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I have a workflow that checks the "Status" field. Certain Statuses will cause it to stop otherwise it will Pause Until a "Required Date". If that date is in the past and a workflow is started it stays paused, will it at some point complete, or should I find another way to deal with required dates being in the past because the item is overdue? Thank you for any help/suggestions with this.

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What you're looking for is a DelayActivity. Depending on how often you want to check the past date you set the interval. Drag the delayActivity from your toolbox (Assuming you are designing in Visual Studio), and create a new event for Initialization.

    private void delayActivity1_InitializeTimeoutDuration(object sender, EventArgs e)
    {
        DelayActivity activity = (DelayActivity)sender;
        activity.TimeoutDuration = new TimeSpan(0, 15, 0);
    }

This link may be helpful and shows how to set the duration through a config file or property http://jasonagraham.wordpress.com/2013/06/19/making-a-sharepoint-workflow-delay-activity-configurable/

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In my experience, if you tell the workflow to pause until a date in the past, the workflow continues on without any intervention required.

If that is not working for you, then you could alter the workflow to check if the calculated date is less than the current date. If it is you continue on, otherwise you pause until that date.

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