diff --git a/discord/file.py b/discord/file.py
index 701418ab4..6f176eef8 100644
--- a/discord/file.py
+++ b/discord/file.py
@@ -23,7 +23,7 @@ DEALINGS IN THE SOFTWARE.
 """
 
 from __future__ import annotations
-from typing import Optional, Union
+from typing import Any, Dict, Optional, Union
 
 import os
 import io
@@ -126,3 +126,14 @@ class File:
         self.fp.close = self._closer
         if self._owner:
             self._closer()
+
+    def to_dict(self, index: int) -> Dict[str, Any]:
+        payload = {
+            'id': index,
+            'filename': self.filename,
+        }
+
+        if self.description is not None:
+            payload['description'] = self.description
+
+        return payload
diff --git a/discord/http.py b/discord/http.py
index a3f83ce81..42aa2199a 100644
--- a/discord/http.py
+++ b/discord/http.py
@@ -52,13 +52,13 @@ import aiohttp
 
 from .errors import HTTPException, Forbidden, NotFound, LoginFailure, DiscordServerError, GatewayNotFound, InvalidArgument
 from .gateway import DiscordClientWebSocketResponse
+from .file import File
 from . import __version__, utils
 from .utils import MISSING
 
 _log = logging.getLogger(__name__)
 
 if TYPE_CHECKING:
-    from .file import File
     from .ui.view import View
     from .embeds import Embed
     from .mentions import AllowedMentions
@@ -147,7 +147,7 @@ def handle_message_parameters(
     files: List[File] = MISSING,
     embed: Optional[Embed] = MISSING,
     embeds: List[Embed] = MISSING,
-    attachments: List[Attachment] = MISSING,
+    attachments: List[Union[Attachment, File]] = MISSING,
     view: Optional[View] = MISSING,
     allowed_mentions: Optional[AllowedMentions] = MISSING,
     message_reference: Optional[message.MessageReference] = MISSING,
@@ -160,6 +160,12 @@ def handle_message_parameters(
     if embeds is not MISSING and embed is not MISSING:
         raise TypeError('Cannot mix embed and embeds keyword arguments.')
 
+    if file is not MISSING:
+        files = [file]
+
+    if attachments is not MISSING and files is not MISSING:
+        raise TypeError('Cannot mix attachments and files keyword arguments.')
+
     payload = {}
     if embeds is not MISSING:
         if len(embeds) > 10:
@@ -190,11 +196,6 @@ def handle_message_parameters(
     if message_reference is not MISSING:
         payload['message_reference'] = message_reference
 
-    if attachments is not MISSING:
-        # Note: This will be overwritten if file or files is provided
-        # However, right now this is only passed via Message.edit not Messageable.send
-        payload['attachments'] = [a.to_dict() for a in attachments]
-
     if stickers is not MISSING:
         if stickers is not None:
             payload['sticker_ids'] = stickers
@@ -224,26 +225,25 @@ def handle_message_parameters(
         except KeyError:
             pass
 
-    multipart = []
-    if file is not MISSING:
-        files = [file]
+    if attachments is MISSING:
+        attachments = files  # type: ignore
+    else:
+        files = [a for a in attachments if isinstance(a, File)]
 
-    if files:
-        for index, file in enumerate(files):
-            attachments_payload = []
-            for index, file in enumerate(files):
-                attachment = {
-                    'id': index,
-                    'filename': file.filename,
-                }
-
-                if file.description is not None:
-                    attachment['description'] = file.description
-
-                attachments_payload.append(attachment)
+    if attachments is not MISSING:
+        file_index = 0
+        attachments_payload = []
+        for attachment in attachments:
+            if isinstance(attachment, File):
+                attachments_payload.append(attachment.to_dict(file_index))
+                file_index += 1
+            else:
+                attachments_payload.append(attachment.to_dict())
 
-            payload['attachments'] = attachments_payload
+        payload['attachments'] = attachments_payload
 
