diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index e59473a5..db74534d 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -40,7 +40,7 @@ jobs:
 
       # Static analysis tools
       - name: Static Code Analysis
-        if: runner.os == 'Linux' && matrix.python-version != '3.8'
+        if: runner.os == 'Linux'
         run: |
           pip install mypy==1.19.1 flake8==7.3.0
           python static_analysis.py
@@ -48,6 +48,12 @@ jobs:
       - name: Run tests
         run: python -m pytest -s -rs
 
+      - name: Check README
+        if: runner.os == 'Linux'
+        run: |
+          python scripts/readme.py
+          git diff --exit-code README.md
+
   release:
     runs-on: ubuntu-latest
 
diff --git a/lean/click.py b/lean/click.py
index 0eb4e86d..128c3040 100644
--- a/lean/click.py
+++ b/lean/click.py
@@ -14,7 +14,7 @@
 from pathlib import Path
 from typing import Optional, List, Callable
 
-from click import Command, Context, Parameter, ParamType, Option as ClickOption
+from click import Choice, Command, Context, Parameter, ParamType, Option as ClickOption
 from click.decorators import FC, option
 
 from lean.constants import DEFAULT_LEAN_CONFIG_FILE_NAME, CONTAINER_LABEL_LEAN_VERSION_NAME
@@ -305,6 +305,20 @@ def _parse_config_option(self, ctx: Context, param: Parameter, value: Optional[P
 
 
 
+class CaseInsensitiveChoice(Choice):
+    """A click.Choice subclass that matches case-insensitively but displays original casing in help text."""
+
+    def __init__(self, choices, **kwargs):
+        super().__init__(choices, case_sensitive=False, **kwargs)
+
+    def get_metavar(self, param, ctx=None) -> str:
+        import enum
+        choices_str = "|".join(c.value if isinstance(c, enum.Enum) else str(c) for c in self.choices)
+        if param is not None and param.required and param.param_type_name == "argument":
+            return f"{{{choices_str}}}"
+        return f"[{choices_str}]"
+
+
 class PathParameter(ParamType):
     """A limited version of click.Path which uses pathlib.Path."""
 
@@ -352,7 +366,7 @@ class DateParameter(ParamType):
 
     name = "date"
 
-    def get_metavar(self, param: Parameter) -> str:
+    def get_metavar(self, param: Parameter, ctx=None) -> str:
         return "[yyyyMMdd]"
 
     def convert(self, value: str, param: Parameter, ctx: Context):
diff --git a/lean/commands/backtest.py b/lean/commands/backtest.py
index 98d6fb3e..bf9a8cac 100644
--- a/lean/commands/backtest.py
+++ b/lean/commands/backtest.py
@@ -13,9 +13,9 @@
 
 from pathlib import Path
 from typing import List, Optional, Tuple
-from click import command, option, argument, Choice
+from click import command, option, argument
 
-from lean.click import LeanCommand, PathParameter, backtest_parameter_option
+from lean.click import LeanCommand, PathParameter, backtest_parameter_option, CaseInsensitiveChoice
 from lean.constants import DEFAULT_ENGINE_IMAGE, LEAN_ROOT_PATH
 from lean.container import container, Logger
 from lean.models.utils import DebuggingMethod
@@ -234,10 +234,10 @@ def _migrate_csharp_csproj(project_dir: Path) -> None:
               default=False,
               help="Run the backtest in a detached Docker container and return immediately")
 @option("--debug",
-              type=Choice(["pycharm", "ptvsd", "debugpy", "vsdbg", "rider", "local-platform"], case_sensitive=False),
+              type=CaseInsensitiveChoice(["pycharm", "ptvsd", "debugpy", "vsdbg", "rider", "local-platform"]),
               help="Enable a certain debugging method (see --help for more information)")
 @option("--data-provider-historical",
-              type=Choice([dp.get_name() for dp in cli_data_downloaders], case_sensitive=False),
+              type=CaseInsensitiveChoice([dp.get_name() for dp in cli_data_downloaders]),
               default="Local",
               help="Update the Lean configuration file to retrieve data from the given historical provider")
 @options_from_json(get_configs_for_options("backtest"))
diff --git a/lean/commands/cloud/live/deploy.py b/lean/commands/cloud/live/deploy.py
index 1fee429c..c667ae40 100644
--- a/lean/commands/cloud/live/deploy.py
+++ b/lean/commands/cloud/live/deploy.py
@@ -12,8 +12,8 @@
 # limitations under the License.
 
