diff --git a/plugins/python-build/bin/python-build b/plugins/python-build/bin/python-build
index 7c4efc7c..f0d30bf2 100755
--- a/plugins/python-build/bin/python-build
+++ b/plugins/python-build/bin/python-build
@@ -1385,8 +1385,9 @@ use_homebrew_readline() {
 }
 
 has_broken_mac_openssl() {
-  is_mac &&
-  [[ "$(/usr/bin/openssl version 2>/dev/null || true)" = "OpenSSL 0.9.8"?* ]] &&
+  is_mac || return 1
+  local openssl_version="$(/usr/bin/openssl version 2>/dev/null || true)"
+  [[ $openssl_version = "OpenSSL 0.9.8"?* || $openssl_version = "LibreSSL"* ]] &&
   ! use_homebrew_openssl
 }