diff --git a/aptly_api/parts/files.py b/aptly_api/parts/files.py
index c71b9e6..d3f5904 100644
--- a/aptly_api/parts/files.py
+++ b/aptly_api/parts/files.py
@@ -4,10 +4,16 @@
 # License, v. 2.0. If a copy of the MPL was not distributed with this
 # file, You can obtain one at http://mozilla.org/MPL/2.0/.
 import os
-from typing import Sequence, List, Tuple, BinaryIO, cast, Optional  # noqa: F401
+from typing import Sequence, List, Tuple, TextIO, BinaryIO, cast, Optional, Union, Dict  # noqa: F401
 
 from aptly_api.base import BaseAPIClient, AptlyAPIException
 
+_tuplefiletype = Union[
+    Tuple[str, Union[TextIO, BinaryIO, str, bytes]],
+    Tuple[str, Union[TextIO, BinaryIO, str, bytes], str],
+    Tuple[str, Union[TextIO, BinaryIO, str, bytes], str, Dict[str, str]]
+]
+
 
 class FilesAPISection(BaseAPIClient):
     def list(self, directory: Optional[str] = None) -> Sequence[str]:
@@ -18,13 +24,16 @@ def list(self, directory: Optional[str] = None) -> Sequence[str]:
 
         return cast(List[str], resp.json())
 
-    def upload(self, destination: str, *files: str) -> Sequence[str]:
-        to_upload = []  # type: List[Tuple[str, BinaryIO]]
+    def upload(self, destination: str, *files: Union[str, _tuplefiletype]) -> Sequence[str]:
+        to_upload = []  # type: List[Tuple[str, Union[BinaryIO, _tuplefiletype]]]
         for f in files:
-            if not os.path.exists(f) or not os.access(f, os.R_OK):
+            if isinstance(f, tuple):
+                to_upload.append((f[0], f),)
+            elif not os.path.exists(f) or not os.access(f, os.R_OK):
                 raise AptlyAPIException("File to upload %s can't be opened or read" % f)
-            fh = open(f, mode="rb")
-            to_upload.append((f, fh),)
+            else:
+                fh = open(f, mode="rb")
+                to_upload.append((f, fh),)
 
         try:
             resp = self.do_post("api/files/%s" % destination,
@@ -33,7 +42,7 @@ def upload(self, destination: str, *files: str) -> Sequence[str]:
             raise
         finally:
             for fn, to_close in to_upload:
-                if not to_close.closed:
+                if not isinstance(to_close, tuple) and not to_close.closed:
                     to_close.close()
 
         return cast(List[str], resp.json())
diff --git a/aptly_api/tests/test_files.py b/aptly_api/tests/test_files.py
index 76f571b..f814534 100644
--- a/aptly_api/tests/test_files.py
+++ b/aptly_api/tests/test_files.py
@@ -45,6 +45,14 @@ def test_upload_failed(self, *, rmock: requests_mock.Mocker) -> None:
         with self.assertRaises(AptlyAPIException):
             self.fapi.upload("test", os.path.join(os.path.dirname(__file__), "testpkg.deb"))
 
+    def test_upload_with_tuples(self, *, rmock: requests_mock.Mocker) -> None:
+        rmock.post("http://test/api/files/test", text='["test/otherpkg.deb", "test/binpkg.deb"]')
+        with open(os.path.join(os.path.dirname(__file__), "testpkg.deb"), "rb") as pkgf:
+            self.assertSequenceEqual(
+                self.fapi.upload("test", ("otherpkg.deb", pkgf), ("binpkg.deb", b"dpkg-contents")),
+                ['test/otherpkg.deb', 'test/binpkg.deb'],
+            )
+
     def test_delete(self, *, rmock: requests_mock.Mocker) -> None:
         rmock.delete("http://test/api/files/test",
                      text='{}')