diff --git a/go.mod b/go.mod
index 0513d67d095..8bb5858aa1e 100644
--- a/go.mod
+++ b/go.mod
@@ -2,7 +2,7 @@ module github.com/cli/cli/v2
 
 go 1.26.0
 
-toolchain go1.26.7
+toolchain go1.26.8
 
 require (
 	charm.land/bubbles/v2 v2.2.1
@@ -18,7 +18,7 @@ require (
 	github.com/cenkalti/backoff/v5 v5.0.3
 	github.com/charmbracelet/glamour v0.10.0
 	github.com/charmbracelet/lipgloss v1.1.1-0.20250404203927-76690c660834
-	github.com/cli/go-gh/v2 v2.15.0
+	github.com/cli/go-gh/v2 v2.16.0
 	github.com/cli/go-internal v0.0.0-20241025142207-6c48bcd5ce24
 	github.com/cli/oauth v1.2.2
 	github.com/cli/safeexec v1.0.1
@@ -57,7 +57,7 @@ require (
 	github.com/vmihailenco/msgpack/v5 v5.4.1
 	github.com/yuin/goldmark v1.8.5
 	github.com/zalando/go-keyring v0.2.8
-	golang.org/x/crypto v0.55.0
+	golang.org/x/crypto v0.56.0
 	golang.org/x/sync v0.22.0
 	golang.org/x/sys v0.47.0
 	golang.org/x/term v0.45.0
diff --git a/go.sum b/go.sum
index 98f3fb40c09..0d36a8f0947 100644
--- a/go.sum
+++ b/go.sum
@@ -145,8 +145,8 @@ github.com/charmbracelet/x/xpty v0.1.3/go.mod h1:poPYpWuLDBFCKmKLDnhBp51ATa0ooD8
 github.com/cli/browser v1.0.0/go.mod h1:IEWkHYbLjkhtjwwWlwTHW2lGxeS5gezEQBMLTwDHf5Q=
 github.com/cli/browser v1.3.0 h1:LejqCrpWr+1pRqmEPDGnTZOjsMe7sehifLynZJuqJpo=
 github.com/cli/browser v1.3.0/go.mod h1:HH8s+fOAxjhQoBUAsKuPCbqUuxZDhQ2/aD+SzsEfBTk=
-github.com/cli/go-gh/v2 v2.15.0 h1:LF5lDLs6yLaUgUlvki/D9syUGYnYaJXjzYXpazTqYdw=
-github.com/cli/go-gh/v2 v2.15.0/go.mod h1:OaJTFtHJapQq670h/3L0vqm4NwZGoJmSAVctWiY+3pQ=
+github.com/cli/go-gh/v2 v2.16.0 h1:xaePUubgeuj4wKz87NIo+zFQtuB6566K8cAGTh0Ctjc=
+github.com/cli/go-gh/v2 v2.16.0/go.mod h1:OaJTFtHJapQq670h/3L0vqm4NwZGoJmSAVctWiY+3pQ=
 github.com/cli/go-internal v0.0.0-20241025142207-6c48bcd5ce24 h1:QDrhR4JA2n3ij9YQN0u5ZeuvRIIvsUGmf5yPlTS0w8E=
 github.com/cli/go-internal v0.0.0-20241025142207-6c48bcd5ce24/go.mod h1:rr9GNING0onuVw8MnracQHn7PcchnFlP882Y0II2KZk=
 github.com/cli/oauth v1.2.2 h1:/qG/wok8jzu66tx7q+duGOIp4DT5P/ACXrdc33UoNUQ=
@@ -561,8 +561,8 @@ go.yaml.in/yaml/v3 v3.0.5 h1:N6y/pJk8buWs9NY5ERU2HSMfm+IuD/OtfdAnq6kESPw=
 go.yaml.in/yaml/v3 v3.0.5/go.mod h1:HVTZu1O7/Vkt2N+BFy8Zza+lnLsABggaTM2ZpNIGuKg=
 golang.org/x/crypto v0.0.0-20190308221718-c2843e01d9a2/go.mod h1:djNgcEr1/C05ACkg1iLfiJU5Ep61QUkGW8qpdssI0+w=
 golang.org/x/crypto v0.0.0-20210921155107-089bfa567519/go.mod h1:GvvjBRRGRdwPK5ydBHafDWAxML/pGHZbMvKqRZ5+Abc=
-golang.org/x/crypto v0.55.0 h1:+KWHjbgOaAQ66dh/YlkZKHlz9ZUlq61AFirAR9ntP8M=
-golang.org/x/crypto v0.55.0/go.mod h1:uq0V9dE/fzQuJtbnL+2EhWOE63vo164FY8xqEnV9xis=
+golang.org/x/crypto v0.56.0 h1:GUh5Ii4J5jtcseSMiRqr1jXCNHoxjeV9Fmekc2oLy6Y=
+golang.org/x/crypto v0.56.0/go.mod h1:OMW5y6CY9l38uPLmxU6l6pwcXp1obtLo3e6gT7gQR2I=
 golang.org/x/exp v0.0.0-20251023183803-a4bb9ffd2546 h1:mgKeJMpvi0yx/sU5GsxQ7p6s2wtOnGAHZWCHUM4KGzY=
 golang.org/x/exp v0.0.0-20251023183803-a4bb9ffd2546/go.mod h1:j/pmGrbnkbPtQfxEe5D0VQhZC6qKbfKifgD0oM7sR70=
 golang.org/x/mod v0.6.0-dev.0.20220419223038-86c51ed26bb4/go.mod h1:jJ57K6gSWd91VN4djpZkiMVwK6gcyfeH4XE8wZrZaV4=
diff --git a/internal/attachments/flags.go b/internal/attachments/flags.go
index c47117c79fc..10e42fd6fca 100644
--- a/internal/attachments/flags.go
+++ b/internal/attachments/flags.go
@@ -6,6 +6,7 @@ import (
 	"os"
 	"strings"
 
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/spf13/cobra"
 	"github.com/spf13/pflag"
 )
@@ -39,6 +40,24 @@ func (f *Flag) Changed() bool {
 	return f.flag.Changed
 }
 
+// RecordTelemetry records how many attachment flags were provided.
+func (f *Flag) RecordTelemetry(command string, recorder ghtelemetry.CommandRecorder) {
+	if recorder == nil || !f.Changed() {
+		return
+	}
+
+	recorder.SetSampleRate(ghtelemetry.SAMPLE_ALL)
+	recorder.Record(ghtelemetry.Event{
+		Type: "attachment_invocation",
+		Dimensions: ghtelemetry.Dimensions{
+			"command": command,
+		},
+		Measures: ghtelemetry.Measures{
+			"attach_count": int64(len(f.values)),
+		},
+	})
+}
+
 // UserAssets validates the files named by the attachment flag, keeping them in
 // the order they were written. It returns nothing when the flag was not passed.
 func (f *Flag) UserAssets() ([]UserAsset, error) {
diff --git a/internal/attachments/flags_test.go b/internal/attachments/flags_test.go
index 1238acc1519..af22157715e 100644
--- a/internal/attachments/flags_test.go
+++ b/internal/attachments/flags_test.go
@@ -7,6 +7,8 @@ import (
 	"strings"
 	"testing"
 
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
+	"github.com/cli/cli/v2/internal/telemetry"
 	"github.com/google/shlex"
 	"github.com/spf13/cobra"
 	"github.com/spf13/pflag"
@@ -88,6 +90,58 @@ func TestAddFlag(t *testing.T) {
 	}
 }
 
