On 01/06/2018 09:11 PM, Yuval Levy wrote:
On 2018-01-06 05:42 PM, Yuval Levy wrote:
I have contacted Outlook.com Deliverability Support and will report back
to the list if the results from the interaction are of public interest.

After reading all the responses, and reading the reference links about Microsoft Smartscreen, I have a really stupid question:

Have you considered encrypting your e-mail traffic?

You are a lawyer. The contents of your mail could be considered sensitive, especially if exposure of the mail could materially affect the legal status of your clients. By encrypting your mail, you instantly remove the idea that the message you are sending is "bulk" in any way, because the methods used to encrypt email involve key-pairs specific to you and your client. Using public keys to encrypt, only the secret private key can be used to decrypt -- and Microsoft wouldn't have access to the secret keys.

But that is a discussion for a different mailing list. PostFix, to the best of my knowledge, doesn't have a way to encrypt content "on the fly". I use EnigMail in Thunderbird, which is a shell for GPG (Gnu Privacy Guard), with those people whose messages need to be kept close to the vest.

Hmmm....need to experiment. Could I write a milter for PostFix that would (1) detect the message body is in plaintext, (2) the recipient address has a public key listed in the key servers, and (3) encrypt the body of the message.

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