Is there anyway for a schedule to evaluate items in a list so that the scheduled workflow will only run on those items which evaluate to 'true'? For example, I'd want a workflow to run nightly, but only on list items when--generically speaking--checkbox Y in the list item=Yes and checkbox X in the list item=No. Is this possible
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Yes it is possible.
I would create a site workflow. Schedule it to run each night.
In that site workflow I would query the list for items matching your criteria.
Then you got a collection of item ID’s do a for each on them starting the list
workflow on them.