diff --git a/.circleci/config.yml b/.circleci/config.yml
index edd87a19d..8a1b5456c 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -137,6 +137,10 @@ jobs:
           working_directory: integration_tests
           environment:
             TESTING: "true"
+      - run:
+          name: "Make sure simple command do not cause any timeout"
+          command: circleci version
+
   test:
     executor: go
     steps:
@@ -378,12 +382,14 @@ workflows:
             - devex-release
       - deploy:
           requires:
+            - cucumber
             - test
             - test_mac
             - coverage
             - lint
             - deploy-test
             - shellcheck/check
+            - vulnerability-scan
           filters:
             branches:
               only: main
diff --git a/Makefile b/Makefile
index 604d50148..a51a58c4a 100644
--- a/Makefile
+++ b/Makefile
@@ -4,7 +4,7 @@ GOOS=$(shell go env GOOS)
 GOARCH=$(shell go env GOARCH)
 
 build: always
-	go build -o build/$(GOOS)/$(GOARCH)/circleci
+	go build -o build/$(GOOS)/$(GOARCH)/circleci -ldflags='-X github.com/CircleCI-Public/circleci-cli/telemetry.SegmentEndpoint=https://api.segment.io'
 
 build-all: build/linux/amd64/circleci build/darwin/amd64/circleci
 
diff --git a/README.md b/README.md
index a955cff70..b57b73873 100644
--- a/README.md
+++ b/README.md
@@ -180,6 +180,20 @@ Please see the [documentation](https://circleci-public.github.io/circleci-cli) o
 
 ## Server compatibility
 
-There are some difference of behavior depending on the version you use:
- - config validation will use the GraphQL API until **Server v4.0.5, v4.1.3, v4.2.0**. The above versions will use the new route `compile-config-with-defaults`
- - `circleci orb validate` will only allow you to validate orbs using other private orbs with the option `--org-slug` from version **Server v4.2.0**
+| Functionality | Impacted commands | Change description | Compatibility with Server |
+| --- | --- | --- | --- |
+| Config compilation and validation | <ul><li>`circleci config validate`</li><li>`circleci config process`</li><li>`circleci local execute`</li> | The config validation has been moved from the GraphQL API to a specific API endpoint | <ul><li>**Server v4.0.5, v4.1.3, v4.2.0 and above**: Commands use the new specific endpoint</li><li>**Previous version**: Commands use the GraphQL API</li></ul> |
+| Orb compilation and validation of orb using private orbs | <ul><li>`circleci orb process`</li><li>`circleci orb validate`</li></ul> | To support the validation of orbs requesting private orbs (see [issue](https://github.com/CircleCI-Public/circleci-cli/issues/751)). A field `ownerId` has been added to the GraphQL orb validation endpoint. Thus allowing the `Impacted commands` to use the `--org-id` parameter to enable the orb compilation / validation  | <ul><li>**Server v4.2.0 and above**: The field is accessible so you can use the parameter</li><li>**Previous versions**: The field does not exist making the functionality unavailable</li></ul> |
+
+## Telemetry
+
+The CircleCI CLI includes a telemetry feature that collects basic errors and feature usage data in order to help us improve the experience for everyone.
+
+Telemetry works on an opt-in basis: when running a command for the first time, you will be asked for consent to enable telemetry. For non-TTY STDIN, telemetry is disabled by default, ensuring that scripts that use the CLI run smoothly.
+
+You can disable or enable telemetry anytime in one of the following ways:
+
+* Run the commands `circleci telemetry enable` or `circleci telemetry disable`
+
+* Set the `CIRCLECI_CLI_TELEMETRY_OPTOUT` environment variable to `1` or `true` to disable it
+
diff --git a/Taskfile.yml b/Taskfile.yml
index ad2d19df9..3cb8bfffc 100644
--- a/Taskfile.yml
+++ b/Taskfile.yml
@@ -47,14 +47,16 @@ tasks:
   build:
     desc: Build main
     cmds:
-      - go build -v -o build/darwin/amd64/circleci .
-  
+      # LDFlags sets the segment endpoint to an empty string thus letting the analytics library set the default endpoint on its own
+      # Not setting the `SegmentEndpoint` variable would let the value in the code ie "http://localhost"
+      - go build -v -o build/$(go env GOOS)/$(go env GOARCH)/circleci -ldflags='-X github.com/CircleCI-Public/circleci-cli/telemetry.SegmentEndpoint=https://api.segment.io' .
+
   build-linux:
     desc: Build main
     cmds:
       - go build -v -o build/linux/amd64/circleci .
- 
+
   cover:
     desc: tests and generates a cover profile
     cmds:
-      - TESTING=true go test -race -coverprofile=coverage.txt ./...
\ No newline at end of file
+      - TESTING=true go test -race -coverprofile=coverage.txt ./...
diff --git a/api/api.go b/api/api.go
index 2dbaca0bd..846626465 100644
--- a/api/api.go
+++ b/api/api.go
@@ -6,11 +6,13 @@ import (
 	"io"
 	"log"
 	"net/http"
+	"net/url"
 	"os"
 	"sort"
 	"strings"
 
 	"github.com/CircleCI-Public/circleci-cli/api/graphql"
+	"github.com/CircleCI-Public/circleci-cli/api/rest"
 	"github.com/CircleCI-Public/circleci-cli/references"
 	"github.com/CircleCI-Public/circleci-cli/settings"
 	"github.com/Masterminds/semver"
@@ -1818,3 +1820,20 @@ func FollowProject(config settings.Config, vcs string, owner string, projectName
 
 	return fr, nil
 }
+
+type Me struct {
+	ID    string `json:"id"`
+	Login string `json:"login"`
+	Name  string `json:"name"`
+}
+
+func GetMe(client *rest.Client) (Me, error) {
+	req, err := client.NewRequest("GET", &url.URL{Path: "me"}, nil)
+	if err != nil {
+		return Me{}, errors.Wrap(err, "Unable to get user info")
+	}
+
+	var me Me
+	_, err = client.DoRequest(req, &me)
+	return me, err
+}
diff --git a/clitest/clitest.go b/clitest/clitest.go
index 6a0010d5c..24b0b25bc 100644
--- a/clitest/clitest.go
+++ b/clitest/clitest.go
@@ -11,9 +11,11 @@ import (
 	"runtime"
 
 	"github.com/CircleCI-Public/circleci-cli/api/graphql"
+	"github.com/CircleCI-Public/circleci-cli/settings"
 	"github.com/onsi/gomega/gexec"
 	"github.com/onsi/gomega/ghttp"
 	"github.com/onsi/gomega/types"
+	"gopkg.in/yaml.v3"
 
 	"github.com/onsi/gomega"
 )
@@ -30,10 +32,12 @@ func ShouldFail() types.GomegaMatcher {
 
 // TempSettings contains useful settings for testing the CLI
 type TempSettings struct {
-	Home       string
-	TestServer *ghttp.Server
-	Config     *TmpFile
-	Update     *TmpFile
+	Home              string
+	TestServer        *ghttp.Server
+	Config            *TmpFile
+	Update            *TmpFile
+	Telemetry         *TmpFile
+	TelemetryDestPath string
 }
 
 // Close should be called in an AfterEach and cleans up the temp directory and server process
@@ -68,6 +72,16 @@ func WithTempSettings() *TempSettings {
 	gomega.Expect(os.Mkdir(settingsPath, 0700)).To(gomega.Succeed())
 
 	tempSettings.Config = OpenTmpFile(settingsPath, "cli.yml")
+	tempSettings.Telemetry = OpenTmpFile(settingsPath, "telemetry.yml")
+	content, err := yaml.Marshal(settings.TelemetrySettings{
+		IsEnabled:         false,
+		HasAnsweredPrompt: true,
+	})
+	gomega.Expect(err).ToNot(gomega.HaveOccurred())
+	_, err = tempSettings.Telemetry.File.Write(content)
+	gomega.Expect(err).ToNot(gomega.HaveOccurred())
+	tempSettings.TelemetryDestPath = filepath.Join(tempSettings.Home, "telemetry-content")
+
 	tempSettings.Update = OpenTmpFile(settingsPath, "update_check.yml")
 
 	tempSettings.TestServer = ghttp.NewServer()
diff --git a/clitest/telemetry.go b/clitest/telemetry.go
new file mode 100644
index 000000000..fc21f85ce
--- /dev/null
+++ b/clitest/telemetry.go
@@ -0,0 +1,19 @@
+package clitest
+
+import (
+	"encoding/json"
+	"os"
+
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+	"github.com/onsi/gomega"
+)
+
+func CompareTelemetryEvent(settings *TempSettings, expected []telemetry.Event) {
+	content, err := os.ReadFile(settings.TelemetryDestPath)
+	gomega.Expect(err).ShouldNot(gomega.HaveOccurred())
+
+	result := []telemetry.Event{}
+	err = json.Unmarshal(content, &result)
+	gomega.Expect(err).ShouldNot(gomega.HaveOccurred())
+	gomega.Expect(result).To(gomega.Equal(expected))
+}
diff --git a/cmd/build.go b/cmd/build.go
index c32ed969c..df4d110c4 100644
--- a/cmd/build.go
+++ b/cmd/build.go
@@ -3,6 +3,7 @@ package cmd
 import (
 	"github.com/CircleCI-Public/circleci-cli/local"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/spf13/cobra"
 )
 
@@ -16,7 +17,14 @@ func newLocalExecuteCommand(config *settings.Config) *cobra.Command {
 			return nil
 		},
 		RunE: func(cmd *cobra.Command, _ []string) error {
-			return local.Execute(cmd.Flags(), config, args)
+			err := local.Execute(cmd.Flags(), config, args)
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateLocalExecuteEvent(telemetry.GetCommandInformation(cmd, true)))
+			}
+
+			return err
 		},
 		Args: cobra.MinimumNArgs(1),
 	}
diff --git a/cmd/cmd_suite_test.go b/cmd/cmd_suite_test.go
index 5f126d986..5e54304ca 100644
--- a/cmd/cmd_suite_test.go
+++ b/cmd/cmd_suite_test.go
@@ -5,6 +5,7 @@ import (
 	"os"
 	"os/exec"
 	"testing"
+	"time"
 
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
@@ -14,6 +15,8 @@ import (
 var pathCLI string
 
 var _ = BeforeSuite(func() {
+	SetDefaultEventuallyTimeout(time.Second * 30)
+
 	var err error
 	pathCLI, err = gexec.Build("github.com/CircleCI-Public/circleci-cli")
 	Ω(err).ShouldNot(HaveOccurred())
diff --git a/cmd/completion.go b/cmd/completion.go
index bc0ff6d53..edeaa58d4 100644
--- a/cmd/completion.go
+++ b/cmd/completion.go
@@ -3,13 +3,21 @@ package cmd
 import (
 	"os"
 
+	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/spf13/cobra"
 )
 
-func newCompletionCommand() *cobra.Command {
+func newCompletionCommand(config *settings.Config) *cobra.Command {
 	completionCmd := &cobra.Command{
 		Use:   "completion",
 		Short: "Generate shell completion scripts",
+		PersistentPreRun: func(cmd *cobra.Command, _ []string) {
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateCompletionCommand(telemetry.GetCommandInformation(cmd, true)))
+			}
+		},
 		Run: func(cmd *cobra.Command, _ []string) {
 			err := cmd.Help()
 			if err != nil {
diff --git a/cmd/config.go b/cmd/config.go
index 690fc78d1..8fdba6194 100644
--- a/cmd/config.go
+++ b/cmd/config.go
@@ -8,14 +8,14 @@ import (
 	"github.com/CircleCI-Public/circleci-config/labeling"
 	"github.com/CircleCI-Public/circleci-config/labeling/codebase"
 
-	"github.com/pkg/errors"
-	"github.com/spf13/cobra"
-	"gopkg.in/yaml.v3"
-
 	"github.com/CircleCI-Public/circleci-cli/config"
 	"github.com/CircleCI-Public/circleci-cli/filetree"
 	"github.com/CircleCI-Public/circleci-cli/proxy"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+	"github.com/pkg/errors"
+	"github.com/spf13/cobra"
+	"gopkg.in/yaml.v3"
 )
 
 // Path to the config.yml file to operate on.
@@ -37,8 +37,14 @@ func newConfigCommand(globalConfig *settings.Config) *cobra.Command {
 	packCommand := &cobra.Command{
 		Use:   "pack <path>",
 		Short: "Pack up your CircleCI configuration into a single file.",
-		RunE: func(_ *cobra.Command, args []string) error {
-			return packConfig(args)
+		RunE: func(cmd *cobra.Command, args []string) error {
+			err := packConfig(args)
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateConfigEvent(telemetry.GetCommandInformation(cmd, true), err))
+			}
+			return err
 		},
 		Args:        cobra.ExactArgs(1),
 		Annotations: make(map[string]string),
@@ -64,13 +70,20 @@ func newConfigCommand(globalConfig *settings.Config) *cobra.Command {
 			if len(args) == 1 {
 				path = args[0]
 			}
-			return compiler.ValidateConfig(config.ValidateConfigOpts{
+
+			err = compiler.ValidateConfig(config.ValidateConfigOpts{
 				ConfigPath:             path,
 				OrgID:                  orgID,
 				OrgSlug:                orgSlug,
 				IgnoreDeprecatedImages: ignoreDeprecatedImages,
 				VerboseOutput:          verboseOutput,
 			})
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateConfigEvent(telemetry.GetCommandInformation(cmd, true), err))
+			}
+
+			return err
 		},
 		Args:        cobra.MaximumNArgs(1),
 		Annotations: make(map[string]string),
@@ -112,6 +125,10 @@ func newConfigCommand(globalConfig *settings.Config) *cobra.Command {
 				PipelineParamsFilePath: pipelineParamsFilePath,
 				VerboseOutput:          verboseOutput,
 			})
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateConfigEvent(telemetry.GetCommandInformation(cmd, true), err))
+			}
 			if err != nil {
 				return err
 			}
diff --git a/cmd/config_test.go b/cmd/config_test.go
index 9168b4146..86c5e8f6d 100644
--- a/cmd/config_test.go
+++ b/cmd/config_test.go
@@ -7,6 +7,7 @@ import (
 	"path/filepath"
 
