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Opportunities are time sensitive (The opportunity is for an advertisement that will run on April 1st) I need a workflow that will change the Opportunity to "closed - Lost" 5 days after the Opportunity "Close Date". I also need to build a report that shows all Opportunities closed by this workflow.

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Use a time-based workflow. The criteria can be something like:

Stage Name not equal to Closed - Won

Add a time-based field update set to 5 days after Close Date.

If you want to be able to identify records that were closed by this process automatically, you'll want a custom field to track this, because workflow updates and manual user edits are indistinguishable otherwise.

I'd add a checkbox with a name similar to "Automatically Expired", and have the workflow field update trigger from the same workflow rule as above.

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