Bug 3492 - SSL handshake with smtp.live.com fails
Summary: SSL handshake with smtp.live.com fails
Status: RESOLVED INVALID
Alias: None
Product: Claws Mail
Classification: Unclassified
Component: SMTP (show other bugs)
Version: 3.9.1
Hardware: PC Windows 7
: P3 normal
Assignee: users
URL:
Depends on:
Blocks:
 
Reported: 2015-08-09 02:57 CEST by libby_hughe5
Modified: 2015-08-09 23:25 CEST (History)
0 users

See Also:


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Description libby_hughe5 2015-08-09 02:57:15 CEST
I'm new to this so sorry if this doesn't constitute a bug, but I don't know where else to go. Been trying all day to send an encrypted email using Claws in Tails. I've been all over the web and the Claws manual and think I've tried every setting with both POP3 (preferred) and IMAP. I've tried inside and outside of tails and every port setting. The result is always the same - 'SSL handshake failed'. This is always with SMTP not POP3 or IMAP. The server is smtp.live.com as I am using a hotmail account. I've tried using both the 'use SSL' and the 'TLS' settings. If this is not a bug, can you please help me overcome this??!
Comment 1 Paul 2015-08-09 10:15:58 CEST
Try the latest release, re-open if the problem remains. http://claws-mail.org/win32/
Comment 2 libby_hughe5 2015-08-09 14:26:58 CEST
Hi,

I've tried Claws 3.12.0 but the problem remains. I tried 3 times, twice without checking the smtp box, once by trying to specify port 465.
Comment 3 Paul 2015-08-09 14:50:59 CEST
what does /Tools/Network Log say during this attempt and failure?
Comment 4 Michael Rasmussen 2015-08-09 14:59:01 CEST
(In reply to comment #3)
> what does /Tools/Network Log say during this attempt and failure?

The server seems to be misconfigured or operating in non-standard mode:

openssl s_client -starttls smtp -connect smtp.live.com:25
CONNECTED(00000003)
depth=2 C = BE, O = GlobalSign nv-sa, OU = Root CA, CN = GlobalSign Root CA
verify return:1
depth=1 C = BE, O = GlobalSign nv-sa, CN = GlobalSign Organization Validation CA - G2
verify return:1
depth=0 C = US, ST = Washington, L = Redmond, O = Microsoft Corporation, CN = *.hotmail.com
verify return:1
---
Certificate chain
 0 s:/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com
   i:/C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - G2
 1 s:/C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - G2
   i:/C=BE/O=GlobalSign nv-sa/OU=Root CA/CN=GlobalSign Root CA
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com
issuer=/C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - G2
---
No client certificate CA names sent
Peer signing digest: SHA1
Server Temp Key: ECDH, P-384, 384 bits
---
SSL handshake has read 3441 bytes and written 564 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-AES256-SHA384
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : ECDHE-RSA-AES256-SHA384
    Session-ID: A00100006361F7877057DC63F119CDA54BEE3E26836C2726EE3971B791713B84
    Session-ID-ctx: 
    Master-Key: E76E17A856A3B99AB61F46BA18C289090F60CFC9069DB2CCDDFD7A7AE774D4B8BC5426DB3BAD743E54B953AFECF9F134
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1439124855
    Timeout   : 300 (sec)
    Verify return code: 0 (ok)
---
250 OK
ehlo mail.datanom.net
quit
^C
[mir@sleipner:~]$ openssl s_client -starttls smtp -crlf -connect smtp.live.com:25
CONNECTED(00000003)
depth=2 C = BE, O = GlobalSign nv-sa, OU = Root CA, CN = GlobalSign Root CA
verify return:1
depth=1 C = BE, O = GlobalSign nv-sa, CN = GlobalSign Organization Validation CA - G2
verify return:1
depth=0 C = US, ST = Washington, L = Redmond, O = Microsoft Corporation, CN = *.hotmail.com
verify return:1
---
Certificate chain
 0 s:/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com
   i:/C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - G2
 1 s:/C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - G2
   i:/C=BE/O=GlobalSign nv-sa/OU=Root CA/CN=GlobalSign Root CA
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com
issuer=/C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - G2
---
No client certificate CA names sent
Peer signing digest: SHA1
Server Temp Key: ECDH, P-384, 384 bits
---
SSL handshake has read 3441 bytes and written 564 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-AES256-SHA384
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : ECDHE-RSA-AES256-SHA384
    Session-ID: 351C0000349861FD1789B7B98777755D0BFD80477BD5F0123C910022E1EC4C89
    Session-ID-ctx: 
    Master-Key: 46B09B750BA559F5D1E076F7E63DDC602C74349354EA4CED68018E5C0FCBC15EACEE8EC78A8CCC5636717D6302202818
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1439124906
    Timeout   : 300 (sec)
    Verify return code: 0 (ok)
---
250 OK

