diff --git a/lib/fluent/plugin/output.rb b/lib/fluent/plugin/output.rb
index 0db896fd4c..45290fda64 100644
--- a/lib/fluent/plugin/output.rb
+++ b/lib/fluent/plugin/output.rb
@@ -1290,16 +1290,17 @@ def update_retry_state(chunk_id, using_secondary, error = nil)
 
           # @retry exists
 
+          # Ensure that the current time is greater than or equal to @retry.next_time to avoid the situation when
+          # @retry.step is called almost as many times as the number of flush threads in a short time.
+          if Time.now >= @retry.next_time
+            @retry.step
+          else
+            @retry.recalc_next_time # to prevent all flush threads from retrying at the same time
+          end
+
           if @retry.limit?
             handle_limit_reached(error)
           else
-            # Ensure that the current time is greater than or equal to @retry.next_time to avoid the situation when
-            # @retry.step is called almost as many times as the number of flush threads in a short time.
-            if Time.now >= @retry.next_time
-              @retry.step
-            else
-              @retry.recalc_next_time # to prevent all flush threads from retrying at the same time
-            end
             if error
               if using_secondary
                 msg = "failed to flush the buffer with secondary output."
@@ -1311,7 +1312,6 @@ def update_retry_state(chunk_id, using_secondary, error = nil)
                 log.warn_backtrace error.backtrace
               end
             end
-            handle_limit_reached(error) if @retry.limit_step?
           end
         end
       end
diff --git a/lib/fluent/plugin_helper/retry_state.rb b/lib/fluent/plugin_helper/retry_state.rb
index 29bcf8c157..82e5689af3 100644
--- a/lib/fluent/plugin_helper/retry_state.rb
+++ b/lib/fluent/plugin_helper/retry_state.rb
@@ -44,6 +44,8 @@ def initialize(title, wait, timeout, forever, max_steps, randomize, randomize_wi
 
           @timeout = timeout
           @timeout_at = @start + timeout
+          @has_reached_timeout = false
+          @has_timed_out = false
           @current = :primary
 
           if randomize_width < 0 || randomize_width > 0.5
@@ -123,7 +125,15 @@ def step
             @current = :secondary
             @secondary_transition_steps = @steps
           end
+
           @next_time = calc_next_time
+
+          if @has_reached_timeout
+            @has_timed_out = @next_time >= @timeout_at
+          else
+            @has_reached_timeout = @next_time >= @timeout_at
+          end
+
           nil
         end
 
@@ -131,24 +141,11 @@ def recalc_next_time
           @next_time = calc_next_time
         end
 
-        # Use @next_time for time by default to keep backward compatibility
-        def limit?(time: @next_time, steps: @steps)
-          timeout?(time) || limit_step?(steps)
-        end
-
-        def timeout?(time = current_time)
-          if @forever
-            false
-          else
-            time >= @timeout_at
-          end
-        end
-
-        def limit_step?(steps = @steps)
+        def limit?
           if @forever
             false
           else
-            !!(@max_steps && steps >= @max_steps)
+            @has_timed_out || !!(@max_steps && @steps >= @max_steps)
           end
         end
       end
diff --git a/test/plugin_helper/test_retry_state.rb b/test/plugin_helper/test_retry_state.rb
index 824151c3a8..b61e5e35db 100644
--- a/test/plugin_helper/test_retry_state.rb
+++ b/test/plugin_helper/test_retry_state.rb
@@ -90,6 +90,7 @@ def ==(obj)
     override_current_time(s, s.next_time)
     s.step
     assert_equal s.timeout_at, s.next_time
+    s.step
     assert s.limit?
   end
 
@@ -115,7 +116,6 @@ def ==(obj)
     assert_equal 5, i
     override_current_time(s, s.next_time)
     s.step
-    assert_equal (s.current_time + 3), s.next_time
     assert s.limit?
   end
 
@@ -179,7 +179,9 @@ def ==(obj)
     assert s.secondary?
 
     s.step
-    assert_equal s.timeout_at, s.next_time
+    assert_equal s.timeout_at, s.next_time # 100
+
+    s.step
     assert s.limit?
   end
 
@@ -285,6 +287,7 @@ def ==(obj)
     assert_equal 3, s.steps
     assert_equal s.timeout_at, s.next_time
 
+    s.step
     assert s.limit?
   end
 
@@ -334,8 +337,6 @@ def ==(obj)
     override_current_time(s, s.next_time)
     s.step
     assert_equal 6, s.steps
-    assert_equal (s.current_time + 10), s.next_time
-
     assert s.limit?
   end
 
@@ -405,7 +406,9 @@ def ==(obj)
     assert s.secondary?
 
     s.step
-    assert_equal s.timeout_at, s.next_time
+    assert_equal s.timeout_at, s.next_time # 100
+
+    s.step
     assert s.limit?
   end
 
@@ -988,15 +991,9 @@ def ==(obj)
         msg << "[#{next_elapsed}s elapsed point] #{retry_count}th-Retry(#{s.secondary? ? "SEC" : "PRI"}) is triggered.\n"
 
         # Update retry statement
-        if s.limit?
-          msg << "--- Reach limit of timeout. ---\n"
-          break
-        end
-
         s.step
-
-        if s.limit_step?
-          msg << "--- Reach limit of max step. ---\n"
+        if s.limit?
+          msg << "--- Reach limit. ---\n"
           break
         end
       end