Re: Problems getting Gmail to use my SMTP server rather than theirs
On Wed, Feb 10, 2010 at 5:54 PM, Rob Tanner rtan...@linfield.edu wrote: TLS is enabled on port 25 of our server and it has a regular Thawte certificate behind it. Tests with Thunderbird using PLAIN authentication (SASL method) work perfectly. From our point of view, all we really want to protect in any SMTP transaction are the user credentials (uid/passwd) and what we are doing is currently sufficient. Google, on the other hand is doing something different or expecting something different and I have no idea what. If you are successfully using a similar setup with Gmail, could you please pass on your wisdom. Watch your postfix logs and start debugging when gmail tries to authenticate against your server The problem is the log files are rather large (a quarter million lines since the 4 am roll this morning, and there are lots of google entries. In other words I've already spent time just trying to find the entries. Any idea about particular keywords that I might look for? . Thanks, Rob An easy way to watch is to tail -f the logfile, tell Gmail to send a message, and then watch the log scroll past. You will see the authorization attempt and your server's response. Also, in your Gmail account, check the submission port. There's a drop down list from which you can choose 25, 465, and 587; it defaults to 587. -- Mike Saldivar Direct Financial Solutions Information Systems Manager Desk: 435-774-8252 Cell: 435-881-3778
Re: Problems getting Gmail to use my SMTP server rather than theirs
On 2/12/2010 11:21 AM, Michael Saldivar wrote: On Wed, Feb 10, 2010 at 5:54 PM, Rob Tanner rtan...@linfield.edu mailto:rtan...@linfield.edu wrote: TLS is enabled on port 25 of our server and it has a regular Thawte certificate behind it. Tests with Thunderbird using PLAIN authentication (SASL method) work perfectly. From our point of view, all we really want to protect in any SMTP transaction are the user credentials (uid/passwd) and what we are doing is currently sufficient. Google, on the other hand is doing something different or expecting something different and I have no idea what. If you are successfully using a similar setup with Gmail, could you please pass on your wisdom. Watch your postfix logs and start debugging when gmail tries to authenticate against your server The problem is the log files are rather large (a quarter million lines since the 4 am roll this morning, and there are lots of google entries. In other words I've already spent time just trying to find the entries. Any idea about particular keywords that I might look for? . Thanks, Rob An easy way to watch is to tail -f the logfile, tell Gmail to send a message, and then watch the log scroll past. You will see the authorization attempt and your server's response. Also, in your Gmail account, check the submission port. There's a drop down list from which you can choose 25, 465, and 587; it defaults to 587. And another great trick for finding stuff in your logs is to tag submission entries with a different syslog_name. # master.cf submission ... smtpd -o syslog_name=postfix-submission ... http://www.postfix.org/postconf.5.html#syslog_name -- Noel Jones
Re: Problems getting Gmail to use my SMTP server rather than theirs
Found a far superior solution. The problem that the powers that be thought it would fix, it wouldn't fix anyway. I finally convinced them of that and so that's the end of that. Nevertheless, thanks to all who replied. -- Rob On 2/12/10 9:30 AM, Noel Jones njo...@megan.vbhcs.org wrote: On 2/12/2010 11:21 AM, Michael Saldivar wrote: On Wed, Feb 10, 2010 at 5:54 PM, Rob Tanner rtan...@linfield.edu mailto:rtan...@linfield.edu wrote: TLS is enabled on port 25 of our server and it has a regular Thawte certificate behind it. Tests with Thunderbird using PLAIN authentication (SASL method) work perfectly. From our point of view, all we really want to protect in any SMTP transaction are the user credentials (uid/passwd) and what we are doing is currently sufficient. Google, on the other hand is doing something different or expecting something different and I have no idea what. If you are successfully using a similar setup with Gmail, could you please pass on your wisdom. Watch your postfix logs and start debugging when gmail tries to authenticate against your server The problem is the log files are rather large (a quarter million lines since the 4 am roll this morning, and there are lots of google entries. In other words I've already spent time just trying to find the entries. Any idea about particular keywords that I might look for? . Thanks, Rob An easy way to watch is to tail -f the logfile, tell Gmail to send a message, and then watch the log scroll past. You will see the authorization attempt and your server's response. Also, in your Gmail account, check the submission port. There's a drop down list from which you can choose 25, 465, and 587; it defaults to 587. And another great trick for finding stuff in your logs is to tag submission entries with a different syslog_name. # master.cf submission ... smtpd -o syslog_name=postfix-submission ... http://www.postfix.org/postconf.5.html#syslog_name -- Noel Jones
