chore: Replace rest-client with httparty for improved maintainability and security

.gitignore

@@ -1,5 +1,7 @@
 .env
 **/*/.env
+# Example test files
+examples/messages/large_test_file.txt
 *.gem
 *.rbc
 .bundle

CHANGELOG.md

@@ -1,6 +1,11 @@
 # Changelog
 
 ### Unreleased
+* Replaced `rest-client` dependency with `httparty` for improved maintainability and security
+  - `rest-client` is no longer actively maintained and has known security vulnerabilities
+  - `httparty` is actively maintained and provides better performance
+  - All existing functionality remains backwards compatible - no customer code changes required
+  - Removed workaround for `rest-client` cookie jar threading bug
 * Added support for new `fields` query parameter values in Messages API:
   - `include_tracking_options`: Returns messages and their tracking settings
   - `raw_mime`: Returns the grant_id, object, id, and raw_mime fields only
@@ -11,6 +16,11 @@
   - `label`: String label describing the message tracking purpose
 * Added support for `raw_mime` field in message responses containing Base64url-encoded message data
 * Added `MessageFields` module with constants for all valid field values to improve developer experience
+* Fixed multipart email sending bug where large attachments would fail due to multipart flag key mismatch (#525)
+  - `FileUtils.handle_message_payload` transforms keys to symbols (`:multipart`)
+  - `HttpClient.build_request` was only checking for string keys (`"multipart"`)
+  - Now checks for both string and symbol keys to maintain full backwards compatibility
+  - Prevents encoding errors when sending emails with attachments larger than 3MB
 
 ### 6.4.0 / 2025-04-30
 * Added support for Notetaker APIs

README.md

@@ -26,7 +26,7 @@ If you have a question about the Nylas Communications Platform, [contact Nylas S
 ### Prerequisites
 
 - Ruby 3.0 or above.
-- Ruby Frameworks: `rest-client` and `yajl-ruby`.
+- Ruby Frameworks: `httparty` and `yajl-ruby`.
 
 ### Install
 

examples/.env.example

@@ -12,4 +12,8 @@ NYLAS_API_URI=https://api.us.nylas.com
 
 # Grant ID - Required for message and event examples
 # You can get this from your Nylas Dashboard after connecting an account
-NYLAS_GRANT_ID=your_grant_id_here
+NYLAS_GRANT_ID=your_grant_id_here
+
+# Send email - Optionl 
+# Used for send examples
+[email protected]

