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How can I access my Outlook Live account using Windows Live Mail in a network using a proxy server (ISA Server)?

 
xentrius
Top 500 Contributor
5 Posts
02/01/10 07:50 PM

I am using Windows Live Mail to access multiple emails. Our Internet connection passes thru Microsoft ISA Server. When I access Live Hotmail it displays my mails. But when I access my Outlook Live account (thru proxy), an error message displays "The connection to the server has failed." with the following details:

Your IMAP command could not be sent to the server, due to non-network errors. This could, for example, indicate a lack of memory on your system.

Configuration:
   Account: *********
   Server: outlook.com
   User name: ************** 
   Protocol: IMAP
   Port: 993
   Secure(SSL): 1
   Code: 800ccc0e

When I try connecting using a PC directly connected to the Internet, it works well. So I'm hypothesizing passing thru a proxy is the problem. Is there a configuration I can do to access my account thru proxy?

xentrius
Top 500 Contributor
5 Posts
08/03/10 09:12 PM

Solution:

 

Because Windows Live Mail does not support TLS on a different port other than TCP port 25:

 

On Proxy Server

  • SMTP proxy must use client port 25 pointing to SMTP Server pod51xxx.outlook.com port 25 (where xxx is the corresponding server assigned to you)
  • IMAP tunnel set to port 993 pointing to IMAP server pod51xxx.outlook.com port 993

On Windows Live Mail

Servers Tab:

  • Set incoming mail server as IMAP
  • Incoming mail (IMAP) and Outgoing mail (SMTP) = set to your proxy server dns or IP address

Advanced Tab:

Server Port Numbers

  • Check This server requires... for both SMTP and IMAP
  • Outgoing mail (SMTP) = 25
  • Incoming mail (IMAP) = 993

Click OK!

In a nutshell: Ignore the TLS setting and Port 587 that you get from the informational display at outlook.com. Tick the box for the SMTP server to use SSL (instead of TLS) and use Port 25 instead of Port 587 for the SMTP server. 

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verified by xentrius

All Replies

02/01/10 08:42 PM

On the ISA servers have you created a Firewall rule IMAP to the destination servers ?

Jon Bradley - MSFT
Outlook Live Answers ... your site for Outlook Live community support!

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suggested by Jon Bradley MSFT
xentrius
Top 500 Contributor
5 Posts
02/08/10 11:44 PM

No, not yet. How can I create a firewall rule IMAP to the destination servers? We are using ISA Server 2006 in a Windows 2003 Enterprise environment.

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03/30/10 03:28 AM

Where  can find the ports& hosts  needs to be opened in cisco firewall for for SMTP and POP3 for our server pod51002.outlook.com

Thanks

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03/30/10 03:28 AM

Where  can find the ports& hosts  needs to be opened in cisco firewall for for SMTP and POP3 for our server pod51002.outlook.com?

 

Thanks

Reply
03/30/10 08:16 AM

Youn should open the following ports

IMAP4=993/TCP (SSL)


SMTP clients to Hub Transport server (for example, end-users using Windows Live Mail)=587 (SMTP)

http://technet.microsoft.com/en-us/library/bb331973.aspx

Jon Bradley - MSFT
Outlook Live Answers ... your site for Outlook Live community support!

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xentrius
Top 500 Contributor
5 Posts
05/12/10 10:08 PM

I did as told but still cannot access my  account using WIndows Live Mail. Any other solution?

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05/12/10 10:25 PM

Hi to test that your isa rules are working correctly ran this test:

Open a command prompt

type "telnet [name of the server in outlook.com] 993" without quotes

if the test succeded imap is open for testing smtp

type "telnet [name of the server in outlook.com] 587" without quotes

if these tests are sucessful you can connect through windows live mail

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xentrius
Top 500 Contributor
5 Posts
05/13/10 06:02 AM
I telnet'd on a live server, it works. I telnet'd in a PC within the network which connects to the Internet via proxy server and it didn't work. =(
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05/14/10 11:22 PM

Then you need to create the rules on the firewall for this ports if the isa server is only acting like a proxy with a single interface i dont think it works

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xentrius
Top 500 Contributor
5 Posts
08/03/10 09:12 PM

Solution:

 

Because Windows Live Mail does not support TLS on a different port other than TCP port 25:

 

On Proxy Server

  • SMTP proxy must use client port 25 pointing to SMTP Server pod51xxx.outlook.com port 25 (where xxx is the corresponding server assigned to you)
  • IMAP tunnel set to port 993 pointing to IMAP server pod51xxx.outlook.com port 993

On Windows Live Mail

Servers Tab:

  • Set incoming mail server as IMAP
  • Incoming mail (IMAP) and Outgoing mail (SMTP) = set to your proxy server dns or IP address

Advanced Tab:

Server Port Numbers

  • Check This server requires... for both SMTP and IMAP
  • Outgoing mail (SMTP) = 25
  • Incoming mail (IMAP) = 993

Click OK!

In a nutshell: Ignore the TLS setting and Port 587 that you get from the informational display at outlook.com. Tick the box for the SMTP server to use SSL (instead of TLS) and use Port 25 instead of Port 587 for the SMTP server. 

Reply
verified by xentrius

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