It skips the 220 banner advertising and does not accept ehlo. From this point it requires auth
mail from: mir@miras.org
550 5.7.3 Requested action aborted; user not authenticated
read:errno=0
Comment 5 Gerard Seibert 2015-08-09 15:01:36 CEST
POP3: Use SSL for POP3 connection

SMTP: Use STARTTLS command to start SSL connection

POP3 Port: 995

POP3 Server: pop-mail.outlook.com

SMTP Port: either 25 or 587 or leave unchecked.

SMTP Server: smtp-mail.outlook.com

IMAP Port: 993

IMAP Server: imap-mail.outlook.com

Both IMAP & POP3 use TLS/SSL encryption

DO NOT USE PORT 465. IT IS DISABLED AND DOES NOT WORK.



POP3 and IMAP use TLS/SSL encryption
Comment 6 daniel 2015-08-09 15:43:27 CEST
a did not try any encryption, but for my outlook.com settings are:
smtp-mail.outlook.com on port 25 or 587 with TLS
Comment 7 libby_hughe5 2015-08-09 20:23:19 CEST
When I apply the settings suggested below, the network log says this:
(perhaps I have made a mistake with the key configuration? I have all 3 PGP plugins loaded, and key pairs in GPA. Sorry if I have made a simple error.

* Account 'emily_sal7@hotmail.com@pop3.live.com': Connecting to SMTP server: smtp-mail.outlook.com:587...
[18:54:56] SMTP< 220 BLU436-SMTP224.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at  Sun, 9 Aug 2015 10:54:55 -0700 
[18:54:56] ESMTP> EHLO localhost
[18:54:56] ESMTP< 250-BLU436-SMTP224.smtp.hotmail.com Hello [213.152.162.84]
[18:54:56] ESMTP< 250-TURN
[18:54:56] ESMTP< 250-SIZE 41943040
[18:54:56] ESMTP< 250-ETRN
[18:54:56] ESMTP< 250-PIPELINING
[18:54:56] ESMTP< 250-DSN
[18:54:56] ESMTP< 250-ENHANCEDSTATUSCODES
[18:54:56] ESMTP< 250-8bitmime
[18:54:56] ESMTP< 250-BINARYMIME
[18:54:56] ESMTP< 250-CHUNKING
[18:54:56] ESMTP< 250-VRFY
[18:54:56] ESMTP< 250-TLS
[18:54:56] ESMTP< 250-STARTTLS
[18:54:56] ESMTP< 250 OK
[18:54:56] ESMTP> STARTTLS
[18:54:56] ESMTP< 220 2.0.0 SMTP server ready
[18:55:04] ESMTP> EHLO localhost
[18:55:05] ESMTP< 250-BLU436-SMTP224.smtp.hotmail.com Hello [213.152.162.84]
[18:55:05] ESMTP< 250-TURN
[18:55:05] ESMTP< 250-SIZE 41943040
[18:55:05] ESMTP< 250-ETRN
[18:55:05] ESMTP< 250-PIPELINING