+func TestFlagRecordTelemetry(t *testing.T) {
+	tests := []struct {
+		name      string
+		input     string
+		wantEvent bool
+		wantCount int64
+	}{
+		{
+			name:  "flag not passed",
+			input: "",
+		},
+		{
+			name:      "one attachment",
+			input:     "--attach ./first.png",
+			wantEvent: true,
+			wantCount: 1,
+		},
+		{
+			name:      "several attachments before validation",
+			input:     "--attach ./first.png --attach ./second.png --attach ./third.png",
+			wantEvent: true,
+			wantCount: 3,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			_, attachFlag := attachCmd(t, tt.input)
+			recorder := &telemetry.CommandRecorderSpy{}
+
+			attachFlag.RecordTelemetry("gh issue comment", recorder)
+
+			if !tt.wantEvent {
+				assert.Empty(t, recorder.Events)
+				assert.Zero(t, recorder.LastSampleRate)
+				return
+			}
+
+			require.Equal(t, ghtelemetry.SAMPLE_ALL, recorder.LastSampleRate)
+			require.Equal(t, []ghtelemetry.Event{{
+				Type: "attachment_invocation",
+				Dimensions: ghtelemetry.Dimensions{
+					"command": "gh issue comment",
+				},
+				Measures: ghtelemetry.Measures{
+					"attach_count": tt.wantCount,
+				},
+			}}, recorder.Events)
+		})
+	}
+}
+
 func TestFlagUserAssets(t *testing.T) {
 	tests := []struct {
 		name      string
diff --git a/internal/config/auth_config_test.go b/internal/config/auth_config_test.go
index 58c938999c7..32884758b69 100644
--- a/internal/config/auth_config_test.go
+++ b/internal/config/auth_config_test.go
@@ -987,38 +987,38 @@ func TestHostForAPIHost(t *testing.T) {
 	}{
 		{
 			name:      "no hosts configure an api_host",
-			lookup:    "api.example.com",
+			lookup:    "api-gateway.example.com",
 			wantFound: false,
 		},
 		{
 			name:      "a host configures the api_host",
-			apiHosts:  map[string]string{"github.com": "api.example.com"},
-			lookup:    "api.example.com",
+			apiHosts:  map[string]string{"github.com": "api-gateway.example.com"},
+			lookup:    "api-gateway.example.com",
 			wantHost:  "github.com",
 			wantFound: true,
 		},
 		{
 			name:      "matching is case insensitive",
-			apiHosts:  map[string]string{"github.com": "API.example.com"},
-			lookup:    "api.example.com",
+			apiHosts:  map[string]string{"github.com": "API-gateway.example.com"},
+			lookup:    "api-gateway.example.com",
 			wantHost:  "github.com",
 			wantFound: true,
 		},
 		{
 			name:      "an unrelated api_host does not match",
-			apiHosts:  map[string]string{"github.com": "api.example.com"},
+			apiHosts:  map[string]string{"github.com": "api-gateway.example.com"},
 			lookup:    "api.other.com",
 			wantFound: false,
 		},
 		{
 			name:      "an empty lookup matches nothing",
-			apiHosts:  map[string]string{"github.com": "api.example.com"},
+			apiHosts:  map[string]string{"github.com": "api-gateway.example.com"},
 			lookup:    "",
 			wantFound: false,
 		},
 		{
 			name:      "the right host is chosen when several configure an api_host",
-			apiHosts:  map[string]string{"github.com": "api.example.com", "ghe.io": "api.ghe.io"},
+			apiHosts:  map[string]string{"github.com": "api-gateway.example.com", "ghe.io": "api.ghe.io"},
 			lookup:    "api.ghe.io",
 			wantHost:  "ghe.io",
 			wantFound: true,
@@ -1028,8 +1028,8 @@ func TestHostForAPIHost(t *testing.T) {
 			// only hopes to catch an ordering regression rather than
 			// guaranteeing it on every run.
 			name:      "the first lexical match is returned when several matches found",
-			apiHosts:  map[string]string{"A.github.com": "api.example.com", "a.github.com": "api.example.com"},
-			lookup:    "api.example.com",
+			apiHosts:  map[string]string{"A.github.com": "api-gateway.example.com", "a.github.com": "api-gateway.example.com"},
+			lookup:    "api-gateway.example.com",
 			wantHost:  "A.github.com",
 			wantFound: true,
 		},
@@ -1084,20 +1084,20 @@ func TestAPIHostForHost(t *testing.T) {
 		},
 		{
 			name:        "the host configures an api_host",
-			apiHost:     "api.example.com",
+			apiHost:     "api-gateway.example.com",
 			lookup:      "github.com",
-			wantAPIHost: "api.example.com",
+			wantAPIHost: "api-gateway.example.com",
 			wantFound:   true,
 		},
 		{
 			name:      "an empty host matches nothing",
-			apiHost:   "api.example.com",
+			apiHost:   "api-gateway.example.com",
 			lookup:    "",
 			wantFound: false,
 		},
 		{
 			name:      "an unknown host matches nothing",
-			apiHost:   "api.example.com",
+			apiHost:   "api-gateway.example.com",
 			lookup:    "ghe.io",
 			wantFound: false,
 		},
diff --git a/internal/config/config.go b/internal/config/config.go
index 8d82017e712..6467fe77d73 100644
--- a/internal/config/config.go
+++ b/internal/config/config.go
@@ -646,10 +646,21 @@ type ConfigOption struct {
 	Description   string
 	DefaultValue  string
 	AllowedValues []string
+	PerHostOnly   bool
 	CurrentValue  func(c gh.Config, hostname string) string
 }
 
 var Options = []ConfigOption{
+	{
+		Key:          apiHostKey,
+		Description:  "experimental: the hostname to use when making API requests for a GitHub host. Note: this is not a security boundary and requests to the canonical host will remain authenticated",
+		DefaultValue: "",
+		PerHostOnly:  true,
+		CurrentValue: func(c gh.Config, hostname string) string {
+			apiHost, _ := c.Authentication().APIHostForHost(hostname)
+			return apiHost
+		},
+	},
 	{
 		Key:           gitProtocolKey,
 		Description:   "the protocol to use for git clone and push operations",
diff --git a/pkg/cmd/api/api.go b/pkg/cmd/api/api.go
index c1bdc911fd4..cb2b86dcc0b 100644
--- a/pkg/cmd/api/api.go
+++ b/pkg/cmd/api/api.go
@@ -18,6 +18,7 @@ import (
 	"github.com/MakeNowJust/heredoc"
 	"github.com/cli/cli/v2/api"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghinstance"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/pkg/cmd/factory"
@@ -34,13 +35,14 @@ const (
 )
 
 type ApiOptions struct {
-	AppVersion    string
-	InvokingAgent string
-	BaseRepo      func() (ghrepo.Interface, error)
-	Branch        func() (string, error)
-	Config        func() (gh.Config, error)
-	HttpClient    func() (*http.Client, error)
-	IO            *iostreams.IOStreams
+	AppVersion        string
+	InvokingAgent     string
+	BaseRepo          func() (ghrepo.Interface, error)
+	Branch            func() (string, error)
+	Config            func() (gh.Config, error)
+	HttpClient        func(api.HTTPClientOptions) (*http.Client, error)
+	IO                *iostreams.IOStreams
+	TelemetryDisabler ghtelemetry.Disabler
 
