diff --git a/packages/cmd/login.go b/packages/cmd/login.go
index 863abf95..dea36b46 100644
--- a/packages/cmd/login.go
+++ b/packages/cmd/login.go
@@ -241,9 +241,18 @@ var loginCmd = &cobra.Command{
 				util.HandleError(err, "Unable to write write to Infisical Config file. Please try again")
 			}
 
+			// Identify the user in PostHog and alias the anonymous machine ID
+			// so that pre-login CLI events are merged into the same person record
+			Telemetry.IdentifyUser(userCredentialsToBeStored.Email)
+
 			// clear backed up secrets from prev account
 			util.DeleteBackupSecrets()
 
+			// Capture login event and flush the PostHog client (including Identify/Alias
+			// events enqueued by IdentifyUser above). This must run before any early
+			// returns so that all enqueued events are flushed via CaptureEvent's Close().
+			Telemetry.CaptureEvent("cli-command:login", posthog.NewProperties().Set("infisical-backend", config.INFISICAL_URL).Set("version", util.CLI_VERSION))
+
 			if plainOutput {
 				util.PrintlnStdout(userCredentialsToBeStored.JTWToken)
 				return
@@ -260,8 +269,6 @@ var loginCmd = &cobra.Command{
 			plainBold.Println("\nQuick links")
 			util.PrintlnStderr("- Learn to inject secrets into your application at https://infisical.com/docs/cli/usage")
 			util.PrintlnStderr("- Stuck? Join our slack for quick support https://infisical.com/slack")
-
-			Telemetry.CaptureEvent("cli-command:login", posthog.NewProperties().Set("infisical-backend", config.INFISICAL_URL).Set("version", util.CLI_VERSION))
 		} else {
 			sdkAuthenticator := util.NewSdkAuthenticator(infisicalClient, cmd)
 
diff --git a/packages/telemetry/telemetry.go b/packages/telemetry/telemetry.go
index ffd74345..d40f5437 100644
--- a/packages/telemetry/telemetry.go
+++ b/packages/telemetry/telemetry.go
@@ -1,6 +1,8 @@
 package telemetry
 
 import (
+	"errors"
+
 	"github.com/Infisical/infisical-merge/packages/util"
 	"github.com/denisbrodbeck/machineid"
 	"github.com/posthog/posthog-go"
@@ -56,27 +58,62 @@ func (t *Telemetry) CaptureEvent(eventName string, properties posthog.Properties
 	}
 }
 
+// IdentifyUser sends a PostHog identify call to enrich the person record
+// with user properties, and aliases the anonymous machine ID to the user's
+// email so that pre-login CLI events are merged into the same person.
+func (t *Telemetry) IdentifyUser(email string) {
+	if !t.isEnabled || email == "" {
+		return
+	}
+
+	// Identify the user with their email as the distinctId
+	t.posthogClient.Enqueue(posthog.Identify{
+		DistinctId: email,
+		Properties: posthog.NewProperties().
+			Set("email", email),
+	})
+
+	// Alias the anonymous machine ID to the user's email so that
+	// any events captured before login are linked to this person
+	machineId, err := machineid.ID()
+	if err == nil && machineId != "" {
+		anonymousId := "anonymous_cli_" + machineId
+		t.posthogClient.Enqueue(posthog.Alias{
+			DistinctId: email,
+			Alias:      anonymousId,
+		})
+	}
+
+	// Note: no Close() here — the caller is responsible for ensuring
+	// CaptureEvent (which calls Close) runs after IdentifyUser to flush
+	// all enqueued events (Identify, Alias, and Capture).
+}
+
 func (t *Telemetry) GetDistinctId() (string, error) {
 	var distinctId string
-	var outputErr error
 
 	machineId, err := machineid.ID()
 	if err != nil {
-		outputErr = err
+		log.Debug().Err(err).Msg("failed to get machine ID for telemetry")
 	}
 
 	infisicalConfig, err := util.GetConfigFile()
 	if err != nil {
-		outputErr = err
+		log.Debug().Err(err).Msg("failed to get config file for telemetry")
 	}
 
 	if infisicalConfig.LoggedInUserEmail != "" {
 		distinctId = infisicalConfig.LoggedInUserEmail
 	} else if machineId != "" {
 		distinctId = "anonymous_cli_" + machineId
-	} else {
-		distinctId = ""
 	}
 
-	return distinctId, outputErr
+	// Only return an error if we could not resolve any distinctId.
+	// Non-critical errors (e.g. machineid failure when email is available)
+	// are logged above but should not prevent event capture.
+	if distinctId == "" {
+		return "", errors.New("unable to resolve a distinct ID for telemetry")
+	}
+
+	return distinctId, nil
 }