fleet/docs/Using Fleet/update-agents.md
Eric 8fb22579ea
Reorganize Fleet documentation (#12871)
Closes: #12611

Changes:
- Added three new documentation sections `/docs/get-started/`,
`/docs/configuration` and `/docs/rest api/`
- Updated folder names: `/docs/Using-Fleet/` » `/docs/Using Fleet` and
`/docs/deploying` » `/docs/deploy/`
- Moved `/docs/using-fleet/process-events.md` to `/articles` and updated
the meta tags to change it into a guide.
- Added support for a new meta tag: `navSection`. This meta tag is used
to organize pages in the sidebar navigation on fleetdm.com/docs
- Moved `docs/using-fleet/application-security.md` and
`docs/using-fleet/security-audits.md` to the security handbook.
- Moved `docs/deploying/load-testing.md` and
`docs/deploying/debugging.md` to the engineering handbook.
- Moved the following files/folders:
- `docs/using-fleet/configuration-files/` »
`docs/configuration/configuration-files/`
- `docs/deploying/configuration.md` »
`docs/configuration/fleet-server-configuration.md`
    -  `docs/using-fleet/rest-api.md` » `docs/rest-api/rest-api.md`
- `docs/using-fleet/monitoring-fleet.md` » `docs/deploy/rest-api.md`
- Updated filenames:
- `docs/using-fleet/permissions.md` »
`docs/using-fleet/manage-access.md`
- `docs/using-fleet/adding-hosts.md` »
`docs/using-fleet/enroll-hosts.md`
    -  `docs/using-fleet/teams.md` » `docs/using-fleet/segment-hosts.md`
- `docs/using-fleet/fleet-ctl-agent-updates.md` »
`docs/using-fleet/update-agents.md`
- `docs/using-fleet/chromeos.md` »
`docs/using-fleet/enroll-chromebooks.md`
- Updated the generated markdown in `server/fleet/gen_activity_doc.go`
and `server/service/osquery_utils/gen_queries_doc.go`
- Updated the navigation sidebar and mobile dropdown links on docs pages
to group pages by their `navSection` meta tag.
- Updated fleetdm.com/docs not to show pages in the `docs/contributing/`
folder in the sidebar navigation
- Added redirects for docs pages that have moved.

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---------

Co-authored-by: Mike Thomas <mthomas@fleetdm.com>
Co-authored-by: Rachael Shaw <r@rachael.wtf>
2023-07-27 17:40:01 -05:00

