diff --git a/docs/source/config.rst b/docs/source/config.rst
index 729e37fc..4f1483a3 100644
--- a/docs/source/config.rst
+++ b/docs/source/config.rst
@@ -211,7 +211,7 @@ configuration.
    able to parse restarts files for a datetime.
 
 ``restart_history``
-    Specifies the number of latest restart files to save
+    Specifies how many of the most recent restart files to retain regardless of `restart_freq`
 
 *The following model-based tags are typically not configured*
 
diff --git a/payu/experiment.py b/payu/experiment.py
index 36a16fe8..15f5f8cb 100644
--- a/payu/experiment.py
+++ b/payu/experiment.py
@@ -198,13 +198,15 @@ def max_output_index(self, output_type="output"):
                 raise
 
         if output_dirs and len(output_dirs):
-            return max([int(d.lstrip(output_type)) for d in output_dirs])
+            return int(output_dirs[-1].lstrip(output_type))
 
     def list_output_dirs(self, output_type="output"):
-        """Return a list of restart or output directories in archive"""
-        naming_pattern = re.compile(fr"^{output_type}[0-9][0-9][0-9]$")
-        return [d for d in os.listdir(self.archive_path)
+        """Return a sorted list of restart or output directories in archive"""
+        naming_pattern = re.compile(fr"^{output_type}[0-9][0-9][0-9]+$")
+        dirs = [d for d in os.listdir(self.archive_path)
                 if naming_pattern.match(d)]
+        dirs.sort(key=lambda d: int(d.lstrip(output_type)))
+        return dirs 
 
     def set_stacksize(self, stacksize):
 
@@ -1003,9 +1005,8 @@ def get_restarts_to_prune(self,
         if not os.path.exists(self.archive_path):
             return []
 
-        # List all and sort restart directories in archive
+        # List all restart directories in archive
         restarts = self.list_output_dirs(output_type='restart')
-        restarts.sort(key=lambda d: int(d.lstrip('restart')))
 
         # TODO: Previous logic was to prune all restarts if self.repeat_run
         # Still need to figure out what should happen in this case
@@ -1043,15 +1044,15 @@ def get_restarts_to_prune(self,
                 restart_path = os.path.join(self.archive_path, restart)
                 try:
                     restart_dt = self.model.get_restart_datetime(restart_path)
-                except NotImplementedError as e:
+                except NotImplementedError:
                     print('payu: error: Date-based restart pruning is not '
                           f'implemented for the {self.model.model_type} '
                           'model. To use integer based restart pruning, '
                           'set restart_freq to an integer value.')
                     raise
-                except Exception as e:
+                except Exception:
                     print('payu: error: Error parsing restart directory ',
-                          f'{restart} for a datetime. Error: {e}')
+                          f'{restart} for a datetime to prune restarts.')
                     raise
 
                 if (next_dt is not None and restart_dt < next_dt):
diff --git a/test/test_prune_restarts.py b/test/test_prune_restarts.py
index ad823b3d..253e02b1 100644
--- a/test/test_prune_restarts.py
+++ b/test/test_prune_restarts.py
@@ -115,7 +115,8 @@ def write_test_config(restart_freq, restart_history=None):
          [1, 2, 3, 4, 5, 6, 7, 8, 9, 10,
           12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22]),
         (1, 1, []),
-        (5, 5, [1, 2, 3, 4, 6, 7, 8, 9, 11, 12, 13, 14, 16, 17, 18, 19]),
+        (5, 3, [1, 2, 3, 4, 6, 7, 8, 9, 11, 12, 13, 14, 16, 17, 18, 19, 21]),
+        (5, 7, [1, 2, 3, 4, 6, 7, 8, 9, 11, 12, 13, 14, 16, 17]),
         (5, None, [1, 2, 3, 4, 6, 7, 8, 9, 11, 12, 13, 14, 16, 17, 18, 19])
     ])
 def test_force_prune_restarts(restart_freq,