bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Ryan Tate via Bug reports for GNU Emacs, the Swiss army knife of text editors]

The internal emacs mail header X-Message-SMTP-Method is described in
section 3.3 of the manual as a way to get "some messages to go via one
mail server, and other messages to go through another." Both examples
given show that this header can be used to communicate a method, server
name, and port.
https://www.gnu.org/software/emacs/manual/html_node/message/Mail-Variables.html

However, emacs, in particular gnus/message.el when sending through
smtpmail.el, fails to adjust the variable smtpmail-smtp-stream type to
match the port. So, for example, if a user selects port 465, the
connection will fail as this is the port for SMTP connections with
TLS.

Port 587 will happen to work as this is the port for SMTP with STARTTLS,
and STARTTLS upgrades can happen in a plain stream type (the smtpmail
default). But emacs will not (and does not provide an option to) force
STARTTLS when port 587 is specified as would occur if 'ssl were supplied
as the value for smtpmail-stream-type. This provides an avenue under
which encryption may be silently dropped. 

There is no warning in the manual that port 465 will not function as
expected using the X-Message-SMTP-Method header.

There is also no mechanism through which a stream may be user specified
via the X-Message-SMTP-Method header.

I believe the ideal solution here is for emacs to either auto-associate
ports with their usual stream types (465->'ssl, 587->'starttls, 25->nil)
or provide a mechanism for stream type to be specified in the header as
the fifth value (after method, machine, port, alt username). Or
auto-associate by default and provide a config variable through which to
override stream type by machine and port.

Personally I am working around this with the following hook. (Due to
changes to emacs in subsequent versions, it needs to work with both
strings and numbers as the port):

(defun set-smtpmail-stream-type-from-port ()
  (when (or (equal smtpmail-smtp-service "465")
	    (equal smtpmail-smtp-service 465))
    (setq smtpmail-stream-type 'ssl))
  (when (or (equal smtpmail-smtp-service "587")
	    (equal smtpmail-smtp-service 587))
    (setq smtpmail-stream-type 'starttls))
  (when (or (equal smtpmail-smtp-service "25")
	    (equal smtpmail-smtp-service 25))
    (setq smtpmail-stream-type nil))
  )

(add-hook 'message-send-mail-hook #'set-smtpmail-stream-type-from-port)



In GNU Emacs 26.1 (build 2, x86_64-pc-linux-gnu, GTK+ Version 3.24.4)
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bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Robert Pluim]

>>>>> On Mon, 04 Nov 2019 23:45:52 -0500, Ryan Tate said:

    Ryan> I believe the ideal solution here is for emacs to either auto-associate
    Ryan> ports with their usual stream types (465->'ssl, 587->'starttls, 25->nil)
    Ryan> or provide a mechanism for stream type to be specified in the header as
    Ryan> the fifth value (after method, machine, port, alt username). Or
    Ryan> auto-associate by default and provide a config variable through which to
    Ryan> override stream type by machine and port.

Iʼm not so sure about the auto association. How about we allow people
to ask for auto-detection? Something like the following (and then we
can discuss whether to turn it on by default, and I can argue that
STARTTLS is evil and we should force everyone to use 465 :-) )

Alternatively we could put this kind of code in open-network-stream,
to allow other protocols to benefit from the same kind of detection.

diff --git a/lisp/mail/smtpmail.el b/lisp/mail/smtpmail.el
index 9cf28fbe8a..75b15a99aa 100644
--- a/lisp/mail/smtpmail.el
+++ b/lisp/mail/smtpmail.el
@@ -98,11 +98,13 @@ smtpmail-stream-type
   "Type of SMTP connections to use.
 This may be either nil (upgrade with STARTTLS if possible),
 `starttls' (refuse to send if STARTTLS isn't available),
-`plain' (never use STARTTLS), or `ssl' (to use TLS/SSL)."
-  :version "24.1"
+`plain' (never use STARTTLS), or `ssl' (to use TLS/SSL), or
+`auto' to derive the stream-type from the port number."
+  :version "27.1"
   :type '(choice (const :tag "Possibly upgrade to STARTTLS" nil)
 		 (const :tag "Always use STARTTLS" starttls)
 		 (const :tag "Never use STARTTLS" plain)
+                 (const :tag "Derive from port number" auto)
 		 (const :tag "Use TLS/SSL" ssl)))
 
