From 3de199f632f055ea326ea53327a802ecf47a48bf Mon Sep 17 00:00:00 2001
From: Aditya kumar singh <143548997+Adityakk9031@users.noreply.github.com>
Date: Sun, 8 Nov 2026 01:09:18 +0530
Subject: [PATCH] fix(type): support nilable elements in ArrayOf and HashOf
 case equality

---
 lib/context_dev/internal/type/array_of.rb     |  2 +-
 lib/context_dev/internal/type/hash_of.rb      |  2 ++
 .../internal/type/base_model_test.rb          | 27 +++++++++++++++++++
 3 files changed, 30 insertions(+), 1 deletion(-)

diff --git a/lib/context_dev/internal/type/array_of.rb b/lib/context_dev/internal/type/array_of.rb
index bc000d46..7f6d09d6 100644
--- a/lib/context_dev/internal/type/array_of.rb
+++ b/lib/context_dev/internal/type/array_of.rb
@@ -38,7 +38,7 @@ def self.[](...) = new(...)
         # @param other [Object]
         #
         # @return [Boolean]
-        def ===(other) = other.is_a?(Array) && other.all?(item_type)
+        def ===(other) = other.is_a?(Array) && other.all? { (nilable? && _1.nil?) || item_type === _1 }
 
         # @api public
         #
diff --git a/lib/context_dev/internal/type/hash_of.rb b/lib/context_dev/internal/type/hash_of.rb
index 31013889..b02ece88 100644
--- a/lib/context_dev/internal/type/hash_of.rb
+++ b/lib/context_dev/internal/type/hash_of.rb
@@ -46,6 +46,8 @@ def ===(other)
               case [key, val]
               in [Symbol | String, ^type]
                 true
+              in [Symbol | String, nil] if nilable?
+                true
               else
                 false
               end
diff --git a/test/context_dev/internal/type/base_model_test.rb b/test/context_dev/internal/type/base_model_test.rb
index f3de30e8..6674368a 100644
--- a/test/context_dev/internal/type/base_model_test.rb
+++ b/test/context_dev/internal/type/base_model_test.rb
@@ -725,3 +725,30 @@ def test_meta_retrieval
     assert_equal({doc: "dawg"}, ub)
   end
 end
+
+class ContextDev::Test::NilableCollectionCaseEqualityTest < Minitest::Test
+  def test_array_of_nilable_case_equality
+    arr_type = ContextDev::Internal::Type::ArrayOf[String, nil?: true]
+    assert_operator(arr_type, :===, ["hello", nil])
+    assert_operator(arr_type, :===, [nil])
+    assert_operator(arr_type, :===, ["hello", "world"])
+    refute_operator(arr_type, :===, ["hello", 123])
+
+    non_nilable = ContextDev::Internal::Type::ArrayOf[String]
+    assert_operator(non_nilable, :===, ["hello", "world"])
+    refute_operator(non_nilable, :===, ["hello", nil])
+  end
+
+  def test_hash_of_nilable_case_equality
+    hash_type = ContextDev::Internal::Type::HashOf[String, nil?: true]
+    assert_operator(hash_type, :===, {a: "hello", b: nil})
+    assert_operator(hash_type, :===, {"a" => "hello", "b" => nil})
+    assert_operator(hash_type, :===, {a: nil})
+    assert_operator(hash_type, :===, {a: "hello"})
+    refute_operator(hash_type, :===, {a: 123})
+
+    non_nilable = ContextDev::Internal::Type::HashOf[String]
+    assert_operator(non_nilable, :===, {a: "hello", b: "world"})
+    refute_operator(non_nilable, :===, {a: "hello", b: nil})
+  end
+end