Azure bug verified with the following script: ----------------------------------- import logging import os from pycloudlib.azure.cloud import Azure api = Azure( tag="test-azure", client_id=os.getenv("UACLIENT_BEHAVE_AZ_CLIENT_ID"), client_secret=os.getenv("UACLIENT_BEHAVE_AZ_CLIENT_SECRET"), tenant_id=os.getenv("UACLIENT_BEHAVE_AZ_TENANT_ID"), subscription_id=os.getenv("UACLIENT_BEHAVE_AZ_SUBSCRIPTION_ID") ) image_id = "Canonical:0001-com-ubuntu-pro-focal:pro-20_04-lts" # Focal pro image key_name = "test-key" private_key_path = "azure-priv-{}.pem".format(key_name) pub_key_path = "azure-pub-{}.txt".format(key_name) pub_key, priv_key = api.create_key_pair( key_name=key_name ) with open(pub_key_path, "w") as stream: stream.write(pub_key) with open(private_key_path, "w") as stream: stream.write(priv_key) os.chmod(pub_key_path, 0o600) os.chmod(private_key_path, 0o600) api.use_key(pub_key_path, private_key_path, key_name) instance = api.launch(image_id) print("--- Creating base instance") print(instance.execute("lsb_release -a")) instance.execute("sh -c 'sudo apt-get update > /dev/null'") instance.execute("sh -c 'sudo apt-get install ubuntu-advantage-tools > /dev/null'") print(instance.execute("ua version")) print(instance.execute("sudo ua enable fips --assume-yes")) print("------------------") print("--- Updating ua package") cmd = "sudo sh -c \"echo 'deb http://archive.ubuntu.com/ubuntu/ {}-proposed restricted main multiverse universe' >> /etc/apt/sources.list.d/proposed-repositories.list\"" instance.execute(cmd.format("focal")) instance.execute("sh -c 'sudo apt-get update > /dev/null'") instance.execute("sh -c 'sudo apt-get install ubuntu-advantage-tools > /dev/null'") print(instance.execute("ua version")) print(instance.execute("sudo ua enable fips --assume-yes")) print("------------------") instance.delete() ------------------------------------- Test output: --- Creating base instance Distributor ID: Ubuntu Description: Ubuntu 20.04.3 LTS Release: 20.04 Codename: focal 27.2.2~20.04.1 One moment, checking your subscription first Updating package lists Installing FIPS packages Updating package lists Could not enable FIPS. ------------------ --- Updating ua package 27.3~20.04.1 One moment, checking your subscription first Ubuntu Focal does not provide an Azure optimized FIPS kernel For help see: https://ubuntu.com/advantage. ------------------