Ideally you’d be able to say:
- always send encrypted to people for whom I hold certs
- always send encrypted to this subset of those people
There is apparently no way of doing this in Outlook 2010-13.
http://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_other/specify-outgoing-mail-encryption-on-a-per/445a57d4-58c9-4122-917f-5491dee3852a?auth=1
Send rules in Outlook are too limited, you cannot even run a script.
Outlook macro would do it I guess, but I have no time to program. Hints here, but the code examples need a way to read a list from disk:
Also at very bottom of same ref, amongst email-send-guard software, the Janus software would appear to be helpful, but availability situation seems strange. Others cost ££.
There are some services which may do it, but as with all services you are v. dependent and they cost:
There are also a few non-service plugins, but none which seem to do it - read near bottom of this link:
Comodo secure email supported it but is discontinued
Any ideas using free software guys?