 from typing import List, Tuple, Optional
-from click import prompt, option, argument, Choice, confirm
-from lean.click import LeanCommand, ensure_options
+from click import prompt, option, argument, confirm
+from lean.click import LeanCommand, ensure_options, CaseInsensitiveChoice
 from lean.components.api.api_client import APIClient
 from lean.components.util.json_modules_handler import non_interactive_config_build_for_name, \
     interactive_config_build
@@ -166,10 +166,10 @@ def _configure_auto_restart(logger: Logger) -> bool:
 @live.command(cls=LeanCommand, default_command=True, name="deploy")
 @argument("project", type=str)
 @option("--brokerage",
-              type=Choice([b.get_name() for b in cloud_brokerages], case_sensitive=False),
+              type=CaseInsensitiveChoice([b.get_name() for b in cloud_brokerages]),
               help="The brokerage to use")
 @option("--data-provider-live",
-              type=Choice([d.get_name() for d in cloud_data_queue_handlers], case_sensitive=False),
+              type=CaseInsensitiveChoice([d.get_name() for d in cloud_data_queue_handlers]),
               multiple=True,
               help="The live data provider to use")
 @options_from_json(get_configs_for_options("live-cloud"))
diff --git a/lean/commands/cloud/optimize.py b/lean/commands/cloud/optimize.py
index d66334ae..cc7efeea 100644
--- a/lean/commands/cloud/optimize.py
+++ b/lean/commands/cloud/optimize.py
@@ -13,9 +13,9 @@
 
 from typing import List, Optional, Tuple
 
-from click import command, option, Choice, argument, confirm
+from click import command, option, argument, confirm
 
-from lean.click import LeanCommand, ensure_options
+from lean.click import LeanCommand, ensure_options, CaseInsensitiveChoice
 from lean.components.config.optimizer_config_manager import NodeType, available_nodes
 from lean.container import container
 from lean.models.api import QCOptimizationBacktest, QCProject, QCCompileWithLogs, QCFullOrganization
@@ -156,7 +156,7 @@ def _display_estimate(cloud_project: QCProject,
               type=str,
               help="The target statistic of the optimization")
 @option("--target-direction",
-              type=Choice(["min", "max"], case_sensitive=False),
+              type=CaseInsensitiveChoice(["min", "max"]),
               help="Whether the target must be minimized or maximized")
 @option("--parameter",
               type=(str, float, float, float),
@@ -167,7 +167,7 @@ def _display_estimate(cloud_project: QCProject,
               multiple=True,
               help="The 'statistic operator value' pairs configuring the constraints of the optimization")
 @option("--node",
-              type=Choice([node.name for node in available_nodes], case_sensitive=False),
+              type=CaseInsensitiveChoice([node.name for node in available_nodes]),
               help="The node type to run the optimization on")
 @option("--parallel-nodes",
               type=int,
diff --git a/lean/commands/create_project.py b/lean/commands/create_project.py
index 2bd9e9bd..6f2d5d4d 100644
--- a/lean/commands/create_project.py
+++ b/lean/commands/create_project.py
@@ -12,9 +12,9 @@
 # limitations under the License.
 
 from pathlib import Path
-from click import Choice, option, argument
+from click import option, argument
 
-from lean.click import LeanCommand
+from lean.click import LeanCommand, CaseInsensitiveChoice
 from lean.commands import lean
 from lean.container import container
 from lean.models.api import QCLanguage
@@ -398,7 +398,7 @@ def _not_identifier_char(text):
 @lean.command(cls=LeanCommand, name="project-create", aliases=["create-project"])
 @argument("name", type=str)
 @option("--language", "-l",
-              type=Choice(container.cli_config_manager.default_language.allowed_values, case_sensitive=False),
+              type=CaseInsensitiveChoice(container.cli_config_manager.default_language.allowed_values),
               help="The language of the project to create")
 def create_project(name: str, language: str) -> None:
     """Create a new project containing starter code.
diff --git a/lean/commands/data/download.py b/lean/commands/data/download.py
index 6b21f402..1657acc2 100644
--- a/lean/commands/data/download.py
+++ b/lean/commands/data/download.py
@@ -15,8 +15,8 @@
 
 from docker.types import Mount
 from typing import Any, Dict, Iterable, List, Optional
-from click import command, option, confirm, pass_context, Context, Choice, prompt
-from lean.click import LeanCommand, ensure_options
+from click import command, option, confirm, pass_context, Context, prompt
+from lean.click import LeanCommand, ensure_options, CaseInsensitiveChoice
 from lean.components.util.json_modules_handler import config_build_for_name
 from lean.constants import DEFAULT_ENGINE_IMAGE
 from lean.container import container
@@ -500,8 +500,8 @@ def _configure_date_option(date_value: str, option_id: str, option_label: str) -
     return date_option.configure_non_interactive(date_value)
 
