diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0049465b9..13b9d75a3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -55,6 +55,7 @@
 * [#2827](https://github.com/ruby-grape/grape/pull/2827): Make the `cascade` DSL getter return the configured value (`cascade false` read back as `true`) - [@ericproulx](https://github.com/ericproulx).
 * [#2829](https://github.com/ruby-grape/grape/pull/2829): Fix a cascading route handing over only to the last route registered for the path, making a middle version (3+ mounted versions with a catch-all) answer 406 - [@ericproulx](https://github.com/ericproulx).
 * [#2826](https://github.com/ruby-grape/grape/pull/2826): Fix `api.version` not being set for the root route of a path-versioned API (`GET /v1`) - [@ericproulx](https://github.com/ericproulx).
+* [#2842](https://github.com/ruby-grape/grape/pull/2842): Warn at definition time when a `rescue_from` class is already covered by one registered earlier in the same scope, since the later handler never runs - [@ericproulx](https://github.com/ericproulx).
 * Your contribution here.
 
 ### 3.3.5 (2026-07-30)
diff --git a/README.md b/README.md
index efae8b900..f8ac3ab84 100644
--- a/README.md
+++ b/README.md
@@ -2747,6 +2747,17 @@ end
 
 In this case ```UserDefinedError``` must be inherited from ```StandardError```.
 
