Originally Posted by
rsteinmetz70112
I think he is talking about an individual tool like a script that would automate it for a single individual, not a website.
Whether it is a website is immaterial. OP is accessing Southwest's website, acting as a third party, for the purpose of online check-in. To me that is exactly what they are prohibiting.
And yes, as OP points out it's not technically illegal. However I don't know that I'd risk my RR points balance over finding out whether Southwest will allow it to go on. (Not to mention giving a stranger access to the information they would need to cancel my reservation).