 
-class QCDataTypeCustomChoice(Choice):
-    def get_metavar(self, param) -> str:
+class QCDataTypeCustomChoice(CaseInsensitiveChoice):
+    def get_metavar(self, param, ctx=None) -> str:
         choices_str = "|".join(QCDataType.get_all_members_except('Open Interest'))
 
         # Use square braces to indicate an option or optional argument.
@@ -521,7 +521,7 @@ def _replace_data_type(ctx, param, value):
 
 @command(cls=LeanCommand, requires_lean_config=True, allow_unknown_options=True, name="download")
 @option("--data-provider-historical",
-        type=Choice([data_downloader.get_name() for data_downloader in cli_data_downloaders], case_sensitive=False),
+        type=CaseInsensitiveChoice([data_downloader.get_name() for data_downloader in cli_data_downloaders]),
         help="The name of the downloader data provider.")
 @options_from_json(get_configs_for_options("download"))
 @option("--dataset", type=str, help="The name of the dataset to download non-interactively")
@@ -530,11 +530,11 @@ def _replace_data_type(ctx, param, value):
 @option("--yes", "-y", "auto_confirm", is_flag=True, default=False,
         help="Automatically confirm payment confirmation prompts")
 @option("--data-type", callback=_replace_data_type,
-        type=QCDataTypeCustomChoice(QCDataType.get_all_members(), case_sensitive=False),
+        type=QCDataTypeCustomChoice(QCDataType.get_all_members()),
         help="Specify the type of historical data")
-@option("--resolution", type=Choice(QCResolution.get_all_members(), case_sensitive=False),
+@option("--resolution", type=CaseInsensitiveChoice(QCResolution.get_all_members()),
         help="Specify the resolution of the historical data")
-@option("--security-type", type=Choice(QCSecurityType.get_all_members(), case_sensitive=False),
+@option("--security-type", type=CaseInsensitiveChoice(QCSecurityType.get_all_members()),
     help="Specify the security type of the historical data")
 @option("--market", type=str,
         help="Specify the market name for tickers (e.g., 'USA', 'NYMEX', 'Binance')"
diff --git a/lean/commands/data/generate.py b/lean/commands/data/generate.py
index 86a4b66d..3346f4f4 100644
--- a/lean/commands/data/generate.py
+++ b/lean/commands/data/generate.py
@@ -14,9 +14,9 @@
 from datetime import datetime
 from typing import Optional
 
-from click import command, option, Choice, IntRange
+from click import command, option, IntRange
 
-from lean.click import DateParameter, LeanCommand, ensure_options
+from lean.click import DateParameter, LeanCommand, ensure_options, CaseInsensitiveChoice
 from lean.constants import DEFAULT_ENGINE_IMAGE
 from lean.container import container
 
@@ -39,15 +39,15 @@
         default="",
         help="Comma separated list of tickers to use for generated data")
 @option("--security-type",
-        type=Choice(["Equity", "Forex", "Cfd", "Future", "Crypto", "Option"], case_sensitive=False),
+        type=CaseInsensitiveChoice(["Equity", "Forex", "Cfd", "Future", "Crypto", "Option"]),
         default="Equity",
         help="The security type to generate data for (defaults to Equity)")
 @option("--resolution",
-        type=Choice(["Tick", "Second", "Minute", "Hour", "Daily"], case_sensitive=False),
+        type=CaseInsensitiveChoice(["Tick", "Second", "Minute", "Hour", "Daily"]),
         default="Minute",
         help="The resolution of the generated data (defaults to Minute)")
 @option("--data-density",
-        type=Choice(["Dense", "Sparse", "VerySparse"], case_sensitive=False),
+        type=CaseInsensitiveChoice(["Dense", "Sparse", "VerySparse"]),
         default="Dense",
         help="The density of the generated data (defaults to Dense)")
 @option("--include-coarse",
@@ -98,7 +98,7 @@
         help="The stochastic process, and returns new pricing engine to run calculations for that option "
              "(defaults to BaroneAdesiWhaleyApproximationEngine)")
 @option("--volatility-model-resolution",
-        type=Choice(["Tick", "Second", "Minute", "Hour", "Daily"], case_sensitive=False),
+        type=CaseInsensitiveChoice(["Tick", "Second", "Minute", "Hour", "Daily"]),
         default="Daily",
         help="The volatility model period span (defaults to Daily)")
 @option("--chain-symbol-count",
diff --git a/lean/commands/init.py b/lean/commands/init.py
index 89dd4a76..461d0dc3 100644
--- a/lean/commands/init.py
+++ b/lean/commands/init.py
@@ -16,7 +16,7 @@
 