[18:55:05] ESMTP< 250-DSN
[18:55:05] ESMTP< 250-ENHANCEDSTATUSCODES
[18:55:05] ESMTP< 250-8bitmime
[18:55:05] ESMTP< 250-BINARYMIME
[18:55:05] ESMTP< 250-CHUNKING
[18:55:05] ESMTP< 250-VRFY
[18:55:05] ESMTP< 250-AUTH LOGIN PLAIN XOAUTH2
[18:55:05] ESMTP< 250 OK
[18:55:05] ESMTP> MAIL FROM:<emily_sal7@hotmail.com> SIZE=1934
[18:55:05] SMTP< 550 5.7.3 Requested action aborted; user not authenticated
** error occurred on SMTP session
*** Error occurred while sending the message:
550 5.7.3 Requested action aborted; user not authenticated
* Account 'emily_sal7@hotmail.com@pop3.live.com': Connecting to SMTP server: smtp-mail.outlook.com:587...
[19:00:35] SMTP< 220 BLU436-SMTP118.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at  Sun, 9 Aug 2015 11:00:34 -0700 
[19:00:35] ESMTP> EHLO localhost
[19:00:35] ESMTP< 250-BLU436-SMTP118.smtp.hotmail.com Hello [213.152.162.84]
[19:00:35] ESMTP< 250-TURN
[19:00:35] ESMTP< 250-SIZE 41943040
[19:00:35] ESMTP< 250-ETRN
[19:00:35] ESMTP< 250-PIPELINING
[19:00:35] ESMTP< 250-DSN
[19:00:35] ESMTP< 250-ENHANCEDSTATUSCODES
[19:00:35] ESMTP< 250-8bitmime
[19:00:35] ESMTP< 250-BINARYMIME
[19:00:35] ESMTP< 250-CHUNKING
[19:00:35] ESMTP< 250-VRFY
[19:00:35] ESMTP< 250-TLS
[19:00:35] ESMTP< 250-STARTTLS
[19:00:35] ESMTP< 250 OK
[19:00:35] ESMTP> STARTTLS
[19:00:35] ESMTP< 220 2.0.0 SMTP server ready
[19:00:36] ESMTP> EHLO localhost
[19:00:36] ESMTP< 250-BLU436-SMTP118.smtp.hotmail.com Hello [213.152.162.84]
[19:00:36] ESMTP< 250-TURN
[19:00:36] ESMTP< 250-SIZE 41943040
[19:00:36] ESMTP< 250-ETRN
[19:00:36] ESMTP< 250-PIPELINING
[19:00:36] ESMTP< 250-DSN
[19:00:36] ESMTP< 250-ENHANCEDSTATUSCODES
[19:00:36] ESMTP< 250-8bitmime
[19:00:36] ESMTP< 250-BINARYMIME
[19:00:36] ESMTP< 250-CHUNKING
[19:00:36] ESMTP< 250-VRFY
[19:00:36] ESMTP< 250-AUTH LOGIN PLAIN XOAUTH2
[19:00:36] ESMTP< 250 OK
[19:00:36] ESMTP> MAIL FROM:<emily_sal7@hotmail.com> SIZE=1934
[19:00:36] SMTP< 550 5.7.3 Requested action aborted; user not authenticated
** error occurred on SMTP session
*** Error occurred while sending the message:
550 5.7.3 Requested action aborted; user not authenticated