 	Hostname            string
 	RequestMethod       string
@@ -65,12 +67,14 @@ type ApiOptions struct {
 
 func NewCmdApi(f *cmdutil.Factory, runF func(*ApiOptions) error) *cobra.Command {
 	opts := ApiOptions{
-		AppVersion:    f.AppVersion,
-		InvokingAgent: f.InvokingAgent,
-		BaseRepo:      f.BaseRepo,
-		Branch:        f.Branch,
-		Config:        f.Config,
-		IO:            f.IOStreams,
+		AppVersion:        f.AppVersion,
+		InvokingAgent:     f.InvokingAgent,
+		BaseRepo:          f.BaseRepo,
+		Branch:            f.Branch,
+		Config:            f.Config,
+		HttpClient:        api.NewHTTPClient,
+		IO:                f.IOStreams,
+		TelemetryDisabler: f.TelemetryDisabler,
 	}
 
 	cmd := &cobra.Command{
@@ -389,25 +393,23 @@ func apiRun(opts *ApiOptions) error {
 	}
 
 	if opts.HttpClient == nil {
-		opts.HttpClient = func() (*http.Client, error) {
-			log := opts.IO.ErrOut
-			if opts.Verbose {
-				log = opts.IO.Out
-			}
-			opts := api.HTTPClientOptions{
-				AppVersion:     opts.AppVersion,
-				InvokingAgent:  opts.InvokingAgent,
-				CacheTTL:       opts.CacheTTL,
-				Config:         cfg.Authentication(),
-				EnableCache:    opts.CacheTTL > 0,
-				Log:            log,
-				LogColorize:    opts.IO.ColorEnabled(),
-				LogVerboseHTTP: opts.Verbose,
-			}
-			return api.NewHTTPClient(opts)
-		}
+		opts.HttpClient = api.NewHTTPClient
 	}
-	httpClient, err := opts.HttpClient()
+	log := opts.IO.ErrOut
+	if opts.Verbose {
+		log = opts.IO.Out
+	}
+	httpClient, err := opts.HttpClient(api.HTTPClientOptions{
+		AppVersion:        opts.AppVersion,
+		InvokingAgent:     opts.InvokingAgent,
+		CacheTTL:          opts.CacheTTL,
+		Config:            cfg.Authentication(),
+		EnableCache:       opts.CacheTTL > 0,
+		Log:               log,
+		LogColorize:       opts.IO.ColorEnabled(),
+		LogVerboseHTTP:    opts.Verbose,
+		TelemetryDisabler: opts.TelemetryDisabler,
+	})
 	if err != nil {
 		return err
 	}
diff --git a/pkg/cmd/api/api_test.go b/pkg/cmd/api/api_test.go
index f5ba71cd324..e67ca517a76 100644
--- a/pkg/cmd/api/api_test.go
+++ b/pkg/cmd/api/api_test.go
@@ -14,11 +14,14 @@ import (
 	"time"
 
 	"github.com/MakeNowJust/heredoc"
+	rootapi "github.com/cli/cli/v2/api"
 	"github.com/cli/cli/v2/git"
 	"github.com/cli/cli/v2/internal/config"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	ghmock "github.com/cli/cli/v2/internal/gh/mock"
 	"github.com/cli/cli/v2/internal/ghrepo"
+	"github.com/cli/cli/v2/internal/telemetry"
 	"github.com/cli/cli/v2/pkg/cmdutil"
 	"github.com/cli/cli/v2/pkg/iostreams"
 	"github.com/cli/go-gh/v2/pkg/template"
@@ -422,6 +425,35 @@ func Test_NewCmdApi_WindowsAbsPath(t *testing.T) {
 	assert.EqualError(t, err, `invalid API endpoint: "C:\users\repos". Your shell might be rewriting URL paths as filesystem paths. To avoid this, omit the leading slash from the endpoint argument`)
 }
 
+func TestNewCmdApiTelemetry(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		fmt.Fprint(w, "{}")
+	}))
+	t.Cleanup(server.Close)
+
+	var payload telemetry.SendTelemetryPayload
+	recorder := telemetry.NewService(func(p telemetry.SendTelemetryPayload) {
+		payload = p
+	})
+	recorder.Record(ghtelemetry.Event{Type: "command"})
+
+	ios, _, _, _ := iostreams.Test()
+	f := &cmdutil.Factory{
+		Config:            func() (gh.Config, error) { return config.NewMockConfig(), nil },
+		IOStreams:         ios,
+		TelemetryDisabler: recorder,
+	}
+	cmd := NewCmdApi(f, nil)
+	cmd.SetArgs([]string{server.URL})
+
+	_, err := cmd.ExecuteC()
+	require.NoError(t, err)
+	recorder.Flush()
+
+	assert.Empty(t, payload.Events)
+}
+
 func Test_apiRun(t *testing.T) {
 	tests := []struct {
 		name         string
@@ -741,7 +773,7 @@ func Test_apiRun(t *testing.T) {
 
 			tt.options.IO = ios
 			tt.options.Config = func() (gh.Config, error) { return config.NewMockConfig(), nil }
-			tt.options.HttpClient = func() (*http.Client, error) {
+			tt.options.HttpClient = func(rootapi.HTTPClientOptions) (*http.Client, error) {
 				var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 					resp := tt.httpResponse
 					resp.Request = req
@@ -810,7 +842,7 @@ func Test_apiRun_paginationREST(t *testing.T) {
 
 	options := ApiOptions{
 		IO: ios,
-		HttpClient: func() (*http.Client, error) {
+		HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 			var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 				resp := responses[requestCount]
 				resp.Request = req
@@ -882,7 +914,7 @@ func Test_apiRun_arrayPaginationREST(t *testing.T) {
 
 	options := ApiOptions{
 		IO: ios,
-		HttpClient: func() (*http.Client, error) {
+		HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 			var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 				resp := responses[requestCount]
 				resp.Request = req
@@ -954,7 +986,7 @@ func Test_apiRun_arrayPaginationREST_with_headers(t *testing.T) {
 
 	options := ApiOptions{
 		IO: ios,
-		HttpClient: func() (*http.Client, error) {
+		HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 			var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 				resp := responses[requestCount]
 				resp.Request = req
@@ -1023,7 +1055,7 @@ func Test_apiRun_paginationGraphQL(t *testing.T) {
 
 	options := ApiOptions{
 		IO: ios,
-		HttpClient: func() (*http.Client, error) {
+		HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 			var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 				resp := responses[requestCount]
 				resp.Request = req
@@ -1122,7 +1154,7 @@ func Test_apiRun_paginationGraphQL_slurp(t *testing.T) {
 
 	options := ApiOptions{
 		IO: ios,
-		HttpClient: func() (*http.Client, error) {
+		HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 			var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 				resp := responses[requestCount]
 				resp.Request = req
@@ -1234,7 +1266,7 @@ func Test_apiRun_paginated_template(t *testing.T) {
 
 	options := ApiOptions{
 		IO: ios,
-		HttpClient: func() (*http.Client, error) {
+		HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 			var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 				resp := responses[requestCount]
 				resp.Request = req
@@ -1293,7 +1325,7 @@ func Test_apiRun_DELETE(t *testing.T) {
 		Config: func() (gh.Config, error) {
 			return config.NewMockConfig(), nil
 		},
-		HttpClient: func() (*http.Client, error) {
+		HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 			var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 				gotRequest = req
 				return &http.Response{StatusCode: 204, Request: req}, nil
@@ -1322,7 +1354,7 @@ func Test_apiRun_HEAD(t *testing.T) {
 		Config: func() (gh.Config, error) {
 			return config.NewMockConfig(), nil
 		},
-		HttpClient: func() (*http.Client, error) {
+		HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 			var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 				return &http.Response{
 					StatusCode: 422,
@@ -1393,7 +1425,7 @@ func Test_apiRun_inputFile(t *testing.T) {
 				RawFields:        []string{"a=b", "c=d"},
 
 				IO: ios,
-				HttpClient: func() (*http.Client, error) {
+				HttpClient: func(rootapi.HTTPClientOptions) (*http.Client, error) {
 					var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 						var err error
 						if bodyBytes, err = io.ReadAll(req.Body); err != nil {
@@ -1889,7 +1921,7 @@ func Test_apiRun_acceptHeader(t *testing.T) {
 			}
 
 			var gotReq *http.Request
-			tt.options.HttpClient = func() (*http.Client, error) {
+			tt.options.HttpClient = func(rootapi.HTTPClientOptions) (*http.Client, error) {
 				var tr roundTripper = func(req *http.Request) (*http.Response, error) {
 					gotReq = req
 					resp := &http.Response{
diff --git a/pkg/cmd/config/list/list_test.go b/pkg/cmd/config/list/list_test.go
index 019d397eec6..3a04647fdac 100644
--- a/pkg/cmd/config/list/list_test.go
+++ b/pkg/cmd/config/list/list_test.go
@@ -82,6 +82,7 @@ func Test_listRun(t *testing.T) {
 			name: "list",
 			config: func() gh.Config {
 				cfg := config.NewMockConfig()
+				cfg.Set("HOST", "api_host", "api-gateway.example.com")
 				cfg.Set("HOST", "git_protocol", "ssh")
 				cfg.Set("HOST", "editor", "/usr/bin/vim")
 				cfg.Set("HOST", "prompt", "disabled")
@@ -93,6 +94,7 @@ func Test_listRun(t *testing.T) {
 			}(),
 			input: &ListOptions{Hostname: "HOST"},
 			stdout: heredoc.Doc(`
+				api_host=api-gateway.example.com
 				git_protocol=ssh
 				editor=/usr/bin/vim
 				prompt=disabled
diff --git a/pkg/cmd/config/set/set.go b/pkg/cmd/config/set/set.go
index 2e4496b86ab..e592d1efc1e 100644
--- a/pkg/cmd/config/set/set.go
+++ b/pkg/cmd/config/set/set.go
@@ -35,6 +35,7 @@ func NewCmdConfigSet(f *cmdutil.Factory, runF func(*SetOptions) error) *cobra.Co
 			$ gh config set editor vim
 			$ gh config set editor "code --wait"
 			$ gh config set git_protocol ssh --host github.com
+			$ gh config set api_host api-gateway.example.com --host example.com
 			$ gh config set prompt disabled
 		`),
 		Args: cobra.ExactArgs(2),
@@ -61,6 +62,10 @@ func NewCmdConfigSet(f *cmdutil.Factory, runF func(*SetOptions) error) *cobra.Co
 }
 
 func setRun(opts *SetOptions) error {
+	if isPerHostOnly(opts.Key) && opts.Hostname == "" {
+		return cmdutil.FlagErrorf("--host required when setting %s", opts.Key)
+	}
+
 	err := ValidateKey(opts.Key)
 	if err != nil {
 		warningIcon := opts.IO.ColorScheme().WarningIcon()
@@ -98,6 +103,16 @@ func ValidateKey(key string) error {
 	return fmt.Errorf("invalid key")
 }
 
+func isPerHostOnly(key string) bool {
+	for _, configKey := range config.Options {
+		if key == configKey.Key {
+			return configKey.PerHostOnly
+		}
+	}
+
+	return false
+}
+
 type InvalidValueError struct {
 	ValidValues []string
 }
diff --git a/pkg/cmd/config/set/set_test.go b/pkg/cmd/config/set/set_test.go
index 80aed28dbe7..a03207cf793 100644
--- a/pkg/cmd/config/set/set_test.go
+++ b/pkg/cmd/config/set/set_test.go
@@ -113,6 +113,26 @@ func Test_setRun(t *testing.T) {
 			},
 			expectedValue: "vim",
 		},
+		{
+			name: "set api_host scoped by host",
+			input: &SetOptions{
+				Config:   config.NewMockConfig(),
+				Hostname: "github.example.com",
+				Key:      "api_host",
+				Value:    "api-gateway.example.com",
+			},
+			expectedValue: "api-gateway.example.com",
+		},
+		{
+			name: "set api_host without hostname",
+			input: &SetOptions{
+				Config: config.NewMockConfig(),
+				Key:    "api_host",
+				Value:  "api-gateway.example.com",
+			},
+			wantsErr: true,
+			errMsg:   "--host required when setting api_host",
+		},
 		{
 			name: "set unknown key",
 			input: &SetOptions{
@@ -196,4 +216,13 @@ func Test_ValidateKey(t *testing.T) {
 
 	err = ValidateKey("browser")
 	assert.NoError(t, err)
+
+	err = ValidateKey("api_host")
+	assert.NoError(t, err)
+}
+
+func Test_isPerHostOnly(t *testing.T) {
+	assert.True(t, isPerHostOnly("api_host"))
+	assert.False(t, isPerHostOnly("editor"))
+	assert.False(t, isPerHostOnly("unknown"))
 }
diff --git a/pkg/cmd/factory/default.go b/pkg/cmd/factory/default.go
index cc10075f203..202f7ae556c 100644
--- a/pkg/cmd/factory/default.go
+++ b/pkg/cmd/factory/default.go
@@ -32,6 +32,7 @@ func New(appVersion string, invokingAgent string, cfgFunc func() (gh.Config, err
 	}
 
 	f.IOStreams = ios
+	f.TelemetryDisabler = telemetryDisabler
 	f.HttpClient = HttpClientFunc(cfgFunc, ios, appVersion, invokingAgent, telemetryDisabler)
 	f.PlainHttpClient = plainHttpClientFunc(ios, appVersion, invokingAgent, telemetryDisabler)
 	f.ExternalHttpClient = externalHttpClientFunc(ios, appVersion)
diff --git a/pkg/cmd/issue/comment/comment.go b/pkg/cmd/issue/comment/comment.go
index c85f17d20ae..3c972d14f20 100644
--- a/pkg/cmd/issue/comment/comment.go
+++ b/pkg/cmd/issue/comment/comment.go
@@ -3,6 +3,7 @@ package comment
 import (
 	"github.com/MakeNowJust/heredoc"
 	"github.com/cli/cli/v2/internal/attachments"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/pkg/cmd/issue/shared"
 	issueShared "github.com/cli/cli/v2/pkg/cmd/issue/shared"
@@ -11,7 +12,7 @@ import (
 	"github.com/spf13/cobra"
 )
 
