Apple iOS - Uwe Gradenegger

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:

The certificates were transferred to the smartphone via the Intune Connector.
Reading encrypted messages works.
However, when enabling encryption for outgoing messages, the following error message is displayed:

There's a problem with one of your S/MIME encryption certificates. Contact your IT help desk for more info.

There is a problem with one of your S/MIME encryption certificates. Contact your IT help desk for more information.

Basics: Name Constraints

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

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

Chrome and Safari limit SSL certificates to one year validity

Apple recently announced that the Safari browser will only accept certificates with a validity of 398 days in the future, provided they were issued from 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 certificate authorities - i.e. whether in future internal SSL certificates will also have to follow these rules, as is the case, for example, with the enforcement of the RFC 2818 by Google was the case.

Configuring a Secure Socket Layer (SSL) Certificate Template for Web Server

Below is a guide to configuring a web server template with recommended settings.