 (defcustom smtpmail-sendto-domain nil
@@ -666,6 +668,16 @@ smtpmail-user-mail-address
 	      (string-match "\\." (cadr parts))
 	      user-mail-address))))
 
+(defun smtpmail-derive-stream-type (stream-type port)
+  (if (equal stream-type 'auto)
+      (cdr (assoc port '((465 . ssl)
+                         ("465" . ssl)
+                         (587 . starttls)
+                         ("587" . starttls)
+                         (25 . nil)
+                         ("25" . nil))))
+    stream-type))
+
 (defun smtpmail-via-smtp (recipient smtpmail-text-buffer
 				    &optional ask-for-password
                                     send-attempts)
@@ -712,7 +724,9 @@ smtpmail-via-smtp
           ;; FIXME: Should we use raw-text-dos coding system to handle the r\n
           ;; for us?
 	  (let ((coding-system-for-read 'binary)
-		(coding-system-for-write 'binary))
+                (coding-system-for-write 'binary)
+                (smtpmail-stream-type
+                 (smtpmail-derive-stream-type smtpmail-stream-type port)))
 	    (setq result
 		  (open-network-stream
 		   "smtpmail" process-buffer host port

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Robert Pluim]

(please keep 38066@debbugs.gnu.org in the CC)

>>>>> On Tue, 05 Nov 2019 11:16:16 -0500, Ryan Tate <ryantate@ryantate.com> said:

    >> Alternatively we could put this kind of code in open-network-stream,
    >> to allow other protocols to benefit from the same kind of detection.

    Ryan> I don't know enough about the open-network-stream corner of emacs so won't argue either
    Ryan> way. At the very least, I think it certainly makes sense with regard to the X-Message-SMTP-Method
    Ryan> header because this is a convenience feature (so some small amount "magic"
    Ryan> seems permissable) and there is no existing way to set the stream type
    Ryan> here. I imagine it could be useful elsewhere in emacs though.

If we do it in the lower layers, then everyone gets to use it, not
just people using X-Message-SMTP-Method or smtpmail-stream-type.

    Ryan> Your patches look good, thank you for writing them! (Do I need to submit
    Ryan> them formally as a patch on this list?)

No, if they gain traction I can commit them. I took a look at
open-network-stream, and itʼs not too hard to do the equivalent there,
although it probably needs to be conditioned on the specified :type
being nil rather than unconditionally overriding it.

diff --git i/lisp/net/gnutls.el w/lisp/net/gnutls.el
index 9b13adaefe..a083e9df6c 100644
--- i/lisp/net/gnutls.el
+++ w/lisp/net/gnutls.el
@@ -202,6 +202,7 @@ open-gnutls-stream
          (process (open-network-stream
                    name buffer host service
                    :nowait nowait
+                   :auto-tls (plist-get parameters :auto-tls)
                    :tls-parameters
                    (and nowait
                         (cons 'gnutls-x509pki
diff --git i/lisp/net/network-stream.el w/lisp/net/network-stream.el
index 4050c83eb0..8b4bd66ef4 100644
--- i/lisp/net/network-stream.el
+++ w/lisp/net/network-stream.el
@@ -73,6 +73,35 @@ network-stream-use-client-certificates
   :type 'boolean
   :version "27.1")
 