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# Self-managed agent updates
[Fleetd](https://fleetdm.com/docs/using-fleet/fleetd) will periodically check the public Fleet update repository and update Orbit, Fleet Desktop, and/or osquery
if it detects a later version.
To override this behavior, users can set a channel for each component or disable updates altogether. Visit [Adding Hosts](https://fleetdm.com/docs/using-fleet/adding-hosts#fleet-desktop) to learn more.
Alternatively, users with a Fleet Premium subscription can self-manage an update server.
## Securing updates
Fleetd utilizes [The Update Framework](https://theupdateframework.io/) to secure the update system. The TUF specification provides a robust framework for establishing trust over the content of updates. See [TUF's security documentation](https://theupdateframework.io/security/) for more details.
Fleet's usage of TUF allows the keys most critical to the security of the system to be stored offline, and provides a simple deployment model for update metadata and content.
There is no server that must be maintained for updates, instead Fleet provides tools via `fleetctl` to manage the static metadata and update assets. These can be served by any static content hosting solution (Apache, nginx, S3, etc.).
## Operations
Update management is handled by the `fleetctl updates` subcommands.
Fleet will prompt for passphrases when needed, or passphrases may be set in the environment variables `FLEET_ROOT_PASSPHRASE`, `FLEET_TARGETS_PASSPHRASE`, `FLEET_SNAPSHOT_PASSPHRASE`, and `FLEET_TIMESTAMP_PASSPHRASE`. Passphrases should be stored separately from keys.
By default, the current working directory is used for the TUF repository. All update commands support a `--path` parameter to use a different directory.
### Initialize the repository
_The root cryptographic key generated in this step is highly sensitive, and critical to the security of the update system. We recommend following these steps from a trusted, offline, ephemeral environment such as [Debian Live](https://www.debian.org/CD/live/) running from a USB stick. Avoid placing the root key in an online environment. Fleet will soon support the use of Hardware security modules (HSMs) to further protect the root key._
For testing purposes it is okay to initialize the repository in an online environment. Be sure to use a clean offline environment with new keys and passphrases when deploying to production.
Initialize the repository:
```
fleetctl updates init
```
Choose and record secure passphrases, _different for each key_. If the passphrases are not already set in the environment, you will be prompted to input them.
Make multiple copies of the `keys` directory to be stored offline on USB drives. These copies contain the root key:
```
cp -r keys <destination>
```
Delete the root key from the `keys` directory:
```
rm keys/root.json
```
Copy the `keys`, `repository`, and `staged` directories to a separate "working" USB drive:
```
cp -r keys repository staged <destination>
```
Shut down the environment.
### Deploy updates
Updates are deployed first by staging the contents and metadata, then publishing.
#### Staging
_Staging targets requires access to the `target`, `snapshot`, and `timestamp` keys. Best practice is to connect the drive containing the keys while staging updates and leave the keys offline at other times._
Use `fleetctl updates add` to stage updates. Fleetd updates the `osqueryd` binary, as well as the `orbit` binary. Updates are staged for each of these separately using the `--name` flag. It is not necessary to update both at the same time.
The following commands will prompt for key passphrases if not specified in the environment.
To stage updates for `osqueryd`:
```
fleetctl updates add --target ./path/to/linux/osqueryd --platform linux --name osqueryd --version 4.6.0 -t 4.6 -t 4 -t stable
```
This will add the `osqueryd` binary located at `./path/to/osqueryd` to the channels `4.6.0`, `4.6`, `4`, and `stable` for the `linux` platform.
In a typical scenario, each platform is staged before the repository is published.
Stage the equivalent macOS update:
```
fleetctl updates add --target ./path/to/macos/osqueryd --platform macos --name osqueryd --version 4.6.0 -t 4.6 -t 4 -t stable
```
A similar process can be used to stage the `orbit` artifacts by substituting `--name orbit`
When updates are staged, publish the repository.
#### Publishing
Publishing updates is as simple as making the contents of the `repository` directory available over HTTP. This can be achieved with [AWS S3](https://docs.aws.amazon.com/AmazonS3/latest/userguide/HostingWebsiteOnS3Setup.html), [Apache](https://access.redhat.com/solutions/67298), [NGINX](https://docs.nginx.com/nginx/admin-guide/web-server/serving-static-content/), or any other static file hosting solution or CDN.
Python's `SimpleHTTPServer` can be used for quick local testing:
```
cd repository && python -m SimpleHTTPServer
```
Or, for Python version 3.0 and greater:
```
cd repository && python -m http.server
```
Run this to host the repository at http://localhost:8000.
#### Update timestamp
Fleetd verifies freshness of the update metadata using the signed [timestamp file](https://theupdateframework.io/metadata/#timestamp-metadata-timestampjson). _This file must be re-signed every two weeks_ (this interval will be made configurable soon).
To update the timestamp metadata:
```
fleetctl updates timestamp
```
_This operation requires the `timestamp` key to be available, along with the corresponding passphrase. Best practice is to keep these keys "online" in a context where they can be used to update the metadata on an interval (via `cron`, AWS Lambda, etc.). This "online" context should be on a separate host from the static file server, to prevent leaking these less sensitive (though still sensitive) keys in the event the static file server is compromised._
### Building packages
Note that `osqueryd` and `orbit` updates must be published before packages can be produced.
Record the root key metadata with a copy of the repository:
```
fleetctl updates roots
```
This output is _not sensitive_ and will be shared in agent deployments to verify the contents of updates and metadata. Provide the JSON output in the `--update-roots` flag of the [Fleetd packager](https://fleetdm.com/docs/using-fleet/fleetd):
### Packaging with Fleetd
See the [Fleetd docs](https://fleetdm.com/docs/using-fleet/fleetd) for more details
You can use `fleetctl package` to generate installer packages of Fleetd (Fleet's bundle of agents that includes a bootstrapped osquery wrapper) to integrate with your Fleet instance.
For example running `fleetctl package --type deb --fleet-url=<fleet url> --enroll-secret=<enroll secret>` will build a `.deb` installer with everything needed
to communicate with your fleet instance.
### Key rotation
Key rotation is supported for each of the update role keys via the `fleetctl updates rotate` command.
Rotation is required for a key if the key has been compromised, or before the key expires.
Compromise of a single key (besides the root key) within the system does not enable an attacker to
push arbitrary updates. Compromise of the root key is a catastrophic failure allowing arbitrary
updates, and for this reason the root key is highly guarded in an offline context. See Section 7.4
of the [_Survivable Key
Compromise_](https://theupdateframework.io/papers/survivable-key-compromise-ccs2010.pdf) paper for a
more in-depth discussion of the implications of key compromise in the TUF system.
To rotate (for example) the targets key:
```
fleetctl updates rotate targets
```
After the key(s) have been rotated, publish the repository in the same fashion as any other update.
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