Re: Problems getting Gmail to use my SMTP server rather than theirs
On 11 February 2010 11:54, Rob Tanner rtan...@linfield.edu wrote: The problem is the log files are rather large (a quarter million lines since the 4 am roll this morning, and there are lots of google entries. In other words I've already spent time just trying to find the entries. Any idea about particular keywords that I might look for? Not really, but I'd be inclined to capture a chunk of the logs while you manually fire off a message from gmail that should go via your server (I think I'm reading this correctly). I don't know what the error messages might look like, perhaps TLS appears in there. Now, I've not used this gmail feature, but perhaps it's connecting to port 587 instead? Do you have the submission port setup, and if so, what settings/restrictions does it have?
Re: Problems getting Gmail to use my SMTP server rather than theirs
Rob Tanner wrote: If you’re familiar with email, you know you can add “Send mail as” identities and when you setup a second identity, you have the option of using Gmail’s SMTP server or the SMTP server for the domain to which the “send as” identity belongs. My problem is I can’t get it to work. The error I get is: *Authentication failed. Please check your username/password. [Server response: Remote server does not support TLS code(500) ] * TLS is enabled on port 25 of our server and it has a regular Thawte certificate behind it. Tests with Thunderbird using PLAIN authentication (SASL method) work perfectly. From our point of view, all we really want to protect in any SMTP transaction are the user credentials (uid/passwd) and what we are doing is currently sufficient. Google, on the other hand is doing something different or expecting something different and I have no idea what. If you are successfully using a similar setup with Gmail, could you please pass on your wisdom. Watch your postfix logs and start debugging when gmail tries to authenticate against your server Thanks, Rob *Rob Tanner *UNIX Services Manager Linfield College, McMinnville Oregon -- Jorge Armando Medina Computación Gráfica de México Web: http://www.e-compugraf.com Tel: 55 51 40 72, Ext: 124 Email: jmed...@e-compugraf.com GPG Key: 1024D/28E40632 2007-07-26 GPG Fingerprint: 59E2 0C7C F128 B550 B3A6 D3AF C574 8422 28E4 0632 signature.asc Description: OpenPGP digital signature
Re: Problems getting Gmail to use my SMTP server rather than theirs
On 2/10/10 4:40 PM, Jorge Armando Medina jmed...@e-compugraf.com wrote: Rob Tanner wrote: If you¹re familiar with email, you know you can add ³Send mail as² identities and when you setup a second identity, you have the option of using Gmail¹s SMTP server or the SMTP server for the domain to which the ³send as² identity belongs. My problem is I can¹t get it to work. The error I get is: *Authentication failed. Please check your username/password. [Server response: Remote server does not support TLS code(500) ] * TLS is enabled on port 25 of our server and it has a regular Thawte certificate behind it. Tests with Thunderbird using PLAIN authentication (SASL method) work perfectly. From our point of view, all we really want to protect in any SMTP transaction are the user credentials (uid/passwd) and what we are doing is currently sufficient. Google, on the other hand is doing something different or expecting something different and I have no idea what. If you are successfully using a similar setup with Gmail, could you please pass on your wisdom. Watch your postfix logs and start debugging when gmail tries to authenticate against your server The problem is the log files are rather large (a quarter million lines since the 4 am roll this morning, and there are lots of google entries. In other words I've already spent time just trying to find the entries. Any idea about particular keywords that I might look for? . Thanks, Rob *Rob Tanner *UNIX Services Manager Linfield College, McMinnville Oregon
