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I've been asked to set up an alert whenever our staff try to send emails to a certain domain, and we're using Outlook 2013/365. I'm just wondering if anyone knows if this is possible and how to do it?

So far I've managed to create a new rule for outgoing messages by going:

Manage Rules & Alerts -> New Rule -> Start from a blank rule: Apply rule on messages I send -> with specific words in the recipient's address -> add the domain (eg @example.com) -> ...

This is where I get stuck.

We're wanting it to be that if we send to a certain domain it pops up asking if the email requires a password, and gives the user an option to cancel sending if it doesn't. We deal with government organizations and they have a new requirement that if we send an email with more than 1 persons details it needs to be in a password protected attachment. So really we just want an honesty prompt asking if the content needs to be in a protected attachment, and if they press yes it cancels sending allowing them to do this.

Can anyone let me know if I can do what I'm wanting, and if so, how?

  • Sounds like you should develop an add-on. My work has something similar with attachments and PII – Ramhound Mar 4 '15 at 1:46
  • @Ramhound so this can't be done with the standard settings? – dpDesignz Mar 4 '15 at 2:00
  • The last two paragraphs sound awkward to me. If Outlook sends email to a specific domain, the e-mail has to be password protected? Otherwise, the e-mail should not be sent (cancelled) by Outlook? Or it is just a honesty policy and users can send as long as they answer it is password protected? If you're asking for VBA scripting help, this should be a StackOver flow question. You could use a transport rule, if your question about e-mail password is something that can be coded and retrieved via rules possibly... exchangeserverpro.com/restrict-outbound-email-transport-rule – Sun Mar 4 '15 at 19:39
  • So we deal with government organizations and they have a new requirement that if we send an email with more than 1 persons details it needs to be in a password protected attachment. So really we just want an honesty prompt asking if the content needs to be in a protected attachment, and if they press yes it cancels sending allowing them to do this. We are not on exchange though so can't do transport rules. :( – dpDesignz Mar 4 '15 at 20:36

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