i stole this from someone else's dotfiles AGAIN

config/awesome/rc.lua

@@ -589,6 +589,30 @@ local startupApps = {
   'keepassxc',
 }
 
-for i, app in ipairs(startupApps) do
-  awful.spawn.once(app)
+local run_once = function(cmd)
+    local findme = cmd
+    local firstspace = cmd:find(' ')
+    if firstspace then
+        findme = cmd:sub(0, firstspace - 1)
+    end
+    awful.spawn.easy_async_with_shell(
+        string.format('pgrep -u $USER -x %s > /dev/null || (%s)', findme, cmd),
+        function(stdout, stderr)
+            -- Debugger 
+            if not stderr or stderr == '' or not debug_mode then
+                return 
+            end
+            naughty.notification({
+                app_name = 'Start-up Applications',
+                title = '<b>Oof! Error detected when starting an application!</b>',
+                message = stderr:gsub('%\n', ''),
+                timeout = 20,
+                icon = require('beautiful').awesome_icon
+            })
+        end
+    )
+end
+
+for _, app in ipairs(startupApps) do
+    run_once(app)
 end