Yes:
Apple canceled their plans to fully encrypt iCloud data after the FBI complained:
https://www.reuters.com/article/us-apple-fbi-icloud-exclusiv...
In the Vault 7 leaks, Little Snitch was something specifically mentioned as being difficult to circumvent. Now, the ability to bypass it is baked into the OS:
https://blog.obdev.at/little-snitch-on-vault-7/
They moved iCloud keys to Chinese servers so the CCP could continue their surveillance:
https://www.reuters.com/article/us-china-apple-icloud-insigh...
During the protests in Hong Kong, Apple took down apps that let people crowdsource tracking of police:
https://www.nytimes.com/2019/10/09/technology/apple-hong-kon...