VirtualSpy's Answers

VMware Email Virtual Appliance ISPConfig

NOTE:  Please click on a sponsor hyperlink if the post was helpful!

Symptoms

I had trouble getting SMTP to go out because the sendmail that I used just would not connect to the AT&T server (my ISP), or gmail either, even after setting the right ports and updating the config file.

Solution

The ISPConfig virtual machine was extrememly easy to setup.  Just fired up the virtual machine, changed the IP address, and the system was running.

In order for the server to resolve the gmail.com domain, I had to flip it to DHCP and back again (/etc/network/interfaces file) to static IP so DNS to recognize the /etc/resolve.conf file with the entry nameserver 68.94.156.1 because it failed when attempting the command “HOST gmail.com” from a terminal.

I was able to login as “admin” and setup my email domain as a “client”, logon as the client administrative user, and create a mailbox.  The cool thing there is that after creating the mailbox I could connect to the server using Outlook Express.

I had to make some changes in order for postfix (the email server) to actually hookup to gmail port 587 with secure authentication.  (There was a LOT of trial-and-error and Internet searching involved.)

sudo nano /etc/postfix/main.cf (…to modify the text file)

smtp_sasl_auth_enable = yes

smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd

smtp_sasl_type = cyrus

smtp_sasl_security_options = noanonymous

relayhost = [smtp.gmail.com]:587

sudo nano sasl_passwd (…to create a new text file)

[smtp.gmail.com]:587     myuser@gmail.com:mypassword

sudo postmap sasl_passwd (…to encrypt the credentials used)

sudo /etc/init.d/postfix reload (…to apply changes)

For some reason, any incoming email gets bounced, but I will save that fight for another day because my objective was to send outgoing mail from the server!  Ideally, it would be cool to setup some family with mailboxes and have them use Outlook Express to connect, but incoming mail must be fixed before I could do that.

NOTE:  Please click on a sponsor hyperlink if the post was helpful!