+    multipart = []
+    if files:
         multipart.append({'name': 'payload_json', 'value': utils._to_json(payload)})
         payload = None
         for index, file in enumerate(files):
@@ -596,7 +596,10 @@ class HTTPClient:
 
     def edit_message(self, channel_id: Snowflake, message_id: Snowflake, *, params: MultipartParameters) -> Response[message.Message]:
         r = Route('PATCH', '/channels/{channel_id}/messages/{message_id}', channel_id=channel_id, message_id=message_id)
-        return self.request(r, json=params.payload)
+        if params.files:
+            return self.request(r, files=params.files, form=params.multipart)
+        else:
+            return self.request(r, json=params.payload)
 
     def add_reaction(self, channel_id: Snowflake, message_id: Snowflake, emoji: str) -> Response[None]:
         r = Route(
diff --git a/discord/interactions.py b/discord/interactions.py
index 57925f2b3..d54756f93 100644
--- a/discord/interactions.py
+++ b/discord/interactions.py
@@ -259,8 +259,7 @@ class Interaction:
         content: Optional[str] = MISSING,
         embeds: List[Embed] = MISSING,
         embed: Optional[Embed] = MISSING,
-        file: File = MISSING,
-        files: List[File] = MISSING,
+        attachments: List[Union[Attachment, File]] = MISSING,
         view: Optional[View] = MISSING,
         allowed_mentions: Optional[AllowedMentions] = None,
     ) -> InteractionMessage:
@@ -283,11 +282,14 @@ class Interaction:
         embed: Optional[:class:`Embed`]
             The embed to edit the message with. ``None`` suppresses the embeds.
             This should not be mixed with the ``embeds`` parameter.
-        file: :class:`File`
-            The file to upload. This cannot be mixed with ``files`` parameter.
-        files: List[:class:`File`]
-            A list of files to send with the content. This cannot be mixed with the
-            ``file`` parameter.
+        attachments: List[Union[:class:`Attachment`, :class:`File`]]
+            A list of attachments to keep in the message as well as new files to upload. If ``[]`` is passed
+            then all attachments are removed.
+ 
+            .. note::
+
+                New files will always appear after current attachments.
+
         allowed_mentions: :class:`AllowedMentions`
             Controls the mentions being processed in this message.
             See :meth:`.abc.Messageable.send` for more information.
@@ -302,7 +304,7 @@ class Interaction:
         Forbidden
             Edited a message that is not yours.
         TypeError
-            You specified both ``embed`` and ``embeds`` or ``file`` and ``files``
+            You specified both ``embed`` and ``embeds``
         ValueError
             The length of ``embeds`` was invalid.
 
@@ -315,8 +317,7 @@ class Interaction:
         previous_mentions: Optional[AllowedMentions] = self._state.allowed_mentions
         params = handle_message_parameters(
             content=content,
-            file=file,
-            files=files,
+            attachments=attachments,
             embed=embed,
             embeds=embeds,
             view=view,
@@ -549,7 +550,7 @@ class InteractionResponse:
         content: Optional[Any] = MISSING,
         embed: Optional[Embed] = MISSING,
         embeds: List[Embed] = MISSING,
-        attachments: List[Attachment] = MISSING,
+        attachments: List[Union[Attachment, File]] = MISSING,
         view: Optional[View] = MISSING,
         allowed_mentions: Optional[AllowedMentions] = MISSING,
     ) -> None:
@@ -567,9 +568,14 @@ class InteractionResponse:
         embed: Optional[:class:`Embed`]
             The embed to edit the message with. ``None`` suppresses the embeds.
             This should not be mixed with the ``embeds`` parameter.
-        attachments: List[:class:`Attachment`]
-            A list of attachments to keep in the message. If ``[]`` is passed
+        attachments: List[Union[:class:`Attachment`, :class:`File`]]
+            A list of attachments to keep in the message as well as new files to upload. If ``[]`` is passed
             then all attachments are removed.
+ 
+            .. note::
+
+                New files will always appear after current attachments.
+
         view: Optional[:class:`~discord.ui.View`]
             The updated view to update this message with. If ``None`` is passed then
             the view is removed.
@@ -667,8 +673,7 @@ class InteractionMessage(Message):
         content: Optional[str] = MISSING,
         embeds: List[Embed] = MISSING,
         embed: Optional[Embed] = MISSING,
-        file: File = MISSING,
-        files: List[File] = MISSING,
+        attachments: List[Union[Attachment, File]] = MISSING,
         view: Optional[View] = MISSING,
         allowed_mentions: Optional[AllowedMentions] = None,
     ) -> InteractionMessage:
@@ -685,11 +690,14 @@ class InteractionMessage(Message):
         embed: Optional[:class:`Embed`]
             The embed to edit the message with. ``None`` suppresses the embeds.
             This should not be mixed with the ``embeds`` parameter.
-        file: :class:`File`
-            The file to upload. This cannot be mixed with ``files`` parameter.
-        files: List[:class:`File`]
-            A list of files to send with the content. This cannot be mixed with the
-            ``file`` parameter.
+        attachments: List[Union[:class:`Attachment`, :class:`File`]]
+            A list of attachments to keep in the message as well as new files to upload. If ``[]`` is passed
+            then all attachments are removed.
+ 
+            .. note::
+
+                New files will always appear after current attachments.
+
         allowed_mentions: :class:`AllowedMentions`
             Controls the mentions being processed in this message.
             See :meth:`.abc.Messageable.send` for more information.
@@ -704,7 +712,7 @@ class InteractionMessage(Message):
         Forbidden
             Edited a message that is not yours.
         TypeError
-            You specified both ``embed`` and ``embeds`` or ``file`` and ``files``
+            You specified both ``embed`` and ``embeds``
         ValueError
             The length of ``embeds`` was invalid.
 