 	"github.com/CircleCI-Public/circleci-cli/clitest"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
 	"github.com/onsi/gomega/gexec"
@@ -29,12 +30,41 @@ var _ = Describe("Config", func() {
 			tempSettings.Close()
 		})
 
+		Describe("telemetry", func() {
+			BeforeEach(func() {
+				tempSettings = clitest.WithTempSettings()
+				command = commandWithHome(pathCLI, tempSettings.Home,
+					"config", "pack",
+					"--skip-update-check",
+					filepath.Join("testdata", "hugo-pack", ".circleci"),
+				)
+				command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+			})
+
+			AfterEach(func() {
+				tempSettings.Close()
+			})
+
+			It("should send telemetry event", func() {
+				session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+				Expect(err).ShouldNot(HaveOccurred())
+
+				Eventually(session).Should(gexec.Exit(0))
+				clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+					telemetry.CreateConfigEvent(telemetry.CommandInfo{
+						Name:      "pack",
+						LocalArgs: map[string]string{"help": "false"},
+					}, nil),
+				})
+			})
+		})
+
 		Describe("a .circleci folder with config.yml and local orbs folder containing the hugo orb", func() {
 			BeforeEach(func() {
 				command = exec.Command(pathCLI,
 					"config", "pack",
 					"--skip-update-check",
-					"testdata/hugo-pack/.circleci")
+					filepath.Join("testdata", "hugo-pack", ".circleci"))
 				results = golden.Get(GinkgoT(), filepath.FromSlash("hugo-pack/result.yml"))
 			})
 
diff --git a/cmd/create_telemetry.go b/cmd/create_telemetry.go
new file mode 100644
index 000000000..645dfe675
--- /dev/null
+++ b/cmd/create_telemetry.go
@@ -0,0 +1,206 @@
+package cmd
+
+import (
+	"fmt"
+	"os"
+	"runtime"
+
+	"github.com/CircleCI-Public/circleci-cli/api"
+	"github.com/CircleCI-Public/circleci-cli/api/rest"
+	"github.com/CircleCI-Public/circleci-cli/prompt"
+	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+	"github.com/CircleCI-Public/circleci-cli/version"
+	"github.com/google/uuid"
+	"github.com/spf13/cobra"
+	"github.com/spf13/pflag"
+	"golang.org/x/term"
+)
+
+var (
+	CreateUUID    = func() string { return uuid.New().String() }
+	isStdinATTY   = term.IsTerminal(int(os.Stdin.Fd()))
+	isStdoutATTY  = term.IsTerminal(int(os.Stdout.Fd()))
+	anonymousUser = telemetry.User{
+		UniqueID: "cli-anonymous-telemetry",
+	}
+)
+
+type telemetryUI interface {
+	AskUserToApproveTelemetry(message string) bool
+}
+
+type telemetryInteractiveUI struct{}
+
+func (telemetryInteractiveUI) AskUserToApproveTelemetry(message string) bool {
+	return prompt.AskUserToConfirmWithDefault(message, true)
+}
+
+type TelemetryAPIClient interface {
+	GetMyUserId() (string, error)
+}
+
+func CreateAPIClient(config *settings.Config) TelemetryAPIClient {
+	return telemetryCircleCIAPI{
+		cli: rest.NewFromConfig(config.Host, config),
+	}
+}
+
+type telemetryCircleCIAPI struct {
+	cli *rest.Client
+}
+
+func (client telemetryCircleCIAPI) GetMyUserId() (string, error) {
+	me, err := api.GetMe(client.cli)
+	if err != nil {
+		return "", err
+	}
+	return me.ID, nil
+}
+
+type nullTelemetryAPIClient struct{}
+
+func (client nullTelemetryAPIClient) GetMyUserId() (string, error) {
+	panic("Should not be called")
+}
+
+// Make sure the user gave their approval for the telemetry and
+func CreateTelemetry(config *settings.Config) telemetry.Client {
+	mockTelemetry := config.MockTelemetry
+	if mockTelemetry == "" {
+		mockTelemetry = os.Getenv("MOCK_TELEMETRY")
+	}
+	if mockTelemetry != "" {
+		return telemetry.CreateFileTelemetry(mockTelemetry)
+	}
+
+	if config.IsTelemetryDisabled || len(os.Getenv("CIRCLECI_CLI_TELEMETRY_OPTOUT")) != 0 {
+		return telemetry.CreateClient(telemetry.User{}, false)
+	}
+
+	var apiClient TelemetryAPIClient = nullTelemetryAPIClient{}
+	if config.HTTPClient != nil {
+		apiClient = telemetryCircleCIAPI{
+			cli: rest.NewFromConfig(config.Host, config),
+		}
+	}
+	ui := telemetryInteractiveUI{}
+
+	telemetrySettings := settings.TelemetrySettings{}
+	user := telemetry.User{
+		IsSelfHosted: config.Host != defaultHost,
+		OS:           runtime.GOOS,
+		Version:      version.Version,
+		TeamName:     "devex",
+	}
+
+	loadTelemetrySettings(&telemetrySettings, &user, apiClient, ui)
+	client := telemetry.CreateClient(user, telemetrySettings.IsEnabled)
+
+	return client
+}
+
+func loadTelemetrySettings(settings *settings.TelemetrySettings, user *telemetry.User, apiClient TelemetryAPIClient, ui telemetryUI) {
+	err := settings.Load()
+	if err != nil && !os.IsNotExist(err) {
+		fmt.Printf("Error loading telemetry configuration: %s\n", err)
+	}
+
+	user.UniqueID = settings.UniqueID
+	user.UserID = settings.UserID
+
+	// If we already have telemetry information or that telemetry is explicitly disabled, skip
+	if settings.HasAnsweredPrompt {
+		// If we have no user id, we try requesting the user id again
+		if settings.UserID == "" && settings.IsEnabled {
+			myID, err := apiClient.GetMyUserId()
+			if err == nil {
+				settings.UserID = myID
+				user.UserID = myID
+				if err := settings.Write(); err != nil {
+					fmt.Printf("Error writing telemetry settings to disk: %s\n", err)
+				}
+			}
+		}
+
+		return
+	}
+
+	// If stdin is not a TTY, stdout is not a TTY or we are in a CI environment, send telemetry event, disable telemetry and return
+	isDisabledByDefault := !isStdinATTY || !isStdoutATTY || os.Getenv("CI") == trueString
+	if isDisabledByDefault {
+		settings.IsEnabled = false
+		err := telemetry.SendTelemetryApproval(anonymousUser, telemetry.NoStdin)
+		if err != nil {
+			fmt.Printf("Error while sending telemetry approval %s\n", err)
+		}
+		return
+	}
+
+	// Else ask user for telemetry approval
+	fmt.Println("CircleCI would like to collect CLI usage data for product improvement purposes.")
+	fmt.Println("")
+	fmt.Println("Participation is voluntary, and your choice can be changed at any time through the command `cli telemetry enable` and `cli telemetry disable`.")
+	fmt.Println("For more information, please see our privacy policy at https://circleci.com/legal/privacy/.")
+	fmt.Println("")
+	settings.IsEnabled = ui.AskUserToApproveTelemetry("Enable telemetry?")
+	settings.HasAnsweredPrompt = true
+
+	// Make sure we have user info and set them
+	if settings.IsEnabled {
+		if settings.UniqueID == "" {
+			settings.UniqueID = CreateUUID()
+		}
+		user.UniqueID = settings.UniqueID
+
+		if settings.UserID == "" {
+			myID, err := apiClient.GetMyUserId()
+			if err == nil {
+				settings.UserID = myID
+			}
+		}
+		user.UserID = settings.UserID
+	} else {
+		*user = anonymousUser
+	}
+
+	// Send telemetry approval event
+	approval := telemetry.Enabled
+	if !settings.IsEnabled {
+		approval = telemetry.Disabled
+	}
+
+	if err := telemetry.SendTelemetryApproval(*user, approval); err != nil {
+		fmt.Printf("Unable to send approval telemetry event: %s\n", err)
+	}
+
+	// Write telemetry
+	if err := settings.Write(); err != nil {
+		fmt.Printf("Error writing telemetry settings to disk: %s\n", err)
+	}
+}
+
+// Utility function used when creating telemetry events.
+// It takes a cobra Command and creates a telemetry.CommandInfo of it
+// If getParent is true, puts both the command's args in `LocalArgs` and the parent's args
+// Else only put the command's args
+// Note: child flags overwrite parent flags with same name
+func GetCommandInformation(cmd *cobra.Command, getParent bool) telemetry.CommandInfo {
+	localArgs := map[string]string{}
+
+	parent := cmd.Parent()
+	if getParent && parent != nil {
+		parent.LocalFlags().VisitAll(func(flag *pflag.Flag) {
+			localArgs[flag.Name] = flag.Value.String()
+		})
+	}
+
+	cmd.LocalFlags().VisitAll(func(flag *pflag.Flag) {
+		localArgs[flag.Name] = flag.Value.String()
+	})
+
+	return telemetry.CommandInfo{
+		Name:      cmd.Name(),
+		LocalArgs: localArgs,
+	}
+}
diff --git a/cmd/create_telemetry_test.go b/cmd/create_telemetry_test.go
new file mode 100644
index 000000000..92b5b9e9f
--- /dev/null
+++ b/cmd/create_telemetry_test.go
@@ -0,0 +1,321 @@
+package cmd
+
+import (
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+	"github.com/spf13/afero"
+	"gotest.tools/v3/assert"
+)
+
+func TestLoadTelemetrySettings(t *testing.T) {
+	// Delete env.CI variable
+	oldEnvCIValue := os.Getenv("CI")
+	os.Setenv("CI", "")
+	defer os.Setenv("CI", oldEnvCIValue)
+
+	// Mock HTTP
+	userId := "id"
+	uniqueId := "unique-id"
+
+	// Mock create UUID
+	oldUUIDCreate := CreateUUID
+	CreateUUID = func() string { return uniqueId }
+	defer (func() { CreateUUID = oldUUIDCreate })()
+
+	// Create test cases
+	type args struct {
+		closeStdin     bool
+		closeStdout    bool
+		env            map[string]string
+		promptApproval bool
+		settings       settings.TelemetrySettings
+	}
+	type want struct {
+		settings        settings.TelemetrySettings
+		fileNotCreated  bool
+		telemetryEvents []telemetry.Event
+	}
+	type testCase struct {
+		name string
+		args args
+		want want
+	}
+
+	testCases := []testCase{
+		{
+			name: "Prompt approval should be saved in settings",
+			args: args{
+				promptApproval: true,
+				settings:       settings.TelemetrySettings{},
+			},
+			want: want{
+				settings: settings.TelemetrySettings{
+					IsEnabled:         true,
+					HasAnsweredPrompt: true,
+					UserID:            userId,
+					UniqueID:          uniqueId,
+				},
+				telemetryEvents: []telemetry.Event{
+					{Object: "cli-telemetry", Action: "enabled",
+						Properties: map[string]interface{}{
+							"UUID":           uniqueId,
+							"user_id":        userId,
+							"is_self_hosted": false,
+						}},
+				},
+			},
+		},
+		{
+			name: "Prompt disapproval should be saved in settings",
+			args: args{
+				promptApproval: false,
+				settings:       settings.TelemetrySettings{},
+			},
+			want: want{
+				settings: settings.TelemetrySettings{
+					IsEnabled:         false,
+					HasAnsweredPrompt: true,
+				},
+				telemetryEvents: []telemetry.Event{
+					{Object: "cli-telemetry", Action: "disabled", Properties: map[string]interface{}{
+						"UUID":           "cli-anonymous-telemetry",
+						"is_self_hosted": false,
+					}},
+				},
+			},
+		},
+		{
+			name: "Does not recreate a unique ID if there is one",
+			args: args{
+				promptApproval: true,
+				settings: settings.TelemetrySettings{
+					UniqueID: "other-id",
+				},
+			},
+			want: want{
+				settings: settings.TelemetrySettings{
+					IsEnabled:         true,
+					HasAnsweredPrompt: true,
+					UserID:            userId,
+					UniqueID:          "other-id",
+				},
+				telemetryEvents: []telemetry.Event{
+					{Object: "cli-telemetry", Action: "enabled", Properties: map[string]interface{}{
+						"UUID":           "other-id",
+						"user_id":        userId,
+						"is_self_hosted": false,
+					}},
+				},
+			},
+		},
+		{
+			name: "Does not change telemetry settings if user already answered prompt",
+			args: args{
+				settings: settings.TelemetrySettings{
+					HasAnsweredPrompt: true,
+				},
+			},
+			want: want{
+				settings: settings.TelemetrySettings{
+					HasAnsweredPrompt: true,
+				},
+				fileNotCreated: true,
+			},
+		},
+		{
+			name: "Does not change telemetry settings if stdin is not a TTY",
+			args: args{closeStdin: true},
+			want: want{
+				fileNotCreated: true,
+				telemetryEvents: []telemetry.Event{
+					{Object: "cli-telemetry", Action: "disabled_default", Properties: map[string]interface{}{
+						"UUID":           "cli-anonymous-telemetry",
+						"is_self_hosted": false,
+					}},
+				},
+			},
+		},
+		{
+			name: "Does not change telemetry settings if stdout is not a TTY",
+			args: args{closeStdout: true},
+			want: want{
+				fileNotCreated: true,
+				telemetryEvents: []telemetry.Event{
+					{Object: "cli-telemetry", Action: "disabled_default", Properties: map[string]interface{}{
+						"UUID":           "cli-anonymous-telemetry",
+						"is_self_hosted": false,
+					}},
+				},
+			},
+		},
+		{
+			name: "Does not change telemetry settings if env.CI == true",
+			args: args{env: map[string]string{"CI": "true"}},
+			want: want{
+				fileNotCreated: true,
+				telemetryEvents: []telemetry.Event{
+					{Object: "cli-telemetry", Action: "disabled_default", Properties: map[string]interface{}{
+						"UUID":           "cli-anonymous-telemetry",
+						"is_self_hosted": false,
+					}},
+				},
+			},
+		},
+		{
+			name: "Should try loading user id if user already answered prompt but has no user id",
+			args: args{
+				settings: settings.TelemetrySettings{
+					HasAnsweredPrompt: true,
+					IsEnabled:         true,
+				},
+			},
+			want: want{
+				settings: settings.TelemetrySettings{
+					HasAnsweredPrompt: true,
+					IsEnabled:         true,
+					UserID:            userId,
+				},
+			},
+		},
+		{
+			name: "Should consider has_answered_prompt before disabled-default scenarios",
+			args: args{
+				env: map[string]string{"CI": "true"},
+				settings: settings.TelemetrySettings{
+					HasAnsweredPrompt: true,
+					IsEnabled:         true,
+				},
+			},
+			want: want{
+				settings: settings.TelemetrySettings{
+					HasAnsweredPrompt: true,
+					IsEnabled:         true,
+					UserID:            userId,
+				},
+			},
+		},
+	}
+
+	for _, tt := range testCases {
+		t.Run(tt.name, func(t *testing.T) {
+			// Mock FS
+			oldFS := settings.FS.Fs
+			settings.FS.Fs = afero.NewMemMapFs()
+			defer (func() { settings.FS.Fs = oldFS })()
+
+			// Mock stdin
+			oldIsStdinOpen := isStdinATTY
+			isStdinATTY = !tt.args.closeStdin
+			defer (func() { isStdinATTY = oldIsStdinOpen })()
+
+			// Mock stdout
+			oldIsStdoutOpen := isStdoutATTY
+			isStdoutATTY = !tt.args.closeStdout
+			defer (func() { isStdoutATTY = oldIsStdoutOpen })()
+
+			// Mock telemetry
+			telemetryClient := testTelemetry{events: make([]telemetry.Event, 0)}
+			oldCreateActiveTelemetry := telemetry.CreateActiveTelemetry
+			telemetry.CreateActiveTelemetry = func(user telemetry.User) telemetry.Client {
+				telemetryClient.User = user
+				return &telemetryClient
+			}
+			defer (func() { telemetry.CreateActiveTelemetry = oldCreateActiveTelemetry })()
+
+			// Mock env
+			if tt.args.env != nil {
+				for k, v := range tt.args.env {
+					oldEnvValue := os.Getenv(k)
+					os.Setenv(k, v)
+					defer os.Setenv(k, oldEnvValue)
+				}
+			}
+
+			// Run tested function
+			loadTelemetrySettings(&tt.args.settings, &telemetry.User{}, telemetryTestAPIClient{userId, nil}, telemetryTestUI{tt.args.promptApproval})
+			assert.DeepEqual(t, &tt.args.settings, &tt.want.settings)
+
+			// Verify good telemetry events were sent
+			expectedEvents := tt.want.telemetryEvents
+			if expectedEvents == nil {
+				expectedEvents = []telemetry.Event{}
+			}
+			assert.DeepEqual(t, telemetryClient.events, expectedEvents)
+
+			// Verify if settings file exist
+			exist, err := settings.FS.Exists(filepath.Join(settings.SettingsPath(), "telemetry.yml"))
+			assert.NilError(t, err)
+			assert.Equal(t, exist, !tt.want.fileNotCreated)
+			if tt.want.fileNotCreated {
+				return
+			}
+
+			// Verify settings file content
+			loaded := settings.TelemetrySettings{}
+			err = loaded.Load()
+			assert.NilError(t, err)
+			assert.DeepEqual(t, &loaded, &tt.want.settings)
+		})
+	}
+}
+
+type testTelemetry struct {
+	events []telemetry.Event
+	User   telemetry.User
+}
+
+func (cli *testTelemetry) Close() error { return nil }
+
+func (cli *testTelemetry) Track(event telemetry.Event) error {
+	newEvent := event
+	properties := map[string]interface{}{}
+	if cli.User.UniqueID != "" {
+		properties["UUID"] = cli.User.UniqueID
+	}
+
+	if cli.User.UserID != "" {
+		properties["user_id"] = cli.User.UserID
+	}
+
+	properties["is_self_hosted"] = cli.User.IsSelfHosted
+
+	if cli.User.OS != "" {
+		properties["os"] = cli.User.OS
+	}
+
+	if cli.User.Version != "" {
+		properties["cli_version"] = cli.User.Version
+	}
+
+	if cli.User.TeamName != "" {
+		properties["team_name"] = cli.User.TeamName
+	}
+
+	if len(properties) > 0 {
+		newEvent.Properties = properties
+	}
+
+	cli.events = append(cli.events, newEvent)
+	return nil
+}
+
+type telemetryTestUI struct {
+	Approved bool
+}
+
+func (ui telemetryTestUI) AskUserToApproveTelemetry(message string) bool {
+	return ui.Approved
+}
+
+type telemetryTestAPIClient struct {
+	id  string
+	err error
+}
+
+func (me telemetryTestAPIClient) GetMyUserId() (string, error) {
+	return me.id, me.err
+}
diff --git a/cmd/diagnostic.go b/cmd/diagnostic.go
index 071ceb257..b8053d63f 100644
--- a/cmd/diagnostic.go
+++ b/cmd/diagnostic.go
@@ -7,6 +7,7 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/api"
 	"github.com/CircleCI-Public/circleci-cli/api/graphql"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/spf13/cobra"
 )
 
