Can't send e-mail via `smtpmail'

Can't send e-mail via `smtpmail'

[Alexander Shukaev]

Hello,

I have the following configuration for `smtpmail':

(setq smtpmail-auth-credentials "~/.authinfo.gpg")

(setq message-send-mail-function 'smtpmail-send-it
      smtpmail-smtp-server "xxx.xxx.xxx"
      smtpmail-smtp-service 587)

plus corresponding 'authinfor.gpg'.  When I send e-mail via `gnus', I
keep getting:

network-stream-open-starttls: make client process failed: Connection
timed out, :name, smtpmail, :buffer, *trace of SMTP session to
xxx.xxx.xxx*, :host, xxx.xxx.xxx, :service, 587

I would love to find out why and how to fix this.  Many thanks to
everyone who assists.

Regards,
Alexander

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Sun, 12 Jul 2015 19:41:21 +0200
> From: Alexander Shukaev <haroogan@gmail.com>
> 
> I have the following configuration for `smtpmail':
> 
> (setq smtpmail-auth-credentials "~/.authinfo.gpg")
> 
> (setq message-send-mail-function 'smtpmail-send-it
>       smtpmail-smtp-server "xxx.xxx.xxx"
>       smtpmail-smtp-service 587)
> 
> plus corresponding 'authinfor.gpg'.  When I send e-mail via `gnus', I
> keep getting:
> 
> network-stream-open-starttls: make client process failed: Connection
> timed out, :name, smtpmail, :buffer, *trace of SMTP session to
> xxx.xxx.xxx*, :host, xxx.xxx.xxx, :service, 587
> 
> I would love to find out why and how to fix this.  Many thanks to
> everyone who assists.

If this is on Windows, then what does this yield:

  M-: (gnutls-available-p) RET

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

> If this is on Windows, then what does this yield:
>
>   M-: (gnutls-available-p) RET
>
>

Was the first what I've checked and its `t'.

Re: Can't send e-mail via `smtpmail'

[Vaidheeswaran C]

This may or may not help.

https://www.gnu.org/software/emacs/manual/html_node/smtpmail/Encryption.html


On Sunday 12 July 2015 11:11 PM, Alexander Shukaev wrote:
> Hello,
> 
> I have the following configuration for `smtpmail':
> 
> (setq smtpmail-auth-credentials "~/.authinfo.gpg")
> 
> (setq message-send-mail-function 'smtpmail-send-it
>       smtpmail-smtp-server "xxx.xxx.xxx"
>       smtpmail-smtp-service 587)
> 
> plus corresponding 'authinfor.gpg'.  When I send e-mail via `gnus', I
> keep getting:
> 
> network-stream-open-starttls: make client process failed: Connection
> timed out, :name, smtpmail, :buffer, *trace of SMTP session to
> xxx.xxx.xxx*, :host, xxx.xxx.xxx, :service, 587
> 
> I would love to find out why and how to fix this.  Many thanks to
> everyone who assists.
> 
> Regards,
> Alexander
> 
> 

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

> This may or may not help.
>
> https://www.gnu.org/software/emacs/manual/html_node/smtpmail/Encryption.html

I've already read this prior posting, but thanks anyway.

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

It might be worth to note that I'm also connecting to the same server
via IMAP + TLS and it works:

Opening connection to xxx.xxx.xxx via tls...
Decrypting ~/.authinfo.gpg...done
Opening connection to xxx.xxx.xxx...done

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Sun, 12 Jul 2015 20:59:35 +0200
> From: Alexander Shukaev <haroogan@gmail.com>
> 
> It might be worth to note that I'm also connecting to the same server
> via IMAP + TLS and it works:
> 
> Opening connection to xxx.xxx.xxx via tls...
> Decrypting ~/.authinfo.gpg...done
> Opening connection to xxx.xxx.xxx...done

smtpmail.el provides a couple of defcustoms to enable detailed logs of
the communications with the server.  Did you try turning that on, and
if so, what did you see in the logs?

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

>> It might be worth to note that I'm also connecting to the same server
>> via IMAP + TLS and it works:
>>
>> Opening connection to xxx.xxx.xxx via tls...
>> Decrypting ~/.authinfo.gpg...done
>> Opening connection to xxx.xxx.xxx...done
>
> smtpmail.el provides a couple of defcustoms to enable detailed logs of
> the communications with the server.  Did you try turning that on, and
> if so, what did you see in the logs?

I've only tried

(setq smtpmail-debug-info t)

but it didn't provide any additional info.  If there are other
variables, then it's probably worth to try them too.

