diff --git a/lib/bundler/cli.rb b/lib/bundler/cli.rb
index 8d9f3a5b7d2ee8..3ff5f68a509ecd 100644
--- a/lib/bundler/cli.rb
+++ b/lib/bundler/cli.rb
@@ -477,6 +477,10 @@ def cache
       into the system wide RubyGems repository.
     D
     def exec(*args)
+      if ARGV.include?("--no-keep-file-descriptors")
+        SharedHelpers.major_deprecation(2, "The `--no-keep-file-descriptors` has been deprecated. `bundle exec` no longer mess with your file descriptors. Close them in the exec'd script if you need to")
+      end
+
       require_relative "cli/exec"
       Exec.new(options, args).run
     end
diff --git a/spec/bundler/other/major_deprecation_spec.rb b/spec/bundler/other/major_deprecation_spec.rb
index 688efbcec8420c..daebdbe1f20b8d 100644
--- a/spec/bundler/other/major_deprecation_spec.rb
+++ b/spec/bundler/other/major_deprecation_spec.rb
@@ -92,6 +92,18 @@
     end
   end
 
+  describe "bundle exec --no-keep-file-descriptors" do
+    before do
+      bundle "exec --no-keep-file-descriptors -e 1", :raise_on_error => false
+    end
+
+    it "is deprecated", :bundler => "< 3" do
+      expect(deprecations).to include "The `--no-keep-file-descriptors` has been deprecated. `bundle exec` no longer mess with your file descriptors. Close them in the exec'd script if you need to"
+    end
+
+    pending "is removed and shows a helpful error message about it", :bundler => "3"
+  end
+
   describe "bundle update --quiet" do
     it "does not print any deprecations" do
       bundle :update, :quiet => true, :raise_on_error => false