diff --git a/lib/rspec/openapi/components_updater.rb b/lib/rspec/openapi/components_updater.rb
index b53b63d7..2db7bba4 100644
--- a/lib/rspec/openapi/components_updater.rb
+++ b/lib/rspec/openapi/components_updater.rb
@@ -14,12 +14,13 @@ def update!(base, fresh)
     nested_refs = find_non_top_level_nested_refs(base, generated_schema_names)
     nested_refs.each do |paths|
       # Slice between the parent name and the element before "$ref"
-      # [..., "Table", "properties", "database",           "$ref"]
-      #       ^idx-1   ^idx          ^size-idx
-      # [..., "Table", "properties", "columns", "items",   "$ref"]
-      #       ^idx-1   ^idx                     ^size-idx
-      idx_properties = paths.size - 1 - paths.reverse.find_index('properties')
-      needle = paths.slice(idx_properties - 1, paths.size - idx_properties)
+      # ["components", "schema", "Table", "properties", "database",                       "$ref"]
+      #  0             1         2 ^....................^
+      # ["components", "schema", "Table", "properties", "columns", "items",               "$ref"]
+      #  0             1         2 ^...............................^
+      # ["components", "schema", "Table", "properties", "owner", "properties", "company", "$ref"]
+      #  0             1         2 ^...........................................^
+      needle = paths.slice(2, paths.size - 3)
       nested_schema = fresh_schemas.dig(*needle)
 
       # Skip if the property using $ref is not found in the parent schema. The property may be removed.
@@ -59,8 +60,8 @@ def paths_to_top_level_refs(base)
 
   def find_non_top_level_nested_refs(base, generated_names)
     nested_refs = [
-      *RSpec::OpenAPI::HashHelper.matched_paths(base, 'components.schemas.*.properties.*.$ref'),
-      *RSpec::OpenAPI::HashHelper.matched_paths(base, 'components.schemas.*.properties.*.*.$ref')
+      *RSpec::OpenAPI::HashHelper.matched_paths_deeply_nested(base, 'components.schemas', 'properties.*.$ref'),
+      *RSpec::OpenAPI::HashHelper.matched_paths_deeply_nested(base, 'components.schemas', 'properties.*.items.$ref')
     ]
     # Reject already-generated schemas to reduce unnecessary loop
     nested_refs.reject do |paths|
diff --git a/lib/rspec/openapi/hash_helper.rb b/lib/rspec/openapi/hash_helper.rb
index fb9e915c..5395ec2b 100644
--- a/lib/rspec/openapi/hash_helper.rb
+++ b/lib/rspec/openapi/hash_helper.rb
@@ -20,4 +20,17 @@ def matched_paths(obj, selector)
     end
     selectors
   end
+
+  def matched_paths_deeply_nested(obj, begin_selector, end_selector)
+    path_depth_sizes = paths_to_all_fields(obj).map(&:size).uniq
+    path_depth_sizes.map do |depth|
+      diff = depth - begin_selector.count('.') - end_selector.count('.')
+      if diff >= 0
+        selector = "#{begin_selector}.#{'*.' * diff}#{end_selector}"
+        matched_paths(obj, selector)
+      else
+        []
+      end
+    end.flatten(1)
+  end
 end
diff --git a/spec/rails/app/controllers/users_controller.rb b/spec/rails/app/controllers/users_controller.rb
new file mode 100644
index 00000000..07814660
--- /dev/null
+++ b/spec/rails/app/controllers/users_controller.rb
@@ -0,0 +1,26 @@
+class UsersController < ApplicationController
+  def show
+    render json: find_user(params[:id])
+  end
+
+  private
+
+  def find_user(id = nil)
+    case id
+    when '1', nil
+      {
+        name: 'John Doe',
+        relations: {
+          avatar: {
+            url: 'https://example.com/avatar.jpg',
+          },
+          pets: [
+            { name: 'doge', age: 8 }
+          ]
+        }
+      }
+    else
+      raise NotFoundError
+    end
+  end
+end
diff --git a/spec/rails/config/routes.rb b/spec/rails/config/routes.rb
index 0ba74542..0daaada7 100644
--- a/spec/rails/config/routes.rb
+++ b/spec/rails/config/routes.rb
@@ -4,6 +4,7 @@
   defaults format: 'json' do
     resources :tables, only: [:index, :show, :create, :update, :destroy]
     resources :images, only: [:index, :show]
+    resources :users,  only: [:show]
 