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Sun, 12 Jul 2015 21:55:01 +0200
> From: Alexander Shukaev <haroogan@gmail.com>
> Cc: help-gnu-emacs <help-gnu-emacs@gnu.org>
> 
> >> It might be worth to note that I'm also connecting to the same server
> >> via IMAP + TLS and it works:
> >>
> >> Opening connection to xxx.xxx.xxx via tls...
> >> Decrypting ~/.authinfo.gpg...done
> >> Opening connection to xxx.xxx.xxx...done
> >
> > smtpmail.el provides a couple of defcustoms to enable detailed logs of
> > the communications with the server.  Did you try turning that on, and
> > if so, what did you see in the logs?
> 
> I've only tried
> 
> (setq smtpmail-debug-info t)
> 
> but it didn't provide any additional info.  If there are other
> variables, then it's probably worth to try them too.

There's one other: smtpmail-debug-verb.

Is smtpmail-send-it at all invoked in this scenario?  Or does the
failure happen before it is called?  If the latter, then smtpmail's
debug facilities will not help you, and I suggest to add 'message'
statements to network-stream-open-starttls to see what goes wrong
there, and why.  (I couldn't even find the place from which the error
message you cite comes.)

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

> Is smtpmail-send-it at all invoked in this scenario?  Or does the
> failure happen before it is called?
>

I've tried `edebug-defun' on `smtpmail-send-it' and it throws me there
every time I try to send a message, so it must happen after that.  In
any case, `smtpmail' debug facilities didn't provide any info (the
trace buffer is empty).  What do we do now?

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

>> Is smtpmail-send-it at all invoked in this scenario?  Or does the
>> failure happen before it is called?
>>
>
> I've tried `edebug-defun' on `smtpmail-send-it' and it throws me there
> every time I try to send a message, so it must happen after that.  In
> any case, `smtpmail' debug facilities didn't provide any info (the
> trace buffer is empty).  What do we do now?

I've just tried Gmail's SMTP and it worked, so the problem should have
something to do with this other server that I'm trying to use.
Interesting... it's actually from Gandi
<https://wiki.gandi.net/en/mail/standard-settings>.  As I said, IMAP
with them works but SMTP does not...

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

>> I've tried `edebug-defun' on `smtpmail-send-it' and it throws me there
>> every time I try to send a message, so it must happen after that.  In
>> any case, `smtpmail' debug facilities didn't provide any info (the
>> trace buffer is empty).  What do we do now?
>
> I've just tried Gmail's SMTP and it worked, so the problem should have
> something to do with this other server that I'm trying to use.
> Interesting... it's actually from Gandi
> <https://wiki.gandi.net/en/mail/standard-settings>.  As I said, IMAP
> with them works but SMTP does not...

Tried with the 'gnutls-cli':

$ gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
Processed 161 CA certificate(s).
Resolving 'mail.gandi.net'...
Connecting to '217.70.184.11:587'...
Connecting to '2001:4b98:c:521::11:587'...
Could not connect to 2001:4b98:c:521::11:587: Connection refused

How's that possible?

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Mon, 13 Jul 2015 15:29:17 +0200
> From: Alexander Shukaev <haroogan@gmail.com>
> Cc: help-gnu-emacs <help-gnu-emacs@gnu.org>
> 
> $ gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
> Processed 161 CA certificate(s).
> Resolving 'mail.gandi.net'...
> Connecting to '217.70.184.11:587'...
> Connecting to '2001:4b98:c:521::11:587'...
> Could not connect to 2001:4b98:c:521::11:587: Connection refused
> 
> How's that possible?

They mention problems with TLS and recommend using SSL, so maybe you
are not alone.  Try googling for similar problems.

Also, perhaps some SMTP/TLS expert here will chime in.

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Mon, 13 Jul 2015 15:29:17 +0200
> From: Alexander Shukaev <haroogan@gmail.com>
> Cc: help-gnu-emacs <help-gnu-emacs@gnu.org>
> 
> Tried with the 'gnutls-cli':
> 
> $ gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
> Processed 161 CA certificate(s).
> Resolving 'mail.gandi.net'...
> Connecting to '217.70.184.11:587'...
> Connecting to '2001:4b98:c:521::11:587'...
> Could not connect to 2001:4b98:c:521::11:587: Connection refused

Doesn't happen here:

  D:\usr\eli>gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
  Processed 158 CA certificate(s).
  Resolving 'mail.gandi.net'...
  Connecting to '217.70.184.11:587'...

  - Simple Client Mode:

  - Received[40]: 220 relay.mail.gandi.net ESMTP Postfix
  EHLO G75VM
  - Sent: 11 bytes
  - Received[168]: 250-relay6-d.mail.gandi.net
  250-PIPELINING
  250-SIZE 35651584
  250-VRFY
  250-ETRN
  250-STARTTLS
  250-AUTH PLAIN LOGIN
  250-ENHANCEDSTATUSCODES
  250-8BITMIME
  250 DSN
  QUIT
  - Sent: 5 bytes
  - Received[15]: 221 2.0.0 Bye
  - Peer has closed the GnuTLS connection

(The "EHLO" and "QUIT" commands were typed by me.)

