re: Credit Card Rewards and Points Discussion

Companion Pass is earned in the calendar year you acquire the necessary requirements.

So if you apply for Southwest cards in November 2018, you shouldn't hit your spending bonus Chase requirement ($2,000 usually) until January 2019 which causes the bonus points to hit your Southwest account in 2019. If you hit it early your points will post in 2018 and then your clock will reset and you'd need 110k points in 2019.

Once you earn the 110k points in the calendar 2019 year, you'll have CP from that point in 2019 through the remainder of the year and through the following year (2020). Hence why people try to to accomplish it as early in a year as possible to get two full years of the benefit.