1 (edited by OMEN 2010-08-05 06:30:23)

Topic: How do I use SMTP over SSL ?

ubuntu 9.10
iredmail Version:  0.6.0

when configuring email client - outlook, thunderbird, i can connect via imaps port 993
but i cannot send via any ssl smtp ports 465 or 587

i get this error

/var/log/mail.warn

Aug  4 23:14:54 mailserver postfix/smtpd[17353]: warning: unknown[192.168.1.29]: SASL LOGIN authentication failed: UGFzc3dvcmQ6

UGFzc3dvcmQ6 is base64 encoding of password
i do not have "password" anywhere on my box

how do i make smtp via ssl work ?


NOTE
using port 25 no ssl, i get same error

2

Re: How do I use SMTP over SSL ?

Did you try port 25 with STARTTLS?

3

Re: How do I use SMTP over SSL ?

yes,
25, 465, 587
ssl, tls, no encryption

4

Re: How do I use SMTP over SSL ?

This works for me with Thunderbird:

Port: 465
Connection security: SSL/TLS

5

Re: How do I use SMTP over SSL ?

Enable SMTP authentication in your client. "My server requires authentication" / "Use name and password".

6

Re: How do I use SMTP over SSL ?

yes i have enabled the smtp auth
thunderbird > authentication > normal password
outlook > this server requires authentication > use the same details as imap

i still get the same problem /var/log/mail.warn

Aug  5 08:52:31 mailserver postfix/smtpd[19424]: warning: unknown[192.168.1.29]: SASL LOGIN authentication failed: UGFzc3dvcmQ6

this is a clean install of ubuntu server 9.10 - nothing was changed before installing iredmail, i just updated apt.

7

Re: How do I use SMTP over SSL ?

Does Thunderbird work for you?

8

Re: How do I use SMTP over SSL ?

no thunderbird does not work for me - as per my previous posts, those are the settings i have tried.

9

Re: How do I use SMTP over SSL ?

Try to debug it yourself: Put your client ip address in postfix main.cf "debug_peer_list = ", restart it and monitor the maillog file, you can simply filter 'TLS' in log file to check whether it works.

10

Re: How do I use SMTP over SSL ?

is this what youre looking for ?

