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I've created a list of "Weekly Activity" where each employee inputs information about what they've done throughout the week. One single item represents one employee's work for 1 week. I have 2 date fields "Date From" and "Date To" which represent the date range.

I'm currently working to make these two fields default to the current week's range when created. However, since it's expected for each employee to create their own item for every week, I was wondering if there's a way that these items can be automatically created for example every Monday Morning at midnight for each employee?

My assumption is that I would have to build some sort of Windows Service Application which connects to SharePoint and generates these on the schedule. However, before I go indulge in that deep of integration (huge subject), is there a way that I can schedule SharePoint to automatically generate a new list item for each user each week?

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Yes there is a way - it would be to create your own timer job, which must be a web application scoped feature. It would contain code to insert items into whatever list you would like. You can then schedule that job to whatever timing is necessary. Some sample timer job projects can be seen here:

http://www.codeproject.com/Tips/634208/Create-and-Deploy-Custom-Timer-Job-Definition-in-S

http://www.sharepointpals.com/post/Step-by-Step-procedures-to-create-a-Timer-Job-in-SharePoint-2013

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The "easiest" way to do this would be a simple PowerShell script which is set up on one of the SharePoint WFEs as a scheudled task in Windows. it can often be easier to get that deployed into a lot of corporate environments rather than cracking open Visual Studio and doing a timer job.

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