@@ -28,8 +29,15 @@ func newDiagnosticCommand(config *settings.Config) *cobra.Command {
 			opts.args = args
 			opts.cl = graphql.NewClient(config.HTTPClient, config.Host, config.Endpoint, config.Token, config.Debug)
 		},
-		RunE: func(_ *cobra.Command, _ []string) error {
-			return diagnostic(opts)
+		RunE: func(cmd *cobra.Command, _ []string) error {
+			err := diagnostic(opts)
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateDiagnosticEvent(err))
+			}
+
+			return err
 		},
 	}
 
diff --git a/cmd/diagnostic_test.go b/cmd/diagnostic_test.go
index f3d48e5d5..21071d3e3 100644
--- a/cmd/diagnostic_test.go
+++ b/cmd/diagnostic_test.go
@@ -8,6 +8,7 @@ import (
 
 	"github.com/CircleCI-Public/circleci-cli/api/graphql"
 	"github.com/CircleCI-Public/circleci-cli/clitest"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
 	"github.com/onsi/gomega/gbytes"
@@ -79,6 +80,24 @@ var _ = Describe("Diagnostic", func() {
 		tempSettings.Close()
 	})
 
+	Describe("telemetry", func() {
+		It("should send telemetry event", func() {
+			command = commandWithHome(pathCLI, tempSettings.Home,
+				"diagnostic",
+				"--skip-update-check",
+				"--host", tempSettings.TestServer.URL())
+			command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+			tempSettings.Config.Write([]byte(`token: mytoken`))
+			session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+			Expect(err).ShouldNot(HaveOccurred())
+
+			Eventually(session).Should(gexec.Exit(0))
+			clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+				telemetry.CreateDiagnosticEvent(nil),
+			})
+		})
+	})
+
 	Describe("existing config file", func() {
 		Describe("token set in config file", func() {
 			BeforeEach(func() {
diff --git a/cmd/follow.go b/cmd/follow.go
index 31eb3bbae..9512423ee 100644
--- a/cmd/follow.go
+++ b/cmd/follow.go
@@ -6,6 +6,7 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/api"
 	"github.com/CircleCI-Public/circleci-cli/git"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/pkg/errors"
 	"github.com/spf13/cobra"
 )
@@ -53,8 +54,15 @@ func followProjectCommand(config *settings.Config) *cobra.Command {
 	followCommand := &cobra.Command{
 		Use:   "follow",
 		Short: "Attempt to follow the project for the current git repository.",
-		RunE: func(_ *cobra.Command, _ []string) error {
-			return followProject(opts)
+		RunE: func(cmd *cobra.Command, _ []string) error {
+			err := followProject(opts)
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateFollowEvent(err))
+			}
+
+			return err
 		},
 	}
 	return followCommand
diff --git a/cmd/info/info.go b/cmd/info/info.go
index 1ed3028fe..fce0bad59 100644
--- a/cmd/info/info.go
+++ b/cmd/info/info.go
@@ -4,6 +4,7 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/api/info"
 	"github.com/CircleCI-Public/circleci-cli/cmd/validator"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/olekukonko/tablewriter"
 
 	"github.com/spf13/cobra"
@@ -41,7 +42,14 @@ func orgInfoCommand(client info.InfoClient, opts infoOptions) *cobra.Command {
 		Long:    `View your Organizations' names and ids.`,
 		PreRunE: opts.validator,
 		RunE: func(cmd *cobra.Command, _ []string) error {
-			return getOrgInformation(cmd, client)
+			err := getOrgInformation(cmd, client)
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateInfoEvent(telemetry.GetCommandInformation(cmd, true), err))
+			}
+
+			return err
 		},
 		Annotations: make(map[string]string),
 		Example:     `circleci info org`,
diff --git a/cmd/info/info_test.go b/cmd/info/info_test.go
index 19bda1417..7b49c8784 100644
--- a/cmd/info/info_test.go
+++ b/cmd/info/info_test.go
@@ -2,6 +2,7 @@ package info
 
 import (
 	"bytes"
+	"context"
 	"fmt"
 	"net/http"
 	"net/http/httptest"
@@ -9,6 +10,7 @@ import (
 
 	"github.com/CircleCI-Public/circleci-cli/cmd/validator"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/spf13/cobra"
 	"gotest.tools/v3/assert"
 )
@@ -106,6 +108,55 @@ func TestFailedValidator(t *testing.T) {
 	assert.Error(t, err, errorMessage)
 }
 
+type testTelemetryClient struct {
+	events []telemetry.Event
+}
+
+func (cli *testTelemetryClient) Track(event telemetry.Event) error {
+	cli.events = append(cli.events, event)
+	return nil
+}
+
+func (cli *testTelemetryClient) Close() error { return nil }
+
+func TestTelemetry(t *testing.T) {
+	telemetryClient := testTelemetryClient{make([]telemetry.Event, 0)}
+	// Test server
+	var serverHandler http.HandlerFunc = func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusOK)
+		_, _ = w.Write([]byte(`[{"id":"id", "name":"name"}]`))
+	}
+	server := httptest.NewServer(serverHandler)
+	defer server.Close()
+
+	// Test command
+	config := &settings.Config{
+		Token:      "testtoken",
+		HTTPClient: http.DefaultClient,
+		Host:       server.URL,
+	}
+	cmd := NewInfoCommand(config, nil)
+	cmd.SetArgs([]string{"org"})
+	ctx := cmd.Context()
+	if ctx == nil {
+		ctx = context.Background()
+	}
+	cmd.SetContext(telemetry.NewContext(ctx, &telemetryClient))
+
+	// Execute
+	err := cmd.Execute()
+
+	assert.NilError(t, err)
+
+	// Read the telemetry events and compare them
+	assert.DeepEqual(t, telemetryClient.events, []telemetry.Event{
+		telemetry.CreateInfoEvent(telemetry.CommandInfo{
+			Name:      "org",
+			LocalArgs: map[string]string{"help": "false"},
+		}, nil),
+	})
+}
+
 func defaultValidator(cmd *cobra.Command, args []string) error {
 	return nil
 }
@@ -115,9 +166,10 @@ func scaffoldCMD(
 	validator validator.Validator,
 ) (*cobra.Command, *bytes.Buffer, *bytes.Buffer) {
 	config := &settings.Config{
-		Token:      "testtoken",
-		HTTPClient: http.DefaultClient,
-		Host:       baseURL,
+		Token:               "testtoken",
+		HTTPClient:          http.DefaultClient,
+		Host:                baseURL,
+		IsTelemetryDisabled: true,
 	}
 	cmd := NewInfoCommand(config, validator)
 
diff --git a/cmd/namespace.go b/cmd/namespace.go
index 0e5fb8cc5..37cf6cbab 100644
--- a/cmd/namespace.go
+++ b/cmd/namespace.go
@@ -8,6 +8,7 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/api/graphql"
 	"github.com/CircleCI-Public/circleci-cli/prompt"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/google/uuid"
 	"github.com/spf13/cobra"
 )
@@ -74,7 +75,14 @@ Please note that at this time all namespaces created in the registry are world-r
 				}
 			}
 
-			return createNamespace(cmd, opts)
+			err := createNamespace(cmd, opts)
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateNamespaceEvent(telemetry.GetCommandInformation(cmd, true)))
+			}
+
+			return err
 		},
 		Args:        cobra.RangeArgs(1, 3),
 		Annotations: make(map[string]string),
diff --git a/cmd/namespace_test.go b/cmd/namespace_test.go
index 189e4901e..216817c96 100644
--- a/cmd/namespace_test.go
+++ b/cmd/namespace_test.go
@@ -6,6 +6,7 @@ import (
 	"os/exec"
 
 	"github.com/CircleCI-Public/circleci-cli/clitest"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
 	"github.com/onsi/gomega/gbytes"
@@ -27,6 +28,42 @@ var _ = Describe("Namespace integration tests", func() {
 		tempSettings.Close()
 	})
 
