diff --git a/discord/ext/commands/flags.py b/discord/ext/commands/flags.py
index 35616c5ea..2085daa96 100644
--- a/discord/ext/commands/flags.py
+++ b/discord/ext/commands/flags.py
@@ -28,7 +28,7 @@ import inspect
 import re
 import sys
 from dataclasses import dataclass, field
-from typing import TYPE_CHECKING, Any, Dict, Iterator, List, Literal, Optional, Pattern, Set, Tuple, Union
+from typing import TYPE_CHECKING, Any, Dict, Iterator, List, Literal, Optional, Pattern, Set, Tuple, Type, Union
 
 from discord.utils import MISSING, maybe_coroutine, resolve_annotation
 
@@ -44,7 +44,7 @@ __all__ = (
 
 
 if TYPE_CHECKING:
-    from typing_extensions import Self
+    from typing_extensions import Self, TypeGuard
 
     from ._types import BotT
     from .context import Context
@@ -76,6 +76,12 @@ class Flag:
         A negative value indicates an unlimited amount of arguments.
     override: :class:`bool`
         Whether multiple given values overrides the previous value.
+    description: :class:`str`
+        The description of the flag.
+    positional: :class:`bool`
+        Whether the flag is positional or not. There can only be one positional flag.
+
+        .. versionadded:: 2.4
     """
 
     name: str = MISSING
@@ -85,6 +91,8 @@ class Flag:
     default: Any = MISSING
     max_args: int = MISSING
     override: bool = MISSING
+    description: str = MISSING
+    positional: bool = MISSING
     cast_to_dict: bool = False
 
     @property
@@ -104,6 +112,8 @@ def flag(
     max_args: int = MISSING,
     override: bool = MISSING,
     converter: Any = MISSING,
+    description: str = MISSING,
+    positional: bool = MISSING,
 ) -> Any:
     """Override default functionality and parameters of the underlying :class:`FlagConverter`
     class attributes.
@@ -128,8 +138,27 @@ def flag(
     converter: Any
         The converter to use for this flag. This replaces the annotation at
         runtime which is transparent to type checkers.
+    description: :class:`str`
+        The description of the flag.
+    positional: :class:`bool`
+        Whether the flag is positional or not. There can only be one positional flag.
+
+        .. versionadded:: 2.4
     """
-    return Flag(name=name, aliases=aliases, default=default, max_args=max_args, override=override, annotation=converter)
+    return Flag(
+        name=name,
+        aliases=aliases,
+        default=default,
+        max_args=max_args,
+        override=override,
+        annotation=converter,
+        description=description,
+        positional=positional,
+    )
+
+
+def is_flag(obj: Any) -> TypeGuard[Type[FlagConverter]]:
+    return hasattr(obj, '__commands_is_flag__')
 
 
 def validate_flag_name(name: str, forbidden: Set[str]) -> None:
@@ -151,6 +180,7 @@ def get_flags(namespace: Dict[str, Any], globals: Dict[str, Any], locals: Dict[s
     flags: Dict[str, Flag] = {}
     cache: Dict[str, Any] = {}
     names: Set[str] = set()
+    positional: Optional[Flag] = None
     for name, annotation in annotations.items():
         flag = namespace.pop(name, MISSING)
         if isinstance(flag, Flag):
@@ -163,6 +193,11 @@ def get_flags(namespace: Dict[str, Any], globals: Dict[str, Any], locals: Dict[s
         if flag.name is MISSING:
             flag.name = name
 
