diff --git a/lib/stripe/api_requestor.rb b/lib/stripe/api_requestor.rb
index cf375dc5f..d4fa7804f 100644
--- a/lib/stripe/api_requestor.rb
+++ b/lib/stripe/api_requestor.rb
@@ -110,7 +110,7 @@ def self.should_retry?(error,
       return false if num_retries >= config.max_network_retries
 
       case error
-      when Net::OpenTimeout, Net::ReadTimeout
+      when Net::OpenTimeout, Net::ReadTimeout, Net::HTTPFatalError
         # Retry on timeout-related problems (either on open or read).
         true
       when EOFError, Errno::ECONNREFUSED, Errno::ECONNRESET, # rubocop:todo Lint/DuplicateBranch
@@ -350,6 +350,7 @@ def last_response_has_key?(object_id)
       Errno::ETIMEDOUT => ERROR_MESSAGE_TIMEOUT_CONNECT,
       SocketError => ERROR_MESSAGE_CONNECTION,
 
+      Net::HTTPFatalError => ERROR_MESSAGE_CONNECTION,
       Net::OpenTimeout => ERROR_MESSAGE_TIMEOUT_CONNECT,
       Net::ReadTimeout => ERROR_MESSAGE_TIMEOUT_READ,
 
diff --git a/test/stripe/api_requestor_test.rb b/test/stripe/api_requestor_test.rb
index c916c6839..f91ccd000 100644
--- a/test/stripe/api_requestor_test.rb
+++ b/test/stripe/api_requestor_test.rb
@@ -317,6 +317,14 @@ class RequestorTest < Test::Unit::TestCase
                                           num_retries: 0)
       end
 
+      should "retry on Net::HTTPFatalError" do
+        response = Net::HTTPResponse::CODE_TO_OBJ["503"].new("1.1", "503", "Service Unavailable")
+        error = Net::HTTPFatalError.new("503 \"Service Unavailable\"", response)
+
+        assert APIRequestor.should_retry?(error,
+                                          num_retries: 0)
+      end
+
       should "retry on SocketError" do
         assert APIRequestor.should_retry?(SocketError.new,
                                           num_retries: 0)
@@ -1178,6 +1186,23 @@ class RequestorTest < Test::Unit::TestCase
             assert_match(/Request was retried 2 times/, err.message)
           end
 
+          should "retry Net::HTTPFatalError failures and raise APIConnectionError if error persists" do
+            APIRequestor.expects(:sleep_time).at_least_once.returns(0)
+
+            response = Net::HTTPResponse::CODE_TO_OBJ["503"].new("1.1", "503", "Service Unavailable")
+            error = Net::HTTPFatalError.new("503 \"Service Unavailable\"", response)
+
+            stub_request(:post, "#{Stripe::DEFAULT_API_BASE}/v1/charges")
+              .to_raise(error)
+
+            client = APIRequestor.new("sk_test_123")
+            err = assert_raises Stripe::APIConnectionError do
+              client.send(request_method, :post, "/v1/charges", :api,
+                          &@read_body_chunk_block)
+            end
+            assert_match(/Request was retried 2 times/, err.message)
+          end
+
           should "retry failed requests and return successful response" do
             APIRequestor.expects(:sleep_time).at_least_once.returns(0)