* Account 'emily_sal7@hotmail.com@pop3.live.com': Connecting to SMTP server: smtp-mail.outlook.com:587...
[19:17:46] SMTP< 220 BLU436-SMTP4.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at  Sun, 9 Aug 2015 11:17:45 -0700 
[19:17:46] ESMTP> EHLO localhost
[19:17:46] ESMTP< 250-BLU436-SMTP4.smtp.hotmail.com Hello [213.152.161.133]
[19:17:46] ESMTP< 250-TURN
[19:17:46] ESMTP< 250-SIZE 41943040
[19:17:46] ESMTP< 250-ETRN
[19:17:46] ESMTP< 250-PIPELINING
[19:17:46] ESMTP< 250-DSN
[19:17:46] ESMTP< 250-ENHANCEDSTATUSCODES
[19:17:46] ESMTP< 250-8bitmime
[19:17:46] ESMTP< 250-BINARYMIME
[19:17:46] ESMTP< 250-CHUNKING
[19:17:46] ESMTP< 250-VRFY
[19:17:46] ESMTP< 250-TLS
[19:17:46] ESMTP< 250-STARTTLS
[19:17:46] ESMTP< 250 OK
[19:17:46] ESMTP> STARTTLS
[19:17:46] ESMTP< 220 2.0.0 SMTP server ready
[19:17:47] ESMTP> EHLO localhost
[19:17:47] ESMTP< 250-BLU436-SMTP4.smtp.hotmail.com Hello [213.152.161.133]
[19:17:47] ESMTP< 250-TURN
[19:17:47] ESMTP< 250-SIZE 41943040
[19:17:47] ESMTP< 250-ETRN
[19:17:47] ESMTP< 250-PIPELINING
[19:17:47] ESMTP< 250-DSN
[19:17:47] ESMTP< 250-ENHANCEDSTATUSCODES
[19:17:47] ESMTP< 250-8bitmime
[19:17:47] ESMTP< 250-BINARYMIME
[19:17:47] ESMTP< 250-CHUNKING
[19:17:47] ESMTP< 250-VRFY
[19:17:47] ESMTP< 250-AUTH LOGIN PLAIN XOAUTH2
[19:17:47] ESMTP< 250 OK
[19:17:47] ESMTP> MAIL FROM:<emily_sal7@hotmail.com> SIZE=1934
[19:17:47] SMTP< 550 5.7.3 Requested action aborted; user not authenticated
** error occurred on SMTP session
*** Error occurred while sending the message:
550 5.7.3 Requested action aborted; user not authenticated
Comment 8 Michael Rasmussen 2015-08-09 20:35:17 CEST
(In reply to comment #7)
> When I apply the settings suggested below, the network log says this:
> (perhaps I have made a mistake with the key configuration? I have all 3 PGP
> plugins loaded, and key pairs in GPA. Sorry if I have made a simple error.
> 
> [19:17:47] SMTP< 550 5.7.3 Requested action aborted; user not authenticated
> ** error occurred on SMTP session
> *** Error occurred while sending the message:
> 550 5.7.3 Requested action aborted; user not authenticated

