diff --git a/upath/_chain.py b/upath/_chain.py
index 83d3db5a..23a25741 100644
--- a/upath/_chain.py
+++ b/upath/_chain.py
@@ -231,14 +231,14 @@ def unchain(
                 proto0 is None or bit == proto0
             ):  # exact match a fsspec protocol
                 proto = bit
-                path_bit = ""
+                path_bit = None
                 extra_so = {}
             elif bit in (m := set(available_implementations(fallback=True))) and (
                 proto0 is None or bit == proto0
             ):
                 self.known_protocols = m
                 proto = bit
-                path_bit = ""
+                path_bit = None
                 extra_so = {}
             else:
                 proto = get_upath_protocol(bit, protocol=proto0)
@@ -246,8 +246,8 @@ def unchain(
                 path_bit = flavour.strip_protocol(bit)
                 extra_so = flavour.get_kwargs_from_url(bit)
             if proto in {"blockcache", "filecache", "simplecache"}:
-                if path_bit:
-                    next_path_overwrite = path_bit
+                if path_bit is not None:
+                    next_path_overwrite = path_bit or "/"
                 path_bit = None
             elif next_path_overwrite is not None:
                 path_bit = next_path_overwrite
diff --git a/upath/_flavour.py b/upath/_flavour.py
index 3274bcb2..842a8350 100644
--- a/upath/_flavour.py
+++ b/upath/_flavour.py
@@ -132,6 +132,7 @@ class WrappedFileSystemFlavour(UPathParser):  # (pathlib_abc.FlavourBase)
             "https",
         },
         "root_marker_override": {
+            "smb": "/",
             "ssh": "/",
             "sftp": "/",
         },
@@ -253,7 +254,7 @@ def stringify_path(pth: JoinablePathLike) -> str:
 
     def strip_protocol(self, pth: JoinablePathLike) -> str:
         pth = self.stringify_path(pth)
-        return self._spec._strip_protocol(pth)
+        return self._spec._strip_protocol(pth) or self.root_marker
 
     def get_kwargs_from_url(self, url: JoinablePathLike) -> dict[str, Any]:
         # NOTE: the public variant is _from_url not _from_urls
@@ -317,6 +318,9 @@ def split(self, path: JoinablePathLike) -> tuple[str, str]:
             tail = stripped_path[1:]
         elif head:
             tail = stripped_path[len(head) + 1 :]
+        elif self.netloc_is_anchor:  # and not head
+            head = stripped_path
+            tail = ""
         else:
             tail = stripped_path
         if (
diff --git a/upath/core.py b/upath/core.py
index 90ac7fef..7c28ba00 100644
--- a/upath/core.py
+++ b/upath/core.py
@@ -573,7 +573,7 @@ def __init__(
         # FIXME: normalization needs to happen in unchain already...
         chain = Chain.from_list(Chain.from_list(segments).to_list())
         if len(args) > 1:
-            flavour = WrappedFileSystemFlavour.from_protocol(protocol)
+            flavour = WrappedFileSystemFlavour.from_protocol(chain.active_path_protocol)
             joined = flavour.join(chain.active_path, *args[1:])
             stripped = flavour.strip_protocol(joined)
             chain = chain.replace(path=stripped)
@@ -963,7 +963,7 @@ def with_segments(self, *pathsegments: JoinablePathLike) -> Self:
         new_instance = type(self)(
             *pathsegments,
             protocol=self._protocol,
-            **self._storage_options,
+            **self.storage_options,
         )
         if hasattr(self, "_fs_cached"):
             new_instance._fs_cached = self._fs_cached
@@ -1090,7 +1090,7 @@ def parent(self) -> Self:
                     self._relative_base,
                     str(self),
                     protocol=self._protocol,
-                    **self._storage_options,
+                    **self.storage_options,
                 )
                 parent = pth.parent
                 parent._relative_base = self._relative_base
@@ -1121,7 +1121,7 @@ def parents(self) -> Sequence[Self]:
                     break
                 parent = parent.parent
                 parents.append(parent)
-            return parents
+            return tuple(parents)
         return super().parents
 
     def joinpath(self, *pathsegments: JoinablePathLike) -> Self:
@@ -1945,14 +1945,14 @@ def __reduce__(self):
             args = (self.__vfspath__(),)
             kwargs = {
                 "protocol": self._protocol,
-                **self._storage_options,
+                **self.storage_options,
             }
         else:
             args = (self._relative_base, self.__vfspath__())
             # Include _relative_base in the state if it's set
             kwargs = {
                 "protocol": self._protocol,
-                **self._storage_options,
+                **self.storage_options,
                 "_relative_base": self._relative_base,
             }
         return _make_instance, (type(self), args, kwargs)
diff --git a/upath/implementations/cloud.py b/upath/implementations/cloud.py
index 02c89db3..7814a456 100644
--- a/upath/implementations/cloud.py
+++ b/upath/implementations/cloud.py
@@ -2,6 +2,7 @@
 
 import sys
 from collections.abc import Iterator
+from collections.abc import Sequence
 from typing import TYPE_CHECKING
 from typing import Any
 
