diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 78c2e9a6d..f81a384a1 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -26,8 +26,7 @@ jobs:
 
       - name: Install dependencies
         run: |
-          python -m pip install --upgrade pip setuptools wheel "coverage[toml]" pytest pytest-asyncio pytest-cov pytest-mock
-          pip install -U -r requirements.txt
+          python -m pip install -e .[test]
 
       - name: Run tests
         shell: bash
diff --git a/discord/app_commands/transformers.py b/discord/app_commands/transformers.py
index 99a45303e..4cecd5a1e 100644
--- a/discord/app_commands/transformers.py
+++ b/discord/app_commands/transformers.py
@@ -750,9 +750,6 @@ def get_supported_annotation(
     if isinstance(annotation, Transformer):
         return (annotation, MISSING, False)
 
-    if hasattr(annotation, '__metadata__'):
-        return get_supported_annotation(annotation.__metadata__[0])
-
     if inspect.isclass(annotation):
         if issubclass(annotation, Transformer):
             return (annotation(), MISSING, False)
diff --git a/discord/ext/commands/core.py b/discord/ext/commands/core.py
index 387d8806e..0a75ddfff 100644
--- a/discord/ext/commands/core.py
+++ b/discord/ext/commands/core.py
@@ -160,12 +160,6 @@ def get_signature_parameters(
         if annotation is Greedy:
             raise TypeError('Unparameterized Greedy[...] is disallowed in signature.')
 
-        if hasattr(annotation, '__metadata__'):
-            # Annotated[X, Y] can access Y via __metadata__
-            metadata = annotation.__metadata__
-            if len(metadata) >= 1:
-                annotation = metadata[0]
-
         params[name] = parameter.replace(annotation=annotation)
 
     return params
diff --git a/discord/ext/commands/flags.py b/discord/ext/commands/flags.py
index 8c418860e..9951e75f3 100644
--- a/discord/ext/commands/flags.py
+++ b/discord/ext/commands/flags.py
@@ -184,11 +184,6 @@ def get_flags(namespace: Dict[str, Any], globals: Dict[str, Any], locals: Dict[s
             flag.name = name
 
         annotation = flag.annotation = resolve_annotation(flag.annotation, globals, locals, cache)
-        if hasattr(annotation, '__metadata__'):
-            # Annotated[X, Y] can access Y via __metadata__
-            metadata = annotation.__metadata__
-            if len(metadata) >= 1:
-                annotation = flag.annotation = metadata[0]
 
         if flag.default is MISSING and hasattr(annotation, '__commands_is_flag__') and annotation._can_be_constructible():
             flag.default = annotation._construct_default
diff --git a/discord/utils.py b/discord/utils.py
index af2d553de..6e27aeac7 100644
--- a/discord/utils.py
+++ b/discord/utils.py
@@ -1062,6 +1062,11 @@ def evaluate_annotation(
         cache[tp] = evaluated
         return evaluated
 
+    if hasattr(tp, '__metadata__'):
+        # Annotated[X, Y] can access Y via __metadata__
+        metadata = tp.__metadata__[0]
+        return evaluate_annotation(metadata, globals, locals, cache)
+
     if hasattr(tp, '__args__'):
         implicit_str = True
         is_literal = False
diff --git a/setup.py b/setup.py
index 5471d06ab..d436a979d 100644
--- a/setup.py
+++ b/setup.py
@@ -39,7 +39,7 @@ extras_require = {
         'sphinx==4.4.0',
         'sphinxcontrib_trio==1.1.2',
         'sphinxcontrib-websupport',
-        'typing-extensions',
+        'typing-extensions>=4.3,<5',
     ],
     'speed': [
         'orjson>=3.5.4',
@@ -52,7 +52,8 @@ extras_require = {
         'pytest',
         'pytest-asyncio',
         'pytest-cov',
-        'pytest-mock'
+        'pytest-mock',
+        'typing-extensions>=4.3,<5',
     ]
 }
 
diff --git a/tests/test_annotated_annotation.py b/tests/test_annotated_annotation.py
new file mode 100644
index 000000000..03fddad1e
--- /dev/null
+++ b/tests/test_annotated_annotation.py
@@ -0,0 +1,61 @@
+"""
+The MIT License (MIT)
+
+Copyright (c) 2015-present Rapptz
+
+Permission is hereby granted, free of charge, to any person obtaining a
+copy of this software and associated documentation files (the "Software"),
+to deal in the Software without restriction, including without limitation
+the rights to use, copy, modify, merge, publish, distribute, sublicense,
+and/or sell copies of the Software, and to permit persons to whom the
+Software is furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in
+all copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS
+OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING
+FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
+DEALINGS IN THE SOFTWARE.
+"""
+
+from __future__ import annotations
+from typing import Optional
+from typing_extensions import Annotated
+
+import discord
+from discord import app_commands
+from discord.ext import commands
+
+import pytest
+
+def test_annotated_annotation():
+    # can't exactly test if the parameter is the same, so just test if it raises something
+    @app_commands.command()
+    async def foo(interaction: discord.Interaction, param: Annotated[float, Optional[int]]):
+        pass
+
+
+    def to_hex(arg: str) -> int:
+        return int(arg, 16)
+
+    class Flag(commands.FlagConverter):
+        thing: Annotated[int, to_hex]
+
+    assert Flag.get_flags()['thing'].annotation == to_hex
+
+    @commands.command()
+    async def bar(ctx: commands.Context, param: Annotated[float, Optional[int]]):
+        pass
+
+    assert bar.clean_params['param'].annotation == Optional[int]
+
+    @commands.command()
+    async def nested(ctx: commands.Context, param: Optional[Annotated[str, int]]):
+        pass
+
+    assert nested.clean_params['param'].annotation == Optional[int]
+