-func NewCmdComment(f *cmdutil.Factory, runF func(*prShared.CommentableOptions) error) *cobra.Command {
+func NewCmdComment(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder, runF func(*prShared.CommentableOptions) error) *cobra.Command {
 	opts := &prShared.CommentableOptions{
 		IO:                        f.IOStreams,
 		HttpClient:                f.HttpClient,
@@ -58,6 +59,8 @@ func NewCmdComment(f *cmdutil.Factory, runF func(*prShared.CommentableOptions) e
 		`),
 		Args: cobra.ExactArgs(1),
 		PreRunE: func(cmd *cobra.Command, args []string) error {
+			opts.AttachFlag.RecordTelemetry(cmd.CommandPath(), telemetry)
+
 			opts.RetrieveCommentable = func() (prShared.Commentable, ghrepo.Interface, error) {
 				// TODO wm: more testing
 				issueNumber, parsedBaseRepo, err := shared.ParseIssueFromArg(args[0])
diff --git a/pkg/cmd/issue/comment/comment_test.go b/pkg/cmd/issue/comment/comment_test.go
index af7ff54f271..08ad22e7757 100644
--- a/pkg/cmd/issue/comment/comment_test.go
+++ b/pkg/cmd/issue/comment/comment_test.go
@@ -14,7 +14,9 @@ import (
 	"github.com/cli/cli/v2/internal/browser"
 	"github.com/cli/cli/v2/internal/config"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
+	"github.com/cli/cli/v2/internal/telemetry"
 	"github.com/cli/cli/v2/pkg/cmd/pr/shared"
 	"github.com/cli/cli/v2/pkg/cmdutil"
 	"github.com/cli/cli/v2/pkg/httpmock"
@@ -408,7 +410,8 @@ func TestNewCmdComment(t *testing.T) {
 			assert.NoError(t, err)
 
 			var gotOpts *shared.CommentableOptions
-			cmd := NewCmdComment(f, func(opts *shared.CommentableOptions) error {
+			recorder := &telemetry.CommandRecorderSpy{}
+			cmd := NewCmdComment(f, recorder, func(opts *shared.CommentableOptions) error {
 				gotOpts = opts
 				return nil
 			})
@@ -420,6 +423,18 @@ func TestNewCmdComment(t *testing.T) {
 			cmd.SetErr(&bytes.Buffer{})
 
 			_, err = cmd.ExecuteC()
+			if cmd.Flags().Changed("attach") {
+				values, flagErr := cmd.Flags().GetStringArray("attach")
+				require.NoError(t, flagErr)
+				require.Equal(t, ghtelemetry.SAMPLE_ALL, recorder.LastSampleRate)
+				require.Len(t, recorder.Events, 1)
+				assert.Equal(t, "attachment_invocation", recorder.Events[0].Type)
+				assert.Equal(t, cmd.CommandPath(), recorder.Events[0].Dimensions["command"])
+				assert.Equal(t, int64(len(values)), recorder.Events[0].Measures["attach_count"])
+			} else {
+				assert.Empty(t, recorder.Events)
+				assert.Zero(t, recorder.LastSampleRate)
+			}
 			if tt.wantsErr {
 				assert.Error(t, err)
 				if tt.wantsErrContains != "" {
diff --git a/pkg/cmd/issue/create/create.go b/pkg/cmd/issue/create/create.go
index 0fd18db0dd6..c0e6adfa481 100644
--- a/pkg/cmd/issue/create/create.go
+++ b/pkg/cmd/issue/create/create.go
@@ -13,6 +13,7 @@ import (
 	"github.com/cli/cli/v2/internal/browser"
 	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/prompter"
 	"github.com/cli/cli/v2/internal/text"
@@ -61,7 +62,7 @@ type CreateOptions struct {
 	Assets     []attachments.UserAsset
 }
 
-func NewCmdCreate(f *cmdutil.Factory, runF func(*CreateOptions) error) *cobra.Command {
+func NewCmdCreate(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder, runF func(*CreateOptions) error) *cobra.Command {
 	opts := &CreateOptions{
 		IO:         f.IOStreams,
 		HttpClient: f.HttpClient,
@@ -120,6 +121,8 @@ func NewCmdCreate(f *cmdutil.Factory, runF func(*CreateOptions) error) *cobra.Co
 		Args:    cmdutil.NoArgsQuoteReminder,
 		Aliases: []string{"new"},
 		RunE: func(cmd *cobra.Command, args []string) error {
+			opts.AttachFlag.RecordTelemetry(cmd.CommandPath(), telemetry)
+
 			// support `-R, --repo` override
 			opts.BaseRepo = f.BaseRepo
 			opts.HasRepoOverride = cmd.Flags().Changed("repo")
diff --git a/pkg/cmd/issue/create/create_test.go b/pkg/cmd/issue/create/create_test.go
index 3f6971ec998..e0463fb9504 100644
--- a/pkg/cmd/issue/create/create_test.go
+++ b/pkg/cmd/issue/create/create_test.go
@@ -18,9 +18,11 @@ import (
 	"github.com/cli/cli/v2/internal/config"
 	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/prompter"
 	"github.com/cli/cli/v2/internal/run"
+	"github.com/cli/cli/v2/internal/telemetry"
 	prShared "github.com/cli/cli/v2/pkg/cmd/pr/shared"
 	"github.com/cli/cli/v2/pkg/cmdutil"
 	"github.com/cli/cli/v2/pkg/httpmock"
@@ -311,7 +313,8 @@ func TestNewCmdCreate(t *testing.T) {
 			}
 
 			var opts *CreateOptions
-			cmd := NewCmdCreate(f, func(o *CreateOptions) error {
+			recorder := &telemetry.CommandRecorderSpy{}
+			cmd := NewCmdCreate(f, recorder, func(o *CreateOptions) error {
 				opts = o
 				return nil
 			})
@@ -322,6 +325,18 @@ func TestNewCmdCreate(t *testing.T) {
 			cmd.SetOut(io.Discard)
 			cmd.SetErr(io.Discard)
 			_, err = cmd.ExecuteC()
+			if cmd.Flags().Changed("attach") {
+				values, flagErr := cmd.Flags().GetStringArray("attach")
+				require.NoError(t, flagErr)
+				require.Equal(t, ghtelemetry.SAMPLE_ALL, recorder.LastSampleRate)
+				require.Len(t, recorder.Events, 1)
+				assert.Equal(t, "attachment_invocation", recorder.Events[0].Type)
+				assert.Equal(t, cmd.CommandPath(), recorder.Events[0].Dimensions["command"])
+				assert.Equal(t, int64(len(values)), recorder.Events[0].Measures["attach_count"])
+			} else {
+				assert.Empty(t, recorder.Events)
+				assert.Zero(t, recorder.LastSampleRate)
+			}
 			if tt.wantsErr {
 				require.Error(t, err)
 				if tt.wantsErrMsg != "" {
@@ -1450,7 +1465,7 @@ func runCommandWithRootDirOverridden(rt http.RoundTripper, isTTY bool, cli strin
 		Prompter: pm,
 	}
 
-	cmd := NewCmdCreate(factory, func(opts *CreateOptions) error {
+	cmd := NewCmdCreate(factory, &telemetry.NoOpService{}, func(opts *CreateOptions) error {
 		opts.RootDirOverride = rootDir
 		opts.Detector = &fd.EnabledDetectorMock{}
 		return createRun(opts)
diff --git a/pkg/cmd/issue/edit/edit.go b/pkg/cmd/issue/edit/edit.go
index 1329e1a5c58..3b8557abee6 100644
--- a/pkg/cmd/issue/edit/edit.go
+++ b/pkg/cmd/issue/edit/edit.go
@@ -15,6 +15,7 @@ import (
 	"github.com/cli/cli/v2/internal/attachments"
 	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/text"
 	issueShared "github.com/cli/cli/v2/pkg/cmd/issue/shared"
@@ -57,7 +58,7 @@ type EditOptions struct {
 	prShared.Editable
 }
 
