diff --git a/.github/workflows/build-test.yml b/.github/workflows/build-test.yml
index ef4277174..219d5c3ce 100644
--- a/.github/workflows/build-test.yml
+++ b/.github/workflows/build-test.yml
@@ -67,7 +67,7 @@ jobs:
 
       - name: Run pytest
         run: |
-          python -m pytest -vv tests --reruns 3 --reruns-delay 30 --only-rerun "(?i)http|timeout"
+          python -m pytest -vv tests --reruns 3 --reruns-delay 30 --only-rerun "(?i)http|timeout|connection"
 
   vanilla-build:
     strategy:
@@ -91,4 +91,4 @@ jobs:
 
       - name: Run pytest
         run: |
-          python -m pytest -vv tests --reruns 3 --reruns-delay 30 --only-rerun "(?i)http|timeout"
+          python -m pytest -vv tests --reruns 3 --reruns-delay 30 --only-rerun "(?i)http|timeout|connection"
diff --git a/src/uproot/_util.py b/src/uproot/_util.py
index 2e4d1331f..61c7f1f51 100644
--- a/src/uproot/_util.py
+++ b/src/uproot/_util.py
@@ -90,6 +90,21 @@ def ensure_numpy(array, types=(numpy.bool_, numpy.integer, numpy.floating)):
         return out
 
 
+def is_file_like(
+    obj, readable: bool = False, writable: bool = False, seekable: bool = False
+) -> bool:
+    return (
+        callable(getattr(obj, "read", None))
+        and callable(getattr(obj, "write", None))
+        and callable(getattr(obj, "seek", None))
+        and callable(getattr(obj, "tell", None))
+        and callable(getattr(obj, "flush", None))
+        and (not readable or not hasattr(obj, "readable") or obj.readable())
+        and (not writable or not hasattr(obj, "writable") or obj.writable())
+        and (not seekable or not hasattr(obj, "seekable") or obj.seekable())
+    )
+
+
 def parse_version(version):
     """
     Converts a semver string into a Version object that can be compared with
diff --git a/src/uproot/sink/file.py b/src/uproot/sink/file.py
index 14c582364..167c8da17 100644
--- a/src/uproot/sink/file.py
+++ b/src/uproot/sink/file.py
@@ -14,6 +14,8 @@
 import numbers
 import os
 
+import uproot._util
+
 
 class FileSink:
     """
@@ -39,16 +41,7 @@ def from_object(cls, obj) -> FileSink:
         as ``io.BytesIO``. The object must be readable, writable, and seekable
         with ``"r+b"`` mode semantics.
         """
-        if (
-            callable(getattr(obj, "read", None))
-            and callable(getattr(obj, "write", None))
-            and callable(getattr(obj, "seek", None))
-            and callable(getattr(obj, "tell", None))
-            and callable(getattr(obj, "flush", None))
-            and (not hasattr(obj, "readable") or obj.readable())
-            and (not hasattr(obj, "writable") or obj.writable())
-            and (not hasattr(obj, "seekable") or obj.seekable())
-        ):
+        if uproot._util.is_file_like(obj, readable=True, writable=True, seekable=True):
             self = cls(None)
             self._file = obj
         else:
diff --git a/src/uproot/writing/writable.py b/src/uproot/writing/writable.py
index e5eb934a7..870e50669 100644
--- a/src/uproot/writing/writable.py
+++ b/src/uproot/writing/writable.py
@@ -73,10 +73,9 @@ def create(file_path: str | IO, **options):
 
 
 def _sink_from_path(
-    file_path_or_object: str | IO, **storage_options
+    file_path_or_object: str | Path | IO, **storage_options
 ) -> uproot.sink.file.FileSink:
-    if not isinstance(file_path_or_object, str):
-        # assume it's a file-like object
+    if uproot._util.is_file_like(file_path_or_object):
         return uproot.sink.file.FileSink.from_object(file_path_or_object)
 
     file_path = uproot._util.regularize_path(file_path_or_object)
@@ -118,7 +117,7 @@ def _sink_from_path(
         ) from None
 
 
-def recreate(file_path: str | IO, **options):
+def recreate(file_path: str | Path | IO, **options):
     """
     Args:
         file_path (str, ``pathlib.Path`` or file-like object): The filesystem path of the
@@ -174,7 +173,7 @@ def recreate(file_path: str | IO, **options):
     ).root_directory
 
 
-def update(file_path: str | IO, **options):
+def update(file_path: str | Path | IO, **options):
     """
     Args:
         file_path (str, ``pathlib.Path`` or file-like object): The filesystem path of the
diff --git a/tests/test_0692_fsspec_writing.py b/tests/test_0692_fsspec_writing.py
index 2f5dc483c..9e089d56b 100644
--- a/tests/test_0692_fsspec_writing.py
+++ b/tests/test_0692_fsspec_writing.py
@@ -5,6 +5,7 @@
 import uproot.source.fsspec
 
 import os
+import pathlib
 import fsspec
 import numpy as np
 
@@ -30,6 +31,22 @@ def test_fsspec_writing_local(tmp_path, scheme):
         assert f["tree"]["x"].array().tolist() == [1, 2, 3]
 
 
+def test_issue_1029(tmp_path):
+    # https://github.com/scikit-hep/uproot5/issues/1029
+    urlpath = os.path.join(tmp_path, "some", "path", "file.root")
+    urlpath = pathlib.Path(urlpath)
+
+    with uproot.recreate(urlpath) as f:
+        f["tree_1"] = {"x": np.array([1, 2, 3])}
+
+    with uproot.update(urlpath) as f:
+        f["tree_2"] = {"y": np.array([4, 5, 6])}
+
+    with uproot.open(urlpath) as f:
+        assert f["tree_1"]["x"].array().tolist() == [1, 2, 3]
+        assert f["tree_2"]["y"].array().tolist() == [4, 5, 6]
+
+
 def test_fsspec_writing_http(server):
     pytest.importorskip("aiohttp")