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Apple have updated their requirements for certificates for their new operating system releases:  https://support.apple.com/en-us/HT210176

One of the The new requirements - the can be broken down in the 3 major sections:

  1. The mandatory presence of a Subject Alternative Name

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  1. Presence of an OID (1.3.6.1.5.5.7.3.1) designating the use of the certificate for TLS Web Server Authentication

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  1. Maximum validity period of 825 days

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Requirement 1 is confirmed to render MDM clients unable to connect to the MDM server when not being met. 

Requirements 2 and 3 are not currently ( as of 24th of September 2019 ) interfering with MDM function when not being met. These two new requirements are not met by newly generated self-signed certificates as of FileWave Server 13.1.3 - so renewing your self-signed certificate will not mitigate this issue permanently. FileWave Server will be updated in a future release to accommodate these new guidelines in order to comply with self-signed certificates. 

If you are using a self-signed certificate on a production server with a publicly resolvable host name , we recommend you purchase a valid 3rdparty certificate that has been signed by a trusted root CA

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