-func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Command {
+func NewCmdEdit(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder, runF func(*EditOptions) error) *cobra.Command {
 	opts := &EditOptions{
 		IO:                 f.IOStreams,
 		HttpClient:         f.HttpClient,
@@ -122,6 +123,8 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 		`),
 		Args: cobra.MinimumNArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
+			opts.AttachFlag.RecordTelemetry(cmd.CommandPath(), telemetry)
+
 			issueNumbers, baseRepo, err := issueShared.ParseIssuesFromArgs(args)
 			if err != nil {
 				return err
diff --git a/pkg/cmd/issue/edit/edit_test.go b/pkg/cmd/issue/edit/edit_test.go
index 54040de3d40..5e80ddc57a3 100644
--- a/pkg/cmd/issue/edit/edit_test.go
+++ b/pkg/cmd/issue/edit/edit_test.go
@@ -20,8 +20,10 @@ import (
 	"github.com/cli/cli/v2/internal/config"
 	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/run"
+	"github.com/cli/cli/v2/internal/telemetry"
 	prShared "github.com/cli/cli/v2/pkg/cmd/pr/shared"
 	"github.com/cli/cli/v2/pkg/cmdutil"
 	"github.com/cli/cli/v2/pkg/httpmock"
@@ -455,7 +457,8 @@ func TestNewCmdEdit(t *testing.T) {
 			assert.NoError(t, err)
 
 			var gotOpts *EditOptions
-			cmd := NewCmdEdit(f, func(opts *EditOptions) error {
+			recorder := &telemetry.CommandRecorderSpy{}
+			cmd := NewCmdEdit(f, recorder, func(opts *EditOptions) error {
 				gotOpts = opts
 				return nil
 			})
@@ -467,6 +470,18 @@ func TestNewCmdEdit(t *testing.T) {
 			cmd.SetErr(&bytes.Buffer{})
 
 			_, err = cmd.ExecuteC()
+			if cmd.Flags().Changed("attach") {
+				values, flagErr := cmd.Flags().GetStringArray("attach")
+				require.NoError(t, flagErr)
+				require.Equal(t, ghtelemetry.SAMPLE_ALL, recorder.LastSampleRate)
+				require.Len(t, recorder.Events, 1)
+				assert.Equal(t, "attachment_invocation", recorder.Events[0].Type)
+				assert.Equal(t, cmd.CommandPath(), recorder.Events[0].Dimensions["command"])
+				assert.Equal(t, int64(len(values)), recorder.Events[0].Measures["attach_count"])
+			} else {
+				assert.Empty(t, recorder.Events)
+				assert.Zero(t, recorder.LastSampleRate)
+			}
 			if tt.wantsErr {
 				require.Error(t, err)
 				if tt.wantsErrMsg != "" {
diff --git a/pkg/cmd/issue/issue.go b/pkg/cmd/issue/issue.go
index eceea35c6df..65f43929cee 100644
--- a/pkg/cmd/issue/issue.go
+++ b/pkg/cmd/issue/issue.go
@@ -2,6 +2,7 @@ package issue
 
 import (
 	"github.com/MakeNowJust/heredoc"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	cmdClose "github.com/cli/cli/v2/pkg/cmd/issue/close"
 	cmdComment "github.com/cli/cli/v2/pkg/cmd/issue/comment"
 	cmdCreate "github.com/cli/cli/v2/pkg/cmd/issue/create"
@@ -20,7 +21,7 @@ import (
 	"github.com/spf13/cobra"
 )
 
-func NewCmdIssue(f *cmdutil.Factory) *cobra.Command {
+func NewCmdIssue(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder) *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "issue <command>",
 		Short: "Manage issues",
@@ -44,16 +45,16 @@ func NewCmdIssue(f *cmdutil.Factory) *cobra.Command {
 
 	cmdutil.AddGroup(cmd, "General commands",
 		cmdList.NewCmdList(f, nil),
-		cmdCreate.NewCmdCreate(f, nil),
+		cmdCreate.NewCmdCreate(f, telemetry, nil),
 		cmdStatus.NewCmdStatus(f, nil),
 	)
 
 	cmdutil.AddGroup(cmd, "Targeted commands",
 		cmdView.NewCmdView(f, nil),
-		cmdComment.NewCmdComment(f, nil),
+		cmdComment.NewCmdComment(f, telemetry, nil),
 		cmdClose.NewCmdClose(f, nil),
 		cmdReopen.NewCmdReopen(f, nil),
-		cmdEdit.NewCmdEdit(f, nil),
+		cmdEdit.NewCmdEdit(f, telemetry, nil),
 		cmdDevelop.NewCmdDevelop(f, nil),
 		cmdLock.NewCmdLock(f, cmd.Name(), nil),
 		cmdLock.NewCmdUnlock(f, cmd.Name(), nil),
diff --git a/pkg/cmd/pr/comment/comment.go b/pkg/cmd/pr/comment/comment.go
index cd9c7927edb..e7f7d504674 100644
--- a/pkg/cmd/pr/comment/comment.go
+++ b/pkg/cmd/pr/comment/comment.go
@@ -3,13 +3,14 @@ package comment
 import (
 	"github.com/MakeNowJust/heredoc"
 	"github.com/cli/cli/v2/internal/attachments"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/pkg/cmd/pr/shared"
 	"github.com/cli/cli/v2/pkg/cmdutil"
 	"github.com/spf13/cobra"
 )
 
-func NewCmdComment(f *cmdutil.Factory, runF func(*shared.CommentableOptions) error) *cobra.Command {
+func NewCmdComment(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder, runF func(*shared.CommentableOptions) error) *cobra.Command {
 	opts := &shared.CommentableOptions{
 		IO:                        f.IOStreams,
 		HttpClient:                f.HttpClient,
@@ -56,6 +57,8 @@ func NewCmdComment(f *cmdutil.Factory, runF func(*shared.CommentableOptions) err
 		`),
 		Args: cobra.MaximumNArgs(1),
 		PreRunE: func(cmd *cobra.Command, args []string) error {
+			opts.AttachFlag.RecordTelemetry(cmd.CommandPath(), telemetry)
+
 			if repoOverride, _ := cmd.Flags().GetString("repo"); repoOverride != "" && len(args) == 0 {
 				return cmdutil.FlagErrorf("argument required when using the --repo flag")
 			}
diff --git a/pkg/cmd/pr/comment/comment_test.go b/pkg/cmd/pr/comment/comment_test.go
index 52b17bee118..c09c83cb32d 100644
--- a/pkg/cmd/pr/comment/comment_test.go
+++ b/pkg/cmd/pr/comment/comment_test.go
@@ -14,7 +14,9 @@ import (
 	"github.com/cli/cli/v2/internal/browser"
 	"github.com/cli/cli/v2/internal/config"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
+	"github.com/cli/cli/v2/internal/telemetry"
 	"github.com/cli/cli/v2/pkg/cmd/pr/shared"
 	"github.com/cli/cli/v2/pkg/cmdutil"
 	"github.com/cli/cli/v2/pkg/httpmock"
@@ -430,7 +432,8 @@ func TestNewCmdComment(t *testing.T) {
 			assert.NoError(t, err)
 
 			var gotOpts *shared.CommentableOptions
-			cmd := NewCmdComment(f, func(opts *shared.CommentableOptions) error {
+			recorder := &telemetry.CommandRecorderSpy{}
+			cmd := NewCmdComment(f, recorder, func(opts *shared.CommentableOptions) error {
 				gotOpts = opts
 				return nil
 			})
@@ -442,6 +445,18 @@ func TestNewCmdComment(t *testing.T) {
 			cmd.SetErr(&bytes.Buffer{})
 
