Added RFD 0144 - Client Tools Updates

rfd/0144-client-tools-updates.md

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+---
+authors: Russell Jones (rjones@goteleport.com) and Bernard Kim (bernard@goteleport.com)
+state: draft
+---
+
+# RFD 0144 - Client Tools Updates
+
+## Required Approvers
+
+* Engineering: @sclevine && @bernardjkim && @r0mant
+* Product: @klizhentas || @xinding33
+* Security: @reedloden
+
+## What/Why
+
+This RFD describes how client tools like `tsh` and `tctl` can be kept up to
+date, either using automatic updates or self-managed updates.
+
+Keeping client tools updated helps with security (fixes for known security
+vulnerabilities are pushed to endpoints), bugs (fixes for resolved issues are
+pushed to endpoints), and compatibility (users no longer have to learn and
+understand [Teleport component
+compatibility](https://goteleport.com/docs/upgrading/overview/#component-compatibility)
+rules).
+
+## Details
+
+### Summary
+
+Client tools like `tsh` and `tctl` will automatically download and install the
+required version for the Teleport cluster.
+
+Enrollment in automatic updates for client tools will be controlled at the
+cluster level. By default all Cloud clusters will be opted into automatic
+updates for client tools. Cluster administrators using MDM software like Jamf
+will be able opt-out manually manage updates.
+
+Self-hosted clusters will be be opted out, but have the option to use the same
+automatic update mechanism.
+
+Inspiration drawn from https://go.dev/doc/toolchain.
+
+### Implementation
+
+#### Client tools
+
+##### Automatic updates
+
+When `tsh login` is executed, client tools will check `/v1/webapi/ping` to
+determine if automatic updates are enabled. If the cluster's required version
+differs from the current binary, client tools will download and re-execute
+using the version required by the cluster. All other `tsh` subcommands (like
+`tsh ssh ...`) will always use the downloaded version.
+
+The original client tools binaries won't be overwritten. Instead, an additional
+binary will be downloaded and stored in `~/.tsh/bin` with `0755` permissions.
+A hash of the binary will be performed and checked against a known value to
+ensure the file has not been corrupted during download. To enable concurrent
+operation of client tools, a locking mechanisms utilizing
+[syscall.Flock](https://pkg.go.dev/syscall#Flock) (for Linux and macOS) and
+[LockFileEx](https://learn.microsoft.com/en-us/windows/win32/api/fileapi/nf-fileapi-lockfileex)
+(for Windows) will be used.
+
+```
+$ tree ~/.tsh
+~/.tsh
+├── bin
+│  ├── tctl
+│  └── tsh
+├── current-profile
+├── keys
+│  └── proxy.example.com
+│     ├── cas
+│     │  └── example.com.pem
+│     ├── certs.pem
+│     ├── foo
+│     ├── foo-ssh
+│     │  └── example.com-cert.pub
+│     ├── foo-x509.pem
+│     └── foo.pub
+├── known_hosts
+└── proxy.example.com.yaml
+```
+
+Users can cancel client tools updates using `Ctrl-C`. This may be needed if the
+user is on a low bandwidth connection (LTE or public Wi-Fi), if the Teleport
+download server is inaccessible, or the user urgently needs to access the
+cluster and can not wait for the update to occur.
+
+```
+$ tsh login --proxy=proxy.example.com
+Client tools are out of date, updating to vX.Y.Z.
+Update progress: [▒▒▒▒▒▒     ] (Ctrl-C to cancel update)
+
+[...]
+```
+
+An environment variable `TELEPORT_TOOLS_VERSION` will be introduced that can be
+`X.Y.Z` (use specific semver version) or `off` (do not update). This
+environment variable can be used as a emergency workaround for a known issue,
+pinning to a specific version in CI/CD, or for debugging.
+
+During re-execution, child process will inherit all environment variables and
+flags. `TELEPORT_TOOLS_VERSION=off` will be added during re-execution to
+prevent infinite loops.
+
+Automatic updates will not be used if `tctl` is connecting to the Auth Service
+over localhost.
+
+> [!NOTE]
+> If a user connects to multiple root clusters, each running a different
+> version of Teleport, client tools will attempt to download the differing
+> version of Teleport each time the user performs a `tsh login`.
+>
+> In practice, the number of users impacted by this would be small. Customer
+> Cloud tenants would be on the same version and this feature is turned off by
+> default for self-hosted cluster.
+>
+> However, for those people in this situation, the recommendation would be to
+> use self-managed updates.
+
+##### Errors and warnings
+
+If cluster administrator has chosen not to enroll client tools in automatic
+updates and does not self-manage client tools updates as outlined in
+[Self-managed client tools updates](#self-managed-client-tools-updates), a
+series of warnings and errors with increasing urgency will be shown to the
+user.
+
+If the version of client tools is within the same major version as advertised
+by the cluster, a warning will be shown to urge the user to enroll in automatic
+updates. Warnings will not prevent the user from using client tools that are
+slightly out of date.
+
+```
+$ tsh login --proxy=proxy.example.com
+Warning: Client tools are out of date, update to vX.Y.Z.
+
+Update Teleport to vX.Y.Z from https://goteleport.com/download or your system
+package manager.