+(defcustom network-stream-auto-tls nil
+  "Whether to automatically try with TLS for certain port
+numbers.  See `network-stream-auto-tls-alist' for the default
+settings."
+  :group 'network
+  :type 'boolean
+  :version "27.1")
+
+(defcustom network-stream-auto-tls-alist
+  '((465 . tls)
+    (587 . starttls)
+    (993 . tls))
+  "Alist used for mapping ports to TLS usage.
+Specifies which port number to map to which TLS behaviour.  See
+`open-network-stream' for a full explanation of the possible
+behaviours."
+  :group 'network
+  :type '(alist :key-type integer
+                :value-type (choice
+                             (const :tag "Possibly upgrade to STARTTLS" nil)
+                             (const :tag "Always use STARTTLS" starttls)
+                             (const :tag "Never use STARTTLS" plain)
+                             (const :tag "Use TLS/SSL" tls)))
+  :version "27.1")
+
 ;;;###autoload
 (defun open-network-stream (name buffer host service &rest parameters)
   "Open a TCP connection to HOST, optionally with encryption.
@@ -175,7 +204,19 @@ open-network-stream
   (unless (featurep 'make-network-process)
     (error "Emacs was compiled without networking support"))
   (let ((type (plist-get parameters :type))
-	(return-list (plist-get parameters :return-list)))
+	(return-list (plist-get parameters :return-list))
+        mapped-type)
+    (when (and network-stream-auto-tls (not (plist-get parameters :auto-tls)))
+      (setq mapped-type (assoc (if (integerp service)
+                                   service
+                                 (string-to-number service))
+                               network-stream-auto-tls-alist))
+      (when mapped-type
+        (setq type (cdr mapped-type)
+              parameters (plist-put
+                          (plist-put parameters :auto-tls t)
+                          :type (cdr mapped-type)))))
+    (message "Auto-TLS %s %s" type mapped-type)
     (if (and (not return-list)
 	     (or (eq type 'plain)
 		 (and (memq type '(nil network))

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Lars Ingebrigtsen]

Robert Pluim <rpluim@gmail.com> writes:

> +(defcustom network-stream-auto-tls-alist
> +  '((465 . tls)
> +    (587 . starttls)
> +    (993 . tls))

I'm not sure I understand the rationale hre.  465 is defined as a TLS
port, so that's what Emacs should talk on that port.  It's like port
443 -- it's also TLS.

-- 
(domestic pets only, the antidote for overdose, milk.)
   bloggy blog: http://lars.ingebrigtsen.no

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Robert Pluim]

>>>>> On Tue, 05 Nov 2019 18:42:39 +0100, Lars Ingebrigtsen <larsi@gnus.org> said:

    Lars> Robert Pluim <rpluim@gmail.com> writes:
    >> +(defcustom network-stream-auto-tls-alist
    >> +  '((465 . tls)
    >> +    (587 . starttls)
    >> +    (993 . tls))

    Lars> I'm not sure I understand the rationale hre.  465 is defined as a TLS
    Lars> port, so that's what Emacs should talk on that port.  It's like port
    Lars> 443 -- it's also TLS.

465 is just a port. And eg

(open-network-stream "google" nil "mail.google.com" 465)

will attempt a STARTTLS connection (and incidentally hang my emacs
:-)). You can override that by passing in :type tls, but in some
situations you canʼt do that, hence the proposed patch.

Unless youʼre suggesting that we unconditionally use tls for 465/443?
Thatʼs another option, but itʼs sure to break someone's setup.

Robert

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Andreas Schwab]

On Nov 05 2019, Robert Pluim wrote:

> +(defcustom network-stream-auto-tls nil
> +  "Whether to automatically try with TLS for certain port

The first line should be a complete sentence.

Andreas.

-- 
Andreas Schwab, schwab@linux-m68k.org
GPG Key fingerprint = 7578 EB47 D4E5 4D69 2510  2552 DF73 E780 A9DA AEC1
"And now for something completely different."