 			_, err = cmd.ExecuteC()
+			if cmd.Flags().Changed("attach") {
+				values, flagErr := cmd.Flags().GetStringArray("attach")
+				require.NoError(t, flagErr)
+				require.Equal(t, ghtelemetry.SAMPLE_ALL, recorder.LastSampleRate)
+				require.Len(t, recorder.Events, 1)
+				assert.Equal(t, "attachment_invocation", recorder.Events[0].Type)
+				assert.Equal(t, cmd.CommandPath(), recorder.Events[0].Dimensions["command"])
+				assert.Equal(t, int64(len(values)), recorder.Events[0].Measures["attach_count"])
+			} else {
+				assert.Empty(t, recorder.Events)
+				assert.Zero(t, recorder.LastSampleRate)
+			}
 			if tt.wantsErr {
 				assert.Error(t, err)
 				if tt.wantsErrContains != "" {
diff --git a/pkg/cmd/pr/create/create.go b/pkg/cmd/pr/create/create.go
index 11706462d28..c365fadebab 100644
--- a/pkg/cmd/pr/create/create.go
+++ b/pkg/cmd/pr/create/create.go
@@ -21,6 +21,7 @@ import (
 	"github.com/cli/cli/v2/internal/browser"
 	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/prompter"
 	"github.com/cli/cli/v2/internal/text"
@@ -195,7 +196,7 @@ type CreateContext struct {
 	GitClient          *git.Client
 }
 
-func NewCmdCreate(f *cmdutil.Factory, runF func(*CreateOptions) error) *cobra.Command {
+func NewCmdCreate(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder, runF func(*CreateOptions) error) *cobra.Command {
 	opts := &CreateOptions{
 		IO:               f.IOStreams,
 		HttpClient:       f.HttpClient,
@@ -274,6 +275,8 @@ func NewCmdCreate(f *cmdutil.Factory, runF func(*CreateOptions) error) *cobra.Co
 		Args:    cmdutil.NoArgsQuoteReminder,
 		Aliases: []string{"new"},
 		RunE: func(cmd *cobra.Command, args []string) error {
+			opts.AttachFlag.RecordTelemetry(cmd.CommandPath(), telemetry)
+
 			opts.Finder = shared.NewFinder(f)
 
 			opts.TitleProvided = cmd.Flags().Changed("title")
diff --git a/pkg/cmd/pr/create/create_test.go b/pkg/cmd/pr/create/create_test.go
index cf5b4ea3c38..e6ecc1047a4 100644
--- a/pkg/cmd/pr/create/create_test.go
+++ b/pkg/cmd/pr/create/create_test.go
@@ -21,9 +21,11 @@ import (
 	"github.com/cli/cli/v2/internal/config"
 	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/prompter"
 	"github.com/cli/cli/v2/internal/run"
+	"github.com/cli/cli/v2/internal/telemetry"
 	"github.com/cli/cli/v2/pkg/cmd/pr/shared"
 	"github.com/cli/cli/v2/pkg/cmdutil"
 	"github.com/cli/cli/v2/pkg/httpmock"
@@ -335,7 +337,8 @@ func TestNewCmdCreate(t *testing.T) {
 			}
 
 			var opts *CreateOptions
-			cmd := NewCmdCreate(f, func(o *CreateOptions) error {
+			recorder := &telemetry.CommandRecorderSpy{}
+			cmd := NewCmdCreate(f, recorder, func(o *CreateOptions) error {
 				opts = o
 				return nil
 			})
@@ -346,6 +349,18 @@ func TestNewCmdCreate(t *testing.T) {
 			cmd.SetOut(stderr)
 			cmd.SetErr(stderr)
 			_, err = cmd.ExecuteC()
+			if cmd.Flags().Changed("attach") {
+				values, flagErr := cmd.Flags().GetStringArray("attach")
+				require.NoError(t, flagErr)
+				require.Equal(t, ghtelemetry.SAMPLE_ALL, recorder.LastSampleRate)
+				require.Len(t, recorder.Events, 1)
+				assert.Equal(t, "attachment_invocation", recorder.Events[0].Type)
+				assert.Equal(t, cmd.CommandPath(), recorder.Events[0].Dimensions["command"])
+				assert.Equal(t, int64(len(values)), recorder.Events[0].Measures["attach_count"])
+			} else {
+				assert.Empty(t, recorder.Events)
+				assert.Zero(t, recorder.LastSampleRate)
+			}
 			if tt.wantsErr {
 				if tt.wantsErrMsg != "" {
 					if tt.wantErrIsNotExist {
diff --git a/pkg/cmd/pr/edit/edit.go b/pkg/cmd/pr/edit/edit.go
index fb4dc268e8a..fb8161f823c 100644
--- a/pkg/cmd/pr/edit/edit.go
+++ b/pkg/cmd/pr/edit/edit.go
@@ -14,6 +14,7 @@ import (
 	"github.com/cli/cli/v2/internal/attachments"
 	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/prompter"
 	shared "github.com/cli/cli/v2/pkg/cmd/pr/shared"
@@ -46,7 +47,7 @@ type EditOptions struct {
 	shared.Editable
 }
 
-func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Command {
+func NewCmdEdit(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder, runF func(*EditOptions) error) *cobra.Command {
 	opts := &EditOptions{
 		IO:              f.IOStreams,
 		HttpClient:      f.HttpClient,
@@ -134,6 +135,8 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 		`),
 		Args: cobra.MaximumNArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
+			opts.AttachFlag.RecordTelemetry(cmd.CommandPath(), telemetry)
+
 			opts.Finder = shared.NewFinder(f)
 
 			// support `-R, --repo` override
diff --git a/pkg/cmd/pr/edit/edit_test.go b/pkg/cmd/pr/edit/edit_test.go
index 64e49e63afb..98cbd60b2d9 100644
--- a/pkg/cmd/pr/edit/edit_test.go
+++ b/pkg/cmd/pr/edit/edit_test.go
@@ -15,7 +15,9 @@ import (
 	"github.com/cli/cli/v2/internal/config"
 	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
+	"github.com/cli/cli/v2/internal/telemetry"
 	shared "github.com/cli/cli/v2/pkg/cmd/pr/shared"
 	"github.com/cli/cli/v2/pkg/cmdutil"
 	"github.com/cli/cli/v2/pkg/httpmock"
@@ -354,7 +356,8 @@ func TestNewCmdEdit(t *testing.T) {
 			assert.NoError(t, err)
 
 			var gotOpts *EditOptions
-			cmd := NewCmdEdit(f, func(opts *EditOptions) error {
+			recorder := &telemetry.CommandRecorderSpy{}
+			cmd := NewCmdEdit(f, recorder, func(opts *EditOptions) error {
 				gotOpts = opts
 				return nil
 			})
@@ -366,6 +369,18 @@ func TestNewCmdEdit(t *testing.T) {
 			cmd.SetErr(&bytes.Buffer{})
 
