Hello, I use my slack box (10.2)to authenticate to my ISP's smtp and pop servers to send and receive mail and it works fine. My other box runs windoze XP ,I configured outlook's smtp and pop setting with the ip address of my slack mail server. In outlook i can view mail which is sent but I cannot send an email to my web accounts. The first test message from outlook to my hotmail account said 550 5.7.1 <username@hotmail.com> Relaying denied. IP name lookup failed [192.168.0.101]. I added this ip address along with the windoze computername to my /etc/hosts file and got 550.5.7.1 <username@hotmail.com> Relaying denied. Proper authentication required. What do I need to add/change?

Thank You,

Raidmax

I'm assuming that you're using sendmail. Have you tried adding the IP address (or subnet) to your /etc/mail/access file and re-generating the database?
Add the following to /etc/mail/access:
Then, re-generate /etc/mail/access.db with:

thanks for the reply gilead...yes i'm using sendmail...added 192.168.0.101 RELAY to /etc/mail/access file and regenerated..I checked the box in outlooks advanced settings that reads My outgoing(SMTP)requires authentication and tested get the following error:



The original message was received at Wed, 18 Apr 2007 19:20:20 -0700 from windoze [192.168.0.101]

----- The following addresses had permanent fatal errors ----- <username@hotmail.com>
(reason: 550 Please configure your mail client to use authentication.)

----- Transcript of session follows -----
... while talking to smtpauth.earthlink.net.:
>>> DATA
<<< 550 Please configure your mail client to use authentication. 550 5.1.1 <username@hotmail.com>... User unknown <<< 503 valid RCPT command must precede DATA

Also i don't know if it matters but I should mentioned that my .mc file has the following added:
FEATURE(masquerade_envelope) FEATURE(genericstable, `hash -o /etc/mail/genericstable')
GENERICS_DOMAIN_FILE(`/etc/mail/genericsdomain')


$ cat /etc/mail/genericstable
myusername myusername@selfip.net
nobody myusername@selfip.net
root webmaster@selfip.net

I haven't used the genericstable for a long time now. It could be that the info being passed to smtpauth.earthlink.net is the changed envelope info instead of the required user name - but that's just a guess.

I'd suggest running ethereal and capturing the data between your box and smtpauth.earthlink.net while you try again. Also, capture the packets from telnet'ing to smtpauth.earthlink.net (port 25) and see what is happening.