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I have traveled with my service dog several times so that is not a problem. This year though I may also be traveling with a puppy as well (I understand he must be in a carrier, there is a fee and he has to have his shots) Am I going to have a hard time with this? Is there anything extra I have to do? Has anyone else done this before?
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I don't have any personal experience with this, but based on reading the policies it sounds like you have a good understanding of the requirements. Just make sure the carrier is an acceptable size and call to pay the pet fee. There's nothing that specifically prohibits what you want to do.
Here's the full policy, which it does appear you've already read. https://www.southwest.com/html/customer-service/traveling-with-animals/pets/index-pol.html
--TheMiddleSeat