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Will my program & the ESHA Database work with SQL Server 2008?
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Yes, the ESHA software programs and Database will work with SQL Server 2008 (including R2).

There are related knowledgebase articles which should walk one through attaching the ESHA Database to an existing instance of SQL Server 2008:
In addition, you may also wish to refer to the article related to installing the Client version of the program.

There is a separate utility called Database Utility that can be installed from the ESHA CD.  Typically, this is not installed by those using their own instance of SQL Server—its purpose was to allow users to have basic maintenance and utility operations on the database (shrink, detach/attach, add users, etc).  The Database Utility does not perform any specific functions that cannot be done in traditional SQL Server tools (SQL Server Management Studio).  Should you have used Database Utility in the past, it will not connect to SQL Server 2008 R2.  That is our only application that will error if (when) you move to SQL Server 2008 R2.

Note -- this does not apply to SQL Server 2005 -- only SQL Server 2008.  The current version (including Database Utility) fully works with SQL Server 2005.

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