Hi Ophira,
Is the milestone a sub work item of the project? In regards to having this setting off, you would want this to be on if the milestone is a sub item of the project.
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Time reporting facility at milestone level for specific projects
If there a way to set a parameter at the project level to enable Time reporting facility at milestone level .
Even though in system settings the "Include leaf milestones and projects in time-sheets" is set to 'OFF'
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