+	Describe("telemetry", func() {
+		It("sends expected event", func() {
+			command = exec.Command(pathCLI,
+				"namespace", "create",
+				"--skip-update-check",
+				"--token", token,
+				"--host", tempSettings.TestServer.URL(),
+				"--integration-testing",
+				"foo-ns",
+				"--org-id", `"bb604b45-b6b0-4b81-ad80-796f15eddf87"`,
+			)
+			command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+
+			tempSettings.TestServer.AppendHandlers(func(res http.ResponseWriter, req *http.Request) {
+				res.WriteHeader(http.StatusOK)
+				_, _ = res.Write([]byte(`{"data":{"organization":{"name":"test-org","id":"bb604b45-b6b0-4b81-ad80-796f15eddf87"}}}`))
+			})
+
+			session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+			Expect(err).ShouldNot(HaveOccurred())
+			Eventually(session).Should(gexec.Exit(0))
+
+			clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+				telemetry.CreateNamespaceEvent(telemetry.CommandInfo{
+					Name: "create",
+					LocalArgs: map[string]string{
+						"help":                "false",
+						"integration-testing": "true",
+						"no-prompt":           "false",
+						"org-id":              "\"bb604b45-b6b0-4b81-ad80-796f15eddf87\"",
+					},
+				}),
+			})
+		})
+	})
+
 	Context("create, with interactive prompts", func() {
 		Describe("registering a namespace with orgID", func() {
 			BeforeEach(func() {
diff --git a/cmd/open.go b/cmd/open.go
index 6f1772b1d..2d9183550 100644
--- a/cmd/open.go
+++ b/cmd/open.go
@@ -6,6 +6,8 @@ import (
 	"strings"
 
 	"github.com/CircleCI-Public/circleci-cli/git"
+	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/pkg/browser"
 	"github.com/pkg/errors"
 	"github.com/spf13/cobra"
@@ -13,7 +15,7 @@ import (
 
 // errorMessage string containing the error message displayed in both the open command and the follow command
 var errorMessage = `
-This command is intended to be run from a git repository with a remote named 'origin' that is hosted on Github or Bitbucket only. 
+This command is intended to be run from a git repository with a remote named 'origin' that is hosted on Github or Bitbucket only.
 We are not currently supporting any other hosts.`
 
 // projectUrl uses the provided values to create the url to open
@@ -39,12 +41,19 @@ func openProjectInBrowser() error {
 }
 
 // newOpenCommand creates the cli command open
-func newOpenCommand() *cobra.Command {
+func newOpenCommand(config *settings.Config) *cobra.Command {
 	openCommand := &cobra.Command{
 		Use:   "open",
 		Short: "Open the current project in the browser.",
-		RunE: func(_ *cobra.Command, _ []string) error {
-			return openProjectInBrowser()
+		RunE: func(cmd *cobra.Command, _ []string) error {
+			err := openProjectInBrowser()
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateOpenEvent(err))
+			}
+
+			return err
 		},
 	}
 	return openCommand
diff --git a/cmd/orb.go b/cmd/orb.go
index d7a011eb3..8a82fe60a 100644
--- a/cmd/orb.go
+++ b/cmd/orb.go
@@ -26,6 +26,7 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/prompt"
 	"github.com/CircleCI-Public/circleci-cli/references"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/CircleCI-Public/circleci-cli/version"
 	"github.com/fatih/color"
 	"github.com/pkg/errors"
@@ -389,6 +390,11 @@ Please note that at this time all orbs created in the registry are world-readabl
 			opts.args = args
 			opts.cl = graphql.NewClient(config.HTTPClient, config.Host, config.Endpoint, config.Token, config.Debug)
 
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateOrbEvent(telemetry.GetCommandInformation(cmd, true)))
+			}
+
 			// PersistentPreRunE overwrites the inherited persistent hook from rootCmd
 			// So we explicitly call it here to retain that behavior.
 			// As of writing this comment, that is only for daily update checks.
diff --git a/cmd/orb_test.go b/cmd/orb_test.go
index 4804d1d6a..9d26392d7 100644
--- a/cmd/orb_test.go
+++ b/cmd/orb_test.go
@@ -16,6 +16,7 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/api"
 	"github.com/CircleCI-Public/circleci-cli/api/graphql"
 	"github.com/CircleCI-Public/circleci-cli/clitest"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/ginkgo/extensions/table"
 	. "github.com/onsi/gomega"
@@ -23,6 +24,57 @@ import (
 	"github.com/onsi/gomega/gexec"
 )
 
+var _ = Describe("Orb telemetry", func() {
+	var (
+		command      *exec.Cmd
+		orb          *clitest.TmpFile
+		tempSettings *clitest.TempSettings
+	)
+
+	BeforeEach(func() {
+		tempSettings = clitest.WithTempSettings()
+		orb = clitest.OpenTmpFile(tempSettings.Home, "orb.yml")
+		command = exec.Command(pathCLI,
+			"orb", "validate", orb.Path,
+			"--skip-update-check",
+			"--token", "token",
+			"--host", tempSettings.TestServer.URL(),
+		)
+		command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+	})
+
+	AfterEach(func() {
+		orb.Close()
+		tempSettings.Close()
+	})
+
+	It("works", func() {
+		orb.Write([]byte(`{}`))
+
+		mockOrbIntrospection(true, "", tempSettings)
+
+		tempSettings.TestServer.AppendHandlers(func(res http.ResponseWriter, req *http.Request) {
+			res.WriteHeader(http.StatusOK)
+			_, _ = res.Write([]byte(`{"orbConfig": {"sourceYaml": "{}", "valid": true, "errors": []} }`))
+		})
+
+		session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+		Expect(err).ShouldNot(HaveOccurred())
+		Eventually(session).Should(gexec.Exit(0))
+
+		clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+			telemetry.CreateOrbEvent(telemetry.CommandInfo{
+				Name: "validate",
+				LocalArgs: map[string]string{
+					"org-slug": "",
+					"help":     "false",
+					"org-id":   "",
+				},
+			}),
+		})
+	})
+})
+
 var _ = Describe("Orb integration tests", func() {
 	Describe("Orb help text", func() {
 		It("shows a link to the docs", func() {
diff --git a/cmd/policy/policy.go b/cmd/policy/policy.go
index 6ccab181c..19147fbc3 100644
--- a/cmd/policy/policy.go
+++ b/cmd/policy/policy.go
@@ -26,15 +26,27 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/api/rest"
 	"github.com/CircleCI-Public/circleci-cli/cmd/validator"
 	"github.com/CircleCI-Public/circleci-cli/config"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+
 	"github.com/CircleCI-Public/circleci-cli/settings"
 )
 
 // NewCommand creates the root policy command with all policy subcommands attached.
 func NewCommand(globalConfig *settings.Config, preRunE validator.Validator) *cobra.Command {
 	cmd := &cobra.Command{
-		Use:               "policy",
-		PersistentPreRunE: preRunE,
-		Short:             "Manage security policies",
+		Use: "policy",
+		PersistentPreRunE: func(cmd *cobra.Command, args []string) error {
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreatePolicyEvent(telemetry.GetCommandInformation(cmd, true)))
+			}
+
+			if preRunE != nil {
+				return preRunE(cmd, args)
+			}
+			return nil
+		},
+		Short: "Manage security policies",
 		Long: `Policies ensures security of build configs via security policy management framework.
 This group of commands allows the management of polices to be verified against build configs.`,
 	}
diff --git a/cmd/policy/policy_test.go b/cmd/policy/policy_test.go
index 227a6a66d..d4c503afc 100644
--- a/cmd/policy/policy_test.go
+++ b/cmd/policy/policy_test.go
@@ -57,7 +57,7 @@ func TestPushPolicyWithPrompt(t *testing.T) {
 	}))
 	defer svr.Close()
 
-	config := &settings.Config{Token: "testtoken", HTTPClient: http.DefaultClient}
+	config := &settings.Config{Token: "testtoken", HTTPClient: http.DefaultClient, IsTelemetryDisabled: true}
 	cmd := NewCommand(config, nil)
 
 	buffer := makeSafeBuffer()
@@ -1389,10 +1389,11 @@ func TestTestRunner(t *testing.T) {
 
 func makeCMD(circleHost string, token string) (*cobra.Command, *bytes.Buffer, *bytes.Buffer) {
 	config := &settings.Config{
-		Host:         circleHost,
-		Token:        token,
-		RestEndpoint: "/api/v2",
-		HTTPClient:   http.DefaultClient,
+		Host:                circleHost,
+		Token:               token,
+		RestEndpoint:        "/api/v2",
+		HTTPClient:          http.DefaultClient,
+		IsTelemetryDisabled: true,
 	}
 
 	cmd := NewCommand(config, nil)
diff --git a/cmd/root.go b/cmd/root.go
index 942278c69..05e028a99 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -1,6 +1,7 @@
 package cmd
 
 import (
+	"context"
 	"fmt"
 	"log"
 	"os"
@@ -14,6 +15,7 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/data"
 	"github.com/CircleCI-Public/circleci-cli/md_docs"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/CircleCI-Public/circleci-cli/version"
 	"github.com/charmbracelet/lipgloss"
 	"github.com/spf13/cobra"
@@ -36,16 +38,23 @@ var rootOptions *settings.Config
 // rootTokenFromFlag stores the value passed in through the flag --token
 var rootTokenFromFlag string
 
-// Execute adds all child commands to rootCmd and
-// sets flags appropriately. This function is called
-// by main.main(). It only needs to happen once to
-// the rootCmd.
-func Execute() {
+// Execute adds all child commands to rootCmd, sets the flags appropriately
+// and put the telemetry client in the command context. This function is
+// called by main.main(). It only needs to happen once to the rootCmd
+func Execute() error {
 	header.SetCommandStr(CommandStr())
 	command := MakeCommands()
-	if err := command.Execute(); err != nil {
-		os.Exit(-1)
+
+	telemetryClient := CreateTelemetry(rootOptions)
+	defer telemetryClient.Close()
+
+	cmdContext := command.Context()
+	if cmdContext == nil {
+		cmdContext = context.Background()
 	}
+	command.SetContext(telemetry.NewContext(cmdContext, telemetryClient))
+
+	return command.Execute()
 }
 
 // Returns a string (e.g. "circleci context list") indicating what
@@ -123,7 +132,7 @@ func MakeCommands() *cobra.Command {
 		Use:   "circleci",
 		Long:  longHelp,
 		Short: rootHelpShort(rootOptions),
-		PersistentPreRunE: func(_ *cobra.Command, _ []string) error {
+		PersistentPreRunE: func(cmd *cobra.Command, _ []string) error {
 			return rootCmdPreRun(rootOptions)
 		},
 	}
@@ -144,7 +153,7 @@ func MakeCommands() *cobra.Command {
 		return validateToken(rootOptions)
 	}
 
-	rootCmd.AddCommand(newOpenCommand())
+	rootCmd.AddCommand(newOpenCommand(rootOptions))
 	rootCmd.AddCommand(newTestsCommand())
 	rootCmd.AddCommand(newContextCommand(rootOptions))
 	rootCmd.AddCommand(project.NewProjectCommand(rootOptions, validator))
@@ -173,8 +182,9 @@ func MakeCommands() *cobra.Command {
 	rootCmd.AddCommand(newStepCommand(rootOptions))
 	rootCmd.AddCommand(newSwitchCommand(rootOptions))
 	rootCmd.AddCommand(newAdminCommand(rootOptions))
-	rootCmd.AddCommand(newCompletionCommand())
+	rootCmd.AddCommand(newCompletionCommand(rootOptions))
 	rootCmd.AddCommand(newEnvCmd())
+	rootCmd.AddCommand(newTelemetryCommand(rootOptions))
 
 	flags := rootCmd.PersistentFlags()
 
@@ -184,8 +194,9 @@ func MakeCommands() *cobra.Command {
 	flags.StringVar(&rootOptions.Endpoint, "endpoint", rootOptions.Endpoint, "URI to your CircleCI GraphQL API endpoint")
 	flags.StringVar(&rootOptions.GitHubAPI, "github-api", "https://api.github.com/", "Change the default endpoint to GitHub API for retrieving updates")
 	flags.BoolVar(&rootOptions.SkipUpdateCheck, "skip-update-check", skipUpdateByDefault(), "Skip the check for updates check run before every command.")
+	flags.StringVar(&rootOptions.MockTelemetry, "mock-telemetry", "", "The path where telemetry must be written")
 
-	hidden := []string{"github-api", "debug", "endpoint"}
+	hidden := []string{"github-api", "debug", "endpoint", "mock-telemetry"}
 
 	for _, f := range hidden {
 		if err := flags.MarkHidden(f); err != nil {
@@ -227,6 +238,7 @@ func rootCmdPreRun(rootOptions *settings.Config) error {
 		fmt.Printf("Error checking for updates: %s\n", err)
 		fmt.Printf("Please contact support.\n\n")
 	}
+
 	return nil
 }
 
diff --git a/cmd/root_test.go b/cmd/root_test.go
index c23982b18..d05a85419 100644
--- a/cmd/root_test.go
+++ b/cmd/root_test.go
@@ -16,7 +16,7 @@ var _ = Describe("Root", func() {
 	Describe("subcommands", func() {
 		It("can create commands", func() {
 			commands := cmd.MakeCommands()
-			Expect(len(commands.Commands())).To(Equal(24))
+			Expect(len(commands.Commands())).To(Equal(25))
 		})
 	})
 
@@ -52,8 +52,7 @@ var _ = Describe("Root", func() {
 
 			Eventually(session.Err.Contents()).Should(BeEmpty())
 
-			Eventually(session.Out).Should(gbytes.Say("update      This command is unavailable on your platform"))
-
+			Eventually(session.Out).Should(gbytes.Say("update\\s+This command is unavailable on your platform"))
 			Eventually(session).Should(gexec.Exit(0))
 		})
 
@@ -92,8 +91,7 @@ var _ = Describe("Root", func() {
 
 			Eventually(session.Err.Contents()).Should(BeEmpty())
 
-			Eventually(session.Out).Should(gbytes.Say("update      Update the tool to the latest version"))
-
+			Eventually(session.Out).Should(gbytes.Say("update\\s+Update the tool to the latest version"))
 			Eventually(session).Should(gexec.Exit(0))
 		})
 	})
diff --git a/cmd/runner/instance.go b/cmd/runner/instance.go
index 28f260937..a4da71338 100644
--- a/cmd/runner/instance.go
+++ b/cmd/runner/instance.go
@@ -9,6 +9,7 @@ import (
 
