ssmtp - possible anomaly with SSL
I recently figured out how to send mail thru my ISP ID using ssmtp. I had previously only been using KMail, and I had it configured to use port 465 SSL LOGIN. I can send mail when I don't use port 465: mailhub=mail.InsightBB.com but if I add the port 465 a,d enable SSL with: UseTLS=YES then I use the -v switch and also -auFreeBSD -apPassword as in smtp -v -auFreeBSD -apPassword free...@insightbb.com and the messages all indicate success, but the mail never arrives. It does when I don't use SSL on port 465. KMail does work with SSL on port 465. -- System Name: laptop2.StevenFriedrich.org Hardware: 2.80GHz Intel Pentium 4 (HTT) with 2 GB memory OS version:FreeBSD 8.1-RELEASE-p1 i386 (6.4 MB kernel) manager(s):kde4-4.5.3 X windows: xorg-7.5X.Org X Server 1.7.5 ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org
Re: ssmtp - possible anomaly with SSL
On Sat, Nov 6, 2010 at 7:23 AM, Steven Friedrich free...@insightbb.comwrote: I recently figured out how to send mail thru my ISP ID using ssmtp. I had previously only been using KMail, and I had it configured to use port 465 SSL LOGIN. I can send mail when I don't use port 465: mailhub=mail.InsightBB.com but if I add the port 465 a,d enable SSL with: UseTLS=YES then I use the -v switch and also -auFreeBSD -apPassword as in smtp -v -auFreeBSD -apPassword free...@insightbb.com and the messages all indicate success, but the mail never arrives. It does when I don't use SSL on port 465. KMail does work with SSL on port 465. What does /var/log/maillog say? Can you post /usr/local/etc/ssmtp.conf? (without password of course) Here is mine and it works fine. MailHub=smtp.gmail.com:587 UseTLS=YES authuser=r*...@xaerolimit.net AuthPass= FromLineOverride=YES Hostname=mail.xaerolimit.net root=*...@xaerolimit.net UseSTARTTLS=YES Did you know... If you play a Windows 2000 CD backwards, you hear satanic messages, but what's worse is when you play it forward ...it installs Windows 2000 -- Alfred Perlstein on chat at freebsd.org http://lists.freebsd.org/mailman/listinfo/freebsd-questions -- System Name: laptop2.StevenFriedrich.org Hardware: 2.80GHz Intel Pentium 4 (HTT) with 2 GB memory OS version:FreeBSD 8.1-RELEASE-p1 i386 (6.4 MB kernel) manager(s):kde4-4.5.3 X windows: xorg-7.5X.Org X Server 1.7.5 ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org
Re: ssmtp - possible anomaly with SSL
On Sat, Nov 06, 2010 at 07:23:39AM -0400, Steven Friedrich wrote: I recently figured out how to send mail thru my ISP ID using ssmtp. I had previously only been using KMail, and I had it configured to use port 465 SSL LOGIN. I can send mail when I don't use port 465: mailhub=mail.InsightBB.com but if I add the port 465 a,d enable SSL with: UseTLS=YES then I use the -v switch and also -auFreeBSD -apPassword as in smtp -v -auFreeBSD -apPassword free...@insightbb.com and the messages all indicate success, but the mail never arrives. It does when I don't use SSL on port 465. KMail does work with SSL on port 465. I'm not entirely clear on what you're using as a mail user agent. Are you still using KMail as your MUA, but using ssmtp to send the emails to your SMTP server, or have you switched MUAs when you started using ssmtp? Chris Brennan suggested you send more information; in addition to answering my question, it might be useful to give us the information Chris requested -- but make sure you obscure any username/password information. -- Chad Perrin [ original content licensed OWL: http://owl.apotheon.org ] pgpU2tev6gfP9.pgp Description: PGP signature
Re: ssmtp - possible anomaly with SSL
On Sat, Nov 6, 2010 at 12:01 PM, Chad Perrin per...@apotheon.com wrote: On Sat, Nov 06, 2010 at 07:23:39AM -0400, Steven Friedrich wrote: I recently figured out how to send mail thru my ISP ID using ssmtp. I had previously only been using KMail, and I had it configured to use port 465 SSL LOGIN. I can send mail when I don't use port 465: mailhub=mail.InsightBB.com but if I add the port 465 a,d enable SSL with: UseTLS=YES then I use the -v switch and also -auFreeBSD -apPassword as in smtp -v -auFreeBSD -apPassword free...@insightbb.com and the messages all indicate success, but the mail never arrives. It does when I don't use SSL on port 465. KMail does work with SSL on port 465. I'm not entirely clear on what you're using as a mail user agent. Are you still using KMail as your MUA, but using ssmtp to send the emails to your SMTP server, or have you switched MUAs when you started using ssmtp? Chris Brennan suggested you send more information; in addition to answering my question, it might be useful to give us the information Chris requested -- but make sure you obscure any username/password information. If you reference my last e-mail, I posted my my working ssmtp.conf (for communicating w/ GMail/Google for Domains). If sSMTP is your only MTA, then using my example will get you up and running very quickly. You can also reference http://wiki.freebsd.org/SecureSSMTP on how to secure it (if this is a (semi-)public machine with more then one user on it. -- Chad Perrin [ original content licensed OWL: http://owl.apotheon.org ] ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org
