The language is unclear but in all practical sense, the CSR $300 travel credit is a card benefit Starting at the moment you own the card - much like the AMEX cards' airline benefits, EXCEPT you dont have to enroll on anything, it is automatic. You do need to enroll the PP benefit either online or calling Chase.

What you are seeing, may be a poor wording of the eligibility period, which has changed from basing on Calendar Year to Membership Year 2+ years ago. That just means, when CSR was first introduced, you can claim the travel credit twice in a single membership year and later cancel the card. There were lots of examples on people taking advantage (or abuse) this feature, either by outright cancel or by downgrade, and still got 2x Travel Credits. Of course Chase noticed such, hence this "loophole" has been eliminated 2+ years ago for those who applied the card after the change put in effect.

Besides, when you really think through this, ALL expensive AF cards have something to offset the AF in their FIRST year ownership immediately started from the date the card is approved. Chase cannot be different else nobody would get the card. This is just a layman's common sense but a common sense that actually makes some sense. Punt intended.

When you actually have the card, go to UR portal thru that card, the first thing you see, in very BIG display too, is a counter of the $300 travel credit, showing you how much you have to use as of this moment.

When an eligible travel expense is posted, the credit also posted at the same time, $ for $ until the $300 is used up. So if the credit has $55 left and your next travel expense is $70, the credit would be at $55 only.

The ONLY change Chase has done aside from changing the eligibility from Calendar year to Membership year back 2 years ago, is to no longer allow point earning on the $300 travel expenses that are completely offset by the $300 Travel Credit.

Slightly off topic - everyone should have known by now, Chase closely monitor the ecosystem of Sapphire cards - it announced the first restriction on how many Sapphire card one can own thru new application, (min 24 months past) right before people were getting ready to X CSR and go with CSP sign up bonus. It then announced the 48 months restriction right before CSR's 24 months life was up... Shouldn't such moves tell us that Chase really closely monitor CSR ownership?

Now we are seeing the rumors on Chase testing the water on raising the fee, and adding some crappy benefits... It remains to be seen how that would fair with the cardholders. At a Net $250 AF, this card is NOT worth it in many people's books, ours incl. My bet is the attrition rate that Chase brags about will go thru the roof and for the first time, there will be retention offers for CSR.