Sending S/MIME encrypted messages with Outlook for iOS is not possible: "There's a problem with one of your S/MIME encryption certificates."

Assume the following scenario:

There's a problem with one of your S/MIME encryption certificates. Contact your IT help desk for more info.
Es gibt ein Problem mit einem ihrer S/MIME-Verschlüsselungszertifikate. Wenden Sie sich für weitere Informationen an Ihren IT-Helpdesk.

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Basics: Name Constraints

Name constraints are part of the X.509 standard and are described in RFC 5280 . They are a tool that can be used as part of qualified subordination to control the scope of a certification authority certificate in a fine-grained manner.

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S/MIME with the Outlook app for Apple iOS and Android only possible with devices managed via Intune

If you want to make S/MIME certificates available to your users on the smartphone as well, you may be surprised to discover that this is not possible with the Outlook app unless you also use Microsoft Intune as a management solution for the devices.

Microsoft has now clarified in the article "Sensitivity labeling and protection in Outlook for iOS and Android " that this is due to the respective system architecture.

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Chrome and Safari limit SSL certificates to one year validity

Apple recently announced that the Safari browser will in future only accept certificates with a validity of 398 days, provided they were issued on or after September 1, 2020.

Mozilla and Google want to implement comparable behavior in their browsers. So the question is whether this change will have an impact on internal certification authorities - i.e. whether in future internal SSL certificates will also have to follow these rules, as was the case, for example, with Google's enforcement of RFC 2818 .

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