What auth method have you configured?

Supported are: 250-AUTH LOGIN PLAIN XOAUTH2

So try plain, login in the listed order.
Comment 9 libby_hughe5 2015-08-09 22:16:44 CEST

(In reply to comment #8)
> (In reply to comment #7)
> > When I apply the settings suggested below, the network log says this:
> > (perhaps I have made a mistake with the key configuration? I have all 3 PGP
> > plugins loaded, and key pairs in GPA. Sorry if I have made a simple error.
> > 
> > [19:17:47] SMTP< 550 5.7.3 Requested action aborted; user not authenticated
> > ** error occurred on SMTP session
> > *** Error occurred while sending the message:
> > 550 5.7.3 Requested action aborted; user not authenticated
> 
> What auth method have you configured?
> 
> Supported are: 250-AUTH LOGIN PLAIN XOAUTH2
> 
> So try plain, login in the listed order.

When I tried that, this happened!:

I realise this is not necessarily a server issue now, but would you have some suggestions as to which email providers i could try to use? I just need to see that it works. I have applied for a riseup account but still waiting. Do you know a provider where i could set up accounts immediately?

* Account 'emily_sal7@hotmail.com@pop3.live.com': Connecting to SMTP server: smtp-mail.outlook.com:587...
[21:02:47] SMTP< 220 BLU436-SMTP177.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at  Sun, 9 Aug 2015 13:02:46 -0700 
[21:02:47] ESMTP> EHLO localhost
[21:02:47] ESMTP< 250-BLU436-SMTP177.smtp.hotmail.com Hello [213.152.162.84]
[21:02:47] ESMTP< 250-TURN
[21:02:47] ESMTP< 250-SIZE 41943040
[21:02:47] ESMTP< 250-ETRN
[21:02:47] ESMTP< 250-PIPELINING
[21:02:47] ESMTP< 250-DSN
[21:02:47] ESMTP< 250-ENHANCEDSTATUSCODES
[21:02:47] ESMTP< 250-8bitmime
[21:02:47] ESMTP< 250-BINARYMIME
[21:02:47] ESMTP< 250-CHUNKING
[21:02:47] ESMTP< 250-VRFY
[21:02:47] ESMTP< 250-TLS
[21:02:47] ESMTP< 250-STARTTLS
[21:02:47] ESMTP< 250 OK
[21:02:47] ESMTP> STARTTLS
[21:02:47] ESMTP< 220 2.0.0 SMTP server ready
[21:02:48] ESMTP> EHLO localhost
[21:02:48] ESMTP< 250-BLU436-SMTP177.smtp.hotmail.com Hello [213.152.162.84]
[21:02:48] ESMTP< 250-TURN
[21:02:48] ESMTP< 250-SIZE 41943040
[21:02:48] ESMTP< 250-ETRN
[21:02:48] ESMTP< 250-PIPELINING
[21:02:48] ESMTP< 250-DSN
[21:02:48] ESMTP< 250-ENHANCEDSTATUSCODES
[21:02:48] ESMTP< 250-8bitmime
[21:02:48] ESMTP< 250-BINARYMIME
[21:02:48] ESMTP< 250-CHUNKING
[21:02:48] ESMTP< 250-VRFY
[21:02:48] ESMTP< 250-AUTH LOGIN PLAIN XOAUTH2
[21:02:49] ESMTP< 250 OK
[21:02:49] ESMTP> [AUTH PLAIN]
[21:02:49] ESMTP< 235 2.7.0 Authentication succeeded
[21:02:49] ESMTP> MAIL FROM:<emily_sal7@hotmail.com> SIZE=1901
[21:02:49] SMTP< 250 2.1.0 emily_sal7@hotmail.com....Sender OK
[21:02:49] SMTP> RCPT TO:<libby_hughe5@hotmail.com>
[21:02:50] SMTP< 250 2.1.5 libby_hughe5@hotmail.com 
[21:02:50] SMTP> DATA
[21:02:50] SMTP< 354 Start mail input; end with <CRLF>.<CRLF>
[21:02:50] SMTP> . (EOM)
[21:02:50] SMTP< 550 5.3.4 Requested action not taken; We noticed some unusual activity in your Hotmail account. To help protect you, we've temporarily blocked your account.
** error occurred on SMTP session
*** Error occurred while sending the message:
550 5.3.4 Requested action not taken; We noticed some unusual activity in your Hotmail account. To help protect you, we've temporarily blocked your account.
Comment 10 Michael Rasmussen 2015-08-09 22:44:25 CEST
(In reply to comment #9)
> 
> I realise this is not necessarily a server issue now, but would you have
> some suggestions as to which email providers i could try to use? I just need
> to see that it works. I have applied for a riseup account but still waiting.
> Do you know a provider where i could set up accounts immediately?
> 
Sorry not. As long as NSA is around I stick to my own mail server.
Comment 11 Paul 2015-08-09 23:25:53 CEST
Please, next time use the users' mailing list for questions and discussions and this bug tracker for bugs. http://www.claws-mail.org/MLs.php