Is Social Security an entitlement? It is under the first connotation of the word, but this gets conflated with another connotation of the word.

There are two connotations to the word entitlement. One is that it is something you are entitled to that you paid into and / or has been promised to you. The other is the attitude of "entitlement," like the concept of being spoiled. The two are different. The two connotations get conflated in discussion.