diff --git a/changelog.md b/changelog.md
index d6eb4e94..cb711fbd 100644
--- a/changelog.md
+++ b/changelog.md
@@ -6,6 +6,7 @@ Features
 * Options to limit size of LLM prompts; cache LLM prompt data.
 * Add startup usage tips.
 * Move `main.ssl_mode` config option to `connection.default_ssl_mode`.
+* Add "unsupported" and "deprecated" `--checkup` sections.
 
 
 Bug Fixes
diff --git a/mycli/config.py b/mycli/config.py
index 90c76b31..a79b1021 100644
--- a/mycli/config.py
+++ b/mycli/config.py
@@ -82,6 +82,7 @@ def read_config_files(
     files: list[str | IO[str]],
     list_values: bool = True,
     ignore_package_defaults: bool = False,
+    ignore_user_options: bool = False,
 ) -> ConfigObj:
     """Read and merge a list of config files."""
 
@@ -90,6 +91,9 @@ def read_config_files(
     else:
         config = create_default_config(list_values=list_values)
 
+    if ignore_user_options:
+        return config
+
     _files = copy(files)
     while _files:
         _file = _files.pop(0)
diff --git a/mycli/main.py b/mycli/main.py
index ea55ab68..6a8c9b9d 100755
--- a/mycli/main.py
+++ b/mycli/main.py
@@ -142,7 +142,10 @@ def __init__(
         # this parallel config exists to
         #  * compare with my.cnf
         #  * support the --checkup feature
+        # todo: after removing my.cnf, create the parallel configs only when --checkup is set
         self.config_without_package_defaults = read_config_files(config_files, ignore_package_defaults=True)
+        # this parallel config exists to compare with my.cnf support the --checkup feature
+        self.config_without_user_options = read_config_files(config_files, ignore_user_options=True)
         self.multi_line = c["main"].as_bool("multi_line")
         self.key_bindings = c["main"]["key_bindings"]
         special.set_timing_enabled(c["main"].as_bool("timing"))
@@ -2272,28 +2275,72 @@ def read_ssh_config(ssh_config_path: str):
 
 
 def do_config_checkup(mycli: MyCli) -> None:
-    did_output = False
+    did_output_missing = False
+    did_output_unsupported = False
+    did_output_deprecated = False
+
+    indent = '    '
+    transitions = {
+        f'{indent}[main]\n{indent}default_character_set': f'{indent}[connection]\n{indent}default_character_set',
+        f'{indent}[main]\n{indent}ssl_mode': f'{indent}[connection]\n{indent}default_ssl_mode',
+    }
 
     if not list(mycli.config.keys()):
         print('\nThe local ~/,myclirc is missing or empty.\n')
-        did_output = True
+        did_output_missing = True
     else:
-        for section_name in mycli.config.keys():
+        for section_name in mycli.config:
             if section_name not in mycli.config_without_package_defaults:
-                if not did_output:
-                    print('\nMissing in user ~/.myclirc:\n')
-                print(f'The entire section:\n\n    [{section_name}]\n')
-                did_output = True
+                if not did_output_missing:
+                    print('\n### Missing in user ~/.myclirc:\n')
+                print(f'The entire section:\n\n{indent}[{section_name}]\n')
+                did_output_missing = True
                 continue
             for item_name in mycli.config[section_name]:
                 if item_name not in mycli.config_without_package_defaults[section_name]:
-                    if not did_output:
-                        print('\nMissing in user ~/.myclirc:\n')
-                    print(f'The item:\n\n    [{section_name}]\n    {item_name} =\n')
-                    did_output = True
-    if did_output:
+                    if not did_output_missing:
+                        print('\n### Missing in user ~/.myclirc:\n')
+                    print(f'The item:\n\n{indent}[{section_name}]\n{indent}{item_name} =\n')
+                    did_output_missing = True
+
+        for section_name in mycli.config_without_package_defaults:
+            if section_name not in mycli.config_without_user_options:
+                if not did_output_unsupported:
+                    print('\n### Unsupported in user ~/.myclirc:\n')
+                did_output_unsupported = True
+                print(f'The entire section:\n\n{indent}[{section_name}]\n')
+                continue
+            for item_name in mycli.config_without_package_defaults[section_name]:
+                if section_name == 'colors' and item_name.startswith('sql.'):
+                    # these are commented out in the package myclirc
+                    continue
+                transition_key = f'{indent}[{section_name}]\n{indent}{item_name}'
+                if transition_key in transitions:
+                    continue
+                if item_name not in mycli.config_without_user_options[section_name]:
+                    if not did_output_unsupported:
+                        print('\n### Unsupported in user ~/.myclirc:\n')
+                    print(f'The item:\n\n{indent}[{section_name}]\n{indent}{item_name} =\n')
+                    did_output_unsupported = True
+
+        for section_name in mycli.config_without_package_defaults:
+            if section_name not in mycli.config_without_user_options:
+                continue
+            for item_name in mycli.config_without_package_defaults[section_name]:
+                if section_name == 'colors' and item_name.startswith('sql.'):
+                    # these are commented out in the package myclirc
+                    continue
+                transition_key = f'{indent}[{section_name}]\n{indent}{item_name}'
+                if transition_key in transitions:
+                    if not did_output_deprecated:
+                        print('\n### Deprecated in user ~/.myclirc:\n')
+                    transition_value = transitions[transition_key]
+                    print(f'It is recommended to transition:\n\n{transition_key}\n\nto\n\n{transition_value}\n')
+                    did_output_deprecated = True
+
+    if did_output_missing or did_output_unsupported or did_output_deprecated:
         print(
-            'For more info on new features, see the commentary and defaults at:\n\n    * https://github.com/dbcli/mycli/blob/main/mycli/myclirc\n'
+            'For more info on supported features, see the commentary and defaults at:\n\n    * https://github.com/dbcli/mycli/blob/main/mycli/myclirc\n'
         )
     else:
         print('User configuration all up to date!')