SMTP AUTH, Sendmail client to Postfix server
 

I'm hoping someone here can help, as I've been beating my head on the wall for a week now with little advancement.

I've found a number of tutorials on setting this up, however none of them have gotten me 100% of the way there.

Here's my situation: home-based Fedora server (Core 8), running sendmail 8.14.2-1. Connecting to hosting company's smtp server over port 587, to bypass Verizon's blocking of port 25.

My /etc/mail/sendmail.mc file looks like this (comment lines removed):

My /etc/mail/auth/client-info file looks like this (username and password obscured):

I can successfully send a mail manually, as shown here:

But when I try to send a mail message from my server, it fails and sends back this bounce message:

I'm at my wit's end (not that long a trip, I'll grant you), can anyone help?

Hi,

Take a look at this thread here at LQ (specially post #2)

Regards

Thanks for the reply bathory, but the URL didn't come through, can you repost?

Oups sorry for that
Here is the link: http://www.linuxquestions.org/questi...t-port-690852/

Regards

I was able to find it, but strangely the URL itself didn't work...it would redirect to some other unrelated post, but I used some of the words from the URL in a search and found the post you were talking about.

Everything mentioned in that post, and the external article referenced, I have done, and it still fails.

Here is the relevant lines from /var/log/maillog from my most recent attempt:

I still think this means my sendmail isn't doing the auth correctly, or at all, but I can't figure out why.

You miss LOGIN from the mechanisms:
but you use it in
Try to use "M:PLAIN" and see if it works.

I added LOGIN to the mechanisms and recreated sendmail.cf, that should have fixed it also, right? I'm loathe to use PLAIN since that is completely in the clear (not that LOGIN is that much better with just base64 encoding)

Still fails:
Could there be something wrong with my SMART_HOST or the various MASQUERADE options?

Hi,

I've reread sendmail documentation and if you want to use base-64 encoded username/password in /etc/mail/authinfo, you have to replace ":" with "=", like this:
HTH

Regards

I'm still getting the following:

(reason: 554 5.7.1 <rickg@datarealm.com>: Relay access denied)

I'm ready to start tearing my hair out.

Hi,

Are you sure you use:
If yes, try to remove the 2nd line, the port and maybe the U part from authinfo:
and see if it works!

Ok, I verified the sendmail.mc lines were as I posted (I had done cut-and-pastes, so was pretty sure).

I removed port from the first line, and the line that had just the port, tested that and it failed. I then removed the U: from the remaining line, and that also failed. I then, on a guess, tried to have both versions of the line...with the FQDN of the host, but with and without the port. That also failed.

Here is the current /etc/mail/auth/client-info file:
Here is the last bounced email showing the failure:

I really appreciate the continued help in trying to diagnose/fix this.

I'm just curious because I've just tested this setup and it works :scratch:

Til now I was using out corporate mail server (on port 25) as a smarthost for sendmail running on my box at home.
So I've changed the relay port in sendmail.mc to 587 and it also worked, when I removed the port from authinfo. I've used tcpdump and saw that sendmail was contacting the smarthost on port 587 in both cases (with or without the port), but in the former case I was getting a DSN with a "No AUTH command command has been given" error.

Maybe your smarthost does not like the from: address, so change it to something other than root@localhost.local domain and test.
I don't know what else to think

Regards

I've been sending test emails just by using the command:

How would I set the from? I though the MASQUERADE options were supposed to do that?

Use:
Apparently masquerade does not work (default for root)

I had to do it this way:

Still failed, no difference in the message.

I've tried running sendmail in a higher level of debugging messages, but I was not able to determine from the output if it was correctly doing authentication or not, do you have any recommendations on that, maybe better diagnostic messages would help.