--tls/smtptls should be renamed --starttls/smtpstarttls and the documentation should be corrected to note that the implementation uses STARTTLS not TLS when this flag is enabled. This type of connection is typically used on port 587. Updating the documentation to clarify this port number would be quite helpful and time saving for users.

The incorrect docs justify elevating the severity of this issue to normal.

A workaround for the lack of support for SMTP+TLS is to use SMTP+STARTTLS, typically on port 587, if available. Some providers do not support this.

The original wishlist item is support for SMTP+TLS; this could be enabled with a new flag --tls/smtptls (same as the old flag) with an implementation that does what --tls/smtptls was originally and incorrectly documented to do: SMTP over a connection that starts with a TLS handshake.

I have merged #586680 #740124 #412914 as they all report users struggling with SMTP+TLS on port 465.

Kind regards,

Ben Caradoc-Davies <b...@transient.nz>
Transient Software Limited <http://transient.nz/>
New Zealand

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