Re: [TLS] Breaking into TLS for enterprise "visibility" (don't do it)

Tony Arcieri <> Sat, 24 March 2018 15:32 UTC

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From: Tony Arcieri <>
Date: Sat, 24 Mar 2018 08:31:49 -0700
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To: Alex C <>
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Subject: Re: [TLS] Breaking into TLS for enterprise "visibility" (don't do it)
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On Fri, Mar 23, 2018 at 11:26 PM, Alex C <>; wrote:

> As I understand it (poorly!) the idea is exactly to have a single system
> on the network that monitors all traffic in cleartext.

And more specifically: to be able to *passively* intercept traffic and
allow it to be decrypted by a central system. "Visibility" with an active
MitM is a solved problem: have the MitM appliance double as an on-the-fly
CA and install its root certificate in the trust stores of all the clients
you intend to MitM.

It's fundamentally impossible to prevent someone from copying all their
> traffic to another system in cleartext. If they're going to do it, they
> will.
> The functionality is exactly the same as what could be achieved by
> installing monitoring software on each endpoint, but the logistics are
> different since the monitoring is centralized.

The response from "visibility" proponents is "endpoint agents are hard".
However, it seems like there is a simple solution to this problem which
should be compatible with their existing monitoring architectures and
require no changes to TLS:

Instrument TLS servers and/or client libraries used by internal enterprise
applications with a little shim that extracts the session master secret,
then makes another TLS connection to a TLS session key escrow service, and
goes "here's the session master secret for a session between X.X.X.X and
Y.Y.Y.Y with nonce ZZZZ...". It could even be encrypted-at-rest to a
particular public key in advance (which could correspond to e.g. an
HSM-backed decryption key).

Enterprises could continue to passively collect TLS sessions in whatever
manner they already do, and decrypt traffic at will, it would just require
looking up the session key for a particular session in a key escrow
database rather than having a single key-to-the-kingdom.

This approach requires no changes to TLS, no changes to how "visibility"
systems collect traffic, and should provide better security in that using
session master secrets better scope the authority conferred to the
decryption service than D-H keys which can grant authority to e.g. resume
TLS sessions.

The downsides are you have to instrument clients and/or servers and have
the decryption service maintain a key escrow database.

However, "visibility" proponents seem unwilling to accept any changes to
anything they presently do today. This is coupled with a sort of artificial
emergency where they claim (or outright lie) that compliance with industry
standards will require them to ship TLS 1.3 everywhere tomorrow. There is a
total unwillingness to compromise, and all sorts of weasel words being
thrown around, from the "visibility" euphemism itself to claims that TLS
1.3 will make them less secure because it makes implementing a
single-point-of-compromise for all their encrypted traffic more difficult.

The reality is for these slow-to-change enterprises, the industry standards
are also slow-to-change. There is no emergency. Many of them are still
using TLS 1.0. The PCI-DSS deadline to adopt TLS 1.1 isn't until this June.
I would challenge any "visibility" proponent to cite *any* industry
standard which will mandate TLS 1.3 any time in the next 5 years.

There is lots of time to solve this problem and better ways to solve it
than introducing codepaths which deliberately break the security of the

Tony Arcieri