Re: Error: -3253 Connection to the server failed or was dropped

On 9/13/07 8:48 PM, in article C30F7CE0.13E52%merb@xxxxxxxxxxxx, "Michael R.
Erb" <merb@xxxxxxxxxxxx> wrote:

For years, I've been "redirecting" emails to a BCC group-list using
Entourage on my Mac. Currently there are 59 addresses in the list but there
has been as many as 80 in the past.

Starting yesterday, I've been unable to redirect emails to my group-list,
getting instead an error message in Entourage that says "Error: -3253
Connection to the server failed or was dropped."

I've called RoadRunner tech support since that is who my smtp server is
through and got nowhere. They told me they only support Outlook and Outlook
Express... and I don't think this has anything to do with my email client at
all. They then suggested I use Webmail. Great, thanks for the awesome tip.
Unfortunately Webmail does not even let you "redirect" an email so it's not
an option.

Just say you use Outlook Express. The directions should be the same.
Directions for menu commands might be a bit different, but you should be
able to make sense for Entourage.

Be that as it may, I don't have a clue how to work around this issue. I've
tried breaking my group-list into two smaller lists of about 30 address
each, but this also elicited the same error message when I tried to send it.
I am not having any problems sending a single email out to specific
addresses but cannot "redirect" an email to my group-list.

My first thought when going over your email, was your ISP has suddenly
started limiting recipients to 50. That's the usual number most ISPs allow,
but since you are getting the error with a smaller number this indicates
something else is causing the problem. I would verify that 30 is allowed
when sending Bcc.

By the way, I was able to successfully send to my 59 address group using
redirect with my Apple "Mail" program on my Mac but I did so through my .mac
account using Apples smtp server. So maybe it is RoadRunner smtp server

Definitely sounds like RR is the problem.

Any thoughts on this?

Your ISP made some security changes and is blocking your redirected mail.

One other thing I would do before calling your ISP back is to monitor your
network traffic to see what their server is actually saying to Entourage
when it fails. This will arm you with enough info they should be able to
answer your questions. The error message you are getting is coming from them
too. What's their response to error message. -3253?

Test your network with tcpflow. Another application I ran into recently that
does the same thing but has a different interface.

EavesDrop....Let it capture some stuff then double-click any of the lines of
text in the main window to see more detail.


See this page for more help monitoring your network:


Here are the short and simple instructions on using tcpflow:

1. Download the Mac OS X version here (freeware).


2. When you install, you will not find a tcpflow window, nor an icon on
your dock. tcpflow is designed to work in the background.

3. To run the test for email, quit all other applications that might be
connecting to the internet like your browser, ftp client.

4. Copy/paste in this command in the Terminal or use the script ²tcpflow
activate² (see below):

sudo /usr/local/bin/tcpflow -i en0 -c

5. Now try to send an email and watch the traffic in the window of the
Terminal. You should see what is happening.

6. For an example see this page:


Script to activate tcpflow:

Download this script and place it in your User's Script folder.


Place the script here:

Users --> Library --> Script folder

If you activate the Script Menu in the Finder you can easily access the
script there. To activate the Script menu, go to your Applications folder in
the Finder. Select the AppleScript folder and open AppleScript Utility. ?
Show Script Menu in menu bar

Select the script to automatically start the Terminal with the correct
command. Enter your password and tcpflow will be activated. Next use
Entourage to send a test message.

Using the script makes it easy to use tcpflow for subsequent testing.

Diane, Microsoft Mac MVP
Entourage Help Page <>
Entourage Help Blog <>