On Mon, Apr 12, 2010 at 10:42 AM, Kenneth Thorman <kenneth.thorman@appinux.com> wrote:

This is the output from the command

root@XXXXXXXX /vol/otrs/bin #openssl s_client -host smtp.gmail.com -port 465
CONNECTED(00000003)
depth=0 /C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
verify error:num=20:unable to get local issuer certificate
verify return:1
depth=0 /C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
verify error:num=27:certificate not trusted
verify return:1
depth=0 /C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
verify error:num=21:unable to verify the first certificate
verify return:1
---
Certificate chain
0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
   i:/C=ZA/ST=Western Cape/L=Cape Town/O=Thawte Consulting cc/OU=Certification Services Division/CN=Thawte Premium Server CA/emailAddress=premium-server@thawte.com
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
issuer=/C=ZA/ST=Western Cape/L=Cape Town/O=Thawte Consulting cc/OU=Certification Services Division/CN=Thawte Premium Server CA/emailAddress=premium-server@thawte.com
---
No client certificate CA names sent
---
SSL handshake has read 1017 bytes and written 315 bytes
---
New, TLSv1/SSLv3, Cipher is RC4-MD5
Server public key is 1024 bit
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol : TLSv1
    Cipher    : RC4-MD5
    Session-ID: 05D147DEFDC2F6B10F47D15EC98B42539BD95BEB13F977A2116C49292DEAFBAD
    Session-ID-ctx:
    Master-Key: A2D70CF49308FC90EC4B82CD1C5EA094F88C909880C73C6B7B71EF9C36C3F446A3BA8F0C1E6C71795155E1F116A1F99D
    Key-Arg   : None
    Krb5 Principal: None
    Start Time: 1271061102
    Timeout   : 300 (sec)
    Verify return code: 21 (unable to verify the first certificate)
---
220 mx.google.com ESMTP t2sm65868gve.19

Now after starting to work the commands

EHLO
250-mx.google.com at your service, [79.125.6.100]
250-SIZE 35651584
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250-ENHANCEDSTATUSCODES
250 PIPELINING
MAIL FROM:XXXXXXXXXXXXx
530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://mail.google.com/support/bin/answer.py?answer=14257 q9sm74150gve.14

....

So I can connect as far as I can see

Regards
Ken

On Mon, Apr 12, 2010 at 10:26 AM, Markus Esche <markus.esche@otrs.com> wrote:

Hi Kenneth,

On 12.04.2010, at 10:21, Kenneth Thorman wrote:
> Config Options: Framework -> Core::Sendmail
> SendmailModule: SMTPS
> SendmailModule::Host: smtp.gmail.com
> SendmailModule::Port: 465
> SendmailModule::AuthUser: XXXXXX@XXXXX.com (a valid username)
> SendmailModule::AuthPassword: XXXXXXXXXXXX (corresponding password to username above)

Could you try the following command:
$ openssl s_client -host smtp.gmail.com -port 465
to get a valid SSL connection to gmail?

And if have SMTP connection up, what if you try authenticate with your
credentials via the openssl prompt?

hth,
Markus

--

Markus Esche
Customer Development

OTRS AG
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