diff --git a/docs/_getting_started/configuration.md b/docs/_getting_started/configuration.md
index e34b30ad6..9e1910726 100644
--- a/docs/_getting_started/configuration.md
+++ b/docs/_getting_started/configuration.md
@@ -202,6 +202,10 @@ RubyLLM.configure do |config|
 
   # Or use Rails logger
   config.logger = Rails.logger  # Overrides log_file and log_level
+
+  # Set custom timeout for log filtering
+  # which is useful when working with large payloads
+  config.log_regexp_timeout = 4 # seconds
 end
 ```
 
@@ -354,6 +358,7 @@ RubyLLM.configure do |config|
   config.log_file = String
   config.log_level = Symbol
   config.log_stream_debug = Boolean
+  config.log_regexp_timeout = Integer
 end
 ```
 
@@ -363,4 +368,4 @@ Now that you've configured RubyLLM, you're ready to:
 
 - [Start chatting with AI models]({% link _core_features/chat.md %})
 - [Work with different providers and models]({% link _advanced/models.md %})
-- [Set up Rails integration]({% link _advanced/rails.md %})
\ No newline at end of file
+- [Set up Rails integration]({% link _advanced/rails.md %})
diff --git a/lib/ruby_llm/configuration.rb b/lib/ruby_llm/configuration.rb
index eda2c3354..dc1cc2e44 100644
--- a/lib/ruby_llm/configuration.rb
+++ b/lib/ruby_llm/configuration.rb
@@ -43,7 +43,8 @@ class Configuration
                   :logger,
                   :log_file,
                   :log_level,
-                  :log_stream_debug
+                  :log_stream_debug,
+                  :log_regexp_timeout
 
     def initialize
       @request_timeout = 120
@@ -64,6 +65,7 @@ def initialize
       @log_file = $stdout
       @log_level = ENV['RUBYLLM_DEBUG'] ? Logger::DEBUG : Logger::INFO
       @log_stream_debug = ENV['RUBYLLM_STREAM_DEBUG'] == 'true'
+      @log_regexp_timeout = Gem::Version.new(RUBY_VERSION) >= Gem::Version.new('3.2.0') ? (Regexp.timeout || 1.0) : nil
     end
 
     def instance_variables
diff --git a/lib/ruby_llm/connection.rb b/lib/ruby_llm/connection.rb
index 52252781c..fd18c8d45 100644
--- a/lib/ruby_llm/connection.rb
+++ b/lib/ruby_llm/connection.rb
@@ -66,8 +66,19 @@ def setup_logging(faraday)
                        errors: true,
                        headers: false,
                        log_level: :debug do |logger|
-        logger.filter(%r{[A-Za-z0-9+/=]{100,}}, 'data":"[BASE64 DATA]"')
-        logger.filter(/[-\d.e,\s]{100,}/, '[EMBEDDINGS ARRAY]')
+        if Gem::Version.new(RUBY_VERSION) >= Gem::Version.new('3.2.0')
+          logger.filter(
+            Regexp.new('[A-Za-z0-9+/=]{100,}', timeout: @config.log_regexp_timeout),
+            'data":"[BASE64 DATA]"'
+          )
+          logger.filter(Regexp.new('[-\\d.e,\\s]{100,}', timeout: @config.log_regexp_timeout), '[EMBEDDINGS ARRAY]')
+        else
+          if @config.log_regexp_timeout
+            RubyLLM.logger.warn("log_regexp_timeout is not supported on Ruby #{RUBY_VERSION}")
+          end
+          logger.filter(Regexp.new('[A-Za-z0-9+/=]{100,}'), 'data":"[BASE64 DATA]"')
+          logger.filter(Regexp.new('[-\\d.e,\\s]{100,}'), '[EMBEDDINGS ARRAY]')
+        end
       end
     end
 
diff --git a/spec/ruby_llm/context_spec.rb b/spec/ruby_llm/context_spec.rb
index 2bbb25626..a05c8a6fd 100644
--- a/spec/ruby_llm/context_spec.rb
+++ b/spec/ruby_llm/context_spec.rb
@@ -10,20 +10,24 @@
       # Get current config values
       original_model = RubyLLM.config.default_model
       original_api_key = RubyLLM.config.openai_api_key
+      original_log_regexp_timeout = RubyLLM.config.log_regexp_timeout
 
       # Create context with modified config
       context = RubyLLM.context do |config|
         config.default_model = 'modified-model'
         config.openai_api_key = 'modified-key'
+        config.log_regexp_timeout = 5.0
       end
 
       # Verify global config is unchanged
       expect(RubyLLM.config.default_model).to eq(original_model)
       expect(RubyLLM.config.openai_api_key).to eq(original_api_key)
+      expect(RubyLLM.config.log_regexp_timeout).to eq(original_log_regexp_timeout)
 
       # Verify context has modified config
       expect(context.config.default_model).to eq('modified-model')
       expect(context.config.openai_api_key).to eq('modified-key')
+      expect(context.config.log_regexp_timeout).to eq(5.0)
     end
   end
 
@@ -95,6 +99,7 @@
     it 'allows multiple contexts with different configurations' do
       context1 = RubyLLM.context do |config|
         config.default_model = 'gpt-4.1-nano'
+        config.log_regexp_timeout = 5.0
       end
 
       context2 = RubyLLM.context do |config|
@@ -105,7 +110,11 @@
       chat2 = context2.chat
 
       expect(chat1.model.id).to eq('gpt-4.1-nano')
+      expect(context1.config.log_regexp_timeout).not_to eq(Regexp.timeout)
+      expect(context1.config.log_regexp_timeout).to eq(5.0)
+
       expect(chat2.model.id).to eq('claude-3-5-haiku-20241022')
+      expect(context2.config.log_regexp_timeout).to eq(Regexp.timeout)
     end
 
     it 'ensures changes in one context do not affect another' do