You need to isolate the problem between IMAIL and Proxy config. 
 
Here is an "off-hours" suggestion.
 
Disable the proxy client on the IMAIL server (temporarily) using start-settings-control panel-WSP Client and uncheck "Enable Win Sock Proxy Client" though you will be prompted for a restart, do not do it.  Change the IP address of your server to that of the proxy server (real Proxy server should be disconnected from the network temporarily) place your IMAIL server on the cable that was connected to the proxy server.  Now let the IMAIL server reboot and when it comes back up you can test the scenario again.  If you still have a problem then we can drop the issue of the proxy server/client config, but if it does not occur again then we know that it is for sure the proxy server config and go on in that way. 
 
  To undo this test and get back to normal just read the paragraph above backwards!  :->
 
I have quite a great deal of experience with troubleshooting firewalls, and proxies and still have to do this sometimes to discover the true nature of a problem.  It is human nature to look for the problems where complexity is and sometimes we over look the "loose wire" so to speak.  Please let me know what you find.  I can maybe be of some more help to you with the proxy server stuff, but if it is an IMAIL problem than I have no idea what could be causing your issue and would not want to appear to hold out some hope for you only to lead you to a dead end.  Let me know what you find >>>
-V  
----- Original Message -----
Sent: Thursday, July 29, 1999 11:14 AM
Subject: [IMail Forum] Iwebmsg and Proxy-sever

I using Imail server with proxy-server, binding the local ports and remote ports for the services POP3, SMTP, IMAP4 and IWEBMSG.
When sending the message using SEND button with iwebmsg, the server accept this connection, but if I use FORWARD button the connection is rejected.
I note with SEND option the Imail server not use SMTPD32 service and Imail server use this service with FORWARD option, this if I use IE 4.0, with IE 3.2 or less, the IWEBMSG every use SMTPD32 service, and in this case I don�t connect.
Accessing IWEBMSG with external computer, connecting in external port of the proxy-server, this option is OK, with IE 4.0 or other.
Accessing Imail server with other client SMTP/POP3, like Outlook Express, this connection is OK (internal and external).
Do you help me ?
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Rodrigo Ot�vio Souza Salles
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