     get '/test_block' => ->(_env) { [200, { 'Content-Type' => 'text/plain' }, ['A TEST']] }
   end
diff --git a/spec/rails/doc/smart/expected.yaml b/spec/rails/doc/smart/expected.yaml
index e8b0bf64..cf4f71b9 100644
--- a/spec/rails/doc/smart/expected.yaml
+++ b/spec/rails/doc/smart/expected.yaml
@@ -134,6 +134,33 @@ paths:
                 storage_size: 12.3
                 created_at: '2020-07-17T00:00:00+00:00'
                 updated_at: '2020-07-17T00:00:00+00:00'
+  "/users/{id}": 
+    get:
+      responses:
+        "200":
+          description: "returns a user"
+          content:
+            "application/json":
+              schema:
+                "$ref": "#/components/schemas/User"
+              example:
+                name: John Doe
+                relations:
+                  avatar:
+                    url: "https://example.com/avatar.jpg"
+                  pets:
+                    - name: doge
+                      age: 8
+      summary: show
+      tags:
+      - User
+      parameters:
+      - name: id
+        in: path
+        required: true
+        schema:
+          type: integer
+        example: 1
 components:
   schemas:
     Table:
@@ -176,3 +203,29 @@ components:
           type: string
         column_type:
           type: string
+    User:
+      type: object
+      properties:
+        name:
+          type: string
+        relations:
+          type: object
+          properties:
+            avatar:
+              "$ref": "#/components/schemas/Avatar"
+            pets:
+              type: array
+              items:
+                "$ref": "#/components/schemas/Pet"
+    Avatar:
+      type: object
+      properties:
+        url:
+          type: string
+    Pet:
+      type: object
+      properties:
+        name:
+          type: string
+        age:
+          type: integer
diff --git a/spec/rails/doc/smart/openapi.yaml b/spec/rails/doc/smart/openapi.yaml
index a4ed6de7..5b1d561d 100644
--- a/spec/rails/doc/smart/openapi.yaml
+++ b/spec/rails/doc/smart/openapi.yaml
@@ -198,6 +198,15 @@ paths:
                 storage_size: 12.3
                 created_at: '2020-07-17T00:00:00+00:00'
                 updated_at: '2020-07-17T00:00:00+00:00'
+  "/users/{id}":
+    get:
+      responses:
+        '200':
+          description: returns a user
+          content:
+            application/json:
+              schema:
+                "$ref": "#/components/schemas/User"
 components:
   schemas:
     Table:
@@ -247,3 +256,17 @@ components:
       properties:
         id:
           type: integer
+    User:
+      type: object
+      properties:
+        name:
+          type: string
+        relations:
+          type: object
+          properties:
+            avatar:
+              "$ref": "#/components/schemas/Avatar"
+            pets:
+              type: array
+              items:
+                "$ref": "#/components/schemas/Pet"
diff --git a/spec/requests/rails_smart_merge_spec.rb b/spec/requests/rails_smart_merge_spec.rb
index 0cf1d20e..c78b4527 100644
--- a/spec/requests/rails_smart_merge_spec.rb
+++ b/spec/requests/rails_smart_merge_spec.rb
@@ -49,3 +49,12 @@
     end
   end
 end
+
+RSpec.describe 'Users', type: :request do
+  describe '#show' do
+    it 'returns a user' do
+      get '/users/1'
+      expect(response.status).to eq(200)
+    end
+  end
+end