+When several classes could match, the one registered **first** in a scope wins — as with the clauses of a Ruby `rescue`. Register the more specific class before the broader one, or the narrower handler never runs:
+
+```ruby
+class Twitter::API < Grape::API
+  rescue_from ArgumentError do ... end   # matched first
+  rescue_from StandardError do ... end   # everything else
+end
+```
+
+Grape warns when a `rescue_from` is registered for a class an earlier one in the same scope already covers. This is about ordering within a scope; a handler in a nested namespace or a mounted API always takes precedence over one inherited from an enclosing scope, whatever the classes are.
+
 Notice that you could combine these two approaches (rescuing custom errors takes precedence). For example, it's useful for handling all exceptions except Grape validation errors.
 
 ```ruby
diff --git a/lib/grape/util/inheritable_setting.rb b/lib/grape/util/inheritable_setting.rb
index 21593255f..25bbcf519 100644
--- a/lib/grape/util/inheritable_setting.rb
+++ b/lib/grape/util/inheritable_setting.rb
@@ -384,6 +384,7 @@ def base_only_rescue_handlers
       def add_rescue_handlers(mapping, subclasses:)
         @rescue_handler_maps ||= {}
         own = (@rescue_handler_maps[subclasses ? :rescue_handlers : :base_only_rescue_handlers] ||= {})
+        ShadowedRescueHandlers.warn_about(own, mapping) if subclasses
         own.merge!(mapping) { |_klass, registered, _new| registered }
       end
 
diff --git a/lib/grape/util/shadowed_rescue_handlers.rb b/lib/grape/util/shadowed_rescue_handlers.rb
new file mode 100644
index 000000000..b5180adc5
--- /dev/null
+++ b/lib/grape/util/shadowed_rescue_handlers.rb
@@ -0,0 +1,49 @@
+# frozen_string_literal: true
+
+module Grape
+  module Util
+    # Diagnostics for +rescue_from+ registrations that can never run.
+    #
+    # Middleware::Error resolves with +find+, so within a scope the first
+    # matching class wins and one registered for a class an earlier handler
+    # already covers is dead code — silently, before this warned:
+    #
+    #   rescue_from StandardError do ... end   # wins
+    #   rescue_from ArgumentError do ... end   # never runs
+    #
+    # Warn rather than reorder: which should win is the author's call, and
+    # +rescue_from :all+ (consulted only after the registered handlers) already
+    # offers "broad first, specific still wins" to anyone who wants it.
+    module ShadowedRescueHandlers
+      module_function
+
+      # @param registered [Hash] the scope's own handlers, in registration order
+      # @param mapping [Hash] the handlers being registered now
+      # @return [void]
+      #
+      # Only a scope's own registrations are compared: across scopes the nearest
+      # one deliberately wins, so an inner +rescue_from StandardError+ shadowing
+      # an outer +rescue_from ArgumentError+ is the documented behaviour rather
+      # than a mistake. Classes sharing a handler object are skipped too, since
+      # +rescue_from A, B+ registers one handler for both and the entry that
+      # loses to the other changes nothing.
+      def warn_about(registered, mapping)
+        return if registered.empty?
+
+        mapping.each do |klass, handler|
+          covered_by, = registered.find { |already, existing| klass <= already && !existing.equal?(handler) }
+          next unless covered_by
+
+          warn(message_for(klass, covered_by))
+        end
+      end
+
+      def message_for(klass, covered_by)
+        return "Grape: rescue_from #{klass} was already registered in this scope; the first handler is kept and this one will never run." if klass == covered_by
+
+        "Grape: rescue_from #{klass} will never run — #{covered_by} was registered earlier in the same scope " \
+          'and is matched first. Register the more specific class before the broader one.'
+      end
+    end
+  end
+end
diff --git a/spec/grape/util/inheritable_setting_spec.rb b/spec/grape/util/inheritable_setting_spec.rb
index 729866879..f057514fe 100644
--- a/spec/grape/util/inheritable_setting_spec.rb
+++ b/spec/grape/util/inheritable_setting_spec.rb
@@ -227,6 +227,62 @@
       subject.add_rescue_handlers({ StandardError => :child }, subclasses: true)
       expect(subject.rescue_handlers).to eq(StandardError => :child)
     end
+
+    # Middleware::Error resolves with #find, so the first matching class in a
+    # scope wins and a narrower one registered after it is dead code.
+    describe 'shadowing warnings' do
+      def add(mapping, subclasses: true)
+        subject.add_rescue_handlers(mapping, subclasses:)
+      end
+
+      it 'warns when a broader class was registered first' do
+        add({ StandardError => :broad })
+
+        expect { add({ ArgumentError => :narrow }) }
+          .to output(/rescue_from ArgumentError will never run — StandardError was registered earlier/).to_stderr
+      end
+
+      it 'warns when the same class is registered twice' do
+        add({ ArgumentError => :first })
+
+        expect { add({ ArgumentError => :second }) }
+          .to output(/rescue_from ArgumentError was already registered in this scope/).to_stderr
+      end
+
+      it 'does not warn when the narrower class was registered first' do
+        add({ ArgumentError => :narrow })
+
+        expect { add({ StandardError => :broad }) }.not_to output.to_stderr
+      end
+
+      it 'does not warn for unrelated classes' do
+        add({ ArgumentError => :one })
+
+        expect { add({ TypeError => :two }) }.not_to output.to_stderr
+      end
+
+      # `rescue_from A, B` registers one handler for both, so the entry that
+      # loses to the other changes nothing.
+      it 'does not warn when both classes share a handler' do
+        expect { add({ StandardError => :shared, ArgumentError => :shared }) }.not_to output.to_stderr
+      end
+
+      # Exact-match handlers are consulted before the subclass-matching ones and
+      # never match a descendant, so they cannot shadow each other.
+      it 'does not warn for exact-match handlers' do
+        add({ StandardError => :broad }, subclasses: false)
+
+        expect { add({ ArgumentError => :narrow }, subclasses: false) }.not_to output.to_stderr
+      end
+
+      # Across scopes the nearest registration deliberately wins.
+      it 'does not warn about a handler inherited from an enclosing scope' do
+        parent = described_class.new.tap { |s| s.add_rescue_handlers({ StandardError => :outer }, subclasses: true) }
+        subject.inherit_from parent
+
+        expect { add({ ArgumentError => :inner }) }.not_to output.to_stderr
+      end
+    end
   end
 
   describe '#route' do