examples/README.md

@@ -10,7 +10,9 @@ examples/
 ├── events/                   # Event-related examples
 │   └── event_notetaker_example.rb    # Example of creating events with Notetaker
 ├── messages/                 # Message-related examples
-│   └── message_fields_example.rb     # Example of using new message fields functionality
+│   ├── message_fields_example.rb     # Example of using new message fields functionality
+│   ├── file_upload_example.rb        # Example of file upload functionality with HTTParty migration
+│   └── send_message_example.rb       # Example of basic message sending functionality
 └── notetaker/               # Standalone Notetaker examples
     ├── README.md            # Notetaker-specific documentation
     └── notetaker_example.rb # Basic Notetaker functionality example
@@ -53,6 +55,31 @@ Before running any example, make sure to:
   export NYLAS_GRANT_ID="your_grant_id"
   ```
 
+- `messages/file_upload_example.rb`: Demonstrates file upload functionality with the HTTParty migration, including:
+  - Sending messages with small attachments (<3MB) - handled as JSON with base64 encoding
+  - Sending messages with large attachments (>3MB) - handled as multipart form data
+  - Creating test files of appropriate sizes for demonstration
+  - File handling logic and processing differences
+  - Verification that HTTParty migration works for both upload methods
+
+  Additional environment variables needed:
+  ```bash
+  export NYLAS_GRANT_ID="your_grant_id"
+  export NYLAS_TEST_EMAIL="[email protected]"  # Email address to send test messages to
+  ```
+
+- `messages/send_message_example.rb`: Demonstrates basic message sending functionality, including:
+  - Sending simple text messages
+  - Handling multiple recipients (TO, CC, BCC)
+  - Sending rich HTML content
+  - Processing responses and error handling
+
+  Additional environment variables needed:
+  ```bash
+  export NYLAS_GRANT_ID="your_grant_id"
+  export NYLAS_TEST_EMAIL="[email protected]"  # Email address to send test messages to
+  ```
+
 ### Notetaker
 - `notetaker/notetaker_example.rb`: Shows basic Notetaker functionality, including:
   - Inviting a Notetaker to a meeting

examples/messages/file_upload_example.rb

@@ -0,0 +1,276 @@
+#!/usr/bin/env ruby
+# frozen_string_literal: true
+
+# Example demonstrating file upload functionality in the Nylas Ruby SDK
+# Tests both small (<3MB) and large (>3MB) file handling with the new HTTParty implementation
+#
+# This example shows how to:
+# 1. Send messages with small attachments (<3MB) - handled as JSON with base64 encoding
+# 2. Send messages with large attachments (>3MB) - handled as multipart form data
+# 3. Create test files of appropriate sizes for demonstration
+# 4. Handle file upload errors and responses
+#
+# Prerequisites:
+# - Ruby 3.0 or later
+# - A Nylas API key
+# - A grant ID (connected email account)
+# - A test email address to send to
+#
+# Environment variables needed:
+# export NYLAS_API_KEY="your_api_key"
+# export NYLAS_GRANT_ID="your_grant_id"
+# export NYLAS_TEST_EMAIL="[email protected]"  # Email address to send test messages to
+# export NYLAS_API_URI="https://api.us.nylas.com"  # Optional
+#
+# Alternatively, create a .env file in the examples directory with:
+# NYLAS_API_KEY=your_api_key
+# NYLAS_GRANT_ID=your_grant_id
+# [email protected]
+# NYLAS_API_URI=https://api.us.nylas.com
+
+$LOAD_PATH.unshift File.expand_path('../../lib', __dir__)
+require "nylas"
+require "json"
+require "tempfile"
+
+# Simple .env file loader
+def load_env_file
+  env_file = File.expand_path('../.env', __dir__)
+  return unless File.exist?(env_file)
+
+  puts "Loading environment variables from .env file..."
+  File.readlines(env_file).each do |line|
+    line = line.strip
+    next if line.empty? || line.start_with?('#')
+
+    key, value = line.split('=', 2)
+    next unless key && value
+
+    # Remove quotes if present
+    value = value.gsub(/\A['"]|['"]\z/, '')
+    ENV[key] = value
+  end
+end
+
+def create_small_test_file
+  puts "\n=== Creating Small Test File (<3MB) ==="
+
+  # Create a 1MB test file
+  content = "A" * (1024 * 1024)  # 1MB of 'A' characters
+
+  temp_file = Tempfile.new(['small_test', '.txt'])
+  temp_file.write(content)
+  temp_file.rewind
+
+  puts "- Created test file: #{temp_file.path}"
+  puts "- File size: #{File.size(temp_file.path)} bytes (#{File.size(temp_file.path) / (1024.0 * 1024).round(2)} MB)"
+  puts "- This will be sent as JSON with base64 encoding"
+
+  temp_file
+end
+
+def find_or_create_large_test_file
+  puts "\n=== Finding Large Test File (>3MB) ==="
+
+  # Look for an existing large file, or create one if needed
+  large_file_path = File.expand_path("large_test_file.txt", __dir__)
+
+  unless File.exist?(large_file_path) && File.size(large_file_path) > 3 * 1024 * 1024
+    puts "- Creating 5MB test file on disk..."
+    content = "B" * (5 * 1024 * 1024)  # 5MB of 'B' characters
+    File.write(large_file_path, content)
+    puts "- Created permanent test file: #{large_file_path}"
+  else
+    puts "- Found existing test file: #{large_file_path}"
+  end
+
+  puts "- File size: #{File.size(large_file_path)} bytes (#{File.size(large_file_path) / (1024.0 * 1024).round(2)} MB)"
+  puts "- This will be sent as multipart form data"
+
+  large_file_path
+end
+
+def send_message_with_small_attachment(nylas, grant_id, recipient_email, test_file)
+  puts "\n=== Sending Message with Small Attachment ==="
+
+  begin
+    # Build the file attachment
+    file_attachment = Nylas::FileUtils.attach_file_request_builder(test_file.path)
+
+    request_body = {
+      subject: "Test Email with Small Attachment (<3MB) - HTTParty Migration Test",
+      to: [{ email: recipient_email }],
+      body: "This is a test email with a small attachment (<3MB) to verify the HTTParty migration works correctly.\n\nFile size: #{File.size(test_file.path)} bytes\nSent at: #{Time.now}",