 from click import command, option, Choice, confirm, prompt
 
-from lean.click import LeanCommand
+from lean.click import LeanCommand, CaseInsensitiveChoice
 from lean.commands.login import get_credentials, validate_credentials, get_lean_config_credentials
 from lean.constants import DEFAULT_DATA_DIRECTORY_NAME, DEFAULT_LEAN_CONFIG_FILE_NAME
 from lean.container import container
@@ -121,7 +121,7 @@ def _download_repository(output_path: Path) -> None:
 @command(cls=LeanCommand)
 @option("--organization", type=str, help="The name or id of the organization the Lean CLI will be scaffolded for")
 @option("--language", "-l",
-        type=Choice(container.cli_config_manager.default_language.allowed_values, case_sensitive=False),
+        type=CaseInsensitiveChoice(container.cli_config_manager.default_language.allowed_values),
         help="The default language to use for new projects")
 def init(organization: Optional[str], language: Optional[str]) -> None:
     """Scaffold a Lean configuration file and data directory."""
diff --git a/lean/commands/live/deploy.py b/lean/commands/live/deploy.py
index be7e8867..bd2efd8c 100644
--- a/lean/commands/live/deploy.py
+++ b/lean/commands/live/deploy.py
@@ -13,8 +13,8 @@
 
 from pathlib import Path
 from typing import List, Optional, Tuple
-from click import option, argument, Choice
-from lean.click import LeanCommand, PathParameter
+from click import option, argument
+from lean.click import LeanCommand, PathParameter, CaseInsensitiveChoice
 from lean.components.util.name_rename import rename_internal_config_to_user_friendly_format
 from lean.constants import DEFAULT_ENGINE_IMAGE
 from lean.container import container
@@ -64,14 +64,14 @@ def _get_history_provider_name(data_provider_live_names: [str]) -> [str]:
               default=False,
               help="Run the live deployment in a detached Docker container and return immediately")
 @option("--brokerage",
-              type=Choice([b.get_name() for b in cli_brokerages], case_sensitive=False),
+              type=CaseInsensitiveChoice([b.get_name() for b in cli_brokerages]),
               help="The brokerage to use")
 @option("--data-provider-live",
-              type=Choice([d.get_name() for d in cli_data_queue_handlers], case_sensitive=False),
+              type=CaseInsensitiveChoice([d.get_name() for d in cli_data_queue_handlers]),
               multiple=True,
               help="The live data provider to use")
 @option("--data-provider-historical",
-              type=Choice([dp.get_name() for dp in cli_data_downloaders if dp.get_id() != "TerminalLinkBrokerage"], case_sensitive=False),
+              type=CaseInsensitiveChoice([dp.get_name() for dp in cli_data_downloaders if dp.get_id() != "TerminalLinkBrokerage"]),
               help="Update the Lean configuration file to retrieve data from the given historical provider")
 @options_from_json(get_configs_for_options("live-cli"))
 @option("--release",
diff --git a/lean/commands/optimize.py b/lean/commands/optimize.py
index 3e659082..7e63e67e 100644
--- a/lean/commands/optimize.py
+++ b/lean/commands/optimize.py
@@ -15,9 +15,9 @@
 from typing import Optional, List, Tuple
 from datetime import datetime, timedelta
 
-from click import command, argument, option, Choice, IntRange
+from click import command, argument, option, IntRange
 
-from lean.click import LeanCommand, PathParameter, ensure_options
+from lean.click import LeanCommand, PathParameter, ensure_options, CaseInsensitiveChoice
 from lean.components.docker.lean_runner import LeanRunner
 from lean.constants import DEFAULT_ENGINE_IMAGE
 from lean.container import container
@@ -81,13 +81,13 @@ def get_filename_timestamp(path: Path) -> datetime:
               type=PathParameter(exists=True, file_okay=True, dir_okay=False),
               help=f"The optimizer configuration file that should be used")
 @option("--strategy",
-              type=Choice(["Grid Search", "Euler Search"], case_sensitive=False),
+              type=CaseInsensitiveChoice(["Grid Search", "Euler Search"]),
               help="The optimization strategy to use")
 @option("--target",
               type=str,
               help="The target statistic of the optimization")
 @option("--target-direction",
-              type=Choice(["min", "max"], case_sensitive=False),
+              type=CaseInsensitiveChoice(["min", "max"]),
               help="Whether the target must be minimized or maximized")
 @option("--parameter",
               type=(str, float, float, float),
@@ -98,7 +98,7 @@ def get_filename_timestamp(path: Path) -> datetime:
               multiple=True,
               help="The 'statistic operator value' pairs configuring the constraints of the optimization")
 @option("--data-provider-historical",
-              type=Choice([dp.get_name() for dp in cli_data_downloaders], case_sensitive=False),
+              type=CaseInsensitiveChoice([dp.get_name() for dp in cli_data_downloaders]),
               default="Local",
               help="Update the Lean configuration file to retrieve data from the given historical provider")
 @option("--download-data",
diff --git a/lean/commands/research.py b/lean/commands/research.py
index 018c618c..49480205 100644
--- a/lean/commands/research.py
+++ b/lean/commands/research.py
@@ -13,8 +13,8 @@
 
