diff --git a/internal/analytics/client.go b/internal/analytics/client.go
index 4c2d33e2..9b0265c9 100644
--- a/internal/analytics/client.go
+++ b/internal/analytics/client.go
@@ -30,6 +30,14 @@ type Tracker interface {
 		optOut bool,
 		step string,
 	)
+	SendSetupFlagToggledEvent(
+		accessToken,
+		baseURI string,
+		optOut,
+		on bool,
+		count int,
+		duration_ms int64,
+	)
 }
 
 type Client struct {
@@ -151,6 +159,27 @@ func (c *Client) SendSetupStepStartedEvent(
 	)
 }
 
+func (c *Client) SendSetupFlagToggledEvent(
+	accessToken,
+	baseURI string,
+	optOut,
+	on bool,
+	count int,
+	duration_ms int64,
+) {
+	c.sendEvent(
+		accessToken,
+		baseURI,
+		optOut,
+		"CLI Setup Flag Toggled",
+		map[string]interface{}{
+			"on":          on,
+			"count":       count,
+			"duration_ms": duration_ms,
+		},
+	)
+}
+
 func (a *Client) Wait() {
 	a.wg.Wait()
 }
@@ -181,6 +210,16 @@ func (c *NoopClient) SendSetupStepStartedEvent(
 ) {
 }
 
+func (c *NoopClient) SendSetupFlagToggledEvent(
+	accessToken,
+	baseURI string,
+	optOut,
+	on bool,
+	count int,
+	duration_ms int64,
+) {
+}
+
 type MockTracker struct {
 	mock.Mock
 	ID string
@@ -245,3 +284,24 @@ func (m *MockTracker) SendSetupStepStartedEvent(
 		},
 	)
 }
+
+func (m *MockTracker) SendSetupFlagToggledEvent(
+	accessToken,
+	baseURI string,
+	optOut,
+	on bool,
+	count int,
+	duration_ms int64,
+) {
+	m.sendEvent(
+		accessToken,
+		baseURI,
+		optOut,
+		"CLI Setup Flag Toggled",
+		map[string]interface{}{
+			"on":          on,
+			"count":       count,
+			"duration_ms": duration_ms,
+		},
+	)
+}
diff --git a/internal/quickstart/container.go b/internal/quickstart/container.go
index 5f4b5729..9b95c4c2 100644
--- a/internal/quickstart/container.go
+++ b/internal/quickstart/container.go
@@ -3,6 +3,7 @@ package quickstart
 import (
 	"fmt"
 	"log"
+	"time"
 
 	"github.com/charmbracelet/bubbles/key"
 	"github.com/charmbracelet/bubbles/spinner"
@@ -53,9 +54,14 @@ type ContainerModel struct {
 	err                error
 	flagKey            string
 	flagsClient        flags.Client
+	flagStatus         bool
+	flagToggled        bool
 	gettingStarted     bool
 	quitting           bool
 	sdk                sdkDetail
+	startTime          time.Time
+	toggleCount        int
+	toggleTime         time.Time
 	totalSteps         int
 	width              int
 }
@@ -78,6 +84,7 @@ func NewContainerModel(
 		environmentsClient: environmentsClient,
 		flagsClient:        flagsClient,
 		gettingStarted:     true,
+		startTime:          time.Now(),
 		totalSteps:         4,
 	}
 }
@@ -165,10 +172,19 @@ func (m ContainerModel) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 	case fetchedFlagStatusMsg:
 		m.currentModel, cmd = m.currentModel.Update(msg)
 		m.err = nil
-	case fetchedSDKInstructionsMsg, selectedSDKMsg, toggledFlagMsg, spinner.TickMsg, createdFlagMsg:
+	case fetchedSDKInstructionsMsg, selectedSDKMsg, spinner.TickMsg, createdFlagMsg:
 		m.gettingStarted = false
 		m.currentModel, cmd = m.currentModel.Update(msg)
 		m.err = nil
+	case toggledFlagMsg:
+		m.gettingStarted = false
+		m.currentModel, cmd = m.currentModel.Update(msg)
+		m.toggleCount++
+		m.flagStatus = msg.on
+		m.toggleTime = msg.time
+		m.flagToggled = true
+		m.err = nil
+		sendEvent = true
 	case showToggleFlagMsg:
 		m.currentModel = NewToggleFlagModel(
 			m.flagsClient,
@@ -192,6 +208,18 @@ func (m ContainerModel) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 			m.analyticsOptOut,
 			m.currentStep.String(),
 		))
+
+		if (m.currentStep == stepToggleFlag) && m.flagToggled {
+			cmd = tea.Batch(cmd, trackSetupFlagToggledEvent(
+				m.analyticsTracker,
+				m.accessToken,
+				m.baseUri,
+				m.analyticsOptOut,
+				m.flagStatus,
+				m.toggleCount,
+				m.toggleTime.Sub(m.startTime).Milliseconds(),
+			))
+		}
 	}
 
 	return m, cmd
diff --git a/internal/quickstart/messages.go b/internal/quickstart/messages.go
index 9b8bf2fd..8d6a06dd 100644
--- a/internal/quickstart/messages.go
+++ b/internal/quickstart/messages.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"encoding/json"
 	"fmt"
+	"time"
 
 	tea "github.com/charmbracelet/bubbletea"
 
@@ -26,7 +27,10 @@ func sendErrMsg(err error) tea.Cmd {
 	}
 }
 
-type toggledFlagMsg struct{}
+type toggledFlagMsg struct {
+	time time.Time
+	on   bool
+}
 
 func toggleFlag(client flags.Client, accessToken, baseUri, flagKey string, enabled bool) tea.Cmd {
 	return func() tea.Msg {
@@ -42,7 +46,10 @@ func toggleFlag(client flags.Client, accessToken, baseUri, flagKey string, enabl
 			return errMsg{err: err}
 		}
 
-		return toggledFlagMsg{}
+		return toggledFlagMsg{
+			time: time.Now(),
+			on:   enabled,
+		}
 	}
 }
 
@@ -251,3 +258,11 @@ func trackSetupStepStartedEvent(tracker analytics.Tracker, accessToken, baseURI
 		return eventTrackedMsg{}
 	}
 }
+
+func trackSetupFlagToggledEvent(tracker analytics.Tracker, accessToken, baseURI string, optOut, on bool, count int, duration_ms int64) tea.Cmd {
+	return func() tea.Msg {
+		tracker.SendSetupFlagToggledEvent(accessToken, baseURI, optOut, on, count, duration_ms)
+
+		return eventTrackedMsg{}
+	}
+}