diff --git a/discord/abc.py b/discord/abc.py
index d699f44702..49c4420306 100644
--- a/discord/abc.py
+++ b/discord/abc.py
@@ -45,7 +45,7 @@
 from .context_managers import Typing
 from .enums import ChannelType
 from .errors import ClientException, InvalidArgument
-from .file import File
+from .file import File, VoiceMessage
 from .flags import MessageFlags
 from .invite import Invite
 from .iterators import HistoryIterator
@@ -1567,7 +1567,7 @@ async def send(
         flags = MessageFlags(
             suppress_embeds=bool(suppress),
             suppress_notifications=bool(silent),
-        ).value
+        )
 
         if stickers is not None:
             stickers = [sticker.id for sticker in stickers]
@@ -1613,27 +1613,7 @@ async def send(
         if file is not None:
             if not isinstance(file, File):
                 raise InvalidArgument("file parameter must be File")
-
-            try:
-                data = await state.http.send_files(
-                    channel.id,
-                    files=[file],
-                    allowed_mentions=allowed_mentions,
-                    content=content,
-                    tts=tts,
-                    embed=embed,
-                    embeds=embeds,
-                    nonce=nonce,
-                    enforce_nonce=enforce_nonce,
-                    message_reference=reference,
-                    stickers=stickers,
-                    components=components,
-                    flags=flags,
-                    poll=poll,
-                )
-            finally:
-                file.close()
-
+            files = [file]
         elif files is not None:
             if len(files) > 10:
                 raise InvalidArgument(
@@ -1642,6 +1622,10 @@ async def send(
             elif not all(isinstance(file, File) for file in files):
                 raise InvalidArgument("files parameter must be a list of File")
 
+        if files is not None:
+            flags = flags + MessageFlags(
+                is_voice_message=any(isinstance(f, VoiceMessage) for f in files)
+            )
             try:
                 data = await state.http.send_files(
                     channel.id,
@@ -1656,7 +1640,7 @@ async def send(
                     message_reference=reference,
                     stickers=stickers,
                     components=components,
-                    flags=flags,
+                    flags=flags.value,
                     poll=poll,
                 )
             finally:
@@ -1675,7 +1659,7 @@ async def send(
                 message_reference=reference,
                 stickers=stickers,
                 components=components,
-                flags=flags,
+                flags=flags.value,
                 poll=poll,
             )
 
diff --git a/discord/file.py b/discord/file.py
index cb1a766bc9..fb0e0908dd 100644
--- a/discord/file.py
+++ b/discord/file.py
@@ -29,7 +29,10 @@
 import os
 from typing import TYPE_CHECKING
 
-__all__ = ("File",)
+__all__ = (
+    "File",
+    "VoiceMessage",
+)
 
 
 class File:
@@ -89,6 +92,7 @@ def __init__(
         description: str | None = None,
         spoiler: bool = False,
     ):
+
         if isinstance(fp, io.IOBase):
             if not (fp.seekable() and fp.readable()):
                 raise ValueError(f"File buffer {fp!r} must be seekable and readable")
@@ -143,3 +147,59 @@ def close(self) -> None:
         self.fp.close = self._closer
         if self._owner:
             self._closer()
+
+
+class VoiceMessage(File):
+    """A special case of the File class that represents a voice message.
+
+    .. versionadded:: 2.7
+
+    .. note::
+
+        Just like File objects VoiceMessage objects are single use and are not meant to be reused in
+        multiple requests.
+
+    Attributes
+    ----------
+    fp: Union[:class:`os.PathLike`, :class:`io.BufferedIOBase`]
+        A audio file-like object opened in binary mode and read mode
+        or a filename representing a file in the hard drive to
+        open.
+
+        .. note::
+
+            If the file-like object passed is opened via ``open`` then the
+            modes 'rb' should be used.
+
+            To pass binary data, consider usage of ``io.BytesIO``.
+
+    filename: Optional[:class:`str`]
+        The filename to display when uploading to Discord.
+        If this is not given then it defaults to ``fp.name`` or if ``fp`` is
+        a string then the ``filename`` will default to the string given.
+    description: Optional[:class:`str`]
+        The description of a file, used by Discord to display alternative text on images.
+    spoiler: :class:`bool`
+        Whether the attachment is a spoiler.
+    waveform: Optional[:class:`str`]
+        The base64 encoded bytearray representing a sampled waveform. Currently only for voice messages
+    duration_secs: Optional[:class:`float`]
+        The duration of the audio file. Currently only for voice messages
+    """
+
+    __slots__ = (
+        "waveform",
+        "duration_secs",
+    )
+
+    def __init__(
+        self,
+        fp: str | bytes | os.PathLike | io.BufferedIOBase,
+        # filename: str | None = None,
+        waveform: str = "",
+        duration_secs: float = 0.0,
+        **kwargs,
+    ):
+        super().__init__(fp, **kwargs)
+        self.waveform = waveform
+        self.duration_secs = duration_secs
diff --git a/discord/http.py b/discord/http.py
index f42bcdc233..e8f461befd 100644
--- a/discord/http.py
+++ b/discord/http.py
@@ -44,6 +44,7 @@
     LoginFailure,
     NotFound,
 )
+from .file import VoiceMessage
 from .gateway import DiscordClientWebSocketResponse
 from .utils import MISSING, warn_deprecated
 