 	"github.com/CircleCI-Public/circleci-cli/api/runner"
 	"github.com/CircleCI-Public/circleci-cli/cmd/validator"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 )
 
 func newRunnerInstanceCommand(o *runnerOpts, preRunE validator.Validator) *cobra.Command {
@@ -25,7 +26,17 @@ func newRunnerInstanceCommand(o *runnerOpts, preRunE validator.Validator) *cobra
 		Aliases: []string{"ls"},
 		Args:    cobra.ExactArgs(1),
 		PreRunE: preRunE,
-		RunE: func(_ *cobra.Command, args []string) error {
+		RunE: func(cmd *cobra.Command, args []string) error {
+			var err error
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				// We defer the call to be sure the `err` has been filled
+				defer (func() {
+					_ = telemetryClient.Track(telemetry.CreateRunnerInstanceEvent(telemetry.GetCommandInformation(cmd, true), err))
+				})()
+			}
+
 			runners, err := o.r.GetRunnerInstances(args[0])
 			if err != nil {
 				return err
diff --git a/cmd/runner/resource_class.go b/cmd/runner/resource_class.go
index 1a727737e..4b68b37ae 100644
--- a/cmd/runner/resource_class.go
+++ b/cmd/runner/resource_class.go
@@ -8,12 +8,19 @@ import (
 
 	"github.com/CircleCI-Public/circleci-cli/api/runner"
 	"github.com/CircleCI-Public/circleci-cli/cmd/validator"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 )
 
 func newResourceClassCommand(o *runnerOpts, preRunE validator.Validator) *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "resource-class",
 		Short: "Operate on runner resource-classes",
+		PersistentPreRun: func(cmd *cobra.Command, _ []string) {
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateRunnerResourceClassEvent(telemetry.GetCommandInformation(cmd, true)))
+			}
+		},
 	}
 
 	genToken := false
diff --git a/cmd/runner/telemetry_test.go b/cmd/runner/telemetry_test.go
new file mode 100644
index 000000000..dcd12874c
--- /dev/null
+++ b/cmd/runner/telemetry_test.go
@@ -0,0 +1,62 @@
+package runner
+
+import (
+	"bytes"
+	"context"
+	"testing"
+
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+	"gotest.tools/v3/assert"
+)
+
+type testTelemetryClient struct {
+	events []telemetry.Event
+}
+
+func (c *testTelemetryClient) Track(event telemetry.Event) error {
+	c.events = append(c.events, event)
+	return nil
+}
+
+func (c *testTelemetryClient) Close() error { return nil }
+
+func Test_RunnerTelemetry(t *testing.T) {
+	t.Run("resource-class", func(t *testing.T) {
+		telemetryClient := &testTelemetryClient{make([]telemetry.Event, 0)}
+		runner := runnerMock{}
+		cmd := newResourceClassCommand(&runnerOpts{r: &runner}, nil)
+		stdout := new(bytes.Buffer)
+		stderr := new(bytes.Buffer)
+		cmd.SetOut(stdout)
+		cmd.SetErr(stderr)
+		ctx := cmd.Context()
+		if ctx == nil {
+			ctx = context.Background()
+		}
+		cmd.SetContext(telemetry.NewContext(ctx, telemetryClient))
+
+		defer runner.reset()
+		defer stdout.Reset()
+		defer stderr.Reset()
+
+		cmd.SetArgs([]string{
+			"create",
+			"my-namespace/my-other-resource-class",
+			"my-description",
+			"--generate-token",
+		})
+
+		err := cmd.Execute()
+		assert.NilError(t, err)
+
+		assert.DeepEqual(t, telemetryClient.events, []telemetry.Event{
+			telemetry.CreateRunnerResourceClassEvent(telemetry.CommandInfo{
+				Name: "create",
+				LocalArgs: map[string]string{
+					"generate-token": "true",
+					"help":           "false",
+				},
+			}),
+		})
+	})
+}
diff --git a/cmd/runner/token.go b/cmd/runner/token.go
index 4771b37e9..60edcbf6e 100644
--- a/cmd/runner/token.go
+++ b/cmd/runner/token.go
@@ -4,6 +4,7 @@ import (
 	"time"
 
 	"github.com/CircleCI-Public/circleci-cli/cmd/validator"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/olekukonko/tablewriter"
 	"github.com/spf13/cobra"
 )
@@ -12,6 +13,12 @@ func newTokenCommand(o *runnerOpts, preRunE validator.Validator) *cobra.Command
 	cmd := &cobra.Command{
 		Use:   "token",
 		Short: "Operate on runner tokens",
+		PersistentPreRun: func(cmd *cobra.Command, _ []string) {
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateRunnerResourceClassEvent(telemetry.GetCommandInformation(cmd, true)))
+			}
+		},
 	}
 
 	cmd.AddCommand(&cobra.Command{
diff --git a/cmd/setup.go b/cmd/setup.go
index 6a2d068b5..efc30288a 100644
--- a/cmd/setup.go
+++ b/cmd/setup.go
@@ -7,6 +7,7 @@ import (
 	"github.com/CircleCI-Public/circleci-cli/api/graphql"
 	"github.com/CircleCI-Public/circleci-cli/prompt"
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/pkg/errors"
 	"github.com/spf13/cobra"
 )
@@ -123,7 +124,13 @@ func newSetupCommand(config *settings.Config) *cobra.Command {
 			opts.args = args
 			opts.cl = graphql.NewClient(config.HTTPClient, config.Host, config.Endpoint, config.Token, config.Debug)
 		},
-		RunE: func(_ *cobra.Command, _ []string) error {
+		RunE: func(cmd *cobra.Command, _ []string) error {
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				// We defer the call to make sure the `opts.cfg.Host` has been filled
+				defer (func() { _ = telemetryClient.Track(telemetry.CreateSetupEvent(opts.cfg.Host != defaultHost)) })()
+			}
+
 			if opts.integrationTesting {
 				opts.tty = setupTestUI{
 					host:            "boondoggle",
diff --git a/cmd/setup_test.go b/cmd/setup_test.go
index 591a6197d..8ae09473c 100644
--- a/cmd/setup_test.go
+++ b/cmd/setup_test.go
@@ -9,12 +9,44 @@ import (
 	"runtime"
 
 	"github.com/CircleCI-Public/circleci-cli/clitest"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
 	"github.com/onsi/gomega/gbytes"
 	"github.com/onsi/gomega/gexec"
 )
 
+var _ = Describe("Setup telemetry", func() {
+	var (
+		command      *exec.Cmd
+		tempSettings *clitest.TempSettings
+	)
+
+	BeforeEach(func() {
+		tempSettings = clitest.WithTempSettings()
+		command = commandWithHome(pathCLI, tempSettings.Home,
+			"setup",
+			"--integration-testing",
+			"--skip-update-check",
+		)
+		command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+	})
+
+	AfterEach(func() {
+		tempSettings.Close()
+	})
+
+	It("should send telemetry event", func() {
+		session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+		Expect(err).ShouldNot(HaveOccurred())
+
+		Eventually(session).Should(gexec.Exit(0))
+		clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+			telemetry.CreateSetupEvent(true),
+		})
+	})
+})
+
 var _ = Describe("Setup with prompts", func() {
 	var (
 		command      *exec.Cmd
diff --git a/cmd/telemetry.go b/cmd/telemetry.go
new file mode 100644
index 000000000..85e231f74
--- /dev/null
+++ b/cmd/telemetry.go
@@ -0,0 +1,79 @@
+package cmd
+
+import (
+	"os"
+
+	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+	"github.com/pkg/errors"
+	"github.com/spf13/cobra"
+)
+
+func newTelemetryCommand(config *settings.Config) *cobra.Command {
+	apiClient := CreateAPIClient(config)
+
+	telemetryEnable := &cobra.Command{
+		Use:   "enable",
+		Short: "Allow telemetry events to be sent to CircleCI servers",
+		RunE: func(cmd *cobra.Command, _ []string) error {
+			err := setIsTelemetryActive(apiClient, true)
+			if telemetryClient, ok := telemetry.FromContext(cmd.Context()); ok {
+				_ = telemetryClient.Track(telemetry.CreateChangeTelemetryStatusEvent("enabled", "telemetry-command", err))
+			}
+			return err
+		},
+		Args: cobra.ExactArgs(0),
+	}
+
+	telemetryDisable := &cobra.Command{
+		Use:   "disable",
+		Short: "Make sure no telemetry events is sent to CircleCI servers",
+		RunE: func(cmd *cobra.Command, _ []string) error {
+			err := setIsTelemetryActive(apiClient, false)
+			if telemetryClient, ok := telemetry.FromContext(cmd.Context()); ok {
+				_ = telemetryClient.Track(telemetry.CreateChangeTelemetryStatusEvent("disabled", "telemetry-command", err))
+			}
+			return err
+		},
+		Args: cobra.ExactArgs(0),
+	}
+
+	telemetryCommand := &cobra.Command{
+		Use:   "telemetry",
+		Short: "Configure telemetry preferences",
+		Long: `Configure telemetry preferences.
+
+Note: If you have not configured your telemetry preferences and call the CLI with a closed stdin, telemetry will be disabled`,
+	}
+
+	telemetryCommand.AddCommand(telemetryEnable)
+	telemetryCommand.AddCommand(telemetryDisable)
+
+	return telemetryCommand
+}
+
+func setIsTelemetryActive(apiClient TelemetryAPIClient, isActive bool) error {
+	settings := settings.TelemetrySettings{}
+	if err := settings.Load(); err != nil && !os.IsNotExist(err) {
+		return errors.Wrap(err, "Loading telemetry configuration")
+	}
+
+	settings.HasAnsweredPrompt = true
+	settings.IsEnabled = isActive
+
+	if settings.UniqueID == "" {
+		settings.UniqueID = CreateUUID()
+	}
+
+	if settings.UserID == "" {
+		if myID, err := apiClient.GetMyUserId(); err == nil {
+			settings.UserID = myID
+		}
+	}
+
+	if err := settings.Write(); err != nil {
+		return errors.Wrap(err, "Writing telemetry configuration")
+	}
+
+	return nil
+}
diff --git a/cmd/telemetry_test.go b/cmd/telemetry_test.go
new file mode 100644
index 000000000..fb8d334db
--- /dev/null
+++ b/cmd/telemetry_test.go
@@ -0,0 +1,58 @@
+package cmd_test
+
+import (
+	"fmt"
+	"os/exec"
+
+	"github.com/CircleCI-Public/circleci-cli/clitest"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+	"github.com/onsi/gomega/gexec"
+
+	. "github.com/onsi/ginkgo"
+	. "github.com/onsi/gomega"
+)
+
+var _ = Describe("Telemetry events on telemetry commands", func() {
+	var (
+		tempSettings *clitest.TempSettings
+		command      *exec.Cmd
+	)
+
+	BeforeEach(func() {
+		tempSettings = clitest.WithTempSettings()
+	})
+
+	AfterEach(func() {
+		tempSettings.Close()
+	})
+
+	Describe("telemetry enable", func() {
+		It("should send an event", func() {
+			command = exec.Command(pathCLI, "telemetry", "enable")
+			command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+
+			session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+			Expect(err).ShouldNot(HaveOccurred())
+			Eventually(session).Should(gexec.Exit(0))
+
+			clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+				telemetry.CreateChangeTelemetryStatusEvent("enabled", "telemetry-command", nil),
+			})
+		})
+	})
+
+	Describe("telemetry disable", func() {
+		It("should send an event", func() {
+			command = exec.Command(pathCLI, "telemetry", "disable")
+			command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+
+			session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+			Expect(err).ShouldNot(HaveOccurred())
+			Eventually(session).Should(gexec.Exit(0))
+
+			clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+				telemetry.CreateChangeTelemetryStatusEvent("disabled", "telemetry-command", nil),
+			})
+		})
+	})
+})
diff --git a/cmd/telemetry_unit_test.go b/cmd/telemetry_unit_test.go
new file mode 100644
index 000000000..468e1ce9d
--- /dev/null
+++ b/cmd/telemetry_unit_test.go
@@ -0,0 +1,143 @@
+package cmd
+
+import (
+	"path/filepath"
+	"testing"
+
+	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/spf13/afero"
+	"gotest.tools/v3/assert"
+)
+
+func TestSetIsTelemetryActive(t *testing.T) {
+	type args struct {
+		apiClient TelemetryAPIClient
+		isActive  bool
+		settings  *settings.TelemetrySettings
+	}
+	type want struct {
+		settings *settings.TelemetrySettings
+	}
+
+	type testCase struct {
+		name string
+		args args
+		want want
+	}
+
+	userId := "user-id"
+	uniqueId := "unique-id"
+
+	testCases := []testCase{
+		{
+			name: "Enabling telemetry with settings should just update the is active field",
+			args: args{
+				apiClient: telemetryTestAPIClient{},
+				isActive:  true,
+				settings: &settings.TelemetrySettings{
+					IsEnabled:         false,
+					HasAnsweredPrompt: true,
+					UniqueID:          uniqueId,
+					UserID:            userId,
+				},
+			},
+			want: want{
+				settings: &settings.TelemetrySettings{
+					IsEnabled:         true,
+					HasAnsweredPrompt: true,
+					UniqueID:          uniqueId,
+					UserID:            userId,
+				},
+			},
+		},
+		{
+			name: "Enabling telemetry without settings should fill the settings fields",
+			args: args{
+				apiClient: telemetryTestAPIClient{id: userId, err: nil},
+				isActive:  true,
+				settings:  nil,
+			},
+			want: want{
+				settings: &settings.TelemetrySettings{
+					IsEnabled:         true,
+					HasAnsweredPrompt: true,
+					UniqueID:          uniqueId,
+					UserID:            userId,
+				},
+			},
+		},
+		{
+			name: "Disabling telemetry with settings should just update the is active field",
+			args: args{
+				apiClient: telemetryTestAPIClient{},
+				isActive:  false,
+				settings: &settings.TelemetrySettings{
+					IsEnabled:         true,
+					HasAnsweredPrompt: true,
+					UniqueID:          uniqueId,
+					UserID:            userId,
+				},
+			},
+			want: want{
+				settings: &settings.TelemetrySettings{
+					IsEnabled:         false,
+					HasAnsweredPrompt: true,
+					UniqueID:          uniqueId,
+					UserID:            userId,
+				},
+			},
+		},
+		{
+			name: "Enabling telemetry without settings should fill the settings fields",
+			args: args{
+				apiClient: telemetryTestAPIClient{id: userId, err: nil},
+				isActive:  false,
+				settings:  nil,
+			},
+			want: want{
+				settings: &settings.TelemetrySettings{
+					IsEnabled:         false,
+					HasAnsweredPrompt: true,
+					UniqueID:          uniqueId,
+					UserID:            userId,
+				},
+			},
+		},
+	}
+
+	// Mock create UUID
+	oldUUIDCreate := CreateUUID
+	CreateUUID = func() string { return uniqueId }
+	defer (func() { CreateUUID = oldUUIDCreate })()
+
+	for _, tt := range testCases {
+		t.Run(tt.name, func(t *testing.T) {
+			// Mock FS
+			oldFS := settings.FS.Fs
+			settings.FS.Fs = afero.NewMemMapFs()
+			defer (func() { settings.FS.Fs = oldFS })()
+
+			if tt.args.settings != nil {
+				err := tt.args.settings.Write()
+				assert.NilError(t, err)
+			}
+
+			err := setIsTelemetryActive(tt.args.apiClient, tt.args.isActive)
+			assert.NilError(t, err)
+
+			exist, err := settings.FS.Exists(filepath.Join(settings.SettingsPath(), "telemetry.yml"))
+			assert.NilError(t, err)
+			if tt.want.settings == nil {
+				assert.Equal(t, exist, false)
+			} else {
+				assert.Equal(t, exist, true)
+
+				loadedSettings := &settings.TelemetrySettings{}
+				err := loadedSettings.Load()
+				assert.NilError(t, err)
+
+				assert.DeepEqual(t, tt.want.settings, loadedSettings)
+			}
+		})
+	}
+}
diff --git a/cmd/update.go b/cmd/update.go
index c43bf33d4..5ef2bcc44 100644
--- a/cmd/update.go
+++ b/cmd/update.go
@@ -5,6 +5,7 @@ import (
 	"time"
 
