Which challenge may arise during the extended roll-out of SSL Inspection?

During the extended roll-out of SSL Inspection, one of the prominent challenges that can arise is related to issues with certificate pinning, developer environments, IoT environments, and services like Office 365.

Certificate pinning is a security mechanism that helps prevent man-in-the-middle attacks by hardcoding the expected certificate of a host within the application. When SSL Inspection is implemented, these pinned certificates may not match the certificates presented by the SSL Inspection service, which can lead to application failures.

Additionally, in developer and IoT environments, applications may not be designed to handle certificate alterations or the added complexity of middleboxes handling SSL/TLS traffic. This might create significant integration challenges as these services may not function properly when SSL Inspection is deployed, potentially causing disruptions in workflows and user experiences.

Moreover, specific services like Office 365 rely heavily on secure connections, and their integration with SSL Inspection can lead to interruptions or malfunction unless meticulously configured. Thus, the implications of certificate pinning and the unique requirements of diverse environments present substantial challenges during the extensive deployment of SSL Inspection.