diff --git a/support/src/utils/unix.cpp b/support/src/utils/unix.cpp
index 69f488a..2b2f2c1 100644
--- a/support/src/utils/unix.cpp
+++ b/support/src/utils/unix.cpp
@@ -311,11 +311,24 @@ auto use_getpwuid(uid_t uid, passwd_callback_t callback) -> result {
 #if defined(PROJECT_ENABLE_PUGIXML)
 auto generate_launchd_plist(const plist_cfg &cfg, bool overwrite_existing)
     -> bool {
+  FIFTHGRID_USES_FUNCTION_NAME();
+
   auto file = utils::path::combine(cfg.plist_path, {cfg.label + ".plist"});
   if (utils::file::file{file}.exists() && not overwrite_existing) {
     return true;
   }
 
+  auto parent_directory = utils::path::get_parent_path(file);
+  if (not utils::file::directory{parent_directory}.create_directory()) {
+    utils::error::handle_error(function_name,
+                               utils::error::create_error_message({
+                                   "failed to create plist parent directory",
+                                   parent_directory,
+                                   std::to_string(errno),
+                               }));
+    return false;
+  }
+
   pugi::xml_document doc;
   auto decl = doc.append_child(pugi::node_declaration);
   decl.append_attribute("version") = "1.0";
@@ -370,26 +383,24 @@ auto generate_launchd_plist(const plist_cfg &cfg, bool overwrite_existing)
 
 #if defined(PROJECT_ENABLE_SPDLOG) || defined(PROJECT_ENABLE_FMT)
 auto launchctl_command(std::string_view label, launchctl_type type) -> int {
+  auto launch_agents_dir = utils::path::combine("~", {
+                                                         "Library",
+                                                         "LaunchAgents",
+                                                     });
   switch (type) {
   case launchctl_type::bootout:
     return system(
         fmt::format("launchctl bootout gui/{} '{}' 1>/dev/null 2>&1", getuid(),
-                    utils::path::combine("~",
-                                         {
-                                             "/Library/LaunchAgents",
-                                             fmt::format("{}.plist", label),
-                                         }))
+                    utils::path::combine(launch_agents_dir,
+                                         {fmt::format("{}.plist", label)}))
             .c_str());
 
   case launchctl_type::bootstrap:
     return system(
         fmt::format("launchctl bootstrap gui/{} '{}' 1>/dev/null 2>&1",
                     getuid(),
-                    utils::path::combine("~",
-                                         {
-                                             "/Library/LaunchAgents",
-                                             fmt::format("{}.plist", label),
-                                         }))
+                    utils::path::combine(launch_agents_dir,
+                                         {fmt::format("{}.plist", label)}))
             .c_str());
 
   case launchctl_type::kickstart: