The Squared Away hat's description is (without clicking on it):
Post 4 answers on 4 separate sites during Winter Bash
Which is unclear for many users, I came across 3 users asking in chat that why they didn't receive the hat, and we looked into their profile and realized that they think it's for 1 answer per site.
I had the same thought in the beginning as well. Could we rephrase it as something along the lines of:
Post 4 answers per site on 4 separate sites during Winter Bash
Or using "each":
Post 4 answers on 4 separate sites each during Winter Bash
Or, maybe rephrase it as something even more clear.