@@ -717,11 +725,62 @@ class InteractionMessage(Message):
             content=content,
             embeds=embeds,
             embed=embed,
-            file=file,
-            files=files,
+            attachments=attachments,
             view=view,
             allowed_mentions=allowed_mentions,
         )
+    
+    async def add_files(self, *files: File) -> InteractionMessage:
+        r"""|coro|
+
+        Adds new files to the end of the message attachments.
+
+        .. versionadded:: 2.0
+
+        Parameters
+        -----------
+        \*files: :class:`File`
+            New files to add to the message.
+
+        Raises
+        -------
+        HTTPException
+            Editing the message failed.
+        Forbidden
+            Tried to edit a message that isn't yours.
+        
+        Returns
+        ---------
+        :class:`InteractionMessage`
+            The newly edited message.
+        """
+        return await self.edit(attachments=[*self.attachments, *files])
+
+    async def remove_attachments(self, *attachments: Attachment) -> InteractionMessage:
+        r"""|coro|
+
+        Removes attachments from the message.
+
+        .. versionadded:: 2.0
+
+        Parameters
+        -----------
+        \*attachments: :class:`Attachment`
+            Attachments to remove from the message.
+        
+        Raises
+        -------
+        HTTPException
+            Editing the message failed.
+        Forbidden
+            Tried to edit a message that isn't yours.
+
+        Returns
+        ---------
+        :class:`InteractionMessage`
+            The newly edited message.
+        """
+        return await self.edit(attachments=[a for a in self.attachments if a not in attachments])
 
     async def delete(self, *, delay: Optional[float] = None) -> None:
         """|coro|
diff --git a/discord/message.py b/discord/message.py
index 58abb2a03..7aaa0aff5 100644
--- a/discord/message.py
+++ b/discord/message.py
@@ -1176,7 +1176,7 @@ class Message(Hashable):
         *,
         content: Optional[str] = ...,
         embed: Optional[Embed] = ...,
-        attachments: List[Attachment] = ...,
+        attachments: List[Union[Attachment, File]] = ...,
         suppress: bool = ...,
         delete_after: Optional[float] = ...,
         allowed_mentions: Optional[AllowedMentions] = ...,
@@ -1190,7 +1190,7 @@ class Message(Hashable):
         *,
         content: Optional[str] = ...,
         embeds: List[Embed] = ...,
-        attachments: List[Attachment] = ...,
+        attachments: List[Union[Attachment, File]] = ...,
         suppress: bool = ...,
         delete_after: Optional[float] = ...,
         allowed_mentions: Optional[AllowedMentions] = ...,
@@ -1203,7 +1203,7 @@ class Message(Hashable):
         content: Optional[str] = MISSING,
         embed: Optional[Embed] = MISSING,
         embeds: List[Embed] = MISSING,
-        attachments: List[Attachment] = MISSING,
+        attachments: List[Union[Attachment, File]] = MISSING,
         suppress: bool = MISSING,
         delete_after: Optional[float] = None,
         allowed_mentions: Optional[AllowedMentions] = MISSING,
@@ -1231,10 +1231,14 @@ class Message(Hashable):
             To remove all embeds ``[]`` should be passed.
 
