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UserData scripts indeed allow you to perform automated configuration tasks or to run scripts after the instance starts. To troubleshoot missing execution of user data scripts on an EC2 Windows instance, you could reference this knowledge article.
In order to further confirm any challenges from the script itself, could you please also try using the same in a test instance with static values (outside of CloudFormation). Having said that, AWS CloudFormation by default does not have a timeout for stack creation.
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