+
+Enroll in automatic updates to keep client tools like tsh and tctl
+automatically updated. https://goteleport.com/docs/upgrading/automatic-updates
+
+[...]
+```
+
+If the version of client tools is 1 major version below the version advertised
+by the cluster, a warning will be shown that indicates some functionality may
+not work.
+
+```
+$ tsh login --proxy=proxy.example.com
+WARNING: Client tools are 1 major version out of date, update to vX.Y.Z.
+
+Some functionality may not work. Update Teleport to vX.Y.Z from
+https://goteleport.com/download or your system package manager.
+
+Enroll in automatic updates to keep client tools like tsh and tctl
+automatically updated. https://goteleport.com/docs/upgrading/automatic-updates
+```
+
+If the version of client tools is 2 (or more) versions lower than the version
+advertised by the cluster or 1 (or more) version greater than the version
+advertised by the cluster, an error will be shown and will require the user to
+use the `--skip-version-check` flag.
+
+```
+$ tsh login --proxy=proxy.example.com
+ERROR: Client tools are N major versions out of date, update to vX.Y.Z.
+
+Your cluster requires {tsh,tctl} vX.Y.Z. Update Teleport from
+https://goteleport.com/download or your system package manager.
+
+Enroll in automatic updates to keep client tools like tsh and tctl
+automatically updated. https://goteleport.com/docs/upgrading/automatic-updates
+
+Use the "--skip-version-check" flag to bypass this check and attempt to connect
+to this cluster.
+```
+
+#### Self-managed client tools updates
+
+Cluster administrators that want to self-manage client tools updates will be
+able to get and watch for changes to client tools versions which can then be
+used to trigger other integrations (using MDM software like Jamf) to update the
+installed version of client tools on endpoints.
+
+```
+$ tctl autoupdate watch
+{"tools_version": "1.0.0"}
+{"tools_version": "1.0.1"}
+{"tools_version": "2.0.0"}
+
+[...]
+```
+
+```
+$ tctl autoupdate get
+{"tools_version": "2.0.0"}
+```
+
+##### Cluster configuration
+
+Enrollment of clients in automatic updates will be enforced at the cluster
+level.
+
+The `cluster_maintenance_config` resource will be updated to allow cluster
+administrators to turn client tools automatic updates `on` or `off`.
+A `autoupdate_version` resource will be added to allow cluster administrators
+to manage the version of tools pushed to clients.
+
+> [!NOTE]
+> Client tools configuration is broken into two resources to [prevent
+> updates](https://github.com/gravitational/teleport/blob/master/lib/modules/modules.go#L332-L355)
+> to `autoupdate_version` on Cloud.
+>
+> While Cloud customers will be able to use `cluster_maintenance_config` to
+> turn client tools automatic updates `off` and self-manage updates, they will
+> not be able to control the version of client tools in `autoupdate_version`.
+> That will continue to be managed by the Teleport Cloud team.
+
+Both resources can either be updated directly or by using `tctl` helper
+functions.
+
+```yaml
+kind: cluster_maintenance_config
+spec:
+  # tools_auto_update allows turning client tools updates on or off at the
+  # cluster level. Only turn client tools automatic updates off if self-managed
+  # updates are in place.
+  tools_auto_update: on|off
+
+  [...]
+```
+```
+$ tctl autoupdate update --set-tools-auto-update=off
+Automatic updates configuration has been updated.
+```
+
+By default, all Cloud clusters will be opted into `tools_auto_update: on`. All
+self-hosted clusters will be opted into `tools_auto_update: off`.
+
+```yaml
+kind: autoupdate_version
+spec:
+  # tools_version is the semver version of client tools the cluster will
+  # advertise.
+  tools_version: X.Y.Z
+```
+```
+$ tctl autoupdate update --set-tools-version=1.0.1
+Automatic updates configuration has been updated.
+```
+
+For Cloud clusters, `tools_version` will always be `X.Y.Z`, with the version
+controlled by the Cloud team.
+
+The above configuration will then be available from the unauthenticated
+endpoint `/v1/webapi/ping` which clients will consult.
+
+```
+$ curl https://proxy.example.com/v1/webapi/ping | jq .
+{
+    "tools_auto_update": true,
+    "tools_version": "X.Y.Z",
+
+    [...]
+}
+```
+
+### Costs
+
+Some additional costs will be incurred as Teleport downloads will increase in
+frequency.
+
+### Out of scope
+
+How Cloud will push changes to `autoupdate_version` is out of scope for this
+RFD and will be handled by a separate Cloud specific RFD.
+
+Automatic updates for Teleport Connect are out of scope for this RFD as it uses
+a different install/update mechanism. For now it will call `tsh` with
+`TELEPORT_TOOLS_VERSION=off` until automatic updates support can be added to
+Connect.
+
+### Security
+
+The initial version of automatic updates will rely on TLS to establish
+connection authenticity to the Teleport download server. The authenticity of
+assets served from the download server is out of scope for this RFD. Cluster
+administrators concerned with the authenticity of assets served from the
+download server can use self-managed updates with system package managers which
+are signed.
+
+Phase 2 will use The Upgrade Framework (TUF) to implement secure updates.