             .. versionadded:: 2.0
-        attachments: List[:class:`Attachment`]
-            A list of attachments to keep in the message. If ``[]`` is passed
+        attachments: List[Union[:class:`Attachment`, :class:`File`]]
+            A list of attachments to keep in the message as well as new files to upload. If ``[]`` is passed
             then all attachments are removed.
 
+            .. note::
+
+                New files will always appear after current attachments.
+
             .. versionadded:: 2.0
         suppress: :class:`bool`
             Whether to suppress embeds for the message. This removes
@@ -1299,6 +1303,58 @@ class Message(Hashable):
 
         return message
 
+    async def add_files(self, *files: File) -> Message:
+        r"""|coro|
+
+        Adds new files to the end of the message attachments.
+
+        .. versionadded:: 2.0
+
+        Parameters
+        -----------
+        \*files: :class:`File`
+            New files to add to the message.
+
+        Raises
+        -------
+        HTTPException
+            Editing the message failed.
+        Forbidden
+            Tried to edit a message that isn't yours.
+
+        Returns
+        --------
+        :class:`Message`
+            The newly edited message.
+        """
+        return await self.edit(attachments=[*self.attachments, *files])
+
+    async def remove_attachments(self, *attachments: Attachment) -> Message:
+        r"""|coro|
+
+        Removes attachments from the message.
+
+        .. versionadded:: 2.0
+
+        Parameters
+        -----------
+        \*attachments: :class:`Attachment`
+            Attachments to remove from the message.
+        
+        Raises
+        -------
+        HTTPException
+            Editing the message failed.
+        Forbidden
+            Tried to edit a message that isn't yours.
+
+        Returns
+        --------
+        :class:`Message`
+            The newly edited message.
+        """
+        return await self.edit(attachments=[a for a in self.attachments if a not in attachments])
+
     async def publish(self) -> None:
         """|coro|
 
@@ -1643,6 +1699,8 @@ class PartialMessage(Hashable):
 
     jump_url: str = Message.jump_url  # type: ignore
     edit = Message.edit
+    add_files = Message.add_files
+    remove_attachments = Message.remove_attachments
     delete = Message.delete
     publish = Message.publish
     pin = Message.pin
diff --git a/discord/webhook/async_.py b/discord/webhook/async_.py
index d63d16cc4..a2f128564 100644
--- a/discord/webhook/async_.py
+++ b/discord/webhook/async_.py
@@ -30,7 +30,7 @@ import json
 import re
 
 from urllib.parse import quote as urlquote
-from typing import Any, Dict, List, Literal, NamedTuple, Optional, TYPE_CHECKING, Tuple, Union, overload
+from typing import Any, Dict, List, Literal, Optional, TYPE_CHECKING, Tuple, Union, overload
 from contextvars import ContextVar
 import weakref
 
@@ -434,7 +434,7 @@ def interaction_message_response_params(
     files: List[File] = MISSING,
     embed: Optional[Embed] = MISSING,
     embeds: List[Embed] = MISSING,
-    attachments: List[Attachment] = MISSING,
+    attachments: List[Union[Attachment, File]] = MISSING,
     view: Optional[View] = MISSING,
     allowed_mentions: Optional[AllowedMentions] = MISSING,
     previous_allowed_mentions: Optional[AllowedMentions] = None,
@@ -444,6 +444,12 @@ def interaction_message_response_params(
     if embeds is not MISSING and embed is not MISSING:
         raise TypeError('Cannot mix embed and embeds keyword arguments.')
 