 			_, err = cmd.ExecuteC()
+			if cmd.Flags().Changed("attach") {
+				values, flagErr := cmd.Flags().GetStringArray("attach")
+				require.NoError(t, flagErr)
+				require.Equal(t, ghtelemetry.SAMPLE_ALL, recorder.LastSampleRate)
+				require.Len(t, recorder.Events, 1)
+				assert.Equal(t, "attachment_invocation", recorder.Events[0].Type)
+				assert.Equal(t, cmd.CommandPath(), recorder.Events[0].Dimensions["command"])
+				assert.Equal(t, int64(len(values)), recorder.Events[0].Measures["attach_count"])
+			} else {
+				assert.Empty(t, recorder.Events)
+				assert.Zero(t, recorder.LastSampleRate)
+			}
 			if tt.wantsErr {
 				assert.Error(t, err)
 				return
diff --git a/pkg/cmd/pr/pr.go b/pkg/cmd/pr/pr.go
index e73193084c0..225b62ca7b7 100644
--- a/pkg/cmd/pr/pr.go
+++ b/pkg/cmd/pr/pr.go
@@ -2,6 +2,7 @@ package pr
 
 import (
 	"github.com/MakeNowJust/heredoc"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	cmdLock "github.com/cli/cli/v2/pkg/cmd/issue/lock"
 	cmdCheckout "github.com/cli/cli/v2/pkg/cmd/pr/checkout"
 	cmdChecks "github.com/cli/cli/v2/pkg/cmd/pr/checks"
@@ -23,7 +24,7 @@ import (
 	"github.com/spf13/cobra"
 )
 
-func NewCmdPR(f *cmdutil.Factory) *cobra.Command {
+func NewCmdPR(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder) *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "pr <command>",
 		Short: "Manage pull requests",
@@ -48,7 +49,7 @@ func NewCmdPR(f *cmdutil.Factory) *cobra.Command {
 
 	cmdutil.AddGroup(cmd, "General commands",
 		cmdList.NewCmdList(f, nil),
-		cmdCreate.NewCmdCreate(f, nil),
+		cmdCreate.NewCmdCreate(f, telemetry, nil),
 		cmdStatus.NewCmdStatus(f, nil),
 	)
 
@@ -61,11 +62,11 @@ func NewCmdPR(f *cmdutil.Factory) *cobra.Command {
 		cmdMerge.NewCmdMerge(f, nil),
 		cmdUpdateBranch.NewCmdUpdateBranch(f, nil),
 		cmdReady.NewCmdReady(f, nil),
-		cmdComment.NewCmdComment(f, nil),
+		cmdComment.NewCmdComment(f, telemetry, nil),
 		cmdClose.NewCmdClose(f, nil),
 		cmdReopen.NewCmdReopen(f, nil),
 		cmdRevert.NewCmdRevert(f, nil),
-		cmdEdit.NewCmdEdit(f, nil),
+		cmdEdit.NewCmdEdit(f, telemetry, nil),
 		cmdLock.NewCmdLock(f, cmd.Name(), nil),
 		cmdLock.NewCmdUnlock(f, cmd.Name(), nil),
 	)
diff --git a/pkg/cmd/root/root.go b/pkg/cmd/root/root.go
index df90bb249f9..985a0d82a41 100644
--- a/pkg/cmd/root/root.go
+++ b/pkg/cmd/root/root.go
@@ -166,9 +166,9 @@ func NewCmdRoot(f *cmdutil.Factory, telemetry ghtelemetry.CommandRecorder, versi
 	cmd.AddCommand(agentTaskCmd.NewCmdAgentTask(&repoResolvingCmdFactory))
 	cmd.AddCommand(browseCmd.NewCmdBrowse(&repoResolvingCmdFactory, nil))
 	cmd.AddCommand(discussionCmd.NewCmdDiscussion(&repoResolvingCmdFactory))
-	cmd.AddCommand(prCmd.NewCmdPR(&repoResolvingCmdFactory))
+	cmd.AddCommand(prCmd.NewCmdPR(&repoResolvingCmdFactory, telemetry))
 	cmd.AddCommand(orgCmd.NewCmdOrg(&repoResolvingCmdFactory))
-	cmd.AddCommand(issueCmd.NewCmdIssue(&repoResolvingCmdFactory))
+	cmd.AddCommand(issueCmd.NewCmdIssue(&repoResolvingCmdFactory, telemetry))
 	cmd.AddCommand(releaseCmd.NewCmdRelease(&repoResolvingCmdFactory))
 	cmd.AddCommand(repoCmd.NewCmdRepo(&repoResolvingCmdFactory))
 	cmd.AddCommand(rulesetCmd.NewCmdRuleset(&repoResolvingCmdFactory))
diff --git a/pkg/cmdutil/factory.go b/pkg/cmdutil/factory.go
index 200314038b2..abbcdf0408b 100644
--- a/pkg/cmdutil/factory.go
+++ b/pkg/cmdutil/factory.go
@@ -7,6 +7,7 @@ import (
 	"github.com/cli/cli/v2/git"
 	"github.com/cli/cli/v2/internal/browser"
 	"github.com/cli/cli/v2/internal/gh"
+	"github.com/cli/cli/v2/internal/gh/ghtelemetry"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/prompter"
 	"github.com/cli/cli/v2/pkg/extensions"
@@ -18,11 +19,12 @@ type Factory struct {
 	ExecutablePath string
 	InvokingAgent  string
 
-	Browser          browser.Browser
-	ExtensionManager extensions.ExtensionManager
-	GitClient        *git.Client
-	IOStreams        *iostreams.IOStreams
-	Prompter         prompter.Prompter
+	Browser           browser.Browser
+	ExtensionManager  extensions.ExtensionManager
+	GitClient         *git.Client
+	IOStreams         *iostreams.IOStreams
+	Prompter          prompter.Prompter
+	TelemetryDisabler ghtelemetry.Disabler
 
 	BaseRepo func() (ghrepo.Interface, error)
 	Branch   func() (string, error)
diff --git a/pkg/extensions/official.go b/pkg/extensions/official.go
index dc6bdc919b0..c45ddc031ce 100644
--- a/pkg/extensions/official.go
+++ b/pkg/extensions/official.go
@@ -25,6 +25,7 @@ func (e *OfficialExtension) Repository() ghrepo.Interface {
 var OfficialExtensions = []OfficialExtension{
 	{Name: "aw", Owner: "github", Repo: "gh-aw"},
 	{Name: "stack", Owner: "github", Repo: "gh-stack"},
+	{Name: "webhook", Owner: "cli", Repo: "gh-webhook"},
 }
 
 // IsOfficial reports whether the given extension command name and owner
diff --git a/pkg/extensions/official_test.go b/pkg/extensions/official_test.go
index 6d16ece2cf9..cb9b699876d 100644
--- a/pkg/extensions/official_test.go
+++ b/pkg/extensions/official_test.go
@@ -27,6 +27,12 @@ func TestIsOfficial(t *testing.T) {
 			extOwner: "github",
 			want:     true,
 		},
+		{
+			name:     "known official extension owned by cli matches",
+			extName:  "webhook",
+			extOwner: "cli",
+			want:     true,
+		},
 		{
 			name:     "official name with different owner is not official",
 			extName:  "stack",