is its detection of which account should be sent from dramatically different from 2007 (note that I said "different", not "better"...a whole new set of headaches replaces the old), but you can also configure it to force a "which account should I send from" prompt.