The NSA has released a security advisory warning of the dangers of TLS inspection:

Transport Layer Security Inspection (TLSI), also known as TLS break and inspect, is a security process that allows enterprises to decrypt traffic, inspect the decrypted content for threats, and then re-encrypt the traffic before it enters or leaves the network. Introducing this capability into an enterprise enhances visibility within boundary security products, but introduces new risks. These risks, while not inconsequential, do have mitigations.

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The primary risk involved with TLSI’s embedded CA is the potential abuse of the CA to issue unauthorized certificates trusted by the TLS clients. Abuse of a trusted CA can allow an adversary to sign malicious code to bypass host IDS/IPSs or to deploy malicious services that impersonate legitimate enterprise services to the hosts.

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A further risk of introducing TLSI is that an adversary can focus their exploitation efforts on a single device where potential traffic of interest is decrypted, rather than try to exploit each location where the data is stored.Setting a policy to enforce that traffic is decrypted and inspected only as authorized, and ensuring that decrypted traffic is contained in an out-of-band, isolated segment of the network prevents unauthorized access to the decrypted traffic.

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To minimize the risks described above, breaking and inspecting TLS traffic should only be conducted once within the enterprise network. Redundant TLSI, wherein a client-server traffic flow is decrypted, inspected, and re-encrypted by one forward proxy and is then forwarded to a second forward proxy for more of the same,should not be performed.Inspecting multiple times can greatly complicate diagnosing network issues with TLS traffic. Also, multi-inspection further obscures certificates when trying to ascertain whether a server should be trusted. In this case, the “outermost” proxy makes the decisions on what server certificates or CAs should be trusted and is the only location where certificate pinning can be performed.Finally, a single TLSI implementation is sufficient for detecting encrypted traffic threats; additional TLSI will have access to the same traffic. If the first TLSI implementation detected a threat, killed the session, and dropped the traffic, then additional TLSI implementations would be rendered useless since they would not even receive the dropped traffic for further inspection. Redundant TLSI increases the risk surface, provides additional opportunities for adversaries to gain unauthorized access to decrypted traffic, and offers no additional benefits.