After downloading the Crackle app and setting up my account, I unlocked this by starting an episode of Comedians in Cars Getting Coffee through the Xbox One version of the app. There are other conditions that may be relevant here, and looking to the community to try narrowing down which ones are relevant:
- The actual show selected may or may not be a factor here. It worked for CiCGC, but may work with any show. Let me know if it pops for you with another program.
- This Achievement may or may not need to be unlocked on the Xbox One. Let me know if you get it to pop using the Xbox 360 version of the app.
If you follow my initial steps, and it doesn't pop, please leave information in the comments to that effect and we will continue to refine the requirements as needed.