The first is a bug, and is related to  Issue 840444 .

The second is not a bug, nor is the latter. That is, UpdateCTPolicy/SetCTPolicy are for Enterprise Policies tied to a specific profile, not for the general browser or apps. In the old code (that is, before https://chromium.googlesource.com/chromium/src/+/9e79cf0ca820c9c83af104df0555550e86ce0048 ), the CTPolicyManager was associated with the TransportSecurityState. Any contexts cloned from the main profile would inherit both the current settings and any future changes. If App Contexts were cloned from the Main Context, then this would propagate settings. I don't know how this works in the S13N world or if this is now handled differently.

In the new world, there is no concept of "cloning" a NetworkContext, so they aren't inherited by apps.  They were before.  I assume the old behavior is the desired one.

Marking this a dupe of  issue 840444  (If we want to hook it up to apps, easy enough to do in the same CL).

Actually, I should unmerge. 840444 is about the NetworkService configuration for CT, this would be about the NetworkContext configuration. I know there's OnNetworkServiceCreated, but what signals exist for a NetworkContext consumer to know to reconfigure a given context (e.g. the ProfileImpl?)

There isn't one...Which is why it should be with the code that creates and manages all settings for NetworkContexts (ProfileNetworkContextService).  All NetworkContext state management should go there or SystemNetworkContextManager.

I see. Doug and John did the design for this, I don't feel qualified to sort it out. Hopefully Eric or Matt may have time.

I can take a look at this.

The following revision refers to this bug:
  https://chromium.googlesource.com/chromium/src.git/+/39d0a6717bf35111459d43f40795d412f0d4a553

commit 39d0a6717bf35111459d43f40795d412f0d4a553
Author: John Abd-El-Malek <jam@chromium.org>
Date: Fri Sep 28 22:14:05 2018

Fix SetCTPolicy not getting called on network service restart.

Bug:  890104 
Change-Id: Id2f726cf4a2052080c1f984cb5844f1d084bf1b0
Reviewed-on: https://chromium-review.googlesource.com/1249732
Commit-Queue: John Abd-El-Malek <jam@chromium.org>
Reviewed-by: Matt Menke <mmenke@chromium.org>
Reviewed-by: Ryan Sleevi <rsleevi@chromium.org>
Cr-Commit-Position: refs/heads/master@{#595230}
[modify] https://crrev.com/39d0a6717bf35111459d43f40795d412f0d4a553/chrome/browser/net/profile_network_context_service.cc
[modify] https://crrev.com/39d0a6717bf35111459d43f40795d412f0d4a553/chrome/browser/net/profile_network_context_service.h
[modify] https://crrev.com/39d0a6717bf35111459d43f40795d412f0d4a553/chrome/browser/policy/policy_browsertest.cc
[modify] https://crrev.com/39d0a6717bf35111459d43f40795d412f0d4a553/chrome/browser/profiles/profile_impl.cc
[modify] https://crrev.com/39d0a6717bf35111459d43f40795d412f0d4a553/chrome/browser/profiles/profile_impl.h