Alpine 2.20 error sending email with Office 365

[ignaci...@gmail.com]

Hi
I'm finding problems to sent emails from Alpine 2.20 on Ubuntu 17.04 with Office 365 (exchange online)

As I can see in several forums it should works with this SMTP Server:
smtp.office365.com/submit/tls/user=yourus...@email.com

I also try with:
smtp.office365.com:587/tls/user=yourus...@email.com

But it shows an error message: Mail not sent. Sending error: 250 2.0.0 resetting

Any suggestion?
Thanks

[Eduardo Chappa]

On Mon, 26 Feb 2018, ignaci...@gmail.com wrote:

> I'm finding problems to sent emails from Alpine 2.20 on Ubuntu 17.04 with Office 365 (exchange online)

> [...]

> But it shows an error message: Mail not sent. Sending error: 250 2.0.0 resetting

Please press M S C and enable

[X] Enable Verbose SMTP Posting

then reproduce the issue, and look at the debug to see the log of the
error. That will show the full error, which is what we need to see.

Thank you.

--
Eduardo
http://repo.or.cz/alpine.git (Git)

[E. Balansay]

On Monday, February 26, 2018 at 11:37:40 AM UTC-8, ignaci...@gmail.com wrote:

> As I can see in several forums it should works with this SMTP Server:
> smtp.office365.com/submit/tls/user=yourus...@email.com
>
> I also try with:
> smtp.office365.com:587/tls/user=yourus...@email.com
>

> Any suggestion?

I too tried those options which did not appear to work. The following does work for me:

smtp.office365.com:587/tls/novalidate-cert/user=user...@domain.com

I also updated the FCC to:
{outlook.office365.com/user=user...@domain.com/ssl/novalidate-cert}Sent Items

This is on Alpine 2.01, running on CentOS release 6.9, Kernal: 2.6.32-642.4.2.el6.x86_64 (for anyone interested, this is homer.u.washington.edu)

Give that a try!

-Edgardo

[dwo...@gmail.com]

Hi everyone!

I got this exact error in alpine 2.20 (250 Resetting), trying to connect to office 365, here, where I work.

I've busted this error in alpine 2.20, doing the debug procedure:
a) Start alpine
b) Setup > Config > SMTP Server
smtp-mail.outlook.com:587/tls/novalidate-cert/user=myu...@company.com
c) In sending preferences, enable "Enable verbose SMTP Posting"
d) then, trying to send an email. Got "250 Reseting".
e) Return to main screen, press J (debug). Then 9 (debug level), then T (time toggle info).
There, I found this:

smtp-mail.outlook.com:587/tls/novalidate-cert/user=us...@company.com

16:46:45.157789: IMAP DEBUG 16:46:45 4/16: MAIL FROM:<user@mylaptop>
16:46:45.526511: IMAP DEBUG 16:46:45 4/16: 250 2.1.0 Sender OK
16:46:45.526544: IMAP DEBUG 16:46:45 4/16: RCPT TO:<test...@gmail.com>
16:46:45.890959: IMAP DEBUG 16:46:45 4/16: 250 2.1.5 Recipient OK
16:46:45.890988: IMAP DEBUG 16:46:45 4/16: DATA

[more lines]

and the error:

16:46:46.251866: IMAP DEBUG 16:46:46 4/16: .
16:46:52.049787: IMAP DEBUG 16:46:52 4/16: 550 5.7.60 SMTP; Client does not have permissions to send as this sender
[SC1PR80MB0671.lamprd
16:46:52.049792: >80.prod.outlook.com]
16:46:52.049805: IMAP DEBUG 16:46:52 4/16: RSET
16:46:52.414803: IMAP DEBUG 16:46:52 4/16: 250 2.0.0 Resetting
16:46:52.414819: Mail not sent. Sending error: 250 2.0.0 Resetting

I found the error "250 Resetting" is just an indication of the connection to email server was dropped (resetted), because the user "< dwonga@dwonga-MacBookProWrk>", is, actually, not allowed as sender in this server.

The solution was changing the email of the sender, doing this:

- Going into Setup, Configuration, "Customized headers" and set it to "From: User <email@company>" (the exact data used as outlook email for logging).
- In "sending preferences", check the option "Enable 8bit ESMTP Negotiation" is enabled, and "Use Sender Instead of X-X-Sender" is disabled (the last one gave errors, due to the way it uses to validate, disable it.

I hope it serves you.

David.

[Eduardo Chappa]

On Mon, 16 Apr 2018, dwo...@gmail.com wrote:

> 16:46:52.049805: IMAP DEBUG 16:46:52 4/16: RSET
> 16:46:52.414803: IMAP DEBUG 16:46:52 4/16: 250 2.0.0 Resetting
> 16:46:52.414819: Mail not sent. Sending error: 250 2.0.0 Resetting
>
> I found the error "250 Resetting" is just an indication of the
> connection to email server was dropped (resetted), because the user "<
> dwonga@dwonga-MacBookProWrk>", is, actually, not allowed as sender in
> this server.

You are right in reading that the problem has to do with the wrong sender.
The resetting part has to do with restarting. RSET is a command the client
gives to the server to tell it that it is going to restart the message.
The server has a bug as the RFC states that the reply must be "250 OK" and
nothing more.

Take a look at RFC 5321 and section 4.1.1.5 for more information.