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RPC over HTTPS with NTLM in pretty weird setup

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Hi,

We are migrating to Exchange from another Exchange-like product, and I still struggle with NTLM authentication for the remote users with Outlook (RCP over HTTPS).

The setup is:
- Firewall with Squid 2.6.18-1ubuntu3 (manually compiled to enable SSL)
- Exchange in the LAN
- Exchange-like product on the firewall, using Apache2 (still in production)

I found some examples on the net to proxy certain URL's to the local Apache and all other to Exchange.

For laptops, this setup works when I use Basic authentication, but that creates annoying password prompts when the laptop user is in the LAN.

Squid.conf:
	visible_hostname mail.company.com
	persistent_connection_after_error on
	
	###############################################################################
	# Exchange 2010
	# extensions for Exchange RPC over HTTPS
	extension_methods RPC_IN_DATA RPC_OUT_DATA
	
	# We listen on 195.xxx.xxx.xxx, our primary line
	# mail.company.com.crt is an official certificate
	https_port 195.xxx.xxx.xxx:443 cert=/etc/ssl/keys/mail.company.com.crt key=/etc/ssl/keys/mail.company.com.pem defaultsite=mail.company.com
	# We also listen on 212.xxx.xxx.xxx, a 2nd line for testing ActiveSync on Exchange
	# 212.xxx.xxx.xxx.crt is a self generated certificate
	https_port 212.xxx.xxx.xxx:443 cert=/etc/ssl/keys/212.xxx.xxx.xxx.crt key=/etc/ssl/keys/212.xxx.xxx.xxx.pem defaultsite=212.xxx.xxx.xxx
	
	# localhost has Apache running, 192.168.xxx.xxx is the Exchange Server
	cache_peer 127.0.0.1 parent 443 0 proxy-only no-query no-digest originserver login=PASS ssl sslflags=DONT_VERIFY_PEER sslcert=/etc/ssl/keys/mail.company.com.pem 	sslkey=/etc/ssl/keys/mail.company.com.pem name=webServer
	cache_peer 192.168.xxx.xxx parent 443 0 proxy-only no-query no-digest originserver front-end-https=on ssl login=PASS sslflags=DONT_VERIFY_PEER name=exchangeServer
	
	# Send the ActiveSync on the main line to the local Apache for the Exchange-like product, which is still in use
	acl web_url url_regex -i mail.company.com/Microsoft-Server-ActiveSync
	
	# Send the webserver URLs to the webserver
	cache_peer_access webServer allow web_url
	# Send everything else to the Exchange server
	cache_peer_access exchangeServer deny web_url

	# This is to protect ourselves
	never_direct allow web_url
	
	# settings caching and logging
	redirect_rewrites_host_header off
	cache_mem 32 MB
	maximum_object_size_in_memory 128 KB
	cache_log none
	cache_store_log none
	
	debug_options ALL, 8
	access_log /var/log/squid/access.log squid
	
	###############################################################################
	# ACL - required to allow
	acl all src 0.0.0.0/0.0.0.0
	
	http_access allow all
	miss_access allow all
	
So far this setup works for ActiveSync via the 2nd line.
Outlook Anywhere (RPC over HTTPS) only gives me this is access.log:
	1265109372.999     23 10.11.11.149 TCP_MISS/401 430 RPC_IN_DATA https://mail.company.com/rpc/rpcproxy.dll? - FIRST_UP_PARENT/exchangeServer text/html
	1265109372.999     20 10.11.11.149 TCP_MISS/401 430 RPC_OUT_DATA https://mail.company.com/rpc/rpcproxy.dll? - FIRST_UP_PARENT/exchangeServer text/html

Any thoughts on this setup?
How to fix NTLM auth for laptop users?

Thanks,

Toni Van Remortel


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