diff --git a/agent/file_safety.py b/agent/file_safety.py
index 789cb3d747..28320edd70 100644
--- a/agent/file_safety.py
+++ b/agent/file_safety.py
@@ -262,15 +262,15 @@ def _classify_write_denial(path: str, *, entry: bool = False) -> Optional[str]:
     # The runtime's own interpreter/venv is never agent-writable (an overwrite
     # bricks the next start exactly like a delete, #58748) — and this must fire
     # BEFORE the approval-gated allow so ~/.ssh-style gating cannot re-open it.
-    from agent.runtime_self_protection import is_protected_path
+    from agent.runtime_self_protection import is_protected_path, split_entry
 
     if is_protected_path(path) or (entry and is_protected_path(path, follow=False)):
         return "credential"
     denial = _classify_resolved_write_denial(homes, resolved)
     if denial or not entry:
         return denial
-    expanded = os.path.expanduser(str(path))
-    entry_path = os.path.join(os.path.realpath(os.path.dirname(expanded) or "."), os.path.basename(expanded))
+    parent, leaf = split_entry(os.path.expanduser(str(path)))
+    entry_path = os.path.join(os.path.realpath(parent or "."), leaf)
     return _classify_resolved_write_denial(homes, entry_path)
 
 
diff --git a/agent/runtime_self_protection.py b/agent/runtime_self_protection.py
index d6917d3a12..fb38911795 100644
--- a/agent/runtime_self_protection.py
+++ b/agent/runtime_self_protection.py
@@ -151,14 +151,25 @@ def _overlaps(a: str, b: str) -> bool:
     return a == b or a.startswith(b + sep) or b.startswith(a + sep)
 
 
+def split_entry(path: str) -> tuple[str, str]:
+    """``os.path.split`` for a directory entry, trailing separators dropped first: an
+    empty leaf (``dir/link/``) would make entry checks degenerate to the link's target.
+    A bare root (``/``, ``C:\\``) is kept as is."""
+    drive, tail = os.path.splitdrive(path)
+    return os.path.split(drive + (tail.rstrip(os.sep + (os.altsep or "")) or tail[:1]))
+
+
 def is_protected_path(path: str, *, follow: bool = True) -> Optional[str]:
     """Description of the protected runtime path ``path`` touches, else ``None``.
 
     ``follow=False`` keeps the final component unresolved (the entry itself, for
     ops that unlink/rename a symlink rather than its target)."""
-    resolved = _normalize_path(path) if follow else _normalize_path(os.path.dirname(path) or ".")
-    if resolved and not follow:
-        resolved = os.path.join(resolved, os.path.basename(path))
+    if follow:
+        resolved = _normalize_path(path)
+    else:
+        parent, leaf = split_entry(path)
+        resolved = _normalize_path(parent or ".")
+        resolved = resolved and os.path.normcase(os.path.join(resolved, leaf))
     if not resolved:
         return None
     for protected, description in _protected():
diff --git a/tests/tools/test_file_operations_delete.py b/tests/tools/test_file_operations_delete.py
index b76d091ff2..81ccb3f3b0 100644
--- a/tests/tools/test_file_operations_delete.py
+++ b/tests/tools/test_file_operations_delete.py
@@ -43,12 +43,13 @@ def test_delete_file_refuses_directory(ops, tmp_path):
 
 
 @pytest.mark.platforms("posix")
-@pytest.mark.parametrize("op", ["delete", "move"])
+@pytest.mark.parametrize("op", ["delete", "delete_trailing_slash", "move"])
 @pytest.mark.parametrize("layout", ["beside_runtime_venv", "link_in_credential_dir"])
 def test_delete_and_move_guard_the_entry_itself(ops, tmp_path, monkeypatch, op, layout):
     """Delete/Move vet the directory entry (parent resolved, leaf kept): a plain file whose
     directory merely CONTAINS the runtime venv (``~/notes.txt``) stays deletable/movable,
-    while a link directly inside a credential dir is refused even though it points outside."""
+    while a link directly inside a credential dir is refused even though it points outside.
+    A trailing separator (``.ssh/link/``) must not empty the leaf and skip the entry check."""
     home, outside = tmp_path / "home", tmp_path / "outside.txt"
     outside.write_text("keep", encoding="utf-8")
     monkeypatch.setenv("HOME", str(home))
@@ -63,7 +64,10 @@ def test_delete_and_move_guard_the_entry_itself(ops, tmp_path, monkeypatch, op,
         entry.symlink_to(outside)
     moved = home / "moved.txt"
 
-    result = ops.delete_file(str(entry)) if op == "delete" else ops.move_file(str(entry), str(moved))
+    if op == "move":
+        result = ops.move_file(str(entry), str(moved))
+    else:
+        result = ops.delete_file(str(entry) + ("/" if op == "delete_trailing_slash" else ""))
 
     if layout == "beside_runtime_venv":
         assert result.error is None, result.error
diff --git a/tests/tools/test_file_tools_cwd_resolution.py b/tests/tools/test_file_tools_cwd_resolution.py
index 82f2cf045e..92b2541d45 100644
--- a/tests/tools/test_file_tools_cwd_resolution.py
+++ b/tests/tools/test_file_tools_cwd_resolution.py
@@ -305,6 +305,8 @@ def test_v4a_patch_applies_to_resolved_workspace_not_backend_cwd(
 @pytest.mark.platforms("posix")
 @pytest.mark.parametrize("header,safe_root,content,dest", [
     ("*** Delete File: local.yaml", False, "shared: true\n", None),
+    # A trailing separator must still name the link, not fall back to its target.
+    ("*** Delete File: local.yaml/", False, "shared: true\n", None),
     ("*** Move File: local.yaml -> old.yaml", False, "shared: true\n", "old.yaml"),
     ("*** Update File: local.yaml\n@@\n-shared: true\n+shared: false\n*** Move File: local.yaml -> old.yaml",
      False, "shared: false\n", "old.yaml"),
diff --git a/tools/file_tools_paths.py b/tools/file_tools_paths.py
index 4e459a5e01..952862ae2d 100644
--- a/tools/file_tools_paths.py
+++ b/tools/file_tools_paths.py
@@ -12,6 +12,8 @@ import sys
 import time
 from pathlib import Path, PurePosixPath
 
+from agent.runtime_self_protection import split_entry
+
 # ``TERMINAL_CWD`` values that mean "not configured" ("." from a stale config;
 # "auto"/"cwd" are wizard placeholders). gateway/run.py sanitizes the same set.
 _TERMINAL_CWD_SENTINELS = frozenset({"", ".", "./", "auto", "cwd"})
@@ -276,7 +278,7 @@ def _resolve_entry_for_task(filepath: str, task_id: str = "default") -> Path | P
     """``_resolve_path_for_task`` for an operation on the directory entry itself (delete,
     rename): the parent is resolved, but a symlink in the last component is kept, since
     resolving it aims the operation at the file the link points to."""
-    parent, name = os.path.split(filepath)
+    parent, name = split_entry(filepath)
     if name in ("", ".", "..") or (not parent and name.startswith("~")):
         return _resolve_path_for_task(filepath, task_id)
     return _resolve_path_for_task(parent or ".", task_id) / name