Re: ssmtp - possible anomaly with SSL
On Saturday 06 November 2010 12:01:53 pm Chad Perrin wrote: On Sat, Nov 06, 2010 at 07:23:39AM -0400, Steven Friedrich wrote: I recently figured out how to send mail thru my ISP ID using ssmtp. I had previously only been using KMail, and I had it configured to use port 465 SSL LOGIN. I can send mail when I don't use port 465: mailhub=mail.InsightBB.com but if I add the port 465 a,d enable SSL with: UseTLS=YES then I use the -v switch and also -auFreeBSD -apPassword as in smtp -v -auFreeBSD -apPassword free...@insightbb.com and the messages all indicate success, but the mail never arrives. It does when I don't use SSL on port 465. KMail does work with SSL on port 465. I'm not entirely clear on what you're using as a mail user agent. Are you still using KMail as your MUA, but using ssmtp to send the emails to your SMTP server, or have you switched MUAs when you started using ssmtp? Chris Brennan suggested you send more information; in addition to answering my question, it might be useful to give us the information Chris requested -- but make sure you obscure any username/password information. I still use KMail for my essential email. However, I want to be able to use send-pr. There is a port called ssmtp, and I use it only for outgoing mail, it allows any userID to send outgoing email using a single ISP account. When my /usr/local/etc/ssmtp.conf is: root=free...@insightbb.com mailhub=mail.InsightBB.com rewriteDomain=InsightBB.com hostname=_HOSTNAME_ I can send an outgoing email to myself so I can prove it works. ssmtp -v free...@insighttbb.com And the verbose output indicates success. I didn't post it, just stated what it was. But when I configure SSL on port 465, it also shows a good exchange, but maybe I didn't wait long enough to see it get thru the ISP's system. So my SSL version of ssmtp.conf is: root=free...@insightbb.com mailhub=mail.InsightBB.com:465 rewriteDomain=InsightBB.com hostname=_HOSTNAME_ # Use SSL/TLS to send secure messages to server. UseTLS=YES The verbose option indicated success when sending an email from root. Let me verify that it wasn't my mistake for not waiting longer... -- System Name: laptop2.StevenFriedrich.org Hardware: 2.80GHz Intel Pentium 4 (HTT) with 2 GB memory OS version:FreeBSD 8.1-RELEASE-p1 i386 (6.4 MB kernel) manager(s):kde4-4.5.3 X windows: xorg-7.5X.Org X Server 1.7.5 ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org
Re: ssmtp - possible anomaly with SSL
On Sat, Nov 6, 2010 at 12:50 PM, Steven Friedrich free...@insightbb.comwrote: On Saturday 06 November 2010 12:01:53 pm Chad Perrin wrote: On Sat, Nov 06, 2010 at 07:23:39AM -0400, Steven Friedrich wrote: I recently figured out how to send mail thru my ISP ID using ssmtp. I had previously only been using KMail, and I had it configured to use port 465 SSL LOGIN. I can send mail when I don't use port 465: mailhub=mail.InsightBB.com but if I add the port 465 a,d enable SSL with: UseTLS=YES then I use the -v switch and also -auFreeBSD -apPassword as in smtp -v -auFreeBSD -apPassword free...@insightbb.com and the messages all indicate success, but the mail never arrives. It does when I don't use SSL on port 465. KMail does work with SSL on port 465. I'm not entirely clear on what you're using as a mail user agent. Are you still using KMail as your MUA, but using ssmtp to send the emails to your SMTP server, or have you switched MUAs when you started using ssmtp? Chris Brennan suggested you send more information; in addition to answering my question, it might be useful to give us the information Chris requested -- but make sure you obscure any username/password information. I still use KMail for my essential email. However, I want to be able to use send-pr. There is a port called ssmtp, and I use it only for outgoing mail, it allows any userID to send outgoing email using a single ISP account. When my /usr/local/etc/ssmtp.conf is: root=free...@insightbb.com mailhub=mail.InsightBB.com rewriteDomain=InsightBB.com hostname=_HOSTNAME_ I can send an outgoing email to myself so I can prove it works. ssmtp -v free...@insighttbb.com And the verbose output indicates success. I didn't post it, just stated what it was. But when I configure SSL on port 465, it also shows a good exchange, but maybe I didn't wait long enough to see it get thru the ISP's system. So my SSL version of ssmtp.conf is: root=free...@insightbb.com mailhub=mail.InsightBB.com:465 rewriteDomain=InsightBB.com hostname=_HOSTNAME_ # Use SSL/TLS to send secure messages to server. UseTLS=YES The verbose option indicated success when sending an email from root. Let me verify that it wasn't my mistake for not waiting longer... -- System Name: laptop2.StevenFriedrich.org Hardware: 2.80GHz Intel Pentium 4 (HTT) with 2 GB memory OS version:FreeBSD 8.1-RELEASE-p1 i386 (6.4 MB kernel) manager(s):kde4-4.5.3 X windows: xorg-7.5X.Org X Server 1.7.5 ___ /var/log/maillog is where you will see success/fail. Your config looks good to me, so I would watch maillog while sending mail and see what crops up. ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org