+    if file is not MISSING:
+        files = [file]
+
+    if attachments is not MISSING and files is not MISSING:
+        raise TypeError('Cannot mix attachments and files keyword arguments.')
+
     data: Optional[Dict[str, Any]] = {
         'tts': tts,
     }
@@ -471,11 +477,6 @@ def interaction_message_response_params(
         else:
             data['components'] = []
 
-    if attachments is not MISSING:
-        # Note: This will be overwritten if file or files is provided
-        # However, right now this is only passed via edit not send
-        data['attachments'] = [a.to_dict() for a in attachments]
-
     if flags is not MISSING:
         data['flags'] = flags.value
 
@@ -487,26 +488,25 @@ def interaction_message_response_params(
     elif previous_allowed_mentions is not None:
         data['allowed_mentions'] = previous_allowed_mentions.to_dict()
 
-    multipart = []
-    if file is not MISSING:
-        files = [file]
-
-    if files:
-        for index, file in enumerate(files):
-            attachments_payload = []
-            for index, file in enumerate(files):
-                attachment = {
-                    'id': index,
-                    'filename': file.filename,
-                }
-
-                if file.description is not None:
-                    attachment['description'] = file.description
+    if attachments is MISSING:
+        attachments = files  # type: ignore
+    else:
+        files = [a for a in attachments if isinstance(a, File)]
 
-                attachments_payload.append(attachment)
+    if attachments is not MISSING:
+        file_index = 0
+        attachments_payload = []
+        for attachment in attachments:
+            if isinstance(attachment, File):
+                attachments_payload.append(attachment.to_dict(file_index))
+                file_index += 1
+            else:
+                attachments_payload.append(attachment.to_dict())
 
-            data['attachments'] = attachments_payload
+        data['attachments'] = attachments_payload
 
+    multipart = []
+    if files:
         data = {'type': type, 'data': data}
         multipart.append({'name': 'payload_json', 'value': utils._to_json(data)})
         data = None
@@ -656,8 +656,7 @@ class WebhookMessage(Message):
         content: Optional[str] = MISSING,
         embeds: List[Embed] = MISSING,
         embed: Optional[Embed] = MISSING,
-        file: File = MISSING,
-        files: List[File] = MISSING,
+        attachments: List[Union[Attachment, File]] = MISSING,
         view: Optional[View] = MISSING,
         allowed_mentions: Optional[AllowedMentions] = None,
     ) -> WebhookMessage:
@@ -679,13 +678,13 @@ class WebhookMessage(Message):
         embed: Optional[:class:`Embed`]
             The embed to edit the message with. ``None`` suppresses the embeds.
             This should not be mixed with the ``embeds`` parameter.
-        file: :class:`File`
-            The file to upload. This cannot be mixed with ``files`` parameter.
+        attachments: List[Union[:class:`Attachment`, :class:`File`]]
+            A list of attachments to keep in the message as well as new files to upload. If ``[]`` is passed
+            then all attachments are removed.
+ 
+            .. note::
 
-            .. versionadded:: 2.0
-        files: List[:class:`File`]
-            A list of files to send with the content. This cannot be mixed with the
-            ``file`` parameter.
+                New files will always appear after current attachments.
 
             .. versionadded:: 2.0
         allowed_mentions: :class:`AllowedMentions`
@@ -704,7 +703,7 @@ class WebhookMessage(Message):
         Forbidden
             Edited a message that is not yours.
         TypeError
-            You specified both ``embed`` and ``embeds`` or ``file`` and ``files``
+            You specified both ``embed`` and ``embeds``
         ValueError
             The length of ``embeds`` was invalid
         InvalidArgument
@@ -720,12 +719,63 @@ class WebhookMessage(Message):
             content=content,
             embeds=embeds,
             embed=embed,
-            file=file,
-            files=files,
+            attachments=attachments,
             view=view,
             allowed_mentions=allowed_mentions,
         )
 
+    async def add_files(self, *files: File) -> WebhookMessage:
+        r"""|coro|
+
+        Adds new files to the end of the message attachments.
+
+        .. versionadded:: 2.0
+
+        Parameters
+        -----------
+        \*files: :class:`File`
+            New files to add to the message.
+
+        Raises
+        -------
+        HTTPException
+            Editing the message failed.
+        Forbidden
+            Tried to edit a message that isn't yours.
+
+        Returns
+        --------
+        :class:`WebhookMessage`
+            The newly edited message.
+        """
+        return await self.edit(attachments=[*self.attachments, *files])
+
+    async def remove_attachments(self, *attachments: Attachment) -> WebhookMessage:
+        r"""|coro|
+
+        Removes attachments from the message.
+
+        .. versionadded:: 2.0
+
+        Parameters
+        -----------
+        \*attachments: :class:`Attachment`
+            Attachments to remove from the message.
+        
+        Raises
+        -------
+        HTTPException
+            Editing the message failed.
+        Forbidden
+            Tried to edit a message that isn't yours.
+
+        Returns
+        --------
+        :class:`WebhookMessage`
+            The newly edited message.
+        """
+        return await self.edit(attachments=[a for a in self.attachments if a not in attachments])
+
     async def delete(self, *, delay: Optional[float] = None) -> None:
         """|coro|
 
