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I want to setup a custom rule on Outlook 2016 so that I cannot send an email to a specific person from a specific account.

I know this sounds crazy, but I have two accounts on Outlook 2016, say from CompanyA and CompanyB. I don't want to send emails from the account with CompanyA to people in CompanyB, by mistake (pretty embarrassing).

I understand Office 2016 has the option to setup rules, but I didn't find a specific rule to effect the above. How can I do so? Please advise.

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2 Answers 2

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Yes, you can add this kind of rule. Add Outlook rule as follows:

  1. Apply rule on messages I send.
  2. If you have two Exchange accounts, you just need to create a rule for each of them. If you have two POP3 accounts for the same store, you can use "through specified account" condition.
  3. Add "with specific words in the recipient's address" condition and add the @companyb.com for CompanyA account or @companya.com for CompanyB account.
  4. Specify "defer delivery by 120 minutes" (maximum value) and "stop processing more rules" actions.

Now, Outlook will leave the message in Outbox for 120 minutes and you can delete or edit and resend it, if it's sent from CompanyA to @companyb.com and vice versa.

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To my knowledge, Outlook Inbox rules cannot be used to achieve the goal. If you are using Exchange accounts, you can do this via using transport rules from the server side.

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