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Dear TheInnovator,
I create a new simple workflow and can't reproduce the issue in our environment.
Could you share the screenshots showing the workflow and the task list with the columns here for our reference?
Note: Remove any private information before uploading the screenshots.
After you change the workflow trigger as manual, can the workflow be ran successfully in your environment?
As the workflow is being replaced with Power Automate, may I know whether you have Power Automate in your environment? If yes, I suggest you create the flow instead of the workflow to get rid of re-creating the workflow with the same process for the future data migration.
SharePoint 2010 workflow retirement - Microsoft Support
Thank you for your effort and time!
Sincerely
Cliff | Microsoft Community Moderator