@@ -82,6 +83,13 @@ def path(self) -> str:
             return self_path + self.root
         return self_path
 
+    @property
+    def parts(self) -> Sequence[str]:
+        parts = super().parts
+        if self._relative_base is None and len(parts) == 2 and not parts[1]:
+            return parts[:1]
+        return parts
+
     def mkdir(
         self, mode: int = 0o777, parents: bool = False, exist_ok: bool = False
     ) -> None:
@@ -171,6 +179,10 @@ def __init__(
             *args, protocol=protocol, chain_parser=chain_parser, **storage_options
         )
 
+    @property
+    def root(self) -> str:
+        return ""
+
     def iterdir(self) -> Iterator[Self]:
         try:
             yield from super().iterdir()
diff --git a/upath/implementations/smb.py b/upath/implementations/smb.py
index c967e370..956fdbad 100644
--- a/upath/implementations/smb.py
+++ b/upath/implementations/smb.py
@@ -42,6 +42,9 @@ def path(self) -> str:
         path = super().path
         if len(path) > 1:
             return path.removesuffix("/")
+        # At root level, return "/" to match anchor
+        if not path and self._relative_base is None:
+            return self.anchor
         return path
 
     def __str__(self) -> str:
diff --git a/upath/tests/cases.py b/upath/tests/cases.py
index 24485e69..dddb9852 100644
--- a/upath/tests/cases.py
+++ b/upath/tests/cases.py
@@ -17,6 +17,7 @@
 from upath import UPath
 from upath._protocol import get_upath_protocol
 from upath._stat import UPathStatResult
+from upath.tests.utils import posixify
 from upath.types import StatResultType
 
 
@@ -248,6 +249,16 @@ def test_parents_are_absolute(self):
         is_absolute = [p.is_absolute() for p in self.path.parents]
         assert all(is_absolute)
 
+    def test_parents_end_at_anchor(self):
+        p = self.path.joinpath("folder1", "file1.txt")
+        assert p.parents[-1].path == posixify(p.anchor)
+
+    def test_anchor_is_its_own_parent(self):
+        p = self.path.joinpath("folder1", "file1.txt")
+        p0 = p.parents[-1]
+        assert p0.path == posixify(p.anchor)
+        assert p0.parent.path == posixify(p.anchor)
+
     def test_private_url_attr_in_sync(self):
         p = self.path
         p1 = self.path.joinpath("c")
diff --git a/upath/tests/implementations/test_data.py b/upath/tests/implementations/test_data.py
index b539e30e..a9e2f4b8 100644
--- a/upath/tests/implementations/test_data.py
+++ b/upath/tests/implementations/test_data.py
@@ -129,6 +129,17 @@ def test_trailing_slash_is_stripped(self):
         with pytest.raises(UnsupportedOperation):
             super().test_trailing_slash_is_stripped()
 
+    @overrides_base
+    def test_parents_end_at_anchor(self):
+        # DataPath does not support joins
+        with pytest.raises(UnsupportedOperation):
+            super().test_parents_end_at_anchor()
+
+    @overrides_base
+    def test_anchor_is_its_own_parent(self):
+        # DataPath does not support joins
+        assert self.path.path == self.path.parent.path
+
     @overrides_base
     def test_private_url_attr_in_sync(self):
         # DataPath does not support joins, so we check on self.path
diff --git a/upath/tests/test_core.py b/upath/tests/test_core.py
index 822cc8c7..9d6d9317 100644
--- a/upath/tests/test_core.py
+++ b/upath/tests/test_core.py
@@ -72,6 +72,22 @@ def test_is_correct_class(self):
     def test_parents_are_absolute(self):
         super().test_parents_are_absolute()
 
+    @overrides_base
+    @pytest.mark.skipif(
+        sys.platform.startswith("win"),
+        reason="mock fs is not well defined on windows",
+    )
+    def test_anchor_is_its_own_parent(self):
+        super().test_anchor_is_its_own_parent()
+
+    @overrides_base
+    @pytest.mark.skipif(
+        sys.platform.startswith("win"),
+        reason="mock fs is not well defined on windows",
+    )
+    def test_parents_end_at_anchor(self):
+        super().test_parents_end_at_anchor()
+
 
 def test_multiple_backend_paths(local_testdir):
     path = "s3://bucket/"