smtp via ssl

S

somedumbguy

I just switched from cable to DSL and am having some problems with my
outgoing mail. I think it may be a certificate problem, but I don't know how
to fix it.

Here's the deal:

Entourage 2004 on my PowerBook. I use this computer at both home and work.
When I set up my DSL last night, I found out that BellSouth now blocks
traffic on port 25, so I can't access my work SMTP server. No problem,
because I can just use the BellSouth SMTP server. Except for the fact that,
when I get to work, I can no longer access the BellSouth SMTP server, and I
have to switch back. Long story short, it seems that I'll have to switch
SMTP servers whenever I go from home to work, or vice versa.

Or so I thought. It seems that I can access my work SMTP server through an
alternate port as long as I'm using SSL. So... I went to account settings,
clicked on advanced options, checked the box to use SSL, checked the box to
use an alternate port, and specified the port to use (465). The problem is
that, when I send mail, it just hangs until it ultimately times out. I
configured Eudora as above and tried the same thing. The first time through,
it popped up a warning window about need a certain certificate, and asked
permission to add it to the keychain. Once I agreed, it started working
perfectly from Eudora.

Any idea why this won't work in Entourage???

Do you think it's possible that I'm getting a similar certificate-related
message from the server, but Entourage is failing to pop up a window through
which I can deal with it? It seems like that would result in an apparent
until it ultimately times out.

Any other suggestions? And, most importantly, how might I fix this???
 
S

somedumbguy

When I set up my DSL last night, I found out that BellSouth now blocks
traffic on port 25, so I can't access my work SMTP server. No problem,
because I can just use the BellSouth SMTP server. Except for the fact that,
when I get to work, I can no longer access the BellSouth SMTP server, and I
have to switch back. Long story short, it seems that I'll have to switch
SMTP servers whenever I go from home to work, or vice versa.

Or so I thought. It seems that I can access my work SMTP server through an
alternate port as long as I'm using SSL. So... I went to account settings,
clicked on advanced options, checked the box to use SSL, checked the box to
use an alternate port, and specified the port to use (465). The problem is
that, when I send mail, it just hangs until it ultimately times out. I
configured Eudora as above and tried the same thing. The first time through,
it popped up a warning window about need a certain certificate, and asked
permission to add it to the keychain. Once I agreed, it started working
perfectly from Eudora.

Any idea why this won't work in Entourage???

Do you think it's possible that I'm getting a similar certificate-related
message from the server, but Entourage is failing to pop up a window through
which I can deal with it? It seems like that would result in an apparent
until it ultimately times out.
Click to expand...

I still don't know what's causing this problem, but I now have a workaround.
I downloaded and installed Eric Clements' SSL Enabler, which serves as a
front end for installing and configuring Stunnel. I then set the local port
to 25, the remote server to my work mail server, and the remote port to the
alternate port (465). I then configured Entourage to use 127.0.0.1 (my own
computer) as the outgoing mail server. This essentially causes Entourage to
contact my computer on port 25, rather than an outside mail server. Stunnel
then redirects the connection to the remote server via the alternate port
via SSL. This solves the problem, but I'd still like to know why Entourage
2004 can't make an effective SSL connection to this server when Eudora can.
 
A

Adam Bailey

When I set up my DSL last night, I found out that BellSouth now blocks
traffic on port 25, so I can't access my work SMTP server. No problem,
because I can just use the BellSouth SMTP server. Except for the fact that,
when I get to work, I can no longer access the BellSouth SMTP server, and I
have to switch back. Long story short, it seems that I'll have to switch
SMTP servers whenever I go from home to work, or vice versa.
[snip]
Click to expand...

I still don't know what's causing this problem, but I now have a workaround.
I downloaded and installed Eric Clements' SSL Enabler, which serves as a
front end for installing and configuring Stunnel.[/QUOTE]

See <http://groups.google.com/[email protected]>.
 
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