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This is a new install that has had update rollup 15 applied on the client side as well as the server side. &nbsp;<br />
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Environment is Windows Web Server 2008 R2 with SQL Server R2 2008. &nbsp;All updates have been applied thus far. &nbsp;<br />
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Client configuration is Windows 7 Ultimate Sp1 64bit , with Outlook 2010 32bit. &nbsp;<br />
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I have been able to auto authenticate and access the CRM site via IE 8 without any trouble in the domain login, via <a href="http://crm.mycompany.com:5555" rel="ugc">http://crm.mycompany.com:5555</a><br />
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When entering this same address into the configuration wizard, it appears to start configuration but then displays the following error Http Error 404: Not Found. &nbsp;<br />
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This is a new install that has had update rollup 15 applied on the client side as well as the server side.  

Environment is Windows Web Server 2008 R2 with SQL Server R2 2008.  All updates have been applied thus far.  

Client configuration is Windows 7 Ultimate Sp1 64bit , with Outlook 2010 32bit.  

I have been able to auto authenticate and access the CRM site via IE 8 without any trouble in the domain login, via http://crm.mycompany.com:5555

When entering this same address into the configuration wizard, it appears to start configuration but then displays the following error Http Error 404: Not Found.  
  

Microsoft Dynamics CRM 4.0 Outlook client - when configuring the Configuration Wizard it fails with Http Error 404: Not Found

Microsoft Dynamics is a line of enterprise resource planning (ERP) and customer relationship management (CRM) software applications. Dynamics can be used with other Microsoft solutions, such as SharePoint, Yammer, Office 365, Azure and Outlook. Dynamics ERP comprises a group of enterprise-resource-planning products includes Dynamics AX (formerly Axapta), a multi-language, multi-currency enterprise software with business management features for financial, human resources, and operations management; Dynamics GP (formerly Great Plains Software); Dynamics NAV (formerly Navision) for financials, supply chain, and people; Dynamics SL (formerly Solomon IV)for project-driven organizations; Dynamics C5 (formerly Concorde C5) for manufacturing, supply chains, analytics and electronic commerce; and Dynamics CRM.

Microsoft Dynamics

Microsoft Outlook is a personal information manager from Microsoft, available as a part of the Microsoft Office suite. Although often used mainly as an email application, it also includes a calendar, task manager, contact manager, note-taker, journal, and web browser.

Outlook

IIS is Internet Information Services, the web server included with Windows Server operating systems. All current versions are built on a modular architecture; modules can be added or removed individually so that those required for specific functionality are installed. The full installation of IIS includes HTTP, security, content, compression, caching, logging and diagnostics.