diff --git a/litestar/app.py b/litestar/app.py
index fa49afdb39..0371924a97 100644
--- a/litestar/app.py
+++ b/litestar/app.py
@@ -4,7 +4,6 @@
 import inspect
 import itertools
 import logging
-import os
 import pdb  # noqa: T100
 import warnings
 from collections import defaultdict
@@ -53,7 +52,7 @@
 from litestar.stores.registry import StoreRegistry
 from litestar.types import Empty, TypeDecodersSequence
 from litestar.types.internal_types import PathParameterDefinition, RouteHandlerMapItem, TemplateConfigType
-from litestar.utils import ensure_async_callable, join_paths, unique
+from litestar.utils import ensure_async_callable, envflag, join_paths, unique
 from litestar.utils.dataclass import extract_dataclass_items
 from litestar.utils.predicates import is_async_callable, is_class_and_subclass
 from litestar.utils.warnings import warn_pdb_on_exception
@@ -334,10 +333,10 @@ def __init__(
             logging_config = LoggingConfig()
 
         if debug is None:
-            debug = os.getenv("LITESTAR_DEBUG", "0") == "1"
+            debug = envflag("LITESTAR_DEBUG")
 
         if pdb_on_exception is None:
-            pdb_on_exception = os.getenv("LITESTAR_PDB", "0") == "1"
+            pdb_on_exception = envflag("LITESTAR_PDB")
 
         config = AppConfig(
             after_exception=list(after_exception or []),
diff --git a/litestar/cli/_utils.py b/litestar/cli/_utils.py
index 729ecabb94..eb39b3fa9e 100644
--- a/litestar/cli/_utils.py
+++ b/litestar/cli/_utils.py
@@ -30,7 +30,7 @@
 
 from litestar import Litestar, __version__
 from litestar.middleware import DefineMiddleware
-from litestar.utils import get_name
+from litestar.utils import envflag, get_name
 
 if sys.version_info >= (3, 10):
     from importlib.metadata import entry_points
@@ -113,7 +113,7 @@ def from_env(cls, app_path: str | None, app_dir: Path | None = None) -> Litestar
             dotenv.load_dotenv()
         app_path = app_path or getenv("LITESTAR_APP")
         app_name = getenv("LITESTAR_APP_NAME") or "Litestar"
-        quiet_console = getenv("LITESTAR_QUIET_CONSOLE") or False
+        quiet_console = envflag("LITESTAR_QUIET_CONSOLE")
         if app_path and getenv("LITESTAR_APP") is None:
             os.environ["LITESTAR_APP"] = app_path
         if app_path:
@@ -345,7 +345,7 @@ def _autodiscovery_paths(base_dir: Path, arbitrary: bool = True) -> Generator[Pa
 
 def _autodiscover_app(cwd: Path) -> LoadedApp:
     app_name = getenv("LITESTAR_APP_NAME") or "Litestar"
-    quiet_console = getenv("LITESTAR_QUIET_CONSOLE") or False
+    quiet_console = envflag("LITESTAR_QUIET_CONSOLE")
     for file_path in _autodiscovery_paths(cwd):
         import_path = _path_to_dotted_path(file_path.relative_to(cwd))
         module = importlib.import_module(import_path)
diff --git a/litestar/cli/commands/core.py b/litestar/cli/commands/core.py
index b0a9753325..30beea0b0a 100644
--- a/litestar/cli/commands/core.py
+++ b/litestar/cli/commands/core.py
@@ -8,6 +8,8 @@
 from contextlib import AbstractContextManager, ExitStack, contextmanager
 from typing import TYPE_CHECKING, Any
 
+from litestar.utils.helpers import envflag
+
 try:
     import rich_click as click
 except ImportError:
@@ -119,7 +121,14 @@ class CommaSplittedPath(click.Path):
 
 
 @click.command(name="version")
-@click.option("-s", "--short", help="Exclude release level and serial information", is_flag=True, default=False)
+@click.option(
+    "-s",
+    "--short",
+    help="Exclude release level and serial information",
+    type=click.BOOL,
+    default=False,
+    is_flag=True,
+)
 def version_command(short: bool) -> None:
     """Show the currently installed Litestar version."""
     from litestar import __version__
@@ -135,7 +144,15 @@ def info_command(app: Litestar) -> None:
 
