diff --git a/lib/msf/core/modules/external/shim.rb b/lib/msf/core/modules/external/shim.rb
index e9dd1a0f63..be79240b65 100644
--- a/lib/msf/core/modules/external/shim.rb
+++ b/lib/msf/core/modules/external/shim.rb
@@ -4,7 +4,11 @@ require 'msf/core/modules/external'
 class Msf::Modules::External::Shim
   def self.generate(module_path, framework)
     mod = Msf::Modules::External.new(module_path, framework: framework)
-    return nil unless mod.meta
+    # first check if meta exists and raise an issue if not, #14281
+    # raise instead of returning nil to avoid confusion
+    unless mod.meta
+      raise LoadError, " Try running file manually to check for errors or dependency issues."
+    end
     case mod.meta['type']
     when 'remote_exploit'
       remote_exploit(mod)
diff --git a/lib/msf/core/modules/loader/base.rb b/lib/msf/core/modules/loader/base.rb
index be290f6e91..d542716fd0 100644
--- a/lib/msf/core/modules/loader/base.rb
+++ b/lib/msf/core/modules/loader/base.rb
@@ -466,9 +466,17 @@ class Msf::Modules::Loader::Base
 
   # Tries to determine if a file might be executable,
   def script_path?(path)
-    File.executable?(path) &&
-      !File.directory?(path) &&
-      ['#!', '//'].include?(File.read(path, 2))
+    # warn users if their external modules aren't marked executable
+    # per #14281
+    if File.directory?(path) || !['#!', '//'].include?(File.read(path, 2))
+      false
+    elsif File.executable?(path)
+      true
+    else
+      # prefer elog since load_error clutters the UI on potential false positives
+      elog("Unable to load module #{path} - LoadError Possible non-executable external module.")
+      false
+    end
   end
 
   # Changes a file name path to a canonical module reference name.