Hi @Anonymous User
Assuming you have signed in on your Mac with the correct NOW account you purchased the Entertainment Pass on, then it should work.
I don't use a PC or Mac but on devices like a fire stick for example when you first download the NOW App and open it up for the first time you are presented with a QR scan code to create an account and purchase a TV Membership and with a fire stick you just close the buy Membership offer and you can then navigate down to the My Account tile box to sign in with your existing NOW account login details.
I believe it's different with a PC or Mac (never used either watching NOW) and once you are signed in on the website with your correct login details then normally you are good to go to watch something with your TV Membership once the NOW Player has already been downloaded.
I am assuming you are not using a VPN or took your Mac if it's a laptop version on holidays recently ?
Also what happens if you temporary try watching on the NOW App on your smartphone for example and then see if it's added to your Continue Watching section on your Mac and if it does click on the Continue Watching to see if it plays on the Mac.