Re: ssmtp - possible anomaly with SSL
On Sat, Nov 06, 2010 at 12:54:39PM -0400, Chris Brennan wrote: On Sat, Nov 6, 2010 at 12:50 PM, Steven Friedrich free...@insightbb.comwrote: I still use KMail for my essential email. Okay, thanks for clarifying, Steven. And the verbose output indicates success. I didn't post it, just stated what it was. But when I configure SSL on port 465, it also shows a good exchange, but maybe I didn't wait long enough to see it get thru the ISP's system. So my SSL version of ssmtp.conf is: root=free...@insightbb.com mailhub=mail.InsightBB.com:465 rewriteDomain=InsightBB.com hostname=_HOSTNAME_ # Use SSL/TLS to send secure messages to server. UseTLS=YES The verbose option indicated success when sending an email from root. Let me verify that it wasn't my mistake for not waiting longer... . . . and you said that setting it to send email through mail.insightbb.com:465 in KMail config works. Right? In addition to Chris Brennan's article references, there's another that I wrote quite some time ago that I think explains ssmtp config for TLS use pretty well: http://blogs.techrepublic.com.com/security/?p=440 From what you said so far, it seems like ssmtp is configured correctly. It seems likely, then, that the problem is with KMail or with something filtering port 465. Does KDE have something going on with firewall management that might be allowing KMail to send stuff on port 465 while outside of KDE's help you cannot? Have you checked to see whether you can send with your TLS settings for ssmtp from outside of KMail? If you are not wedded to ssmtp per se, you could always try msmtp instead: http://blogs.techrepublic.com.com/opensource/?p=1842 It does much the same sort of stuff as ssmtp, but is a bit more feature rich, and appears to be more actively maintained than ssmtp. /var/log/maillog is where you will see success/fail. Your config looks good to me, so I would watch maillog while sending mail and see what crops up. It appears that Chris Brennan knows a bit about this subject. Yes, that file may prove useful in troubleshooting this issue. If you are having trouble figuring out whether maillog has anything to offer for hints, you might want to paste its contents into pastebin and give us a link to it there so we can give it a look (after checking to make sure you are not pasting any sensitive data, of course). -- Chad Perrin [ original content licensed OWL: http://owl.apotheon.org ] pgp4vEGMWEDJJ.pgp Description: PGP signature
Re: ssmtp - possible anomaly with SSL
I should port this wiki to @doc On Nov 6, 2010, at 9:30 AM, Chris Brennan xa...@xaerolimit.net wrote: On Sat, Nov 6, 2010 at 12:01 PM, Chad Perrin per...@apotheon.com wrote: On Sat, Nov 06, 2010 at 07:23:39AM -0400, Steven Friedrich wrote: I recently figured out how to send mail thru my ISP ID using ssmtp. I had previously only been using KMail, and I had it configured to use port 465 SSL LOGIN. I can send mail when I don't use port 465: mailhub=mail.InsightBB.com but if I add the port 465 a,d enable SSL with: UseTLS=YES then I use the -v switch and also -auFreeBSD -apPassword as in smtp -v -auFreeBSD -apPassword free...@insightbb.com and the messages all indicate success, but the mail never arrives. It does when I don't use SSL on port 465. KMail does work with SSL on port 465. I'm not entirely clear on what you're using as a mail user agent. Are you still using KMail as your MUA, but using ssmtp to send the emails to your SMTP server, or have you switched MUAs when you started using ssmtp? Chris Brennan suggested you send more information; in addition to answering my question, it might be useful to give us the information Chris requested -- but make sure you obscure any username/password information. If you reference my last e-mail, I posted my my working ssmtp.conf (for communicating w/ GMail/Google for Domains). If sSMTP is your only MTA, then using my example will get you up and running very quickly. You can also reference http://wiki.freebsd.org/SecureSSMTP on how to secure it (if this is a (semi-)public machine with more then one user on it. -- Chad Perrin [ original content licensed OWL: http://owl.apotheon.org ] ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org
Re: ssmtp - possible anomaly with SSL
On Sat, Nov 6, 2010 at 5:28 PM, Jason Helfman jhelf...@experts-exchange.com wrote: I should port this wiki to @doc if you need an extra pair of eyes, I shall provide mine and what little free time I may have. Did you know... If you play a Windows 2000 CD backwards, you hear satanic messages, but what's worse is when you play it forward ...it installs Windows 2000 -- Alfred Perlstein on chat at freebsd.org http://lists.freebsd.org/mailman/listinfo/freebsd-questions ___ freebsd-questions@freebsd.org mailing list http://lists.freebsd.org/mailman/listinfo/freebsd-questions To unsubscribe, send any mail to freebsd-questions-unsubscr...@freebsd.org
