Outlook anywhere prompting for password

By ron ·
I have Exchange 2003 running on a small business server with Outlook 2007 clients. 6 existing users can successfully connect using outlook anywhere ussing http with basic authentication. I added 2 new users, connected to Exchange connected to the LAN, enered the same connection info as existing users. The problem is the when the 2 new users are out of the office, Outlook will not accept their username/password to connect to exchange.
This has me stumped, any ideas?

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Are they using VPN to sign in?.

Please post back if you have any more problems or questions.

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Outlook anywhere prompting for password

by ron In reply to Are they using VPN to sig ...

No, they are using http over rpc found in "Outlook Anywhere"

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Re-check with this info....

This feature requires you to use a Microsoft Exchange Server 2003 or Exchange Server 2007 account. Most home and personal accounts do not use Microsoft Exchange. For more information about Microsoft Exchange accounts and how to determine which version of Exchange your account connects to, see the links in the See Also section.

In a local area network (LAN) (LAN: A computer network technology designed to connect computers separated by a short distance. A local area network (LAN) can be connected to the Internet and can also be configured as an intranet.) environment, communicates with Exchange by using remote procedure call (RPC) (remote procedure call (RPC): In programming, a request by one program to a second program on a remote system. The second program generally performs a task and returns the results of that task to the first program.) with Transmission Control Protocol/Internet Protocol (TCP/IP). This method provides quick and efficient access in a corporate network. However, access to Exchange when you are outside of your organization's firewall, such as when you are at home or traveling, usually requires a virtual private network (VPN) (virtual private network (VPN): Extension of a private network encompassing encapsulated, encrypted, and authenticated links across shared or public networks. VPN connections provide remote access and connections to private networks over the Internet.) connection to the organization's network. A VPN provides you with a connection within an organization's network and within its firewall. A VPN also enables access to more network services than those required for just e-mail access.
For remote connections, Outlook offers Outlook Anywhere, an alternative to VPN connections that allows you to use Outlook just as you normally do at your organization, without the need for any special connections or hardware, such as smart cards and security tokens. Outlook can connect to Exchange through the Internet by using remote procedure call (RPC) over HTTP. The Outlook Anywhere feature allows you to access your Exchange account remotely from the Internet when you are working outside your organization's firewall.
System requirements

There are several minimum requirements for using Outlook Anywhere. If your computer and Exchange do not meet all requirements for this feature, these options will not be available. The requirements include:

* Your computer must have Microsoft Windows XP Service Pack 2 or a later service pack.
* Your account be hosted on Microsoft Exchange Server 2003 or Microsoft Exchange Server 2007 running on Microsoft Windows Server 2003.
* Your Exchange administrator must configure the server to permit connections via HTTP. For more information about configuring this feature, see the Microsoft Office Resource Kit and the Microsoft Exchange documentation.

Enable Outlook Anywhere in Outlook

Your Exchange administrator can automatically configure all copies of Outlook in your organization or provide a special executable script file that enables Outlook Anywhere. You can also manually configure Outlook Anywhere if the system requirements are met and you have the correct URL and security information from your Exchange administrator.

1. On the Tools menu, click Account Settings, select the Exchange account, and then click Change.
2. Click More Settings, and then click the Connection tab.
3. Under Outlook Anywhere, select the Connect to Microsoft Exchange using HTTP check box.

Note If the Outlook Anywhere section is not available, your computer is probably not running Windows XP Service Pack 2 or a later service pack.
# To specify a proxy server, click Exchange Proxy Settings.
Callout 1 Type the URL provided by your Exchange administrator.
Callout 2 If your Exchange administrator tells you to use a Secure Sockets Layer (SSL) connection, select the Connect using SSL only check box.
Callout 3 If your Exchange administrator instructs you to do so, select the Only connect to proxy servers that have this principal name in their certificate check box, and then type msstd: followed by the URL provided by the administrator.
# Under Proxy authentication settings, click Basic Authentication or NTLM Authentication as instructed by your Exchange administrator.
Note If you click Basic Authentication or NTLM Authentication and an LM Compatibility Level of less than 2, you will be prompted for a password each time a connection is made to Exchange. With Basic Authentication, the password is sent in clear text. For increased security, we recommend that you select the NTLM Authentication and Connect using SSL only options.

Please post back if you have any more problems or questions.
If this info is useful, please mark it helpful. Thanks

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TCP Protocol Connection Limit

TCP Protocol Connection Limit

The TCP protocol has a requirement that each connection have a unique ordered list, also known as an n-tuple, which consists of source address, source port, destination address, and destination port. All incoming connections use the same destination address or port, so the number of incoming connections is limited by the non-paged pool size. Each outgoing connection consumes a port on an address. The TCP port is a 16-bit number, so there are at most 65,535 ports.

The change to 64-bit hardware in Exchange 2007 exposed this scalability limit. In Exchange 2003, the memory constraints in 32-bit hardware hide this limit and because of those memory constraints, memory availability would be exhausted before the TCP connection limit could be reached. Now, with 64-bit hardware and an almost endless amount of memory, Exchange is no longer limited in this area and can therefore hit the TCP connection limitation. Usually, this affects enterprise customers who are running at very high scale and who are trying to maximize as much scale-up from their hardware as possible.

Please post back if you have any more problems or questions.
If this info is useful, please mark it helpful. Thanks

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What finally worked for me

by Cymon In reply to Outlook anywhere promptin ...

I had this same problem as well as the exact same configurations--including current OA users working just fine. Seems to be an extremely rare problem, so I was very disapointed when the private message link led to err 404!
But I finally solved it and perhaps someone reading this will save a day's work...

Basically, DON'T assume as I did that your server configuration is all correct. In my case, I had to follow the instructions at (part of the checklist at which I started going through) and after that it worked instantly. It seems this problem may have something to do with installing a service pack over a working setup.

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