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Any idea how I can set an alert to warn site owner if content is out of date?

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I would suggest the use of native policies (like in our case the expiration policy) that you can attach to a specific content type and trigger an action / workflow when the policy is met. In this case it will be when an item's age is reached. (eg :

What I've been doing for a customer is a custom field "review date" which allow them to pick a date when the content should be reviewed (because different type of content got different life time and even within the same content type it was not consistent) associated with a daily timer job that was looking for item reaching the dreaded date. As soon as found, it was sending an email to the content creator with a cc to the site collection administrator.

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You should first think on what actually is the 'Content' you want to set alerts.

If they are records in document library\ lists, You can set retention policy. First, Create a workflow for the list to send email to the site owner. Now, under information management policies, you can Enable Retention > Add a retention stage > Set date to expire>Under actions, select start workflow> Select workflow to send email alert.

If they are lists\sites, you can create a custom timer job to scan the content and send emails.

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