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/CircleCI-Public/circleci-cli/update"
 	"github.com/CircleCI-Public/circleci-cli/version"
 
@@ -28,8 +29,13 @@ func newUpdateCommand(config *settings.Config) *cobra.Command {
 	update := &cobra.Command{
 		Use:   "update",
 		Short: "Update the tool to the latest version",
-		PersistentPreRun: func(_ *cobra.Command, _ []string) {
+		PersistentPreRun: func(cmd *cobra.Command, _ []string) {
 			opts.cfg.SkipUpdateCheck = true
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateUpdateEvent(telemetry.GetCommandInformation(cmd, cmd.Name() != "update")))
+			}
 		},
 		PreRun: func(cmd *cobra.Command, args []string) {
 			opts.args = args
@@ -43,9 +49,6 @@ func newUpdateCommand(config *settings.Config) *cobra.Command {
 		Use:    "check",
 		Hidden: true,
 		Short:  "Check if there are any updates available",
-		PersistentPreRun: func(_ *cobra.Command, _ []string) {
-			opts.cfg.SkipUpdateCheck = true
-		},
 		PreRun: func(cmd *cobra.Command, args []string) {
 			opts.args = args
 			opts.dryRun = true
@@ -59,9 +62,6 @@ func newUpdateCommand(config *settings.Config) *cobra.Command {
 		Use:    "install",
 		Hidden: true,
 		Short:  "Update the tool to the latest version",
-		PersistentPreRun: func(_ *cobra.Command, _ []string) {
-			opts.cfg.SkipUpdateCheck = true
-		},
 		PreRun: func(cmd *cobra.Command, args []string) {
 			opts.args = args
 		},
@@ -74,9 +74,6 @@ func newUpdateCommand(config *settings.Config) *cobra.Command {
 		Use:    "build-agent",
 		Hidden: true,
 		Short:  "This command has no effect, and is kept for backwards compatibility",
-		PersistentPreRun: func(_ *cobra.Command, _ []string) {
-			opts.cfg.SkipUpdateCheck = true
-		},
 		PreRun: func(cmd *cobra.Command, args []string) {
 			opts.args = args
 		},
diff --git a/cmd/update_test.go b/cmd/update_test.go
index 431987119..6ed7aa5dd 100644
--- a/cmd/update_test.go
+++ b/cmd/update_test.go
@@ -1,11 +1,13 @@
 package cmd_test
 
 import (
+	"fmt"
 	"net/http"
 	"os/exec"
 	"path/filepath"
 
 	"github.com/CircleCI-Public/circleci-cli/clitest"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
 	"github.com/onsi/gomega/gbytes"
@@ -70,6 +72,69 @@ var _ = Describe("Update", func() {
 		tempSettings.Close()
 	})
 