@@ -1470,8 +1520,7 @@ class Webhook(BaseWebhook):
         content: Optional[str] = MISSING,
         embeds: List[Embed] = MISSING,
         embed: Optional[Embed] = MISSING,
-        file: File = MISSING,
-        files: List[File] = MISSING,
+        attachments: List[Union[Attachment, File]] = MISSING,
         view: Optional[View] = MISSING,
         allowed_mentions: Optional[AllowedMentions] = None,
     ) -> WebhookMessage:
@@ -1498,13 +1547,9 @@ class Webhook(BaseWebhook):
         embed: Optional[:class:`Embed`]
             The embed to edit the message with. ``None`` suppresses the embeds.
             This should not be mixed with the ``embeds`` parameter.
-        file: :class:`File`
-            The file to upload. This cannot be mixed with ``files`` parameter.
-
-            .. versionadded:: 2.0
-        files: List[:class:`File`]
-            A list of files to send with the content. This cannot be mixed with the
-            ``file`` parameter.
+        attachments: List[Union[:class:`Attachment`, :class:`File`]]
+            A list of attachments to keep in the message as well as new files to upload. If ``[]`` is passed
+            then all attachments are removed.
 
             .. versionadded:: 2.0
         allowed_mentions: :class:`AllowedMentions`
@@ -1524,7 +1569,7 @@ class Webhook(BaseWebhook):
         Forbidden
             Edited a message that is not yours.
         TypeError
-            You specified both ``embed`` and ``embeds`` or ``file`` and ``files``
+            You specified both ``embed`` and ``embeds``
         ValueError
             The length of ``embeds`` was invalid
         InvalidArgument
@@ -1549,8 +1594,7 @@ class Webhook(BaseWebhook):
         previous_mentions: Optional[AllowedMentions] = getattr(self._state, 'allowed_mentions', None)
         params = handle_message_parameters(
             content=content,
-            file=file,
-            files=files,
+            attachments=attachments,
             embed=embed,
             embeds=embeds,
             view=view,
diff --git a/discord/webhook/sync.py b/discord/webhook/sync.py
index bf79c2c1b..c2adf3f6c 100644
--- a/discord/webhook/sync.py
+++ b/discord/webhook/sync.py
@@ -59,6 +59,7 @@ if TYPE_CHECKING:
     from ..file import File
     from ..embeds import Embed
     from ..mentions import AllowedMentions
+    from ..message import Attachment
     from ..types.webhook import (
         Webhook as WebhookPayload,
     )
@@ -381,8 +382,7 @@ class SyncWebhookMessage(Message):
         content: Optional[str] = MISSING,
         embeds: List[Embed] = MISSING,
         embed: Optional[Embed] = MISSING,
-        file: File = MISSING,
-        files: List[File] = MISSING,
+        attachments: List[Union[Attachment, File]] = MISSING,
         allowed_mentions: Optional[AllowedMentions] = None,
     ) -> SyncWebhookMessage:
         """Edits the message.
@@ -396,11 +396,15 @@ class SyncWebhookMessage(Message):
         embed: Optional[:class:`Embed`]
             The embed to edit the message with. ``None`` suppresses the embeds.
             This should not be mixed with the ``embeds`` parameter.
-        file: :class:`File`
-            The file to upload. This cannot be mixed with ``files`` parameter.
-        files: List[:class:`File`]
-            A list of files to send with the content. This cannot be mixed with the
-            ``file`` parameter.
+        attachments: List[Union[:class:`Attachment`, :class:`File`]]
+            A list of attachments to keep in the message as well as new files to upload. If ``[]`` is passed
+            then all attachments are removed.
+
+            .. note::
+
+                New files will always appear after current attachments.
+
+            .. versionadded:: 2.0
         allowed_mentions: :class:`AllowedMentions`
             Controls the mentions being processed in this message.
             See :meth:`.abc.Messageable.send` for more information.
@@ -412,7 +416,7 @@ class SyncWebhookMessage(Message):
         Forbidden
             Edited a message that is not yours.
         TypeError
-            You specified both ``embed`` and ``embeds`` or ``file`` and ``files``
+            You specified both ``embed`` and ``embeds``
         ValueError
             The length of ``embeds`` was invalid
         InvalidArgument
@@ -428,11 +432,58 @@ class SyncWebhookMessage(Message):
             content=content,
             embeds=embeds,
             embed=embed,
-            file=file,
-            files=files,
+            attachments=attachments,
             allowed_mentions=allowed_mentions,
         )
 
