Moving at the Speed of Creativity

For our residential high speed
connection provided by Cox Communications in West Texas, all outgoing email SMTP
connections (not authenticated through an external Exchange server apparently)
are blocked unless the Cox SMTP server address is used. Cox does not require (at
this time in our area) authenticated SMTP, so that means any email program that
sends out email can work fine as long as the Cox SMTP mail server address is
used– when the Internet connection is made through Cox’s service. Other
providers, like Verizon, are href="http://www2.verizon.net/help/dsl/?problem=14481"
target="NewWindow">doing the same thing but require SMTP
authentication — so you have to use the userid/password from Verizon
to send out email. If someone comes to visit and wants to send out email from
their laptop using a third-party email application, they can use the Cox SMTP
server address to send email too. This doesn’t work as nicely for a Verizon
internet connection, however, since it requires SMTP authentication. This is a
bit of a hassle in the case of Cox, but certainly workable. When people use the
webmail interface for their email program with either ISP, this is not an issue
however– those email services work over different webserver ports that are not
blocked or affected by the ISPs’ anti-spam
policies.

What this means practically
is that in my current email client of choice ( href="http://www.microsoft.com/mac/products/entourage2004/entourage2004.aspx?pid=entourage2004"
target="NewWindow">Microsoft Entourage), I have to create separate
accounts with different SMTP mail settings depending on my location. This is not
that big of a pain to setup, and once setup it is simple to change the account I
am using to send email. I have one account to use when I am at home (using the
Cox SMTP server address), and another when I am
away.

Now on Spring Break, using
public internet connections as well as the wireless internet connection of the
friends we are staying with, I have run into 2 related problems with sending
email that I have had to work
around:

1- The Yahoo mail service
restricts the maximum number of mail recipients for a single message, again to
try and cut down on SPAM. When I use the Cox SMTP mail server from home this is
not a problem: Cox presently does not require SMTP authentication or limit the
number of recipients for a mail message. But, when I am on the road and away
from home, I cannot use the Cox SMTP mail server. So this requires a
workaround.

2- Some ISPs (like
Verizon) attempt to block 100% of SMTP mailservers that are not their own. So
when connected with these services (like our friends are at their house) it is
not an option to use any of the SMTP mail servers I have used in the past,
including Yahoo’s. Again a workaround is
needed.

WORKAROUNDS

1-
Using the webmail interface for Yahoo mail is a partial workaround but not a
complete one. I have many addresses in Entourage that are not included in my
Yahoo mail account, so I really want to use Entourage to send my mail.
Additionally, Yahoo does limit the maximum of email recipients for a message
even when you use their webmail
interface.

2- I have found my
Microsoft Exchange mail server account still allows me to send email via
Entourage when I am connected to the Internet through various ISPs, so I could
use that mail account and bypass at least the first of the above problems.
However, I try to only send work-related email using that account, so this is
not a real good solution for me. I need to use a SMTP server that will let me
send from my personal email
account(s).

3- The best workaround I
have found so far is using a combination of two
approaches:

A) Activating a built-in
feature of my UNIX based Macintosh, the href="http://www.reitter-it-media.de/software/osxpostfix.html#panther"
target="NewWindow">Postfix service which uses my own computer as an SMTP
server.

B) Using an
inexpensive commercial VPN service ( target="NewWindow">HotSpotVPN) to establish a VPN connection so the
local ISP doesn’t block my local computer acting as a SMTP server. I found that
without a VPN connection, the Postfix SMTP server doesn’t work– and I assume
that is because of restrictions imposed by the
ISP.

Thanks to href="http://www.edsupport.cc/mguhlin/artifacts/writings/2004/utilities.htm#4"
target="NewWindow">Miguel Guhlin for the link to instructions on
Postfix, this procedure required several commands from the UNIX
terminal (yikes!) but really wasn’t hard at all to do. This took about 3 minutes
total to configure.

I read about
HotSpotVPN in the href="http://www.macworld.com/2005/02/features/macsecuritymain/index2.php"
target="NewWindow">February 2005 edition of MacWorld — not only
will using a VPN service like this most likely allow a local SMTP server like I
have described here, but it will also provide a level of encryption for all your
wireless communication that href="http://wifinetnews.com/archives/003340.html" target="NewWindow">can be
sniffed/intercepted by others less easily. There is a small monthly
fee for this service ($9 per month), but given the security benefits as well as
the third-party-mailclient-SMTP benefits described here, at this point it looks
to me like it is a very worthwhile
expense.

So, in order to send out
emails to large recipient lists when away from home, now that these
configuration changes have been made to Entourage my procedures
are:

1) Connect to HotSpotVPN with a
mouseclick
2) Compose a new mail message
and change the account to a new one I created that uses my local machine’s SMTP
service
3) Send the
message!

This solution requires a
somewhat ridiculous level of geekiness to accomplish, but at least it works, and
I would say the technical geekiness required here is not at an obscene level–
so I would recommend this to others who have encountered similar problems and,
like me, are fortunate to be running such a powerful, flexible, and
user-friendly operating system like target="NewWindow">Mac OS X….