We just have a C160 (upgraded to version 6.5.3-007) installed. The priority is getting the email encryption working.
I created a content filter with a [secure] in the subject line. I disabled everything on the default policy. I then inserted a new policy above the default, with everything else disabled except the content filter I created above. Because I don't want it interfere with everyone else, I add myself into the current users list. I sent a few test messages to my outside account. It worked as supposed. Email with [secure] got encrypted and one with no [secure] arrived as normal. I also sent mail from another account that not on the current users list to verify if this person is affected by the policy. Email from this other account is not encrypted doesn't matter if it has [secure] in the subject line or not. This is good so far.
I then added another person into the current users list so he can test it out. This is where the problem occured. Everything he sent got encrypted. I then used my email account that was working earlier. I got the same problem.
Well, I deleted everything and re-created the policy this time with both my name and his name in the current users list. Mail sent from both account work as supposed. To verify, I added a third account into the list. After that, all three account got the same problem. Everything sent got encrypted.
Is it a known bug or I am not supposed to add user into the list after the policy is created.
From your clear description, I would definitely say that is a bug. Even if a "new user" is added to this custom Encryption policy that you created in the outbound mail policy, this new user should **only** match the outgoing content filter you created if the Subject line contains the [secure] keyword.
It's a very simple and straight forward outgoing policy and outgoing content filter.
I would recommend this, open a case with the Email customer support and they should be able to run a test over the phone with you very quickly and examine the logs to see what is happening and why it's mis-firing.
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