diff --git a/changes/4711-fleetctl-preview-cleanup-osquery-socket b/changes/4711-fleetctl-preview-cleanup-osquery-socket
new file mode 100644
index 0000000000..546984ae89
--- /dev/null
+++ b/changes/4711-fleetctl-preview-cleanup-osquery-socket
@@ -0,0 +1 @@
+* Fleetctl preview to clean up osquery socket files before running fleet-osquery.
diff --git a/cmd/fleetctl/preview.go b/cmd/fleetctl/preview.go
index 1da907a141..be119e9311 100644
--- a/cmd/fleetctl/preview.go
+++ b/cmd/fleetctl/preview.go
@@ -629,6 +629,9 @@ func downloadOrbitAndStart(destDir, enrollSecret, address, orbitChannel, osquery
 	if err := os.RemoveAll(path.Join(destDir, "orbit.db")); err != nil {
 		fmt.Println("Warning: clearing orbit db dir:", err)
 	}
+	if err := cleanUpSocketFiles(destDir); err != nil {
+		fmt.Println("Warning: cleaning up socket files:", err)
+	}
 
 	updateOpt := update.DefaultOptions
 
@@ -673,6 +676,26 @@ func downloadOrbitAndStart(destDir, enrollSecret, address, orbitChannel, osquery
 	return nil
 }
 
+// cleanUpSocketFiles cleans up fleet-osqueryd's socket file
+// ("orbit-osquery.em") and osquery extension socket files
+// ("orbit-osquery.em.*").
+func cleanUpSocketFiles(path string) error {
+	entries, err := os.ReadDir(path)
+	if err != nil {
+		return fmt.Errorf("read dir: %w", err)
+	}
+	for _, entry := range entries {
+		if !strings.HasPrefix(entry.Name(), "orbit-osquery.em") {
+			continue
+		}
+		entryPath := filepath.Join(path, entry.Name())
+		if err := os.Remove(entryPath); err != nil {
+			return fmt.Errorf("remove %q: %w", entryPath, err)
+		}
+	}
+	return nil
+}
+
 func stopOrbit(destDir string) error {
 	err := killFromPIDFile(destDir, "osquery.pid", "osqueryd")
 	if err != nil {