@@ -410,9 +411,36 @@ async def close(self) -> None:
     # login management
 
     async def static_login(self, token: str) -> user.User:
+        # TODO: Remove This When Testing Is Done
+        import logging
+
+        async def on_request_start(
+            session, context, params: aiohttp.TraceRequestStartParams
+        ):
+            # breakpoint()
+            logging.getLogger("aiohttp.client").debug(
+                f"Starting request <{params}> <{session}> <{context}>"
+            )
+
+        async def on_request_chunk_sent(
+            session, context, params: aiohttp.TraceRequestChunkSentParams
+        ):
+            with open("output.txt", "a") as file:
+                if byte := str(params.chunk).find(r"\x", 100) != -1:
+                    file.write(str(params.chunk)[:byte] + "\n")
+                else:
+                    file.write(str(params.chunk) + "\n")
+            # logging.getLogger('aiohttp.client').debug(f'Sent Chunk <{params}>')
+
+        trace_config = aiohttp.TraceConfig()
+        trace_config.on_request_start.append(on_request_start)
+        trace_config.on_request_chunk_sent.append(on_request_chunk_sent)
+
         # Necessary to get aiohttp to stop complaining about session creation
         self.__session = aiohttp.ClientSession(
-            connector=self.connector, ws_response_class=DiscordClientWebSocketResponse
+            connector=self.connector,
+            ws_response_class=DiscordClientWebSocketResponse,
+            trace_configs=[trace_config],
         )
         old_token = self.token
         self.token = token
@@ -567,13 +595,17 @@ def send_multipart_helper(
         attachments = []
         form.append({"name": "payload_json"})
         for index, file in enumerate(files):
-            attachments.append(
-                {
-                    "id": index,
-                    "filename": file.filename,
-                    "description": file.description,
-                }
-            )
+            attachment_info = {
+                "id": index,
+                "filename": file.filename,
+                "description": file.description,
+            }
+            if isinstance(file, VoiceMessage):
+                attachment_info.update(
+                    waveform=file.waveform,
+                    duration_secs=file.duration_secs,
+                )
+            attachments.append(attachment_info)
             form.append(
                 {
                     "name": f"files[{index}]",
@@ -633,13 +665,17 @@ def edit_multipart_helper(
         attachments = []
         form.append({"name": "payload_json"})
         for index, file in enumerate(files):
-            attachments.append(
-                {
-                    "id": index,
-                    "filename": file.filename,
-                    "description": file.description,
-                }
-            )
+            attachment_info = {
+                "id": index,
+                "filename": file.filename,
+                "description": file.description,
+            }
+            if isinstance(file, VoiceMessage):
+                attachment_info.update(
+                    waveform=file.waveform,
+                    duration_secs=file.duration_secs,
+                )
+            attachments.append(attachment_info)
             form.append(
                 {
                     "name": f"files[{index}]",
diff --git a/discord/interactions.py b/discord/interactions.py
index e7d7fade3e..5aa849bc7e 100644
--- a/discord/interactions.py
+++ b/discord/interactions.py
@@ -37,7 +37,7 @@
     try_enum,
 )
 from .errors import ClientException, InteractionResponded, InvalidArgument
-from .file import File
+from .file import File, VoiceMessage
 from .flags import MessageFlags
 from .guild import Guild
 from .member import Member
@@ -915,8 +915,7 @@ async def send_message(
         if content is not None:
             payload["content"] = str(content)
 