Aug  5 10:02:52 mailserver postfix/postfix-script[19610]: refreshing the Postfix mail system
Aug  5 10:02:52 mailserver postfix/master[15799]: reload -- version 0.6.0, configuration /etc/postfix
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: connect from unknown[192.168.1.29]
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: send attr request = seed
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: send attr size = 32
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: private/tlsmgr: wanted attribute: status
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute name: status
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute value: 0
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: private/tlsmgr: wanted attribute: seed
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute name: seed
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute value: sfY4P8E2xj+aQERFtTVSqhwhXBKZQZ8SsXGEgegXkAM=
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: private/tlsmgr: wanted attribute: (list terminator)
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute name: (end)
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_create: SASL service=smtp, realm=(null)
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: name_mask: noanonymous
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_connect: Connecting
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_connect: auth reply: MECH?PLAIN?plaintext
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: name_mask: plaintext
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_connect: auth reply: MECH?LOGIN?plaintext
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: name_mask: plaintext
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_connect: auth reply: VERSION?1?0
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_connect: auth reply: SPID?16059
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_connect: auth reply: CUID?215
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_connect: auth reply: DONE
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_mech_filter: keep mechanism: PLAIN
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_mech_filter: keep mechanism: LOGIN
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: match_hostname: unknown ~? 127.0.0.0/8
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: match_hostaddr: 192.168.1.29 ~? 127.0.0.0/8
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: match_list_match: unknown: no match
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: match_list_match: 192.168.1.29: no match
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: auto_clnt_open: connected to private/anvil
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: send attr request = connect
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: send attr ident = smtps:192.168.1.29
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: private/anvil: wanted attribute: status
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute name: status
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute value: 0
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: private/anvil: wanted attribute: count
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute name: count
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute value: 1
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: private/anvil: wanted attribute: rate
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute name: rate
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute value: 1
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: private/anvil: wanted attribute: (list terminator)
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: input attribute name: (end)
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 220 mailserver.domain.com ESMTP iRedMail (Ubuntu)
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: watchdog_pat: 0x7fe871c19fe0
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: < unknown[192.168.1.29]: EHLO [127.0.0.1]
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250-mailserver.domain.com
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250-PIPELINING
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250-SIZE 10240000
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250-ETRN
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250-AUTH PLAIN LOGIN
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: match_list_match: unknown: no match
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: match_list_match: 192.168.1.29: no match
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250-AUTH=PLAIN LOGIN
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250-ENHANCEDSTATUSCODES
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250-8BITMIME
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 250 DSN
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: watchdog_pat: 0x7fe871c19fe0
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: < unknown[192.168.1.29]: AUTH PLAIN AHd3dwBkb29yYmVsbDc=
Aug  5 10:03:05 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_first: sasl_method PLAIN, init_response AHd3dwBkb29yYmVsbDc=
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: xsasl_dovecot_handle_reply: auth reply: FAIL?1?user=www@domain.com
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: warning: unknown[192.168.1.29]: SASL PLAIN authentication failed: 
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 535 5.7.8 Error: authentication failed: 
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: watchdog_pat: 0x7fe871c19fe0
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: < unknown[192.168.1.29]: AUTH LOGIN
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: xsasl_dovecot_server_first: sasl_method LOGIN
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: xsasl_dovecot_handle_reply: auth reply: CONT?2?VXNlcm5hbWU6
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 334 VXNlcm5hbWU6
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: < unknown[192.168.1.29]: d3d3
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: xsasl_dovecot_handle_reply: auth reply: CONT?2?base64 of "Password"
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 334 base64 of "Password"
Aug  5 10:03:07 mailserver postfix/smtpd[19617]: < unknown[192.168.1.29]: base64 Of Real Password
Aug  5 10:03:09 mailserver postfix/smtpd[19617]: xsasl_dovecot_handle_reply: auth reply: FAIL?2?user=www@domain.com
Aug  5 10:03:09 mailserver postfix/smtpd[19617]: warning: unknown[192.168.1.29]: SASL LOGIN authentication failed: base64 of "Password"
Aug  5 10:03:09 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 535 5.7.8 Error: authentication failed: base64 of "Password"
Aug  5 10:03:09 mailserver postfix/smtpd[19617]: watchdog_pat: 0x7fe871c19fe0
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: < unknown[192.168.1.29]: QUIT
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: > unknown[192.168.1.29]: 221 2.0.0 Bye
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: match_hostname: unknown ~? 127.0.0.0/8
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: match_hostaddr: 192.168.1.29 ~? 127.0.0.0/8
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: match_list_match: unknown: no match
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: match_list_match: 192.168.1.29: no match
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: send attr request = disconnect
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: send attr ident = smtps:192.168.1.29
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: private/anvil: wanted attribute: status
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: input attribute name: status
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: input attribute value: 0
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: private/anvil: wanted attribute: (list terminator)
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: input attribute name: (end)
Aug  5 10:03:11 mailserver postfix/smtpd[19617]: disconnect from unknown[192.168.1.29]

i have changed base64 encoded values

this was in my /var/log/syslog

11

Re: How do I use SMTP over SSL ?

I have these content in my maillog:

May 18 07:05:27 r6 postfix/smtpd[2944]: send attr encryption_protocol = TLSv1
May 18 07:05:27 r6 postfix/smtpd[2944]: send attr encryption_cipher = DHE-RSA-AES256-SHA
May 18 07:05:27 r6 postfix/smtpd[2944]: send attr encryption_keysize = 256 

12

Re: How do I use SMTP over SSL ?

well as i said before its a clean install.
openldap backend

13

Re: How do I use SMTP over SSL ?

Can you please take a screenshot of SMTP server setting in Thunderbird?

14

Re: How do I use SMTP over SSL ?

as i have said before i have tried every setting
logging in with user@hostname, user
entering server dns address, server ip address,

the client recognises the certificate and informs me that it is invalid.

in my mail.warn i keep getting "password" encoded in bas64 as the password being sent - and its NOT the password entered in smtp settings.

15

Re: How do I use SMTP over SSL ?

NOTE

i can send emails from webmail on the iredmail box perfectly fine !

16

Re: How do I use SMTP over SSL ?

i use iRedMail with default settings, thunderbird works fine. Check attached image to see my smtp settings in thunderbird.

Did you change any setting? What's the version number of your Postfix?

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