+    def add_files(self, *files: File) -> SyncWebhookMessage:
+        r"""Adds new files to the end of the message attachments.
+
+        .. versionadded:: 2.0
+
+        Parameters
+        -----------
+        \*files: :class:`File`
+            New files to add to the message.
+
+        Raises
+        -------
+        HTTPException
+            Editing the message failed.
+        Forbidden
+            Tried to edit a message that isn't yours.
+
+        Returns
+        --------
+        :class:`SyncWebhookMessage`
+            The newly edited message.
+        """
+        return self.edit(attachments=[*self.attachments, *files])
+
+    def remove_attachments(self, *attachments: Attachment) -> SyncWebhookMessage:
+        r"""Removes attachments from the message.
+
+        .. versionadded:: 2.0
+
+        Parameters
+        -----------
+        \*attachments: :class:`Attachment`
+            Attachments to remove from the message.
+        
+        Raises
+        -------
+        HTTPException
+            Editing the message failed.
+        Forbidden
+            Tried to edit a message that isn't yours.
+
+        Returns
+        --------
+        :class:`SyncWebhookMessage`
+            The newly edited message.
+        """
+        return self.edit(attachments=[a for a in self.attachments if a not in attachments])
+
     def delete(self, *, delay: Optional[float] = None) -> None:
         """Deletes the message.
 
@@ -966,8 +1017,7 @@ class SyncWebhook(BaseWebhook):
         content: Optional[str] = MISSING,
         embeds: List[Embed] = MISSING,
         embed: Optional[Embed] = MISSING,
-        file: File = MISSING,
-        files: List[File] = MISSING,
+        attachments: List[Union[Attachment, File]] = MISSING,
         allowed_mentions: Optional[AllowedMentions] = None,
     ) -> SyncWebhookMessage:
         """Edits a message owned by this webhook.
@@ -988,11 +1038,11 @@ class SyncWebhook(BaseWebhook):
         embed: Optional[:class:`Embed`]
             The embed to edit the message with. ``None`` suppresses the embeds.
             This should not be mixed with the ``embeds`` parameter.
-        file: :class:`File`
-            The file to upload. This cannot be mixed with ``files`` parameter.
-        files: List[:class:`File`]
-            A list of files to send with the content. This cannot be mixed with the
-            ``file`` parameter.
+        attachments: List[Union[:class:`Attachment`, :class:`File`]]
+            A list of attachments to keep in the message as well as new files to upload. If ``[]`` is passed
+            then all attachments are removed.
+
+            .. versionadded:: 2.0
         allowed_mentions: :class:`AllowedMentions`
             Controls the mentions being processed in this message.
             See :meth:`.abc.Messageable.send` for more information.
@@ -1004,7 +1054,7 @@ class SyncWebhook(BaseWebhook):
         Forbidden
             Edited a message that is not yours.
         TypeError
-            You specified both ``embed`` and ``embeds`` or ``file`` and ``files``
+            You specified both ``embed`` and ``embeds``
         ValueError
             The length of ``embeds`` was invalid
         InvalidArgument
@@ -1017,8 +1067,7 @@ class SyncWebhook(BaseWebhook):
         previous_mentions: Optional[AllowedMentions] = getattr(self._state, 'allowed_mentions', None)
         params = handle_message_parameters(
             content=content,
-            file=file,
-            files=files,
+            attachments=attachments,
             embed=embed,
             embeds=embeds,
             allowed_mentions=allowed_mentions,