We like to let all our moms know that TSA is very likely to do special inspections on the coolers - specifically the cooling units inside - since they don't see them every day and and may be curious. The cooling units use evaporation technology and don't contain any hazardous materials like dry ice - which is usually their main concern.
Be prepared and allow extra time for TSA inspection. Just know that you're not required to put your milk through the x-ray scanner - you do have the ability to opt out but it will mean that they'll take you aside for inspection.
A couple valuable resources are:
Milk Stork's Airport Security Guide
https://www.tsa.gov/travel/special-procedures/traveling-children
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