So it looks like something is wrong with your connectivity, or maybe
with your port of GnuTLS.

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Mon, 13 Jul 2015 19:09:01 +0300
> From: Eli Zaretskii <eliz@gnu.org>
> 
> > Date: Mon, 13 Jul 2015 15:29:17 +0200
> > From: Alexander Shukaev <haroogan@gmail.com>
> > Cc: help-gnu-emacs <help-gnu-emacs@gnu.org>
> > 
> > Tried with the 'gnutls-cli':
> > 
> > $ gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
> > Processed 161 CA certificate(s).
> > Resolving 'mail.gandi.net'...
> > Connecting to '217.70.184.11:587'...
> > Connecting to '2001:4b98:c:521::11:587'...
> > Could not connect to 2001:4b98:c:521::11:587: Connection refused
                         ^^^^^^^^^^^^^^^^^^^
Btw, the above is an IPv6 address, whereas my port of GnuTLS only
supports IPv4.  Maybe that's the problem here.  (I know nothing about
these issues.)

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

>> Date: Mon, 13 Jul 2015 19:09:01 +0300
>> From: Eli Zaretskii <eliz@gnu.org>
>>
>> > Date: Mon, 13 Jul 2015 15:29:17 +0200
>> > From: Alexander Shukaev <haroogan@gmail.com>
>> > Cc: help-gnu-emacs <help-gnu-emacs@gnu.org>
>> >
>> > Tried with the 'gnutls-cli':
>> >
>> > $ gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
>> > Processed 161 CA certificate(s).
>> > Resolving 'mail.gandi.net'...
>> > Connecting to '217.70.184.11:587'...
>> > Connecting to '2001:4b98:c:521::11:587'...
>> > Could not connect to 2001:4b98:c:521::11:587: Connection refused
>                          ^^^^^^^^^^^^^^^^^^^
> Btw, the above is an IPv6 address, whereas my port of GnuTLS only
> supports IPv4.  Maybe that's the problem here.  (I know nothing about
> these issues.)
>
It's amazing...  Today I'm in another city.  I didn't change anything
in my configuration, only the internet end-point from where I send
e-mails, and now it works:

$ gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
Processed 161 CA certificate(s).
Resolving 'mail.gandi.net'...
Connecting to '217.70.184.11:587'...

- Simple Client Mode:

- Received[40]: 220 relay.mail.gandi.net ESMTP Postfix
EHLO
- Sent: 5 bytes
- Received[27]: 501 Syntax: EHLO hostname
QUIT
- Sent: 5 bytes
- Received[15]: 221 2.0.0 Bye
- Peer has closed the GnuTLS connection

Similarly, sending with `smtpmail' works as well.  Kek, how come?
Something wrong with DNS at the previous place?

Re: Can't send e-mail via `smtpmail'

[Yuri Khan]

On Wed, Jul 15, 2015 at 2:40 AM, Alexander Shukaev <haroogan@gmail.com> wrote:

>>> > $ gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
>>> > Processed 161 CA certificate(s).
>>> > Resolving 'mail.gandi.net'...
>>> > Connecting to '217.70.184.11:587'...
>>> > Connecting to '2001:4b98:c:521::11:587'...
>>> > Could not connect to 2001:4b98:c:521::11:587: Connection refused

> $ gnutls-cli --verbose --starttls --tofu -p 587 mail.gandi.net
> Processed 161 CA certificate(s).
> Resolving 'mail.gandi.net'...
> Connecting to '217.70.184.11:587'...

[…]

> Similarly, sending with `smtpmail' works as well.  Kek, how come?
> Something wrong with DNS at the previous place?

As seen in the quotes above, the IP address is identical, so DNS is
OK. But, in similar cases where you cannot connect, you might want to
run a traceroute to the target IP and note where the latter stops.
Might be your provider not liking the server, or a temporary glitch
along the way.

Re: Can't send e-mail via `smtpmail'

[Robert Thorpe]

Alexander Shukaev <haroogan@gmail.com> writes:
...
> Similarly, sending with `smtpmail' works as well.  Kek, how come?
> Something wrong with DNS at the previous place?

Some email providers have a policy of only accepting so many
connection requests to the same account per day.  When tinkering with
settings people often exceed this maximum.  That means that even though
they've got their settings right they still can't get a connection until
the next day.  You may have been hit by this problem.

