Outlook to send separate e-mails when subject contains "confidential"

Hello Experts,

I use the Sharefile Outlook Plugin to send confidential files to my clients, and in addition to having my clients as recipients of the e-mails, I also CC and BCC other staff at my office, so they can then save that correspondence in a folder in our document repository in the network.

I would like the following to be done, if possible from one e-mail:


Instruct Outlook to send separate e-mails, when the subject contains the word "Confidential", and if the domain of the e-mail addresses is the same as my e-mail address, then send e-mail as is, with attachments to intra-office recipients only.


Then, once the regular e-mail has been sent to all intra-office recipients, call and apply the Sharefile Outlook Plug-in and send to all recipients outside of the office
The Sharefile plugin converts all attachments into a secure link, where the e-mail recipients have to connect to our website and download files.

Thank you very much in advance for any help you can provide.
Who is Participating?
RobConnect With a Mentor Owner (Aidellio)Commented:

You're wanting Outlook to replicate essentially what it does by BCC?  For the first part of your question why do you not just bcc to everyone you need to rather than send separate emails?

I can't see you being able to do this without writing your own plugin and even then when dealing with a 3rd party will complicate things.

Really the best solution is to compose two emails, one for internal staff and one for external and BCC both.  Or BCC everyone with the sharefile link, that way your email servers aren't getting bloated with attachments.

SuraDalbinAccountantAuthor Commented:
Thank you Rob, that makes sense.
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