diff --git a/python/lib/sift_py/file_attachment/__init__.py b/python/lib/sift_py/file_attachment/__init__.py
new file mode 100644
index 00000000..e69de29b
diff --git a/python/lib/sift_py/file_attachment/_internal/__init__.py b/python/lib/sift_py/file_attachment/_internal/__init__.py
new file mode 100644
index 00000000..e69de29b
diff --git a/python/lib/sift_py/file_attachment/_internal/upload.py b/python/lib/sift_py/file_attachment/_internal/upload.py
new file mode 100644
index 00000000..a85e6c69
--- /dev/null
+++ b/python/lib/sift_py/file_attachment/_internal/upload.py
@@ -0,0 +1,109 @@
+from typing import Any, Dict, Optional, Tuple
+from requests_toolbelt import MultipartEncoder
+from pathlib import Path
+from urllib.parse import urljoin, urlparse
+
+from sift_py._internal.convert.json import to_json
+from sift_py.file_attachment.entity import Entity
+from sift_py.file_attachment.metadata import Metadata
+from sift_py.rest import SiftRestConfig
+
+import mimetypes
+import requests
+
+
+class UploadService:
+    UPLOAD_PATH = "/api/v0/remote-files/upload"
+    UPLOAD_BULK_PATH = "/api/v0/remote-files/upload:bulk"
+
+    _upload_uri: str
+    _upload_bulk_uri: str
+    _apikey: str
+
+    def __init__(self, restconf: SiftRestConfig):
+        base_uri = self.__class__._compute_uri(restconf)
+        self._upload_uri = urljoin(base_uri, self.UPLOAD_PATH)
+        self._upload_bulk_uri = urljoin(base_uri, self.UPLOAD_BULK_PATH)
+        self._apikey = restconf["apikey"]
+
+    def upload_attachment(
+        self,
+        path: str,
+        entity: Entity,
+        metadata: Metadata,
+        description: Optional[str] = None,
+        organization_id: Optional[str] = None,
+    ) -> str:
+        posix_path = Path(path)
+
+        if not posix_path.is_file():
+            raise Exception(f"Provided path, '{path}', must be a regular file")
+
+        file_name, mimetype, content_encoding = self.__class__._mime_and_content_type_from_path(
+            posix_path
+        )
+
+        if not mimetype:
+            raise Exception(f"The MIME-type of '{posix_path}' could not be computed")
+
+        with open(path, "rb") as file:
+            form_fields: Dict[str, Any] = {
+                "entityId": entity.entity_id,
+                "entityType": entity.entity_type.value,
+                "metadata": to_json(metadata),
+            }
+
+            if content_encoding:
+                form_fields["file"] = (
+                    file_name,
+                    file,
+                    mimetype,
+                    {
+                        "Content-Encoding": content_encoding,
+                    },
+                )
+            else:
+                form_fields["file"] = (file_name, file, mimetype)
+
+            if organization_id:
+                form_fields["organizationId"] = organization_id
+
+            if description:
+                form_fields["description"] = description
+
+            form_data = MultipartEncoder(fields=form_fields)
+
+            # https://github.com/requests/toolbelt/issues/312
+            # Issue above is reason for the type ignoring
+            response = requests.post(
+                url=self._upload_uri,
+                data=form_data,  # type: ignore
+                headers={
+                    "Authorization": f"Bearer {self._apikey}",
+                    "Content-Type": form_data.content_type,
+                },
+            )
+
+            if response.status_code != 200:
+                raise Exception(response.text)
+
+            return response.json().get("remoteFile").get("remoteFileId")
+
+    @staticmethod
+    def _mime_and_content_type_from_path(path: Path) -> Tuple[str, Optional[str], Optional[str]]:
+        file_name = path.name
+        mime, encoding = mimetypes.guess_type(path)
+        return file_name, mime, encoding
+
+    @classmethod
+    def _compute_uri(cls, restconf: SiftRestConfig) -> str:
+        uri = restconf["uri"]
+        parsed_uri = urlparse(uri)
+
+        if parsed_uri.scheme != "":
+            raise Exception(f"The URL scheme '{parsed_uri.scheme}' should not be included")
+
+        if restconf.get("use_ssl", True):
+            return f"https://{uri}"
+
+        return f"http://{uri}"
diff --git a/python/lib/sift_py/file_attachment/entity.py b/python/lib/sift_py/file_attachment/entity.py
new file mode 100644
index 00000000..7fe39d94
--- /dev/null
+++ b/python/lib/sift_py/file_attachment/entity.py
@@ -0,0 +1,21 @@
+"""
+Entities represent things that files can be attached to.
+"""
+
+from __future__ import annotations
+from enum import Enum
+
+
+class Entity:
+    entity_id: str
+    entity_type: EntityType
+
+    def __init__(self, entity_id: str, entity_type: EntityType):
+        self.entity_id = entity_id
+        self.entity_type = entity_type
+
+
+class EntityType(Enum):
+    RUN = "runs"
+    ANNOTATION = "annotations"
+    ANNOTATION_LOG = "annotation_logs"
diff --git a/python/lib/sift_py/file_attachment/metadata.py b/python/lib/sift_py/file_attachment/metadata.py
new file mode 100644
index 00000000..525c02c1
--- /dev/null
+++ b/python/lib/sift_py/file_attachment/metadata.py
@@ -0,0 +1,73 @@
+from __future__ import annotations
+from typing import Any, Type
+from typing_extensions import Self
+from sift.remote_files.v1.remote_files_pb2 import (
+    ImageMetadata as ImageMetadataPb,
+    VideoMetadata as VideoMetadataPb,
+)
+from sift_py._internal.convert.protobuf import AsProtobuf
+from sift_py._internal.convert.json import AsJson
+
+
+class Metadata(AsJson): ...