 from pathlib import Path
 from typing import Optional, Tuple
-from click import command, argument, option, Choice
-from lean.click import LeanCommand, PathParameter
+from click import command, argument, option
+from lean.click import LeanCommand, PathParameter, CaseInsensitiveChoice
 from lean.components.docker.lean_runner import LeanRunner
 from lean.constants import DEFAULT_RESEARCH_IMAGE, LEAN_ROOT_PATH
 from lean.container import container
@@ -38,7 +38,7 @@ def _check_docker_output(chunk: str, port: int) -> None:
 @argument("project", type=PathParameter(exists=True, file_okay=False, dir_okay=True))
 @option("--port", type=int, default=8888, help="The port to run Jupyter Lab on (defaults to 8888)")
 @option("--data-provider-historical",
-              type=Choice([dp.get_name() for dp in cli_data_downloaders], case_sensitive=False),
+              type=CaseInsensitiveChoice([dp.get_name() for dp in cli_data_downloaders]),
               default="Local",
               help="Update the Lean configuration file to retrieve data from the given historical provider")
 @options_from_json(get_configs_for_options("research"))
diff --git a/lean/models/click_options.py b/lean/models/click_options.py
index 65526334..5531395c 100644
--- a/lean/models/click_options.py
+++ b/lean/models/click_options.py
@@ -13,8 +13,8 @@
 
 
 from typing import List, Dict
-from click import option, Choice
-from lean.click import PathParameter
+from click import option
+from lean.click import PathParameter, CaseInsensitiveChoice
 from lean.models.cli import cli_brokerages, cli_data_downloaders, cli_data_queue_handlers
 from lean.models.cloud import cloud_brokerages, cloud_data_queue_handlers
 from lean.models.configuration import Configuration, InfoConfiguration, InternalInputUserInput
@@ -59,7 +59,7 @@ def get_click_option_type(configuration: Configuration):
         # Skip validation if no predefined choices in config and user provided input manually
         if not configuration._choices:
             return str
-        return Choice(configuration._choices, case_sensitive=False)
+        return CaseInsensitiveChoice(configuration._choices)
     elif configuration._input_method == "prompt":
         return configuration.get_input_type()
     elif configuration._input_method == "prompt-password":
diff --git a/lean/models/configuration.py b/lean/models/configuration.py
index 67b79e05..e7a61e27 100644
--- a/lean/models/configuration.py
+++ b/lean/models/configuration.py
@@ -13,7 +13,8 @@
 
 from pathlib import Path
 from typing import Any, Dict, List
-from click import prompt, Choice
+from click import prompt
+from lean.click import CaseInsensitiveChoice
 from abc import ABC, abstractmethod
 from lean.components.util.logger import Logger
 from lean.click import PathParameter
@@ -294,7 +295,7 @@ def ask_user_for_input(self, default_value, logger: Logger, hide_input: bool = F
         return prompt(
             self._prompt_info,
             default_value,
-            type=Choice(self._choices, case_sensitive=False)
+            type=CaseInsensitiveChoice(self._choices)
         )
 
 
diff --git a/scripts/readme.py b/scripts/readme.py
index 61071cde..c6402247 100644
--- a/scripts/readme.py
+++ b/scripts/readme.py
@@ -24,6 +24,7 @@
 
 from click import Command, Group
 from click.testing import CliRunner
+from pydantic import ConfigDict
 
 from lean.commands import lean
 from lean.models.pydantic import WrappedBaseModel
@@ -31,12 +32,11 @@
 from lean.container import container
 
 class NamedCommand(WrappedBaseModel):
+    model_config = ConfigDict(arbitrary_types_allowed=True)
+
     name: str
     command: Command
 
-    class Config:
-        arbitrary_types_allowed = True
-
 
 def get_commands(group: Group, parent_names: List[str] = []) -> List[NamedCommand]:
     """Returns all lean commands by name.