diff --git a/clients/algoliasearch-client-ruby/lib/algolia/error.rb b/clients/algoliasearch-client-ruby/lib/algolia/error.rb
index 85a7447e343..a2cc8658328 100644
--- a/clients/algoliasearch-client-ruby/lib/algolia/error.rb
+++ b/clients/algoliasearch-client-ruby/lib/algolia/error.rb
@@ -10,6 +10,15 @@ class AlgoliaError < StandardError
   # Used when hosts are unreachable
   #
   class AlgoliaUnreachableHostError < AlgoliaError
+    attr_reader :errors
+
+    def initialize(message, errors = [])
+      errors.last&.tap do |last_error|
+        message += " Last error for #{last_error[:host]}: #{last_error[:error]}"
+      end
+      super(message)
+      @errors = errors
+    end
   end
 
   # An exception class raised when the REST API returns an error.
diff --git a/clients/algoliasearch-client-ruby/lib/algolia/logger_helper.rb b/clients/algoliasearch-client-ruby/lib/algolia/logger_helper.rb
index c968bf687b4..3652ae3d2cb 100644
--- a/clients/algoliasearch-client-ruby/lib/algolia/logger_helper.rb
+++ b/clients/algoliasearch-client-ruby/lib/algolia/logger_helper.rb
@@ -5,8 +5,17 @@ class LoggerHelper
     # @param debug_file [nil|String] file used to output the logs
     #
     def self.create(debug_file = nil)
-      file = debug_file || (ENV["ALGOLIA_DEBUG"] ? File.new("debug.log", "a+") : $stderr)
-      instance = ::Logger.new(file)
+      file = debug_file
+
+      if file.nil? && ENV["ALGOLIA_DEBUG"]
+        begin
+          file = File.new("debug.log", "a+")
+        rescue Errno::EACCES, Errno::ENOENT => e
+          puts "Failed to open debug.log: #{e.message}. Falling back to $stderr."
+        end
+      end
+
+      instance = ::Logger.new(file || $stderr)
       instance.progname = "algolia"
       instance
     end
diff --git a/clients/algoliasearch-client-ruby/lib/algolia/transport/transport.rb b/clients/algoliasearch-client-ruby/lib/algolia/transport/transport.rb
index 61839f0c623..14c7e4169bb 100644
--- a/clients/algoliasearch-client-ruby/lib/algolia/transport/transport.rb
+++ b/clients/algoliasearch-client-ruby/lib/algolia/transport/transport.rb
@@ -39,6 +39,8 @@ def initialize(config, requester)
       # @return [Response] response of the request
       #
       def request(call_type, method, path, body, opts = {})
+        retry_errors = []
+
         @retry_strategy.get_tryable_hosts(call_type).each do |host|
           opts[:timeout] ||= get_timeout(call_type) * (host.retry_count + 1)
           opts[:connect_timeout] ||= @config.connect_timeout * (host.retry_count + 1)
@@ -71,10 +73,14 @@ def request(call_type, method, path, body, opts = {})
             raise Algolia::AlgoliaHttpError.new(response.status, decoded_error[:message])
           end
 
-          return response unless outcome == RETRY
+          if outcome == RETRY
+            retry_errors << {host: host.url, error: response.error}
+          else
+            return response
+          end
         end
 
-        raise Algolia::AlgoliaUnreachableHostError, "Unreachable hosts"
+        raise Algolia::AlgoliaUnreachableHostError.new("Unreachable hosts.", retry_errors)
       end
 
       private