release: 0.35.2

.release-please-manifest.json

@@ -1,3 +1,3 @@
 {
-  ".": "0.35.1"
+  ".": "0.35.2"
 }

CHANGELOG.md

@@ -1,5 +1,14 @@
 # Changelog
 
+## 0.35.2 (2025-11-05)
+
+Full Changelog: [v0.35.1...v0.35.2](https://github.com/openai/openai-ruby/compare/v0.35.1...v0.35.2)
+
+### Bug Fixes
+
+* better thread safety via early initializing SSL store during HTTP client creation ([e7d9a3d](https://github.com/openai/openai-ruby/commit/e7d9a3d70c0930ac248b4da680296213cb3e163d))
+* schema generation ([#862](https://github.com/openai/openai-ruby/issues/862)) ([2c9b91a](https://github.com/openai/openai-ruby/commit/2c9b91acc79262dd56ef52854ad64384f172984b))
+
 ## 0.35.1 (2025-11-04)
 
 Full Changelog: [v0.35.0...v0.35.1](https://github.com/openai/openai-ruby/compare/v0.35.0...v0.35.1)

Gemfile.lock

@@ -11,7 +11,7 @@ GIT
 PATH
   remote: .
   specs:
-    openai (0.35.1)
+    openai (0.35.2)
       connection_pool
 
 GEM

README.md

@@ -15,7 +15,7 @@ To use this gem, install via Bundler by adding the following to your application
 <!-- x-release-please-start-version -->
 
 ```ruby
-gem "openai", "~> 0.35.1"
+gem "openai", "~> 0.35.2"
 ```
 
 <!-- x-release-please-end -->

lib/openai.rb

@@ -8,6 +8,7 @@
 require "etc"
 require "json"
 require "net/http"
+require "openssl"
 require "pathname"
 require "rbconfig"
 require "securerandom"

lib/openai/helpers/structured_output/union_of.rb

@@ -21,6 +21,7 @@ class UnionOf
         #
         # @return [Hash{Symbol=>Object}]
         def to_json_schema_inner(state:)
+          # rubocop:disable Metrics/BlockLength
           OpenAI::Helpers::StructuredOutput::JsonSchemaConverter.cache_def!(state, type: self) do
             path = state.fetch(:path)
             mergeable_keys = {[:anyOf] => 0, [:type] => 0}
@@ -33,7 +34,9 @@ def to_json_schema_inner(state:)
             end
 
             schemas.each do |schema|
-              mergeable_keys.each_key { mergeable_keys[_1] += 1 if schema.keys == _1 }
+              mergeable_keys.each_key do
+                mergeable_keys[_1] += 1 if schema.keys == _1 && schema[_1].is_a?(Array)
+              end
             end
             mergeable = mergeable_keys.any? { _1.last == schemas.length }
             if mergeable
@@ -48,6 +51,7 @@ def to_json_schema_inner(state:)
               }
             end
           end
+          # rubocop:enable Metrics/BlockLength
         end
 
         private_class_method :new

lib/openai/internal/transport/pooled_net_requester.rb

@@ -16,10 +16,11 @@ class PooledNetRequester
         class << self
           # @api private
           #
+          # @param cert_store [OpenSSL::X509::Store]
           # @param url [URI::Generic]
           #
           # @return [Net::HTTP]
-          def connect(url)
+          def connect(cert_store:, url:)
             port =
               case [url.port, url.scheme]
               in [Integer, _]
@@ -33,6 +34,8 @@ def connect(url)
             Net::HTTP.new(url.host, port).tap do
               _1.use_ssl = %w[https wss].include?(url.scheme)
               _1.max_retries = 0
+
+              (_1.cert_store = cert_store) if _1.use_ssl?
             end
           end
 
@@ -102,7 +105,7 @@ def build_request(request, &blk)
           pool =
             @mutex.synchronize do
               @pools[origin] ||= ConnectionPool.new(size: @size) do
-                self.class.connect(url)
+                self.class.connect(cert_store: @cert_store, url: url)
               end
             end
 
@@ -192,6 +195,7 @@ def execute(request)
         def initialize(size: self.class::DEFAULT_MAX_CONNECTIONS)
           @mutex = Mutex.new
           @size = size
+          @cert_store = OpenSSL::X509::Store.new.tap(&:set_default_paths)
           @pools = {}
         end
 

lib/openai/version.rb

@@ -1,5 +1,5 @@
 # frozen_string_literal: true
 
 module OpenAI
-  VERSION = "0.35.1"
+  VERSION = "0.35.2"
 end

manifest.yaml

@@ -6,6 +6,7 @@ dependencies:
   - etc
   - json
   - net/http
+  - openssl
   - pathname
   - rbconfig
   - securerandom

rbi/openai/internal/transport/pooled_net_requester.rbi

@@ -26,8 +26,12 @@ module OpenAI
 
         class << self
           # @api private
-          sig { params(url: URI::Generic).returns(Net::HTTP) }
-          def connect(url)
+          sig do
+            params(cert_store: OpenSSL::X509::Store, url: URI::Generic).returns(
+              Net::HTTP
+            )
+          end
+          def connect(cert_store:, url:)
           end
 
           # @api private

sig/openai/internal/transport/pooled_net_requester.rbs

@@ -17,7 +17,10 @@ module OpenAI
 
         DEFAULT_MAX_CONNECTIONS: Integer
 
-        def self.connect: (URI::Generic url) -> top
+        def self.connect: (
+          cert_store: OpenSSL::X509::Store,
+          url: URI::Generic
+        ) -> top
 
         def self.calibrate_socket_timeout: (top conn, Float deadline) -> void
 

test/openai/helpers/structured_output_test.rb

@@ -39,6 +39,7 @@ class M3 < OpenAI::Helpers::StructuredOutput::BaseModel
   U1 = OpenAI::Helpers::StructuredOutput::UnionOf[Integer, A1]
   U2 = OpenAI::Helpers::StructuredOutput::UnionOf[M2, M3]
   U3 = OpenAI::Helpers::StructuredOutput::UnionOf[A1, A1]
+  U4 = OpenAI::Helpers::StructuredOutput::UnionOf[String, NilClass]
 
   def test_coerce
     cases = {
@@ -117,6 +118,12 @@ def test_to_schema
             additionalProperties: false
           }
         ]
+      },
+      U4 => {
+        anyOf: [
+          {type: "string"},
+          {type: "null"}
+        ]
       }
     }
     cases.each do |input, expected|