+	Describe("telemetry", func() {
+		It("should send telemetry event when calling parent command", func() {
+			updateCLI, err := gexec.Build("github.com/CircleCI-Public/circleci-cli")
+			Expect(err).ShouldNot(HaveOccurred())
+
+			command = exec.Command(updateCLI,
+				"update",
+				"--github-api", tempSettings.TestServer.URL(),
+			)
+			command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+
+			assetBytes := golden.Get(GinkgoT(), filepath.FromSlash("update/foo.zip"))
+			assetResponse := string(assetBytes)
+
+			tempSettings.TestServer.AppendHandlers(
+				ghttp.CombineHandlers(
+					ghttp.VerifyRequest(http.MethodGet, "/repos/CircleCI-Public/circleci-cli/releases"),
+					ghttp.RespondWith(http.StatusOK, response),
+				),
+				ghttp.CombineHandlers(
+					ghttp.VerifyRequest(http.MethodGet, "/repos/CircleCI-Public/circleci-cli/releases/assets/1"),
+					ghttp.RespondWith(http.StatusOK, assetResponse),
+				),
+			)
+
+			session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+			Expect(err).ShouldNot(HaveOccurred())
+
+			Eventually(session).Should(gexec.Exit(0))
+			clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+				telemetry.CreateUpdateEvent(telemetry.CommandInfo{
+					Name: "update",
+					LocalArgs: map[string]string{
+						"check": "false",
+						"help":  "false",
+					},
+				}),
+			})
+		})
+
+		It("should send telemetry event when calling child command", func() {
+			command = exec.Command(pathCLI,
+				"update",
+				"check",
+				"--github-api", tempSettings.TestServer.URL(),
+			)
+			command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+			session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+			Expect(err).ShouldNot(HaveOccurred())
+
+			Eventually(session).Should(gexec.Exit(0))
+			clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+				telemetry.CreateUpdateEvent(telemetry.CommandInfo{
+					Name: "check",
+					LocalArgs: map[string]string{
+						"check": "false",
+						"help":  "false",
+					},
+				}),
+			})
+		})
+	})
+
 	Describe("update --check", func() {
 		BeforeEach(func() {
 			command = exec.Command(pathCLI,
diff --git a/cmd/version.go b/cmd/version.go
index 756e5e6ce..e2cd566ce 100644
--- a/cmd/version.go
+++ b/cmd/version.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 
 	"github.com/CircleCI-Public/circleci-cli/settings"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
 	"github.com/CircleCI-Public/circleci-cli/version"
 	"github.com/spf13/cobra"
 )
@@ -24,11 +25,18 @@ func newVersionCommand(config *settings.Config) *cobra.Command {
 		PersistentPreRun: func(_ *cobra.Command, _ []string) {
 			opts.cfg.SkipUpdateCheck = true
 		},
-		PreRun: func(cmd *cobra.Command, args []string) {
+		PreRun: func(_ *cobra.Command, args []string) {
 			opts.args = args
 		},
-		Run: func(_ *cobra.Command, _ []string) {
-			fmt.Printf("%s+%s (%s)\n", version.Version, version.Commit, version.PackageManager())
+		Run: func(cmd *cobra.Command, _ []string) {
+			version := fmt.Sprintf("%s+%s (%s)", version.Version, version.Commit, version.PackageManager())
+
+			telemetryClient, ok := telemetry.FromContext(cmd.Context())
+			if ok {
+				_ = telemetryClient.Track(telemetry.CreateVersionEvent(version))
+			}
+
+			fmt.Printf("%s\n", version)
 		},
 	}
 }
diff --git a/cmd/version_test.go b/cmd/version_test.go
new file mode 100644
index 000000000..e64cf051e
--- /dev/null
+++ b/cmd/version_test.go
@@ -0,0 +1,39 @@
+package cmd_test
+
+import (
+	"fmt"
+	"os/exec"
+
+	"github.com/CircleCI-Public/circleci-cli/clitest"
+	"github.com/CircleCI-Public/circleci-cli/telemetry"
+	. "github.com/onsi/ginkgo"
+	. "github.com/onsi/gomega"
+	"github.com/onsi/gomega/gexec"
+)
+
+var _ = Describe("Version telemetry", func() {
+	var (
+		command      *exec.Cmd
+		tempSettings *clitest.TempSettings
+	)
+
+	BeforeEach(func() {
+		tempSettings = clitest.WithTempSettings()
+		command = commandWithHome(pathCLI, tempSettings.Home, "version")
+		command.Env = append(command.Env, fmt.Sprintf("MOCK_TELEMETRY=%s", tempSettings.TelemetryDestPath))
+	})
+
+	AfterEach(func() {
+		tempSettings.Close()
+	})
+
+	It("should send a telemetry event", func() {
+		session, err := gexec.Start(command, GinkgoWriter, GinkgoWriter)
+		Expect(err).ShouldNot(HaveOccurred())
+
+		Eventually(session).Should(gexec.Exit(0))
+		clitest.CompareTelemetryEvent(tempSettings, []telemetry.Event{
+			telemetry.CreateVersionEvent("0.0.0-dev+dirty-local-tree (source)"),
+		})
+	})
+})
diff --git a/go.mod b/go.mod
index f305f8565..710386a9d 100644
--- a/go.mod
+++ b/go.mod
@@ -37,6 +37,8 @@ require (
 	github.com/charmbracelet/lipgloss v0.5.0
 	github.com/erikgeiser/promptkit v0.7.0
 	github.com/hexops/gotextdiff v1.0.3
+	github.com/segmentio/analytics-go v3.1.0+incompatible
+	github.com/spf13/afero v1.9.5
 	github.com/stretchr/testify v1.8.3
 	golang.org/x/exp v0.0.0-20230713183714-613f0c0eb8a1
 	golang.org/x/term v0.10.0
@@ -50,6 +52,7 @@ require (
 	github.com/agnivade/levenshtein v1.1.1 // indirect
 	github.com/atotto/clipboard v0.1.4 // indirect
 	github.com/beorn7/perks v1.0.1 // indirect
+	github.com/bmizerany/assert v0.0.0-20160611221934-b7ed37b82869 // indirect
 	github.com/cespare/xxhash/v2 v2.2.0 // indirect
 	github.com/charmbracelet/bubbles v0.11.0 // indirect
 	github.com/charmbracelet/bubbletea v0.21.0 // indirect
@@ -94,6 +97,7 @@ require (
 	github.com/prometheus/procfs v0.11.0 // indirect
 	github.com/rcrowley/go-metrics v0.0.0-20201227073835-cf1acfcdf475 // indirect
 	github.com/rivo/uniseg v0.2.0 // indirect
+	github.com/segmentio/backo-go v1.0.1 // indirect
 	github.com/sergi/go-diff v1.1.0 // indirect
 	github.com/sirupsen/logrus v1.9.3 // indirect
 	github.com/skeema/knownhosts v1.1.1 // indirect
@@ -101,6 +105,7 @@ require (
 	github.com/xanzy/ssh-agent v0.3.3 // indirect
 	github.com/xeipuuv/gojsonpointer v0.0.0-20190905194746-02993c407bfb // indirect
 	github.com/xeipuuv/gojsonreference v0.0.0-20180127040603-bd5ef7bd5415 // indirect
+	github.com/xtgo/uuid v0.0.0-20140804021211-a0b114877d4c // indirect
 	github.com/yashtewari/glob-intersection v0.2.0 // indirect
 	go.opentelemetry.io/otel v1.16.0 // indirect
 	go.opentelemetry.io/otel/metric v1.16.0 // indirect
diff --git a/go.sum b/go.sum
index 7ab560a5e..4d5d49640 100644
--- a/go.sum
+++ b/go.sum
@@ -1,5 +1,45 @@
+cloud.google.com/go v0.26.0/go.mod h1:aQUYkXzVsufM+DwF1aE+0xfcU+56JwCaLick0ClmMTw=
+cloud.google.com/go v0.34.0/go.mod h1:aQUYkXzVsufM+DwF1aE+0xfcU+56JwCaLick0ClmMTw=
+cloud.google.com/go v0.38.0/go.mod h1:990N+gfupTy94rShfmMCWGDn0LpTmnzTp2qbd1dvSRU=
+cloud.google.com/go v0.44.1/go.mod h1:iSa0KzasP4Uvy3f1mN/7PiObzGgflwredwwASm/v6AU=
+cloud.google.com/go v0.44.2/go.mod h1:60680Gw3Yr4ikxnPRS/oxxkBccT6SA1yMk63TGekxKY=
+cloud.google.com/go v0.44.3/go.mod h1:60680Gw3Yr4ikxnPRS/oxxkBccT6SA1yMk63TGekxKY=
+cloud.google.com/go v0.45.1/go.mod h1:RpBamKRgapWJb87xiFSdk4g1CME7QZg3uwTez+TSTjc=
+cloud.google.com/go v0.46.3/go.mod h1:a6bKKbmY7er1mI7TEI4lsAkts/mkhTSZK8w33B4RAg0=
+cloud.google.com/go v0.50.0/go.mod h1:r9sluTvynVuxRIOHXQEHMFffphuXHOMZMycpNR5e6To=
+cloud.google.com/go v0.52.0/go.mod h1:pXajvRH/6o3+F9jDHZWQ5PbGhn+o8w9qiu/CffaVdO4=
+cloud.google.com/go v0.53.0/go.mod h1:fp/UouUEsRkN6ryDKNW/Upv/JBKnv6WDthjR6+vze6M=
+cloud.google.com/go v0.54.0/go.mod h1:1rq2OEkV3YMf6n/9ZvGWI3GWw0VoqH/1x2nd8Is/bPc=
+cloud.google.com/go v0.56.0/go.mod h1:jr7tqZxxKOVYizybht9+26Z/gUq7tiRzu+ACVAMbKVk=
+cloud.google.com/go v0.57.0/go.mod h1:oXiQ6Rzq3RAkkY7N6t3TcE6jE+CIBBbA36lwQ1JyzZs=
+cloud.google.com/go v0.62.0/go.mod h1:jmCYTdRCQuc1PHIIJ/maLInMho30T/Y0M4hTdTShOYc=
+cloud.google.com/go v0.65.0/go.mod h1:O5N8zS7uWy9vkA9vayVHs65eM1ubvY4h553ofrNHObY=
+cloud.google.com/go v0.72.0/go.mod h1:M+5Vjvlc2wnp6tjzE102Dw08nGShTscUx2nZMufOKPI=
+cloud.google.com/go v0.74.0/go.mod h1:VV1xSbzvo+9QJOxLDaJfTjx5e+MePCpCWwvftOeQmWk=
+cloud.google.com/go v0.75.0/go.mod h1:VGuuCn7PG0dwsd5XPVm2Mm3wlh3EL55/79EKB6hlPTY=
+cloud.google.com/go/bigquery v1.0.1/go.mod h1:i/xbL2UlR5RvWAURpBYZTtm/cXjCha9lbfbpx4poX+o=
+cloud.google.com/go/bigquery v1.3.0/go.mod h1:PjpwJnslEMmckchkHFfq+HTD2DmtT67aNFKH1/VBDHE=
+cloud.google.com/go/bigquery v1.4.0/go.mod h1:S8dzgnTigyfTmLBfrtrhyYhwRxG72rYxvftPBK2Dvzc=
+cloud.google.com/go/bigquery v1.5.0/go.mod h1:snEHRnqQbz117VIFhE8bmtwIDY80NLUZUMb4Nv6dBIg=
+cloud.google.com/go/bigquery v1.7.0/go.mod h1://okPTzCYNXSlb24MZs83e2Do+h+VXtc4gLoIoXIAPc=
+cloud.google.com/go/bigquery v1.8.0/go.mod h1:J5hqkt3O0uAFnINi6JXValWIb1v0goeZM77hZzJN/fQ=
+cloud.google.com/go/datastore v1.0.0/go.mod h1:LXYbyblFSglQ5pkeyhO+Qmw7ukd3C+pD7TKLgZqpHYE=
+cloud.google.com/go/datastore v1.1.0/go.mod h1:umbIZjpQpHh4hmRpGhH4tLFup+FVzqBi1b3c64qFpCk=
+cloud.google.com/go/pubsub v1.0.1/go.mod h1:R0Gpsv3s54REJCy4fxDixWD93lHJMoZTyQ2kNxGRt3I=
+cloud.google.com/go/pubsub v1.1.0/go.mod h1:EwwdRX2sKPjnvnqCa270oGRyludottCI76h+R3AArQw=
+cloud.google.com/go/pubsub v1.2.0/go.mod h1:jhfEVHT8odbXTkndysNHCcx0awwzvfOlguIAii9o8iA=
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@@ -32,11 +72,14 @@ github.com/beorn7/perks v1.0.1 h1:VlbKKnNfV8bJzeqoa4cOKqO6bYr3WgKZxO8Z16+hsOM=
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@@ -47,9 +90,16 @@ github.com/charmbracelet/bubbletea v0.21.0/go.mod h1:GgmJMec61d08zXsOhqRC/AiOx4K
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@@ -65,6 +115,12 @@ github.com/dustin/go-humanize v1.0.1 h1:GzkhY7T5VNhEkwH0PVJgjz+fX1rhBrR7pRT3mDkp
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@@ -87,6 +143,9 @@ github.com/go-git/go-billy/v5 v5.4.1/go.mod h1:vjbugF6Fz7JIflbVpl1hJsGjSHNltrSw4
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@@ -98,26 +157,51 @@ github.com/go-task/slim-sprig v0.0.0-20210107165309-348f09dbbbc0/go.mod h1:fyg78
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@@ -125,17 +209,39 @@ github.com/google/go-github v15.0.0+incompatible h1:jlPg2Cpsxb/FyEV/MFiIE9tW/2RA
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@@ -144,11 +250,15 @@ github.com/inconshreveable/mousetrap v1.1.0 h1:wN+x4NVGpMsO7ErUn/mUI3vEoE6Jt13X2
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@@ -220,10 +330,12 @@ github.com/pkg/browser v0.0.0-20180916011732-0a3d74bf9ce4/go.mod h1:4OwLy04Bl9Ef
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@@ -237,10 +349,15 @@ github.com/rhysd/go-github-selfupdate v0.0.0-20180520142321-41c1bbb0804a/go.mod
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@@ -248,6 +365,8 @@ github.com/sirupsen/logrus v1.9.3 h1:dueUQJ1C2q9oE3F7wvmSGAaVtTmUizReu6fjN8uqzbQ
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@@ -273,10 +392,21 @@ github.com/xeipuuv/gojsonpointer v0.0.0-20190905194746-02993c407bfb h1:zGWFAtiMc
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@@ -292,26 +422,87 @@ go.opentelemetry.io/otel/trace v1.16.0 h1:8JRpaObFoW0pxuVPapkgH8UhHQj+bJW8jJsCZE
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 google.golang.org/genproto/googleapis/api v0.0.0-20230724170836-66ad5b6ff146 h1:P60zJj7Yxq1VhZIxpRO7A5lDFyy07D6Dqa+HCixuFBM=
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 google.golang.org/protobuf v1.26.0-rc.1/go.mod h1:jlhhOSvTdKEhbULTjvd4ARK9grFBp09yW+WbY/TyQbw=
 google.golang.org/protobuf v1.26.0/go.mod h1:9q0QmTI4eRPtz6boOQmLYwt+qCgq0jsYwAQnmE0givc=
 google.golang.org/protobuf v1.31.0 h1:g0LDEJHgrBl9N9r17Ru3sqWhkIx2NB67okBHPwC7hs8=
 google.golang.org/protobuf v1.31.0/go.mod h1:HV8QOd/L58Z+nl8r43ehVNZIU/HEI6OcFqwMG9pJV4I=
 gopkg.in/check.v1 v0.0.0-20161208181325-20d25e280405/go.mod h1:Co6ibVJAznAaIkqp8huTwlJQCZ016jof/cbN4VW5Yz0=
+gopkg.in/check.v1 v1.0.0-20180628173108-788fd7840127/go.mod h1:Co6ibVJAznAaIkqp8huTwlJQCZ016jof/cbN4VW5Yz0=
 gopkg.in/check.v1 v1.0.0-20190902080502-41f04d3bba15/go.mod h1:Co6ibVJAznAaIkqp8huTwlJQCZ016jof/cbN4VW5Yz0=
 gopkg.in/check.v1 v1.0.0-20201130134442-10cb98267c6c h1:Hei/4ADfdWqJk1ZMxUNpqntNwaWcugrBjAiHlqqRiVk=
 gopkg.in/check.v1 v1.0.0-20201130134442-10cb98267c6c/go.mod h1:JHkPIbrfpd72SG/EVd6muEfDQjcINNoR0C8j2r3qZ4Q=
+gopkg.in/errgo.v2 v2.1.0/go.mod h1:hNsd1EY+bozCKY1Ytp96fpM3vjJbqLJn88ws8XvfDNI=
 gopkg.in/fsnotify.v1 v1.4.7/go.mod h1:Tz8NjZHkW78fSQdbUxIjBTcgA1z1m8ZHf0WmKUhAMys=
 gopkg.in/tomb.v1 v1.0.0-20141024135613-dd632973f1e7 h1:uRGJdciOHaEIrze2W8Q3AKkepLTh2hOroT7a+7czfdQ=
 gopkg.in/tomb.v1 v1.0.0-20141024135613-dd632973f1e7/go.mod h1:dt/ZhP58zS4L8KSrWDmTeBkI65Dw0HsyUHuEVlX15mw=
@@ -423,3 +790,13 @@ gopkg.in/yaml.v3 v3.0.1 h1:fxVm/GzAzEWqLHuvctI91KS9hhNmmWOoWu0XTYJS7CA=
 gopkg.in/yaml.v3 v3.0.1/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=
 gotest.tools/v3 v3.0.3 h1:4AuOwCGf4lLR9u3YOe2awrHygurzhO/HeQ6laiA6Sx0=
 gotest.tools/v3 v3.0.3/go.mod h1:Z7Lb0S5l+klDB31fvDQX8ss/FlKDxtlFlw3Oa8Ymbl8=
+honnef.co/go/tools v0.0.0-20190102054323-c2f93a96b099/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=
+honnef.co/go/tools v0.0.0-20190106161140-3f1c8253044a/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=
+honnef.co/go/tools v0.0.0-20190418001031-e561f6794a2a/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=
+honnef.co/go/tools v0.0.0-20190523083050-ea95bdfd59fc/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=
+honnef.co/go/tools v0.0.1-2019.2.3/go.mod h1:a3bituU0lyd329TUQxRnasdCoJDkEUEAqEt0JzvZhAg=
+honnef.co/go/tools v0.0.1-2020.1.3/go.mod h1:X/FiERA/W4tHapMX5mGpAtMSVEeEUOyHaw9vFzvIQ3k=
+honnef.co/go/tools v0.0.1-2020.1.4/go.mod h1:X/FiERA/W4tHapMX5mGpAtMSVEeEUOyHaw9vFzvIQ3k=
+rsc.io/binaryregexp v0.2.0/go.mod h1:qTv7/COck+e2FymRvadv62gMdZztPaShugOCi3I+8D8=
+rsc.io/quote/v3 v3.1.0/go.mod h1:yEA65RcK8LyAZtP9Kv3t0HmxON59tX3rD+tICJqUlj0=
+rsc.io/sampler v1.3.0/go.mod h1:T1hPZKmBbMNahiBKFy5HrXp6adAjACjK9JXDnKaTXpA=
diff --git a/main.go b/main.go
index 8948a918d..9a733aa63 100644
--- a/main.go
+++ b/main.go
@@ -1,10 +1,14 @@
 package main
 
 import (
+	"os"
+
 	"github.com/CircleCI-Public/circleci-cli/cmd"
 )
 
 func main() {
 	// See cmd/root.go for Execute()
-	cmd.Execute()
+	if err := cmd.Execute(); err != nil {
+		os.Exit(-1)
+	}
 }
diff --git a/prompt/prompt.go b/prompt/prompt.go
index cb2bd52dd..c9613386c 100644
--- a/prompt/prompt.go
+++ b/prompt/prompt.go
@@ -36,3 +36,14 @@ func AskUserToConfirm(message string) bool {
 	result, err := input.RunPrompt()
 	return err == nil && result
 }
+
+func AskUserToConfirmWithDefault(message string, defaultValue bool) bool {
+	def := confirmation.No
+	if defaultValue {
+		def = confirmation.Yes
+	}
+
+	input := confirmation.New(message, def)
+	result, err := input.RunPrompt()
+	return err == nil && result
+}
diff --git a/settings/settings.go b/settings/settings.go
index 36928fac5..7a9e7f0e4 100644
--- a/settings/settings.go
+++ b/settings/settings.go
@@ -17,25 +17,37 @@ import (
 	yaml "gopkg.in/yaml.v3"
 
 	"github.com/CircleCI-Public/circleci-cli/data"
+	"github.com/spf13/afero"
+)
+
+var (
+	FS afero.Afero = afero.Afero{
+		Fs: afero.NewOsFs(),
+	}
 )
 
 // Config is used to represent the current state of a CLI instance.
 type Config struct {
-	Host            string            `yaml:"host"`
-	DlHost          string            `yaml:"-"`
-	Endpoint        string            `yaml:"endpoint"`
-	Token           string            `yaml:"token"`
-	RestEndpoint    string            `yaml:"rest_endpoint"`
-	TLSCert         string            `yaml:"tls_cert"`
-	TLSInsecure     bool              `yaml:"tls_insecure"`
-	HTTPClient      *http.Client      `yaml:"-"`
-	Data            *data.DataBag     `yaml:"-"`
-	Debug           bool              `yaml:"-"`
-	Address         string            `yaml:"-"`
-	FileUsed        string            `yaml:"-"`
-	GitHubAPI       string            `yaml:"-"`
-	SkipUpdateCheck bool              `yaml:"-"`
-	OrbPublishing   OrbPublishingInfo `yaml:"orb_publishing"`
+	Host            string        `yaml:"host"`
+	DlHost          string        `yaml:"-"`
+	Endpoint        string        `yaml:"endpoint"`
+	Token           string        `yaml:"token"`
+	RestEndpoint    string        `yaml:"rest_endpoint"`
+	TLSCert         string        `yaml:"tls_cert"`
+	TLSInsecure     bool          `yaml:"tls_insecure"`
+	HTTPClient      *http.Client  `yaml:"-"`
+	Data            *data.DataBag `yaml:"-"`
+	Debug           bool          `yaml:"-"`
+	Address         string        `yaml:"-"`
+	FileUsed        string        `yaml:"-"`
+	GitHubAPI       string        `yaml:"-"`
+	SkipUpdateCheck bool          `yaml:"-"`
+	// Parameter used to disable telemetry from tests
+	IsTelemetryDisabled bool `yaml:"-"`
+	// If this value is defined, the telemetry will write all its events a file
+	// The value of this field is the path where the telemetry will be written
+	MockTelemetry string            `yaml:"-"`
+	OrbPublishing OrbPublishingInfo `yaml:"orb_publishing"`
 }
 
 type OrbPublishingInfo struct {
@@ -50,6 +62,14 @@ type UpdateCheck struct {
 	FileUsed        string    `yaml:"-"`
 }
 