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Lars Ingebrigtsen]

Robert Pluim <rpluim@gmail.com> writes:

>     Lars> I'm not sure I understand the rationale hre.  465 is defined as a TLS
>     Lars> port, so that's what Emacs should talk on that port.  It's like port
>     Lars> 443 -- it's also TLS.
>
> 465 is just a port. And eg
>
> (open-network-stream "google" nil "mail.google.com" 465)
>
> will attempt a STARTTLS connection (and incidentally hang my emacs
> :-)). You can override that by passing in :type tls, but in some
> situations you canʼt do that, hence the proposed patch.
>
> Unless youʼre suggesting that we unconditionally use tls for 465/443?
> Thatʼs another option, but itʼs sure to break someone's setup.

465 is a TLS port in an SMTP context, and 443 is a TLS port in an HTTP
context.  Outside those contexts, they're not anything in particular, of
course.

-- 
(domestic pets only, the antidote for overdose, milk.)
   bloggy blog: http://lars.ingebrigtsen.no

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Robert Pluim]

>>>>> On Tue, 05 Nov 2019 19:23:58 +0100, Lars Ingebrigtsen <larsi@gnus.org> said:

    Lars> Robert Pluim <rpluim@gmail.com> writes:
    Lars> I'm not sure I understand the rationale hre.  465 is defined as a TLS
    Lars> port, so that's what Emacs should talk on that port.  It's like port
    Lars> 443 -- it's also TLS.
    >> 
    >> 465 is just a port. And eg
    >> 
    >> (open-network-stream "google" nil "mail.google.com" 465)
    >> 
    >> will attempt a STARTTLS connection (and incidentally hang my emacs
    >> :-)). You can override that by passing in :type tls, but in some
    >> situations you canʼt do that, hence the proposed patch.
    >> 
    >> Unless youʼre suggesting that we unconditionally use tls for 465/443?
    >> Thatʼs another option, but itʼs sure to break someone's setup.

    Lars> 465 is a TLS port in an SMTP context, and 443 is a TLS port in an HTTP
    Lars> context.  Outside those contexts, they're not anything in particular, of
    Lars> course.

So youʼre suggesting we do autodetection in smtpmail and nnimap only
(and probably a few more besides)?

Robert

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Lars Ingebrigtsen]

Robert Pluim <rpluim@gmail.com> writes:

>     Lars> 465 is a TLS port in an SMTP context, and 443 is a TLS port
>     Lars> in an HTTP context.  Outside those contexts, they're not
>     Lars> anything in particular, of course.
>
> So youʼre suggesting we do autodetection in smtpmail and nnimap only
> (and probably a few more besides)?

When smtpmail contacts port 465, it should set the type to 'ssl, yes.
(And the same for nnimap and 993.)

-- 
(domestic pets only, the antidote for overdose, milk.)
   bloggy blog: http://lars.ingebrigtsen.no

bug#38066: 26.1; X-Message-SMTP-Method header does not affect smtpmail-stream-type

[Lars Ingebrigtsen]

Lars Ingebrigtsen <larsi@gnus.org> writes:

> Robert Pluim <rpluim@gmail.com> writes:
>
>>     Lars> 465 is a TLS port in an SMTP context, and 443 is a TLS port
>>     Lars> in an HTTP context.  Outside those contexts, they're not
>>     Lars> anything in particular, of course.
>>
>> So youʼre suggesting we do autodetection in smtpmail and nnimap only
>> (and probably a few more besides)?
>
> When smtpmail contacts port 465, it should set the type to 'ssl, yes.
> (And the same for nnimap and 993.)

I've now done this on the trunk.

I think Robert's suggestion to add more DWIM logic at a lower level is
interesting, but I think it makes sense to handle this at a higher
(protocol) level -- and I think the Message level is the most flexible.

-- 
(domestic pets only, the antidote for overdose, milk.)
   bloggy blog: http://lars.ingebrigtsen.no