My understanding is that you must purchase an item* to get the prompt - it's not an option you enable/disable in Settings. Canada is on the supported list of content in the cloud for iTunes purchases. (Movies / TV Shows / Music.)
*...including movies, individual TV show episodes, TV Season Passes, and completed seasons.
MacBook Pro (15-inch, Mid 2012) 2.3 GHz Core i7, 16GB, 256GB M4 SSD
iPhone 8 - 64GB S/G • Sound System Audio Engine A2 • Display UltraSharp U2412M 24"
Custom Built Gaming PC Kaby Lake Edition | 16GB DDR4 | GTX 1070 8G