 
 @click.command(name="run")
-@click.option("-r", "--reload", help="Reload server on changes", default=False, is_flag=True, envvar="LITESTAR_RELOAD")
+@click.option(
+    "-r",
+    "--reload",
+    help="Reload server on changes",
+    envvar="LITESTAR_RELOAD",
+    type=click.BOOL,
+    default=False,
+    is_flag=True,
+)
 @click.option(
     "-R",
     "--reload-dir",
@@ -195,15 +212,39 @@ def info_command(app: Litestar) -> None:
     show_default=True,
     envvar="LITESTAR_UNIX_DOMAIN_SOCKET",
 )
-@click.option("-d", "--debug", help="Run app in debug mode", is_flag=True, envvar="LITESTAR_DEBUG")
-@click.option("-P", "--pdb", "--use-pdb", help="Drop into PDB on an exception", is_flag=True, envvar="LITESTAR_PDB")
+@click.option(
+    "-d",
+    "--debug",
+    help="Run app in debug mode",
+    envvar="LITESTAR_DEBUG",
+    type=click.BOOL,
+    is_flag=True,
+)
+@click.option(
+    "-P",
+    "--pdb",
+    "--use-pdb",
+    help="Drop into PDB on an exception",
+    envvar="LITESTAR_PDB",
+    type=click.BOOL,
+    is_flag=True,
+)
 @click.option("--ssl-certfile", help="Location of the SSL cert file", default=None, envvar="LITESTAR_SSL_CERT_PATH")
 @click.option("--ssl-keyfile", help="Location of the SSL key file", default=None, envvar="LITESTAR_SSL_KEY_PATH")
 @click.option(
     "--create-self-signed-cert",
     help="If certificate and key are not found at specified locations, create a self-signed certificate and a key",
-    is_flag=True,
     envvar="LITESTAR_CREATE_SELF_SIGNED_CERT",
+    type=click.BOOL,
+    is_flag=True,
+)
+@click.option(
+    "-q",
+    "--quiet-console",
+    envvar="LITESTAR_QUIET_CONSOLE",
+    help="Suppress formatted console output (useful for non-TTY environments, logs, and CI/CD",
+    type=click.BOOL,
+    is_flag=True,
 )
 def run_command(
     reload: bool,
@@ -220,6 +261,7 @@ def run_command(
     ssl_certfile: str | None,
     ssl_keyfile: str | None,
     create_self_signed_cert: bool,
+    quiet_console: bool,
     ctx: click.Context,
 ) -> None:
     """Run a Litestar app. (requires 'uvicorn' to be installed).
@@ -234,7 +276,9 @@ def run_command(
 
     if pdb:
         os.environ["LITESTAR_PDB"] = "1"
-    quiet_console = os.getenv("LITESTAR_QUIET_CONSOLE") or False
+
+    quiet_console = bool(envflag("LITESTAR_QUIET_CONSOLE"))
+
     if not UVICORN_INSTALLED:
         console.print(
             r"uvicorn is not installed. Please install the standard group, litestar\[standard], to use this command."
@@ -307,7 +351,7 @@ def run_command(
 
 
 @click.command(name="routes")
-@click.option("--schema", help="Include schema routes", is_flag=True, default=False)
+@click.option("--schema", help="Include schema routes", is_flag=True, default=False, type=click.BOOL)
 @click.option("--exclude", help="routes to exclude via regex", type=str, is_flag=False, multiple=True)
 def routes_command(app: Litestar, exclude: tuple[str, ...], schema: bool) -> None:  # pragma: no cover
     """Display information about the application's routes."""
diff --git a/litestar/utils/__init__.py b/litestar/utils/__init__.py
index 4cc9d1429b..3fccb3dd3f 100644
--- a/litestar/utils/__init__.py
+++ b/litestar/utils/__init__.py
@@ -1,6 +1,6 @@
 from litestar.utils.deprecation import deprecated, warn_deprecation
 
