diff --git a/cmd/tailscaled/install_darwin.go b/cmd/tailscaled/install_darwin.go
index c373c78e8..2a4132852 100644
--- a/cmd/tailscaled/install_darwin.go
+++ b/cmd/tailscaled/install_darwin.go
@@ -73,9 +73,18 @@ func uninstallSystemDaemonDarwin(args []string) (ret error) {
 		}
 	}
 
-	err = os.Remove(sysPlist)
-	if os.IsNotExist(err) {
-		err = nil
+	if err := os.Remove(sysPlist); err != nil {
+		if os.IsNotExist(err) {
+			err = nil
+		}
+		if ret == nil {
+			ret = err
+		}
+	}
+	if err := os.Remove(targetBin); err != nil {
+		if os.IsNotExist(err) {
+			err = nil
+		}
 		if ret == nil {
 			ret = err
 		}
@@ -93,6 +102,9 @@ func installSystemDaemonDarwin(args []string) (err error) {
 		}
 	}()
 
+	// Best effort:
+	uninstallSystemDaemonDarwin(nil)
+
 	// Copy ourselves to /usr/local/bin/tailscaled.
 	if err := os.MkdirAll(filepath.Dir(targetBin), 0755); err != nil {
 		return err
@@ -127,9 +139,6 @@ func installSystemDaemonDarwin(args []string) (err error) {
 		return err
 	}
 
-	// Best effort:
-	uninstallSystemDaemonDarwin(nil)
-
 	if err := ioutil.WriteFile(sysPlist, []byte(darwinLaunchdPlist), 0700); err != nil {
 		return err
 	}