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RE: CRM 2011 - Outlook Client cannot connect

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I would recommend reviewing the Claims based authentication whitepaper. A few things I see here are NTLM must be enabled, you are using an HTTP port 55555 and if you have HTTPS configured, you need to be using an HTTPS port such as 443. Also, it is recommended to use a separate internal and external URL as an endpoint instead of the servername:port format

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