To set the context, let's assume that the customer's Salesforce instance already has the below fields created:
AND ( OR(NOT(IsClosed), NOT(IsWon)), (TODAY() > Opportunity_Expiration_Date__c))
Here we are checking if the opportunity is not closed or won and if it has crossed the expiration date.
With the above fields created, let's now look at the approach to updating the "Urgent Opportunity" picklist from "No" to "Yes".
We will be using a Scheduled flow which would run on a daily basis to update the Opportunity picklist field from "No" to "Yes". The reason we go with scheduled flow is that it will help to query all opportunities that have crossed their expiration even if they did not get updated on that day. Hence, to cover this outlier situation, a scheduled flow is being considered.
The design of the Scheduled Flow is as below:
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