diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4ce5face0..c83660b57 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@
 #### Fixes
 
 * [#2767](https://github.com/ruby-grape/grape/pull/2767): Update rubocop to 1.88.0 and rubocop-rspec to 3.10.2 - [@ericproulx](https://github.com/ericproulx).
+* [#2773](https://github.com/ruby-grape/grape/pull/2773): Fix middleware build crash when a top-level `::Options` constant is in scope - [@ericproulx](https://github.com/ericproulx).
 * Your contribution here.
 
 ### 3.3.1 (2026-06-28)
diff --git a/lib/grape/middleware/base.rb b/lib/grape/middleware/base.rb
index f47ec752e..975208952 100644
--- a/lib/grape/middleware/base.rb
+++ b/lib/grape/middleware/base.rb
@@ -16,10 +16,8 @@ class Base
       #   subclass's `DEFAULT_OPTIONS` Hash (legacy path) and frozen.
       def initialize(app, **options)
         @app = app
-        if self.class.const_defined?(:Options)
-          # Search ancestors so subclasses (e.g. Versioner::Path → Versioner::Base)
-          # inherit their parent's Options Data class without redeclaring it.
-          @config = self.class::Options.new(**options)
+        if (config_class = options_data_class)
+          @config = config_class.new(**options)
           @options = @config.to_h.freeze
         else
           @options = merge_default_options(options).freeze
@@ -92,9 +90,25 @@ def merge_headers(response)
 
       def merge_default_options(options)
         return default_options.deep_merge(options) if respond_to?(:default_options)
-        return self.class::DEFAULT_OPTIONS.deep_merge(options) if self.class.const_defined?(:DEFAULT_OPTIONS)
 
-        options
+        default_options_constant&.deep_merge(options) || options
+      end
+
+      # self.class::Options honours middleware inheritance (e.g. Versioner::Path
+      # → Versioner::Base) and, unlike const_defined?, never resolves a
+      # top-level ::Options on Object. Absent an own/inherited Options class,
+      # the lookup raises NameError and we fall back to the legacy path.
+      def options_data_class
+        self.class::Options
+      rescue NameError
+        nil
+      end
+
+      # Same idea as {#options_data_class} for the legacy DEFAULT_OPTIONS Hash.
+      def default_options_constant
+        self.class::DEFAULT_OPTIONS
+      rescue NameError
+        nil
       end
 
       def try_scrub(obj)
diff --git a/spec/grape/middleware/base_spec.rb b/spec/grape/middleware/base_spec.rb
index 0884f50ab..8bd9f59e8 100644
--- a/spec/grape/middleware/base_spec.rb
+++ b/spec/grape/middleware/base_spec.rb
@@ -153,6 +153,74 @@
         expect(example_ware.new(blank_app, monkey: false).options[:monkey]).to be false
       end
     end
+
+    context 'when an unrelated top-level ::Options constant is in scope' do
+      # The `options` gem (a transitive dep of e.g. progress_bar) defines a
+      # global ::Options. const_defined?(:Options) reaches it through Object,
+      # but `self.class::Options` does not, so the naive guard raised NameError.
+      before { stub_const('Options', Module.new) }
+
+      let(:example_ware) do
+        Class.new(Grape::Middleware::Base) do
+          const_set(:DEFAULT_OPTIONS, { monkey: true }.freeze)
+        end
+      end
+
+      it 'builds without resolving the global ::Options' do
+        expect { example_ware.new(blank_app) }.not_to raise_error
+      end
+
+      it 'falls back to the legacy DEFAULT_OPTIONS path' do
+        expect(example_ware.new(blank_app).options[:monkey]).to be true
+      end
+
+      it 'does not expose a config object' do
+        expect(example_ware.new(blank_app).config).to be_nil
+      end
+    end
+
+    context 'when an unrelated top-level ::DEFAULT_OPTIONS constant is in scope' do
+      before { stub_const('DEFAULT_OPTIONS', { monkey: true }.freeze) }
+
+      let(:example_ware) { Class.new(described_class) }
+
+      it 'ignores the global ::DEFAULT_OPTIONS' do
+        expect(example_ware.new(blank_app).options).not_to have_key(:monkey)
+      end
+    end
+
+    context 'when a middleware declares its own Options Data class' do
+      let(:example_ware) do
+        Class.new(Grape::Middleware::Base) do
+          self::Options = Data.define(:monkey)
+        end
+      end
+
+      it 'routes options through the Options value object' do
+        instance = example_ware.new(blank_app, monkey: true)
+        expect(instance.config.monkey).to be true
+        expect(instance.options[:monkey]).to be true
+      end
+
+      it 'still resolves its own Options when a global ::Options is in scope' do
+        stub_const('Options', Module.new)
+        expect(example_ware.new(blank_app, monkey: true).config.monkey).to be true
+      end
+    end
+
+    context 'when a middleware inherits its parent Options Data class' do
+      let(:parent_ware) do
+        Class.new(Grape::Middleware::Base) do
+          self::Options = Data.define(:monkey)
+        end
+      end
+
+      let(:child_ware) { Class.new(parent_ware) }
+
+      it 'inherits the ancestor Options without redeclaring it' do
+        expect(child_ware.new(blank_app, monkey: true).config.monkey).to be true
+      end
+    end
   end
 
   context 'header' do