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diff --git a/doc/rtd/topics/boot.rst b/doc/rtd/topics/boot.rst
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+++ b/doc/rtd/topics/boot.rst
@@ -157,4 +157,90 @@ finished, the ``cloud-init status`` subcommand can help block external
scripts until cloud-init is done without having to write your own systemd
units dependency chains. See :ref:`cli_status` for more info.
+First Boot Determination
+************************
+
+cloud-init has to determine whether or not the current boot is the first boot
+of a new instance or not, so that it applies the appropriate configuration. On
+an instance's first boot, it should run all "per-instance" configuration,
+whereas on a subsequent boot it should run only "per-boot" configuration. This
+section describes how cloud-init performs this determination, as well as why it
+is necessary.
+
+When it runs, cloud-init stores a cache of its internal state for use across
+stages and boots.
+
+If this cache is present, then cloud-init has run on this system before.
+[#not-present]_ There are two cases where this could occur. Most commonly,
+the instance has been rebooted, and this is a second/subsequent boot.
+Alternatively, the filesystem has been attached to a *new* instance, and this
+is an instance's first boot. The most obvious case where this happens is when
+an instance is launched from an image captured from a launched instance.
+
+By default, cloud-init attempts to determine which case it is running in by
+checking the instance ID in the cache against the instance ID it determines at
+runtime. If they do not match, then this is an instance's first boot;
+otherwise, it's a subsequent boot. Internally, cloud-init refers to this
+behavior as ``check``.
+
+This behavior is required for images captured from launched instances to
+behave correctly, and so is the default which generic cloud images ship with.
+However, there are cases where it can cause problems. [#problems]_ For these
+cases, cloud-init has support for modifying its behavior to trust the instance
+ID that is present in the system unconditionally. This means that cloud-init
+will never detect a new instance when the cache is present, and it follows that
+the only way to cause cloud-init to detect a new instance (and therefore its
+first boot) is to manually remove cloud-init's cache. Internally, this
+behavior is referred to as ``trust``.
+
+To configure which of these behaviors to use, cloud-init exposes the
+``manual_cache_clean`` configuration option. When ``false`` (the default),
+cloud-init will ``check`` and clean the cache if the instance IDs do not match
+(this is the default, as discussed above). When ``true``, cloud-init will
+``trust`` the existing cache (and therefore not clean it).
+
+Manual Cache Cleaning
+=====================
+
+cloud-init ships a command for manually cleaning the cache: ``cloud-init
+clean``. See :ref:`cli_clean`'s documentation for further details.
+
+Reverting ``manual_cache_clean`` Setting
+========================================
+
+Currently there is no support for switching an instance that is launched with
+``manual_cache_clean: true`` from ``trust`` behavior to ``check`` behavior,
+other than manually cleaning the cache.
+
+.. warning:: If you want to capture an instance that is currently in ``trust``
+ mode as an image for launching other instances, you **must** manually clean
+ the cache. If you do not do so, then instances launched from the captured
+ image will all detect their first boot as a subsequent boot of the captured
+ instance, and will not apply any per-instance configuration.
+
+ This is a functional issue, but also a potential security one: cloud-init is
+ responsible for rotating SSH host keys on first boot, and this will not
+ happen on these instances.
+
+.. [#not-present] It follows that if this cache is not present, cloud-init has
+ not run on this system before, so this is unambiguously this instance's
+ first boot.
+
+.. [#problems] A couple of ways in which this strict reliance on the presence
+ of a datasource has been observed to cause problems:
+
+ * If a cloud's metadata service is flaky and cloud-init cannot obtain the
+ instance ID locally on that platform, cloud-init's instance ID
+ determination will sometimes fail to determine the current instance ID,
+ which makes it impossible to determine if this is an instance's first or
+ subsequent boot (`#1885527`_).
+ * If cloud-init is used to provision a physical appliance or device and an
+ attacker can present a datasource to the device with a different instance
+ ID, then cloud-init's default behavior will detect this as an instance's
+ first boot and reset the device using the attacker's configuration
+ (this has been observed with the NoCloud datasource in `#1879530`_).
+
+.. _#1885527: https://bugs.launchpad.net/ubuntu/+source/cloud-init/+bug/1885527
+.. _#1879530: https://bugs.launchpad.net/ubuntu/+source/cloud-init/+bug/1879530
+
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