+
+
+class VideoMetadata(AsProtobuf, Metadata):
+    width: int
+    height: int
+    duration_seconds: float
+
+    def __init__(self, width: int, height: int, duration_seconds: float):
+        self.width = width
+        self.height = height
+        self.duration_seconds = duration_seconds
+
+    def as_pb(self, klass: Type[VideoMetadataPb]) -> VideoMetadataPb:
+        return klass(
+            width=self.width,
+            height=self.height,
+            duration_seconds=self.duration_seconds,
+        )
+
+    @classmethod
+    def from_pb(cls, message: VideoMetadataPb) -> Self:
+        return cls(
+            width=message.width,
+            height=message.height,
+            duration_seconds=message.duration_seconds,
+        )
+
+    def as_json(self) -> Any:
+        return {
+            "height": self.height,
+            "width": self.width,
+            "duration_seconds": self.duration_seconds,
+        }
+
+
+class ImageMetadata(AsProtobuf, Metadata):
+    width: int
+    height: int
+
+    def __init__(self, width: int, height: int):
+        self.width = width
+        self.height = height
+
+    def as_pb(self, klass: Type[ImageMetadataPb]) -> ImageMetadataPb:
+        return klass(
+            width=self.width,
+            height=self.height,
+        )
+
+    @classmethod
+    def from_pb(cls, message: ImageMetadataPb) -> Self:
+        return cls(
+            width=message.width,
+            height=message.height,
+        )
+
+    def as_json(self) -> Any:
+        return {
+            "height": self.height,
+            "width": self.width,
+        }
diff --git a/python/lib/sift_py/file_attachment/service.py b/python/lib/sift_py/file_attachment/service.py
new file mode 100644
index 00000000..9e029067
--- /dev/null
+++ b/python/lib/sift_py/file_attachment/service.py
@@ -0,0 +1,40 @@
+from typing import Optional, cast
+from sift.remote_files.v1.remote_files_pb2_grpc import RemoteFileServiceStub
+from sift_py.file_attachment._internal.upload import UploadService
+from sift_py.file_attachment.entity import Entity
+from sift_py.file_attachment.metadata import Metadata
+from sift_py.grpc.transport import SiftChannel
+from sift.remote_files.v1.remote_files_pb2 import (
+    RemoteFile,
+    GetRemoteFileRequest,
+    GetRemoteFileResponse,
+)
+from sift_py.rest import SiftRestConfig
+
+
+class FileAttachmentService:
+    _remote_file_service_stub: RemoteFileServiceStub
+    _upload_service: UploadService
+
+    def __init__(self, channel: SiftChannel, restconf: SiftRestConfig):
+        self._remote_file_service_stub = RemoteFileServiceStub(channel)
+        self._upload_service = UploadService(restconf)
+
+    def upload_attachment(
+        self,
+        path: str,
+        entity: Entity,
+        metadata: Metadata,
+        description: Optional[str] = None,
+        organization_id: Optional[str] = None,
+    ) -> RemoteFile:
+        remote_file_id = self._upload_service.upload_attachment(
+            path,
+            entity,
+            metadata,
+            description,
+            organization_id,
+        )
+        req = GetRemoteFileRequest(remote_file_id=remote_file_id)
+        res = cast(GetRemoteFileResponse, self._remote_file_service_stub.GetRemoteFile(req))
+        return res.remote_file
diff --git a/python/lib/sift_py/rest.py b/python/lib/sift_py/rest.py
new file mode 100644
index 00000000..9157c1ab
--- /dev/null
+++ b/python/lib/sift_py/rest.py
@@ -0,0 +1,15 @@
+from typing import TypedDict
+from typing_extensions import NotRequired
+
+
+class SiftRestConfig(TypedDict):
+    """
+    Config class used to to interact with services that use Sift's REST API.`.
+    - `uri`: The URI of Sift's REST API. The scheme portion of the URI i.e. `https://` should be ommitted.
+    - `apikey`: User-generated API key generated via the Sift application.
+    - `use_ssl`: INTERNAL USE. Meant to be used for local development.
+    """
+
+    uri: str
+    apikey: str
+    use_ssl: NotRequired[bool]
diff --git a/python/pyproject.toml b/python/pyproject.toml
index 541eeb65..ccdfdc24 100644
--- a/python/pyproject.toml
+++ b/python/pyproject.toml
@@ -77,6 +77,11 @@ module = "grpc"
 ignore_missing_imports = true
 ignore_errors = true
 
+[[tool.mypy.overrides]]
+module = "grpc.aio"
+ignore_missing_imports = true
+ignore_errors = true
+
 [[tool.mypy.overrides]]
 module = "requests_toolbelt"
 ignore_missing_imports = true