+        if flag.positional:
+            if positional is not None:
+                raise TypeError(f"{flag.name!r} positional flag conflicts with {positional.name!r} flag.")
+            positional = flag
+
         annotation = flag.annotation = resolve_annotation(flag.annotation, globals, locals, cache)
 
         if flag.default is MISSING and hasattr(annotation, '__commands_is_flag__') and annotation._can_be_constructible():
@@ -250,6 +285,7 @@ class FlagsMeta(type):
         __commands_flag_case_insensitive__: bool
         __commands_flag_delimiter__: str
         __commands_flag_prefix__: str
+        __commands_flag_positional__: Optional[Flag]
 
     def __new__(
         cls,
@@ -304,9 +340,13 @@ class FlagsMeta(type):
         delimiter = attrs.setdefault('__commands_flag_delimiter__', ':')
         prefix = attrs.setdefault('__commands_flag_prefix__', '')
 
+        positional: Optional[Flag] = None
         for flag_name, flag in get_flags(attrs, global_ns, local_ns).items():
             flags[flag_name] = flag
             aliases.update({alias_name: flag_name for alias_name in flag.aliases})
+            if flag.positional:
+                positional = flag
+        attrs['__commands_flag_positional__'] = positional
 
         forbidden = set(delimiter).union(prefix)
         for flag_name in flags:
@@ -480,10 +520,25 @@ class FlagConverter(metaclass=FlagsMeta):
         result: Dict[str, List[str]] = {}
         flags = cls.__commands_flags__
         aliases = cls.__commands_flag_aliases__
+        positional_flag = cls.__commands_flag_positional__
         last_position = 0
         last_flag: Optional[Flag] = None
 
         case_insensitive = cls.__commands_flag_case_insensitive__
+
+        if positional_flag is not None:
+            match = cls.__commands_flag_regex__.search(argument)
+            if match is not None:
+                begin, end = match.span(0)
+                value = argument[:begin].strip()
+            else:
+                value = argument.strip()
+                last_position = len(argument)
+
+            if value:
+                name = positional_flag.name.casefold() if case_insensitive else positional_flag.name
+                result[name] = [value]
+
         for match in cls.__commands_flag_regex__.finditer(argument):
             begin, end = match.span(0)
             key = match.group('flag')
diff --git a/docs/ext/commands/commands.rst b/docs/ext/commands/commands.rst
index f4504c3fd..68fe4deef 100644
--- a/docs/ext/commands/commands.rst
+++ b/docs/ext/commands/commands.rst
@@ -767,6 +767,19 @@ This tells the parser that the ``members`` attribute is mapped to a flag named `
 the default value is an empty list. For greater customisability, the default can either be a value or a callable
 that takes the :class:`~ext.commands.Context` as a sole parameter. This callable can either be a function or a coroutine.
 
+A positional flag can be defined by setting the :attr:`~ext.commands.Flag.positional` attribute to ``True``. This
+tells the parser that the content provided before the parsing occurs is part of the flag. This is useful for commands that
+require a parameter to be used first and the flags are optional, such as the following:
+
+.. code-block:: python3
+
+    class BanFlags(commands.FlagConverter):
+        members: List[discord.Member] = commands.flag(name='member', positional=True, default=lambda ctx: [])
+        reason: Optional[str] = None
+
+.. note::
+    Only one positional flag is allowed in a flag converter.
+
 In order to customise the flag syntax we also have a few options that can be passed to the class parameter list:
 
 .. code-block:: python3
@@ -786,11 +799,16 @@ In order to customise the flag syntax we also have a few options that can be pas
         nsfw: Optional[bool]
         slowmode: Optional[int]
 
+    # Hello there --bold True
+    class Greeting(commands.FlagConverter):
+        text: str = commands.flag(positional=True)
+        bold: bool = False
+
 .. note::
 
     Despite the similarities in these examples to command like arguments, the syntax and parser is not
     a command line parser. The syntax is mainly inspired by Discord's search bar input and as a result
-    all flags need a corresponding value.
+    all flags need a corresponding value unless part of a positional flag.
 
 Flag converters will only raise :exc:`~ext.commands.FlagError` derived exceptions. If an error is raised while
 converting a flag, :exc:`~ext.commands.BadFlagArgument` is raised instead and the original exception