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I signed up for the record breaking Alibaba Cloud DirectMail service that allows me to send email from an SMTP clients such as Outlook/Squirrelmail

However, whenever I send emails with the service e.g. to my Google account, I realize that the email is not encrypted.

I get the message, "aliyun.com did not encrypt this message"

What should I do to ensure the emails are encrypted?

See the screenshot with the error

Francis Ndungu
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  • What did you do to think it would be encrypted? What do you know about email encryption? You know that it is the task of the email client to encrypt the email? – RalfFriedl Sep 13 '18 at 05:49
  • Since port 25 is disabled by default on Alibaba Cloud for security reasons, I used the recommended port 465 which supports SSL but this didn't encrypt the email either. – Francis Ndungu Sep 13 '18 at 20:40
  • Are you talking about transport encryption or about end-to-end encryption? – RalfFriedl Sep 13 '18 at 21:48
  • I think this is TLS as the secure channel should be established when one SMTP host is delivering email to another SMTP host. – Francis Ndungu Sep 16 '18 at 08:24
  • Then ask their support whether or why not they use TLS on outgoing emails. – RalfFriedl Sep 16 '18 at 08:56

2 Answers2

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I think the encrypted function you wanted is not in the server side.it is during transfer to outside and for the email content. I suggest you to add a security e-mail gateway to realize this function.

Wenson Ding
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I have written a number of articles about Alibaba Cloud DirectMail on my website. These may help you understand the product (service). Alibaba Cloud Articles You can also find these articles on Alibaba's Blog website Alibaba Cloud Blog

There are two types of encryption when it comes to email. Envelope Encryption, meaning that the email itself is encrypted and Data in Transit, the phase when emails are being delivered from on email server to another.

Alibaba DirecMail does not provide Envelope Encryption. This is a feature of the email client to encrypt an email. DirectMail will process an email encrypted or unencrypted.

Alibaba DirectMail does support encryption for Data in Transit to their servers. This means the path from your email client to their server. This is optional and you enable this by selecting an encrypted port such as 465.

The last item to think about is email data transfers between email servers. An email can go from the origin server thru several servers on its way to the destination inbox. You have no control over this process. Most enterprise class email systems will attach email headers that you can review to see if encryption was used as part of the transport protocol between servers.

If your goal is to encrypt your emails, select an email client that supports email encryption. This sounds simple, but in the real world email encryption is a pain to manage. I instead recommend creating a text file with your secrets and then encrypting the file. Attach the encrypted file as part of your normal unencrypted email.

John Hanley
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