-from .helpers import get_enum_string_value, get_name, unique_name_for_scope, url_quote
+from .helpers import envflag, get_enum_string_value, get_name, unique_name_for_scope, url_quote
 from .path import join_paths, normalize_path
 from .predicates import (
     is_annotated_type,
@@ -29,6 +29,7 @@
     "AsyncIteratorWrapper",
     "deprecated",
     "ensure_async_callable",
+    "envflag",
     "find_index",
     "get_enum_string_value",
     "get_name",
diff --git a/litestar/utils/helpers.py b/litestar/utils/helpers.py
index 10602e2a00..ada18a8de3 100644
--- a/litestar/utils/helpers.py
+++ b/litestar/utils/helpers.py
@@ -1,10 +1,12 @@
 from __future__ import annotations
 
+import os
 from enum import Enum
 from functools import partial
 from typing import TYPE_CHECKING, TypeVar, cast
 from urllib.parse import quote
 
+from litestar.exceptions import LitestarException
 from litestar.utils.typing import get_origin_or_inner_type
 
 if TYPE_CHECKING:
@@ -102,3 +104,33 @@ def get_exception_group() -> type[BaseException]:
         from exceptiongroup import ExceptionGroup as _ExceptionGroup  # pyright: ignore
 
         return cast("type[BaseException]", _ExceptionGroup)
+
+
+def envflag(varname: str) -> bool | None:
+    """Parse an environment variable as a boolean flag.
+
+    Args:
+        varname: The name of the environment variable to check.
+
+    Returns:
+        True for truthy values (1, true, t, yes, y, on),
+        False for falsy values (0, false, f, no, n, off),
+        or empty string, None if not set.
+
+    Raises:
+        LitestarException: If the value is not a recognized boolean.
+    """
+    if varname not in os.environ:
+        return None
+
+    envvar = os.environ.get(varname)
+    if not envvar:
+        return False
+
+    norm = envvar.strip().lower()
+    if norm in {"1", "true", "t", "yes", "y", "on"}:
+        return True
+    if norm in {"0", "false", "f", "no", "n", "off"}:
+        return False
+
+    raise LitestarException(f"Invalid value for {varname}: '{norm}' is not a valid boolean.")
diff --git a/litestar/utils/warnings.py b/litestar/utils/warnings.py
index 2322245ce6..1337a4ac30 100644
--- a/litestar/utils/warnings.py
+++ b/litestar/utils/warnings.py
@@ -1,10 +1,10 @@
 from __future__ import annotations
 
-import os
 import warnings
 from typing import TYPE_CHECKING
 
 from litestar.exceptions import LitestarWarning
+from litestar.utils import envflag
 
 if TYPE_CHECKING:
     import re
@@ -13,7 +13,7 @@
 
 
 def warn_implicit_sync_to_thread(source: AnyCallable, stacklevel: int = 2) -> None:
-    if os.getenv("LITESTAR_WARN_IMPLICIT_SYNC_TO_THREAD") == "0":
+    if not envflag("LITESTAR_WARN_IMPLICIT_SYNC_TO_THREAD"):
         return
 
     warnings.warn(
@@ -29,7 +29,7 @@ def warn_implicit_sync_to_thread(source: AnyCallable, stacklevel: int = 2) -> No
 
 
 def warn_sync_to_thread_with_async_callable(source: AnyCallable, stacklevel: int = 2) -> None:
-    if os.getenv("LITESTAR_WARN_SYNC_TO_THREAD_WITH_ASYNC") == "0":
+    if not envflag("LITESTAR_WARN_SYNC_TO_THREAD_WITH_ASYNC"):
         return
 
     warnings.warn(
@@ -42,7 +42,7 @@ def warn_sync_to_thread_with_async_callable(source: AnyCallable, stacklevel: int
 
 
 def warn_sync_to_thread_with_generator(source: AnyGenerator, stacklevel: int = 2) -> None:
-    if os.getenv("LITESTAR_WARN_SYNC_TO_THREAD_WITH_GENERATOR") == "0":
+    if not envflag("LITESTAR_WARN_SYNC_TO_THREAD_WITH_GENERATOR"):
         return
 
