Add version check on application boot

Checks for PWB updates when the Rails server starts and logs the result:
- If running latest: "[PWB Version] Running latest version (2.2.0)"
- If outdated: "[PWB Version] Update available! Current: X, Latest: Y..."

The check runs in a background thread to avoid blocking server startup.
Calls the PWB version check API at propertywebbuilder.com.

🤖 Generated with [Claude Code](https://claude.com/claude-code)

Co-Authored-By: Claude <noreply@anthropic.com>

Author: etewiah

app/services/pwb/version_check_service.rb

@@ -0,0 +1,127 @@
+# frozen_string_literal: true
+
+module Pwb
+  # Service for checking if a newer version of PropertyWebBuilder is available.
+  #
+  # Calls the PWB version check API endpoint to compare the current version
+  # against the latest release.
+  #
+  # Usage:
+  #   # Check for updates and log if available
+  #   Pwb::VersionCheckService.check_and_log
+  #
+  #   # Get version info without logging
+  #   info = Pwb::VersionCheckService.check
+  #   puts info[:latest_version] if info[:update_available]
+  #
+  class VersionCheckService
+    VERSION_CHECK_URL = 'https://propertywebbuilder.com/api_public/v4/version_check'
+    REQUEST_TIMEOUT = 5 # seconds
+
+    class << self
+      # Check for updates and log a message if a new version is available
+      #
+      # @return [Hash, nil] version info hash or nil if check failed
+      def check_and_log
+        info = check
+        return nil unless info
+
+        if info[:update_available]
+          log_update_available(info)
+        else
+          Rails.logger.info "[PWB Version] Running latest version (#{Pwb::VERSION})"
+        end
+
+        info
+      rescue StandardError => e
+        Rails.logger.debug "[PWB Version] Check failed: #{e.message}"
+        nil
+      end
+
+      # Check for updates by calling the version check API
+      #
+      # @return [Hash, nil] version info hash or nil if check failed
+      # @example Return value
+      #   {
+      #     incoming_version: "2.1.0",
+      #     latest_version: "2.2.0",
+      #     latest_release_date: "2025-12-21",
+      #     is_latest: false,
+      #     update_available: true,
+      #     versions_behind: 1
+      #   }
+      def check
+        response = fetch_version_info
+        return nil unless response
+
+        parse_response(response)
+      rescue StandardError => e
+        Rails.logger.debug "[PWB Version] API call failed: #{e.message}"
+        nil
+      end
+
+      # Get the current PWB version
+      #
+      # @return [String] the current version string
+      def current_version
+        Pwb::VERSION
+      end
+
+      private
+
+      def fetch_version_info
+        uri = URI("#{VERSION_CHECK_URL}?version=#{current_version}")
+
+        http = Net::HTTP.new(uri.host, uri.port)
+        http.use_ssl = true
+        http.open_timeout = REQUEST_TIMEOUT
+        http.read_timeout = REQUEST_TIMEOUT
+
+        # Skip strict SSL verification for version check (read-only, non-sensitive)
+        # This works around OpenSSL 3.6+ CRL verification issues on macOS
+        # See: config/initializers/ssl_crl_fix.rb
+        http.verify_mode = OpenSSL::SSL::VERIFY_NONE
+
+        request = Net::HTTP::Get.new(uri)
+        request['Accept'] = 'application/json'
+        request['User-Agent'] = "PropertyWebBuilder/#{current_version}"
+
+        response = http.request(request)
+
+        return nil unless response.is_a?(Net::HTTPSuccess)
+
+        response.body
+      end
+
+      def parse_response(json_string)
+        data = JSON.parse(json_string, symbolize_names: true)
+
+        {
+          incoming_version: data[:incoming_version],
+          latest_version: data[:latest_version],
+          latest_release_date: data[:latest_release_date],
+          is_latest: data[:is_latest],
+          is_known_version: data[:is_known_version],
+          update_available: data[:update_available],
+          versions_behind: data[:versions_behind]
+        }
+      rescue JSON::ParserError => e
+        Rails.logger.debug "[PWB Version] Failed to parse response: #{e.message}"
+        nil
+      end
+
+      def log_update_available(info)
+        message = <<~MSG.squish
+          [PWB Version] Update available!
+          Current: #{info[:incoming_version]},
+          Latest: #{info[:latest_version]}
+          (#{info[:versions_behind]} version(s) behind,
+          released #{info[:latest_release_date]}).
+          Visit https://github.com/etewiah/property_web_builder for upgrade instructions.
+        MSG
+
+        Rails.logger.info message
+      end
+    end
+  end
+end

config/initializers/version_check.rb

@@ -0,0 +1,26 @@
+# frozen_string_literal: true
+
+# Check for PWB updates on application boot
+#
+# This runs asynchronously to avoid slowing down server startup.
+# Only runs on first boot (not on Rails console or rake tasks).
+
+Rails.application.config.after_initialize do
+  # Only check in server context, not in console/rake/test
+  next unless defined?(Rails::Server) || ENV['PWB_FORCE_VERSION_CHECK']
+
+  # Skip in test environment
+  next if Rails.env.test?
+
+  # Run the check in a background thread to avoid blocking boot
+  Thread.new do
+    # Small delay to let the server finish initializing
+    sleep 2
+
+    begin
+      Pwb::VersionCheckService.check_and_log
+    rescue StandardError => e
+      Rails.logger.debug "[PWB Version] Startup check failed: #{e.message}"
+    end
+  end
+end