First, thanks for the detailed help you have given me. I’ve dug in and learned a lot about email servers, security and studied differences between ssl/tls and starttls to understand how this would affect what I’m trying to do.
three key points to ensure we agree:
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SSL vs. TLS: SSL and its successor, TLS, are protocols that encrypt internet traffic to make it secure for communication.
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Starttls is the command to force an ssl connection
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You stated Plone only supports SMTP and starttls. This means we should see Plone talk to the smtp server – give the command ‘starttls” which forces an ssl connection and then goes from there
Second, I’d like to ask a basic question (I’m going to post this as a new question to the entire community): what commercial email service do you use that works with Plone? I can move my email server (or entire site) as required to fix this issue. I don’t want to keep imposing on you if I can make a change that fixes the issue.
Steps I’ve Taken
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Created two new emails with different domains on different servers.
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Went to //email/testTo: to test for STARTTLS connection (I noted you stated Plone only supports SMTP and starttls so I figured this was a key issue to check). (Note: in this test I did not compel or direct TLS (two of the settings available)
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Below is a portion of the readout when checking wayne@rileydog.info. The key parts of the readout were the same for both emails.
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Key point is both smtp servers replied: “starttls command works on this server” then “connection converted to ssl”. This shows the starttls has successfully forced an ssl connection. (my new understanding of what “starttls command” does.
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as best I can tell this means Plone should be able to connect
Thoughts? Is no one else having this issue??
below is the relevant portion of the log file
Trying TLS on in1-smtp.messagingengine.com[66.111.4.73:25] (10)
[000.009] Server answered
[001.078] < 220 mx4.messagingengine.com ESMTP mx. No UCE permitted.
[001.078] We are allowed to connect
[001.078] > EHLO www12-azure.checktls.com
[001.090] < 250-mx4.messagingengine.com
250-PIPELINING
250-SIZE 73000000
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 CHUNKING
[001.090] We can use this server
[001.090] TLS is an option on this server
[001.090] > STARTTLS
[001.099] < 220 2.0.0 Ready to start TLS
[001.100] STARTTLS command works on this server
[001.120] Connection converted to SSL