diff --git a/boxcli/midcobra/telemetry.go b/boxcli/midcobra/telemetry.go
index a90e5cd490f..17aaf0fc726 100644
--- a/boxcli/midcobra/telemetry.go
+++ b/boxcli/midcobra/telemetry.go
@@ -59,7 +59,11 @@ func (m *telemetryMiddleware) postRun(cmd *cobra.Command, args []string, runErr
 		return
 	}
 
-	segmentClient, _ := segment.NewWithConfig(m.opts.TelemetryKey, segment.Config{Verbose: false})
+	segmentClient, _ := segment.NewWithConfig(m.opts.TelemetryKey,
+		segment.Config{
+			Verbose:   false,
+			BatchSize: 1, // We're in a short lived program, so batching doesn't make sense
+		})
 
 	defer func() {
 		_ = segmentClient.Close()
@@ -70,15 +74,19 @@ func (m *telemetryMiddleware) postRun(cmd *cobra.Command, args []string, runErr
 		return // Ignore invalid commands
 	}
 
-	trackEvent(segmentClient, &event{
+	evt := &event{
 		AppName:     m.opts.AppName,
 		AppVersion:  m.opts.AppVersion,
 		Command:     subcmd.CommandPath(),
 		CommandArgs: subargs,
 		DeviceID:    deviceID(),
 		Duration:    time.Since(m.startTime),
-		Failed:      runErr != nil,
-	})
+	}
+	if runErr != nil {
+		evt.Failed = true
+		evt.FailedMsg = runErr.Error()
+	}
+	trackEvent(segmentClient, evt)
 }
 
 func deviceID() string {
@@ -104,6 +112,7 @@ type event struct {
 	DeviceID    string
 	Duration    time.Duration
 	Failed      bool
+	FailedMsg   string
 }
 
 func trackEvent(client segment.Client, evt *event) {
@@ -126,6 +135,7 @@ func trackEvent(client segment.Client, evt *event) {
 			Set("command", evt.Command).
 			Set("command_args", evt.CommandArgs).
 			Set("failed", evt.Failed).
+			Set("failed_msg", evt.FailedMsg).
 			Set("duration", evt.Duration.Milliseconds()),
 	})
 }