+// TelemetrySettings is used to represent telemetry related settings
+type TelemetrySettings struct {
+	IsEnabled         bool   `yaml:"is_enabled"`
+	HasAnsweredPrompt bool   `yaml:"has_answered_prompt"`
+	UniqueID          string `yaml:"unique_id"`
+	UserID            string `yaml:"user_id"`
+}
+
 // Load will read the update check settings from the user's disk and then deserialize it into the current instance.
 func (upd *UpdateCheck) Load() error {
 	path := filepath.Join(SettingsPath(), updateCheckFilename())
@@ -80,6 +100,35 @@ func (upd *UpdateCheck) WriteToDisk() error {
 	return err
 }
 
+// Load will read the telemetry settings from the user's disk and then deserialize it into the current instance.
+func (tel *TelemetrySettings) Load() error {
+	path := filepath.Join(SettingsPath(), telemetryFilename())
+
+	if err := ensureSettingsFileExists(path); err != nil {
+		return err
+	}
+
+	content, err := FS.ReadFile(path) // #nosec
+	if err != nil {
+		return err
+	}
+
+	err = yaml.Unmarshal(content, &tel)
+	return err
+}
+
+// WriteToDisk will write the telemetry settings to disk by serializing the YAML
+func (tel *TelemetrySettings) Write() error {
+	enc, err := yaml.Marshal(&tel)
+	if err != nil {
+		return err
+	}
+
+	path := filepath.Join(SettingsPath(), telemetryFilename())
+	err = FS.WriteFile(path, enc, 0600)
+	return err
+}
+
 // Load will read the config from the user's disk and then evaluate possible configuration from the environment.
 func (cfg *Config) Load() error {
 	if err := cfg.LoadFromDisk(); err != nil {
@@ -161,6 +210,11 @@ func configFilename() string {
 	return "cli.yml"
 }
 
+// telemetryFilename returns the name of the cli telemetry file
+func telemetryFilename() string {
+	return "telemetry.yml"
+}
+
 // settingsPath returns the path of the CLI settings directory
 func SettingsPath() string {
 	// TODO: Make this configurable
diff --git a/telemetry/context.go b/telemetry/context.go
new file mode 100644
index 000000000..4e245f101
--- /dev/null
+++ b/telemetry/context.go
@@ -0,0 +1,16 @@
+package telemetry
+
+import "context"
+
+type contextKey string
+
+const telemetryClientContextKey contextKey = "telemetryClientContextKey"
+
+func NewContext(ctx context.Context, client Client) context.Context {
+	return context.WithValue(ctx, telemetryClientContextKey, client)
+}
+
+func FromContext(ctx context.Context) (Client, bool) {
+	client, ok := ctx.Value(telemetryClientContextKey).(Client)
+	return client, ok
+}
diff --git a/telemetry/events.go b/telemetry/events.go
new file mode 100644
index 000000000..dfdc61330
--- /dev/null
+++ b/telemetry/events.go
@@ -0,0 +1,149 @@
+package telemetry
+
+import "fmt"
+
+// This file contains all the telemetry event constructors
+// All the events are referenced in the following file:
+// https://circleci.atlassian.net/wiki/spaces/DE/pages/6760694125/CLI+segment+event+tracking
+// If you want to add an event, first make sure it appears in this file
+
+type CommandInfo struct {
+	Name      string
+	LocalArgs map[string]string
+}
+
+func createEventFromCommandInfo(name string, cmdInfo CommandInfo) Event {
+	properties := map[string]interface{}{}
+	for key, value := range cmdInfo.LocalArgs {
+		properties[fmt.Sprintf("cmd.flag.%s", key)] = value
+	}
+	properties["has_been_executed"] = false
+
+	return Event{
+		Object:     fmt.Sprintf("cli-%s", name),
+		Action:     cmdInfo.Name,
+		Properties: properties,
+	}
+}
+
+func errorToProperties(err error) map[string]interface{} {
+	properties := map[string]interface{}{
+		"has_been_executed": true,
+	}
+
+	if err != nil {
+		properties["error"] = err.Error()
+	}
+	return properties
+}
+
+func CreateSetupEvent(isServerCustomer bool) Event {
+	return Event{
+		Object: "cli-setup",
+		Action: "setup",
+		Properties: map[string]interface{}{
+			"is_server_customer": isServerCustomer,
+			"has_been_executed":  true,
+		},
+	}
+}
+
+func CreateVersionEvent(version string) Event {
+	return Event{
+		Object: "cli-version",
+		Action: "version",
+		Properties: map[string]interface{}{
+			"version":           version,
+			"has_been_executed": true,
+		},
+	}
+}
+
+func CreateUpdateEvent(cmdInfo CommandInfo) Event {
+	return createEventFromCommandInfo("update", cmdInfo)
+}
+
+func CreateDiagnosticEvent(err error) Event {
+	return Event{
+		Object: "cli-diagnostic", Action: "diagnostic", Properties: errorToProperties(err),
+	}
+}
+
+func CreateFollowEvent(err error) Event {
+	return Event{
+		Object: "cli-follow", Action: "follow", Properties: errorToProperties(err),
+	}
+}
+
+func CreateOpenEvent(err error) Event {
+	return Event{Object: "cli-open", Action: "open", Properties: errorToProperties(err)}
+}
+
+func CreateCompletionCommand(cmdInfo CommandInfo) Event {
+	return createEventFromCommandInfo("completion", cmdInfo)
+}
+
+func CreateConfigEvent(cmdInfo CommandInfo, err error) Event {
+	event := createEventFromCommandInfo("config", cmdInfo)
+	if err != nil {
+		event.Properties["error"] = err.Error()
+		event.Properties["has_been_executed"] = true
+	}
+	return event
+}
+
+func CreateLocalExecuteEvent(cmdInfo CommandInfo) Event {
+	return createEventFromCommandInfo("local", cmdInfo)
+}
+
+func CreateNamespaceEvent(cmdInfo CommandInfo) Event {
+	return createEventFromCommandInfo("namespace", cmdInfo)
+}
+
+func CreateOrbEvent(cmdInfo CommandInfo) Event {
+	return createEventFromCommandInfo("orb", cmdInfo)
+}
+
+func CreatePolicyEvent(cmdInfo CommandInfo) Event {
+	return createEventFromCommandInfo("policy", cmdInfo)
+}
+
+func CreateRunnerInstanceEvent(cmdInfo CommandInfo, err error) Event {
+	event := createEventFromCommandInfo("runner-instance", cmdInfo)
+	if err != nil {
+		event.Properties["error"] = err.Error()
+		event.Properties["has_been_executed"] = true
+	}
+	return event
+}
+
+func CreateRunnerResourceClassEvent(cmdInfo CommandInfo) Event {
+	return createEventFromCommandInfo("runner-resource-class", cmdInfo)
+}
+
+func CreateRunnerToken(cmdInfo CommandInfo) Event {
+	return createEventFromCommandInfo("runner-resource-class", cmdInfo)
+}
+
+func CreateInfoEvent(cmdInfo CommandInfo, err error) Event {
+	event := createEventFromCommandInfo("info", cmdInfo)
+	if err != nil {
+		event.Properties["error"] = err.Error()
+		event.Properties["has_been_executed"] = true
+	}
+	return event
+}
+
+func CreateChangeTelemetryStatusEvent(action string, origin string, err error) Event {
+	event := Event{
+		Object: "cli-telemetry",
+		Action: action,
+		Properties: map[string]interface{}{
+			"origin": origin,
+		},
+	}
+	if err != nil {
+		event.Properties["error"] = err.Error()
+	}
+	return event
+}
diff --git a/telemetry/telemetry.go b/telemetry/telemetry.go
new file mode 100644
index 000000000..928e59dd8
--- /dev/null
+++ b/telemetry/telemetry.go
@@ -0,0 +1,197 @@
+package telemetry
+
+import (
+	"encoding/json"
+	"fmt"
+	"io"
+	"os"
+
+	"github.com/segmentio/analytics-go"
+)
+
+var (
+	// Overwrite this function for tests
+	CreateActiveTelemetry = newSegmentClient
+
+	SegmentEndpoint = "http://localhost:33457"
+	segmentKey      = "AbgkrgN4cbRhAVEwlzMkHbwvrXnxHh35"
+)
+
+type Approval string
+
+const (
+	Enabled  Approval = "enabled"
+	Disabled Approval = "disabled"
+	NoStdin  Approval = "disabled_default"
+)
+
+type Client interface {
+	io.Closer
+	// Send a telemetry event. This method is not to be called directly. Use config.Track instead
+	Track(event Event) error
+}
+
+// A segment event to be sent to the telemetry
+// Important: this is not meant to be constructed directly apart in tests
+// If you want to create a new event, add its constructor in ./events.go
+type Event struct {
+	Object     string                 `json:"object"`
+	Action     string                 `json:"action"`
+	Properties map[string]interface{} `json:"properties"`
+}
+
+type User struct {
+	UniqueID     string
+	UserID       string
+	IsSelfHosted bool
+	OS           string
+	Version      string
+	TeamName     string
+}
+
+// Create a telemetry client to be used to send telemetry events
+func CreateClient(user User, enabled bool) Client {
+	if !enabled {
+		return nullClient{}
+	}
+
+	return CreateActiveTelemetry(user)
+}
+
+// Sends the user's approval event
+func SendTelemetryApproval(user User, approval Approval) error {
+	client := CreateActiveTelemetry(user)
+	defer client.Close()
+
+	return client.Track(CreateChangeTelemetryStatusEvent(string(approval), "first-time-prompt", nil))
+}
+
+// Null client
+// Used when telemetry is disabled
+
+func CreateNullClient() Client {
+	return nullClient{}
+}
+
+type nullClient struct{}
+
+func (cli nullClient) Close() error { return nil }
+
+func (cli nullClient) Track(_ Event) error { return nil }
+
+// Segment client
+// Used when telemetry is enabled
+
+// Nil segment logger
+type nilSegmentEmptyLogger struct{}
+
+func (nilSegmentEmptyLogger) Logf(format string, args ...interface{})   {}
+func (nilSegmentEmptyLogger) Errorf(format string, args ...interface{}) {}
+
+type segmentClient struct {
+	analyticsClient analytics.Client
+	user            User
+}
+
+func newSegmentClient(user User) Client {
+	cli, err := analytics.NewWithConfig(segmentKey, analytics.Config{
+		Endpoint: SegmentEndpoint,
+		Logger:   nilSegmentEmptyLogger{},
+	})
+
+	if err != nil {
+		return CreateNullClient()
+	}
+
+	if len(user.UniqueID) == 0 {
+		return CreateNullClient()
+	}
+
+	err = cli.Enqueue(
+		analytics.Identify{
+			UserId: user.UniqueID,
+			Traits: analytics.NewTraits().Set("os", user.OS),
+		},
+	)
+	if err != nil {
+		fmt.Printf("Error while identifying with telemetry: %s\n", err)
+	}
+
+	return &segmentClient{cli, user}
+}
+
+func (segment *segmentClient) Track(event Event) error {
+	if event.Properties == nil {
+		event.Properties = make(map[string]interface{})
+	}
+	if event.Action != "" {
+		event.Properties["action"] = event.Action
+	}
+
+	if segment.user.UniqueID != "" {
+		event.Properties["anonymous_id"] = segment.user.UniqueID
+	}
+
+	if segment.user.UserID != "" {
+		event.Properties["cci_user_id"] = segment.user.UserID
+	}
+
+	event.Properties["is_self_hosted"] = segment.user.IsSelfHosted
+
+	if segment.user.OS != "" {
+		event.Properties["os"] = segment.user.OS
+	}
+
+	if segment.user.Version != "" {
+		event.Properties["cli_version"] = segment.user.Version
+	}
+
+	if segment.user.TeamName != "" {
+		event.Properties["team_name"] = segment.user.TeamName
+	}
+
+	return segment.analyticsClient.Enqueue(analytics.Track{
+		UserId:     segment.user.UniqueID,
+		Event:      event.Object,
+		Properties: event.Properties,
+	})
+}
+
+func (segment *segmentClient) Close() error {
+	return segment.analyticsClient.Close()
+}
+
+// File telemetry
+// Used for E2E tests
+
+type fileTelemetry struct {
+	filePath string
+	events   []Event
+}
+
+func CreateFileTelemetry(filePath string) Client {
+	return &fileTelemetry{filePath, make([]Event, 0)}
+}
+
+func (cli *fileTelemetry) Track(event Event) error {
+	cli.events = append(cli.events, event)
+	return nil
+}
+
+func (cli *fileTelemetry) Close() error {
+	file, err := os.OpenFile(cli.filePath, os.O_CREATE|os.O_WRONLY, 0666)
+	if err != nil {
+		return err
+	}
+
+	content, err := json.Marshal(&cli.events)
+	if err != nil {
+		return err
+	}
+
+	if _, err = file.Write(content); err != nil {
+		return err
+	}
+
+	return file.Close()
+}
diff --git a/telemetry/utils.go b/telemetry/utils.go
new file mode 100644
index 000000000..2201887ad
--- /dev/null
+++ b/telemetry/utils.go
@@ -0,0 +1,31 @@
+package telemetry
+
+import (
+	"github.com/spf13/cobra"
+	"github.com/spf13/pflag"
+)
+
+// Utility function used when creating telemetry events.
+// It takes a cobra Command and creates a telemetry.CommandInfo of it
+// If getParent is true, puts both the command's args in `LocalArgs` and the parent's args
+// Else only put the command's args
+// Note: child flags overwrite parent flags with same name
+func GetCommandInformation(cmd *cobra.Command, getParent bool) CommandInfo {
+	localArgs := map[string]string{}
+
+	parent := cmd.Parent()
+	if getParent && parent != nil {
+		parent.LocalFlags().VisitAll(func(flag *pflag.Flag) {
+			localArgs[flag.Name] = flag.Value.String()
+		})
+	}
+
+	cmd.LocalFlags().VisitAll(func(flag *pflag.Flag) {
+		localArgs[flag.Name] = flag.Value.String()
+	})
+
+	return CommandInfo{
+		Name:      cmd.Name(),
+		LocalArgs: localArgs,
+	}
+}