You can accomplish this from Outlook by using the Outlook Encryption Plug-in, or by setting up a content filter on your appliance and using subject line keywords to accomplish encryption.
1) Create a content filter under Mail Policies -> Incoming Content Filters -OR- Outgoing Content Filters, with the following properties:
Condition:
Subject Header: Contains: (?i)\[SEND SECURE\] -OR- (?i)\[encrypt\] -OR- (?i)\[keyword of choice\]
Condition:
Subject Header: Contains: (?i)\[SEND SECURE\] -OR- (?i)\[encrypt\] -OR- (?i)\[keyword of choice\]
Action:
Encrypt and Deliver
(example from web GUI):
Condition details:
Actions details:
* Q: Why does the output reflect as “\\”? You will need to have the line written as:
(?i)\[SEND SECURE\]
This will AUTOMATICALLY convert to show as:
subject == "(?i)\\[SEND SECURE\\]”
* Q: What does (?i) do? Case insensitivity. Allows for “[SEND SECURE]”, “[send secure]”, “[SeNd SeCuRe]”, etc.
2) Enable the new content filter for all relevant policies under Mail Policies -> Outgoing Mail Policies
3) Submit/Commit the changes
I hope this helps!
-Robert
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