diff --git a/changelog.md b/changelog.md
index c8ff509a..0f275c4b 100644
--- a/changelog.md
+++ b/changelog.md
@@ -1,3 +1,11 @@
+Upcoming (TBD)
+==============
+
+Features
+---------
+* Add a dependencies section to `--checkup`.
+
+
 1.63.0 (2026/03/12)
 ==============
 
diff --git a/mycli/main.py b/mycli/main.py
index a3ee11f3..5a8390ca 100755
--- a/mycli/main.py
+++ b/mycli/main.py
@@ -79,6 +79,7 @@
 from mycli.key_bindings import mycli_bindings
 from mycli.lexer import MyCliLexer
 from mycli.packages import special
+from mycli.packages.checkup import do_checkup
 from mycli.packages.filepaths import dir_path_exists, guess_socket_location
 from mycli.packages.hybrid_redirection import get_redirect_components, is_redirect_command
 from mycli.packages.parseutils import is_destructive, is_dropping_database, is_valid_connection_scheme
@@ -2130,7 +2131,7 @@ def get_password_from_file(password_file: str | None) -> str | None:
     )
 
     if checkup:
-        do_config_checkup(mycli)
+        do_checkup(mycli)
         sys.exit(0)
 
     if csv and batch_format not in [None, 'csv']:
@@ -2688,110 +2689,5 @@ def read_ssh_config(ssh_config_path: str):
         return ssh_config
 
 
-def do_config_checkup(mycli: MyCli) -> None:
-    did_output_missing = False
-    did_output_unsupported = False
-    did_output_deprecated = False
-
-    print('\n### External executables:\n')
-    for executable in [
-        'less',
-        'fzf',
-        'pygmentize',
-    ]:
-        if shutil.which(executable):
-            print(f'The "{executable}" executable was found — good!')
-        else:
-            print(f'The recommended "{executable}" executable was not found — some functionality will suffer.')
-
-    print('\n### Environment variables:\n')
-    for variable in [
-        'EDITOR',
-        'VISUAL',
-    ]:
-        if value := os.environ.get(variable):
-            print(f'The ${variable} environment variable was set to "{value}" — good!')
-        else:
-            print(f'The ${variable} environment variable was not set — some functionality will suffer.')
-
-    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',
-    }
-    reverse_transitions = {v: k for k, v in transitions.items()}
-
-    if not list(mycli.config.keys()):
-        print('\n### Missing file:\n')
-        print('The local ~/,myclirc is missing or empty.\n')
-        did_output_missing = True
-    else:
-        for section_name in mycli.config:
-            if section_name not in mycli.config_without_package_defaults:
-                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]:
-                transition_key = f'{indent}[{section_name}]\n{indent}{item_name}'
-                if transition_key in reverse_transitions:
-                    continue
-                if item_name not in mycli.config_without_package_defaults[section_name]:
-                    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
-                if section_name in [
-                    'favorite_queries',
-                    'init-commands',
-                    'alias_dsn',
-                    'alias_dsn.init-commands',
-                ]:
-                    # these are free-entry sections, so a comparison per item is not meaningful
-                    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(f'For more info on supported features, see the commentary and defaults at:\n\n    * {REPO_URL}/blob/main/mycli/myclirc\n')
-    else:
-        print('\n### Configuration:\n')
-        print('User configuration all up to date!\n')
-
-
 if __name__ == "__main__":
     cli()
diff --git a/mycli/packages/checkup.py b/mycli/packages/checkup.py
new file mode 100644
index 00000000..29e61355
--- /dev/null
+++ b/mycli/packages/checkup.py
@@ -0,0 +1,156 @@
+import importlib.metadata
+import json
+import os
+import shutil
+import sys
+import urllib.error
+import urllib.request
+
+from mycli.constants import REPO_URL
+
+PYPI_API_BASE = 'https://pypi.org/pypi'
+
+
+def pypi_api_fetch(fragment: str) -> dict:
+    fragment = fragment.lstrip('/')
+    url = f'{PYPI_API_BASE}/{fragment}'
+    try:
+        with urllib.request.urlopen(url, timeout=5) as response:
+            return json.loads(response.read().decode('utf8'))
+    except urllib.error.URLError:
+        print(f'Failed to connect to PyPi on {url}', file=sys.stderr)
+        return {}
+
+
+def _dependencies_checkup() -> None:
+    print('\n### Key Python dependencies:\n')
+    for dependency in [
+        'cli_helpers',
+        'click',
+        'prompt_toolkit',
+        'pymysql',
+        'tabulate',
+    ]:
+        try:
+            installed_version = importlib.metadata.version(dependency)
+        except importlib.metadata.PackageNotFoundError:
+            installed_version = None
+        pypi_profile = pypi_api_fetch(f'/{dependency}/json')
+        latest_version = pypi_profile.get('info', {}).get('version', None)
+        print(f'{dependency} version {installed_version} (latest {latest_version})')
+
+
+def _executables_checkup() -> None:
+    print('\n### External executables:\n')
+    for executable in [
+        'less',
+        'fzf',
+        'pygmentize',
+    ]:
+        if shutil.which(executable):
+            print(f'The "{executable}" executable was found — good!')
+        else:
+            print(f'The recommended "{executable}" executable was not found — some functionality will suffer.')
+
+
+def _environment_checkup() -> None:
+    print('\n### Environment variables:\n')
+    for variable in [
+        'EDITOR',
+        'VISUAL',
+    ]:
+        if value := os.environ.get(variable):
+            print(f'The ${variable} environment variable was set to "{value}" — good!')
+        else:
+            print(f'The ${variable} environment variable was not set — some functionality will suffer.')
+
+
+def _configuration_checkup(mycli) -> None:
+    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',
+    }
+    reverse_transitions = {v: k for k, v in transitions.items()}
+
+    if not list(mycli.config.keys()):
+        print('\n### Missing file:\n')
+        print('The local ~/,myclirc is missing or empty.\n')
+        did_output_missing = True
+    else:
+        for section_name in mycli.config:
+            if section_name not in mycli.config_without_package_defaults:
+                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]:
+                transition_key = f'{indent}[{section_name}]\n{indent}{item_name}'
+                if transition_key in reverse_transitions:
+                    continue
+                if item_name not in mycli.config_without_package_defaults[section_name]:
+                    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
+                if section_name in [
+                    'favorite_queries',
+                    'init-commands',
+                    'alias_dsn',
+                    'alias_dsn.init-commands',
+                ]:
+                    # these are free-entry sections, so a comparison per item is not meaningful
+                    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(f'For more info on supported features, see the commentary and defaults at:\n\n    * {REPO_URL}/blob/main/mycli/myclirc\n')
+    else:
+        print('\n### Configuration:\n')
+        print('User configuration all up to date!\n')
+
+
+def do_checkup(mycli) -> None:
+    _dependencies_checkup()
+    _executables_checkup()
+    _environment_checkup()
+    _configuration_checkup(mycli)