+      attachments: [file_attachment]
+    }
+
+    puts "- Sending message with small attachment..."
+    puts "- Recipient: #{recipient_email}"
+    puts "- Attachment size: #{File.size(test_file.path)} bytes"
+    puts "- Expected handling: JSON with base64 encoding"
+
+    response, request_id = nylas.messages.send(
+      identifier: grant_id,
+      request_body: request_body
+    )
+
+    puts "✅ Message sent successfully!"
+    puts "- Message ID: #{response[:id]}"
+    puts "- Request ID: #{request_id}"
+    puts "- Grant ID: #{response[:grant_id]}"
+
+    response
+  rescue => e
+    puts "❌ Failed to send message with small attachment: #{e.message}"
+    puts "- Error class: #{e.class}"
+    raise
+  end
+end
+
+def send_message_with_large_attachment(nylas, grant_id, recipient_email, test_file_path)
+  puts "\n=== Sending Message with Large Attachment ==="
+
+  begin
+    # Build the file attachment
+    file_attachment = Nylas::FileUtils.attach_file_request_builder(test_file_path)
+
+    request_body = {
+      subject: "Test Email with Large Attachment (>3MB) - HTTParty Migration Test",
+      to: [{ email: recipient_email }],
+      body: "This is a test email with a large attachment (>3MB) to verify the HTTParty migration works correctly.\n\nFile size: #{File.size(test_file_path)} bytes\nSent at: #{Time.now}",
+      attachments: [file_attachment]
+    }
+
+    puts "- Sending message with large attachment..."
+    puts "- Recipient: #{recipient_email}"
+    puts "- Attachment size: #{File.size(test_file_path)} bytes"
+    puts "- Expected handling: Multipart form data"
+
+    response, request_id = nylas.messages.send(
+      identifier: grant_id,
+      request_body: request_body
+    )
+
+    puts "✅ Message sent successfully!"
+    puts "- Message ID: #{response[:id]}"
+    puts "- Request ID: #{request_id}"
+    puts "- Grant ID: #{response[:grant_id]}"
+
+    response
+  rescue => e
+    puts "❌ Failed to send message with large attachment: #{e.message}"
+    puts "- Error class: #{e.class}"
+    raise
+  end
+end
+
+def demonstrate_file_utils_handling
+  puts "\n=== Demonstrating File Handling Logic ==="
+
+  # Create temporary files to test the file handling logic
+  small_file = create_small_test_file
+  large_file_path = find_or_create_large_test_file
+
+  begin
+    # Test small file handling
+    small_attachment = Nylas::FileUtils.attach_file_request_builder(small_file.path)
+    puts "- Small file attachment structure: #{small_attachment.keys}"
+
+    # Test large file handling  
+    large_attachment = Nylas::FileUtils.attach_file_request_builder(large_file_path)
+    puts "- Large file attachment structure: #{large_attachment.keys}"
+
+    # Demonstrate the SDK's file size handling
+    small_payload = {
+      subject: "test",
+      attachments: [small_attachment]
+    }
+
+    large_payload = {
+      subject: "test", 
+      attachments: [large_attachment]
+    }
+
+    # Show how the SDK determines handling method
+    small_handling, small_files = Nylas::FileUtils.handle_message_payload(small_payload)
+    large_handling, large_files = Nylas::FileUtils.handle_message_payload(large_payload)
+
+    puts "- Small file handling method: #{small_handling['multipart'] ? 'Form Data' : 'JSON'}"
+    puts "- Large file handling method: #{large_handling['multipart'] ? 'Form Data' : 'JSON'}"
+
+  ensure
+    small_file.close
+    small_file.unlink
+    # Note: We keep the large file on disk for future use
+  end
+end
+
+def main
+  # Load .env file if it exists
+  load_env_file
+
+  # Check for required environment variables
+  api_key = ENV["NYLAS_API_KEY"]
+  grant_id = ENV["NYLAS_GRANT_ID"] 
+  test_email = ENV["NYLAS_TEST_EMAIL"]
+
+  raise "NYLAS_API_KEY environment variable is not set" unless api_key
+  raise "NYLAS_GRANT_ID environment variable is not set" unless grant_id
+  raise "NYLAS_TEST_EMAIL environment variable is not set" unless test_email
+
+  puts "=== Nylas File Upload Example - HTTParty Migration Test ==="
+  puts "Using API key: #{api_key[0..4]}..."
+  puts "Using grant ID: #{grant_id[0..8]}..."
+  puts "Test email recipient: #{test_email}"
+
+  # Initialize the Nylas client
+  nylas = Nylas::Client.new(
+    api_key: api_key,
+    api_uri: ENV["NYLAS_API_URI"] || "https://api.us.nylas.com"
+  )
+
+  begin
+    # Demonstrate file handling logic
+    demonstrate_file_utils_handling
+
+    # Create test files
+    small_file = create_small_test_file
+    large_file_path = find_or_create_large_test_file
+
+    begin
+      # Test 1: Send message with small attachment
+      small_response = send_message_with_small_attachment(nylas, grant_id, test_email, small_file)
+
+      # Test 2: Send message with large attachment  
+      large_response = send_message_with_large_attachment(nylas, grant_id, test_email, large_file_path)
+
+      puts "\n=== Summary ==="
+      puts "✅ Both small and large file uploads completed successfully!"
+      puts "- Small file message ID: #{small_response[:id]}"
+      puts "- Large file message ID: #{large_response[:id]}"
+      puts "- HTTParty migration verified for both file handling methods"
+
+    ensure
+      # Clean up temporary small file only
+      small_file.close
+      small_file.unlink
+      puts "\n🧹 Cleaned up temporary small file (large file kept on disk for reuse)"
+    end
+
+  rescue => e
+    puts "\n❌ Example failed: #{e.message}"
+    puts "- #{e.backtrace.first}"
+    exit 1
+  end
+
+  puts "\n🎉 File upload example completed successfully!"
+  puts "This confirms that the HTTParty migration properly handles:"
+  puts "- Small files (<3MB): JSON with base64 encoding"
+  puts "- Large files (>3MB): Multipart form data"
+  puts "- File attachment building and processing"
+  puts "- HTTP request execution with different payload types"
+end
+
+if __FILE__ == $0
+  main
+end