BR,
Robert Thorpe

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Mon, 13 Jul 2015 13:27:37 +0200
> From: Alexander Shukaev <haroogan@gmail.com>
> Cc: help-gnu-emacs <help-gnu-emacs@gnu.org>
> 
> > Is smtpmail-send-it at all invoked in this scenario?  Or does the
> > failure happen before it is called?
> >
> 
> I've tried `edebug-defun' on `smtpmail-send-it' and it throws me there
> every time I try to send a message, so it must happen after that.  In
> any case, `smtpmail' debug facilities didn't provide any info (the
> trace buffer is empty).  What do we do now?

I'd start with setting debug-on-error non-nil, so that the Lisp
backtrace could show which function errors out.

Re: Can't send e-mail via `smtpmail'

[Alexander Shukaev]

>> > Is smtpmail-send-it at all invoked in this scenario?  Or does the
>> > failure happen before it is called?
>> >
>>
>> I've tried `edebug-defun' on `smtpmail-send-it' and it throws me there
>> every time I try to send a message, so it must happen after that.  In
>> any case, `smtpmail' debug facilities didn't provide any info (the
>> trace buffer is empty).  What do we do now?
>
> I'd start with setting debug-on-error non-nil, so that the Lisp
> backtrace could show which function errors out.
>

Here is the result:

Debugger entered--Lisp error: (file-error "make client process failed"
"Connection timed out" :name "smtpmail" :buffer #<buffer *trace of
SMTP session to mail.gandi.net*> :host "mail.gandi.net" :service 587)
  make-network-process(:name "smtpmail" :buffer #<buffer *trace of
SMTP session to mail.gandi.net*> :host "mail.gandi.net" :service 587)
  network-stream-open-starttls("smtpmail" #<buffer *trace of SMTP
session to mail.gandi.net*> "mail.gandi.net" 587 (:type nil
:return-list t :warn-unless-encrypted nil :capability-command "EHLO
G75VW
\n" :end-of-command "^[0-9]+ .*
\n" :success "^2.*\n" :always-query-capabilities t :starttls-function
#[(capabilities) "\301\302\b\"\205
  open-network-stream("smtpmail" #<buffer *trace of SMTP session to
mail.gandi.net*> "mail.gandi.net" 587 :type nil :return-list t
:warn-unless-encrypted nil :capability-command "EHLO G75VW
\n" :end-of-command "^[0-9]+ .*
\n" :success "^2.*\n" :always-query-capabilities t :starttls-function
#[(capabilities) "\301\302\b\"\205\b\b
  smtpmail-via-smtp(("...@...") #<buffer  smtpmail temp>)
  smtpmail-send-it()
  message-multi-smtp-send-mail()
  gnus-agent-send-mail()
  message-send-mail(nil)
  message-send-via-mail(nil)
  message-send(nil)
  message-send-and-exit(nil)
  funcall-interactively(message-send-and-exit nil)
  call-interactively(message-send-and-exit nil nil)
  command-execute(message-send-and-exit)

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Mon, 13 Jul 2015 17:29:30 +0200
> From: Alexander Shukaev <haroogan@gmail.com>
> Cc: help-gnu-emacs <help-gnu-emacs@gnu.org>
> 
> Debugger entered--Lisp error: (file-error "make client process failed"
> "Connection timed out" :name "smtpmail" :buffer #<buffer *trace of
> SMTP session to mail.gandi.net*> :host "mail.gandi.net" :service 587)
>   make-network-process(:name "smtpmail" :buffer #<buffer *trace of
> SMTP session to mail.gandi.net*> :host "mail.gandi.net" :service 587)
>   network-stream-open-starttls("smtpmail" #<buffer *trace of SMTP
> session to mail.gandi.net*> "mail.gandi.net" 587 (:type nil
> :return-list t :warn-unless-encrypted nil :capability-command "EHLO
> G75VW
> \n" :end-of-command "^[0-9]+ .*
> \n" :success "^2.*\n" :always-query-capabilities t :starttls-function
> #[(capabilities) "\301\302\b\"\205
>   open-network-stream("smtpmail" #<buffer *trace of SMTP session to
> mail.gandi.net*> "mail.gandi.net" 587 :type nil :return-list t
> :warn-unless-encrypted nil :capability-command "EHLO G75VW
> \n" :end-of-command "^[0-9]+ .*
> \n" :success "^2.*\n" :always-query-capabilities t :starttls-function
> #[(capabilities) "\301\302\b\"\205\b\b
>   smtpmail-via-smtp(("...@...") #<buffer  smtpmail temp>)
>   smtpmail-send-it()

My interpretation of this is that the server didn't respond.

What do you see in the trace buffer it mentions above?

Re: Can't send e-mail via `smtpmail'

[Eli Zaretskii]

> Date: Mon, 13 Jul 2015 17:43:09 +0200
> From: Alexander Shukaev <haroogan@gmail.com>
> 
> As I said previously, that buffer is empty.

What happens if you connect to that server using telnet?