-        if ephemeral:
-            payload["flags"] = 64
+        flags = MessageFlags(ephemeral=ephemeral)
 
         if view is not None:
             payload["components"] = view.to_components()
@@ -954,6 +953,11 @@ async def send_message(
             elif not all(isinstance(file, File) for file in files):
                 raise InvalidArgument("files parameter must be a list of File")
 
+            if any(isinstance(file, VoiceMessage) for file in files):
+                flags = flags + MessageFlags(is_voice_message=True)
+
+        payload["flags"] = flags.value
+
         parent = self._parent
         adapter = async_context.get()
         http = parent._state.http
diff --git a/discord/webhook/async_.py b/discord/webhook/async_.py
index 090f7c96f2..1daa44d458 100644
--- a/discord/webhook/async_.py
+++ b/discord/webhook/async_.py
@@ -47,6 +47,7 @@
     InvalidArgument,
     NotFound,
 )
+from ..file import VoiceMessage
 from ..flags import MessageFlags
 from ..http import Route
 from ..message import Attachment, Message
@@ -507,13 +508,17 @@ def create_interaction_response(
         attachments = []
         files = files or []
         for index, file in enumerate(files):
-            attachments.append(
-                {
-                    "id": index,
-                    "filename": file.filename,
-                    "description": file.description,
-                }
-            )
+            attachment_info = {
+                "id": index,
+                "filename": file.filename,
+                "description": file.description,
+            }
+            if isinstance(file, VoiceMessage):
+                attachment_info.update(
+                    waveform=file.waveform,
+                    duration_secs=file.duration_secs,
+                )
+            attachments.append(attachment_info)
             form.append(
                 {
                     "name": f"files[{index}]",
@@ -522,6 +527,8 @@ def create_interaction_response(
                     "content_type": "application/octet-stream",
                 }
             )
+        if files and any(isinstance(f, VoiceMessage) for f in files):
+            payload["flags"] = MessageFlags(is_voice_message=True).value
         payload["attachments"] = attachments
         form[0]["value"] = utils._to_json(payload)
 
@@ -658,8 +665,10 @@ def handle_message_parameters(
     if username:
         payload["username"] = username
 
-    flags = MessageFlags(suppress_embeds=suppress, ephemeral=ephemeral)
-    payload["flags"] = flags.value
+    flags = MessageFlags(
+        suppress_embeds=suppress,
+        ephemeral=ephemeral,
+    )
 
     if applied_tags is not MISSING:
         payload["applied_tags"] = applied_tags
@@ -680,6 +689,7 @@ def handle_message_parameters(
         files = [file]
 
     if files:
+        voice_message = False
         for index, file in enumerate(files):
             multipart_files.append(
                 {
@@ -689,17 +699,26 @@ def handle_message_parameters(
                     "content_type": "application/octet-stream",
                 }
             )
-            _attachments.append(
-                {
-                    "id": index,
-                    "filename": file.filename,
-                    "description": file.description,
-                }
-            )
+            attachment_info = {
+                "id": index,
+                "filename": file.filename,
+                "description": file.description,
+            }
+            if isinstance(file, VoiceMessage):
+                voice_message = True
+                attachment_info.update(
+                    waveform=file.waveform,
+                    duration_secs=file.duration_secs,
+                )
+            _attachments.append(attachment_info)
+        if voice_message:
+            flags = flags + MessageFlags(is_voice_message=True)
 
     if _attachments:
         payload["attachments"] = _attachments
 
+    payload["flags"] = flags.value
+
     if multipart_files:
         multipart.append({"name": "payload_json", "value": utils._to_json(payload)})
         payload = None