If possible I would remove passcodes from the device, then try again. Also check you cert is valid https://documentation.meraki.com/SM/Device_Enrollment/Apple_MDM_Push_Certificate Then I would start by verifying there is no blocking of the iOS updates https://documentation.meraki.com/zGeneral_Administration/Other_Topics/Blocking_or_Rate_Limiting_iOS_Updates Then review this doc, and try the per Client basis option https://documentation.meraki.com/SM/Apps_and_Software/Deploying_OS_Updates_with_Systems_Manager Some good info on troubleshooting iOS devices with SM https://documentation.meraki.com/SM/Other_Topics/Systems_Manager_Logging_and_Troubleshooting Then I would try doing a packet capture went you are sending the update command https://documentation.meraki.com/zGeneral_Administration/Other_Topics/Packet_Captures_on_Mobile_Devices
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