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Our CRM 2011 on-premise setup is such that users create records offline (using Outlook CRM client) and then synchronize them to the server once they are online.

Is there column that timestamps when a particular record (e.g., a sales order) was synchronized to the server? I know I can look at the CreatedOn column, but I can't tell if that is the time when the record was created on the user's machine, or on the server?

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You should look at the ModifiedOn field. It will be set to the UTC time when the record was last modified. In the case of a newly created record, that has not been updated, ModifiedOn will equal CreatedOn. Those values are set by the server clock.

I don't recommend ever relying on the local system clock to match the server clock. Do a retrieve of the record from the server and compare the ModifiedOn to the locally stored record to determine if it has been updated.

You can also do a MAX(ModifiedOn) of local records and then query the server for all records with a ModifiedOn greater than the max.