     warnings.warn(
@@ -73,7 +73,7 @@ def warn_middleware_excluded_on_all_routes(
 
 
 def warn_signature_namespace_override(signature_key: str, stacklevel: int = 2) -> None:
-    if os.getenv("LITESTAR_WARN_SIGNATURE_NAMESPACE_OVERRIDE") == "0":
+    if not envflag("LITESTAR_WARN_SIGNATURE_NAMESPACE_OVERRIDE"):
         return
 
     warnings.warn(
diff --git a/tests/unit/test_utils/test_helpers.py b/tests/unit/test_utils/test_helpers.py
index 988b4ac512..aaefcbd7ce 100644
--- a/tests/unit/test_utils/test_helpers.py
+++ b/tests/unit/test_utils/test_helpers.py
@@ -3,7 +3,8 @@
 
 import pytest
 
-from litestar.utils.helpers import get_name, unique_name_for_scope, unwrap_partial
+from litestar.exceptions import LitestarException
+from litestar.utils.helpers import envflag, get_name, unique_name_for_scope, unwrap_partial
 
 T = TypeVar("T")
 
@@ -45,3 +46,44 @@ def test_unique_name_for_scope() -> None:
     assert unique_name_for_scope("a", ["a", "a_0", "b"]) == "a_1"
 
     assert unique_name_for_scope("b", ["a", "a_0", "b"]) == "b_0"
+
+
+def test_envflag_truthy_values(monkeypatch: pytest.MonkeyPatch) -> None:
+    for value in ("1", "true", "t", "yes", "y", "on", "YeS", "oN", "TRUE", "T"):
+        monkeypatch.setenv("TEST_FLAG", value)
+        assert envflag("TEST_FLAG") is True
+        monkeypatch.delenv("TEST_FLAG")
+
+
+def test_envflag_falsy_values(monkeypatch: pytest.MonkeyPatch) -> None:
+    for value in ("0", "false", "f", "no", "n", "off", "", "OfF", "fAlSe", "NO"):
+        monkeypatch.setenv("TEST_FLAG", value)
+        assert envflag("TEST_FLAG") is False
+        monkeypatch.delenv("TEST_FLAG")
+
+
+def test_envflag_invalid_value(monkeypatch: pytest.MonkeyPatch) -> None:
+    for value in ("2", "Tru", "Fals", "maybe", "invalid", "O"):
+        monkeypatch.setenv("TEST_FLAG", value)
+        with pytest.raises(LitestarException):
+            envflag("TEST_FLAG")
+
+
+def test_envflag_missing() -> None:
+    assert envflag("NONEXISTENT_VAR") is None
+
+
+def test_envflag_overrides(monkeypatch: pytest.MonkeyPatch) -> None:
+    monkeypatch.setenv("TEST_FLAG", "true")
+    assert envflag("TEST_FLAG") is True
+    monkeypatch.delenv("TEST_FLAG")
+
+    monkeypatch.setenv("TEST_FLAG", "0")
+    assert envflag("TEST_FLAG") is False
+    monkeypatch.delenv("TEST_FLAG")
+
+
+def test_envflag_empty_string(monkeypatch: pytest.MonkeyPatch) -> None:
+    monkeypatch.setenv("TEST_FLAG", "")
+    assert envflag("TEST_FLAG") is False
+    monkeypatch.delenv("TEST_FLAG")
diff --git a/tools/sphinx_ext/run_examples.py b/tools/sphinx_ext/run_examples.py
index 75ff281ba6..0537e3fa4d 100644
--- a/tools/sphinx_ext/run_examples.py
+++ b/tools/sphinx_ext/run_examples.py
@@ -22,6 +22,7 @@
 from sphinx.addnodes import highlightlang
 
 from litestar import Litestar
+from litestar.utils import envflag
 
 if TYPE_CHECKING:
     from collections.abc import Generator
@@ -34,7 +35,7 @@
 
 logger = logging.getLogger("sphinx")
 
-ignore_missing_output = os.getenv("LITESTAR_DOCS_IGNORE_MISSING_EXAMPLE_OUTPUT", "") == "1"
+ignore_missing_output = envflag("LITESTAR_DOCS_IGNORE_MISSING_EXAMPLE_OUTPUT")
 
 
 class StartupError(RuntimeError):