diff --git a/src/anthropic/lib/tools/_skills.py b/src/anthropic/lib/tools/_skills.py
index 0a1e9e537..8792ad7dc 100644
--- a/src/anthropic/lib/tools/_skills.py
+++ b/src/anthropic/lib/tools/_skills.py
@@ -274,9 +274,23 @@ async def download_session_skills(
             adest = anyio.Path(dest)
             if await adest.is_symlink():
                 await adest.unlink()
+            # If the directory already exists and contains the expected version,
+            # skip the download. This prevents race conditions and redundant
+            # work when multiple sessions share a workdir.
+            version_file = dest / ".version"
+            if await adest.is_dir() and await anyio.Path(version_file).exists():
+                try:
+                    if (await anyio.Path(version_file).read_text()).strip() == version_id:
+                        log.info("skill skill_id=%s version=%s already exists at %s; skipping", skill.skill_id, version_id, dest)
+                        downloaded.append(dest)
+                        continue
+                except Exception:
+                    pass
+
             # ``shutil.rmtree`` is blocking; keep it off the event loop.
             await run_sync(partial(shutil.rmtree, dest, ignore_errors=True))
             await _download_and_extract(client, skill.skill_id, version_id, dest)
+            await anyio.Path(version_file).write_text(version_id)
             downloaded.append(dest)
             log.info("downloaded skill skill_id=%s version=%s -> %s", skill.skill_id, version_id, dest)
         except Exception as e:
diff --git a/src/anthropic/lib/tools/agent_toolset.py b/src/anthropic/lib/tools/agent_toolset.py
index ccb662457..0d4d56272 100644
--- a/src/anthropic/lib/tools/agent_toolset.py
+++ b/src/anthropic/lib/tools/agent_toolset.py
@@ -274,6 +274,10 @@ class AgentToolContext:
     max_file_bytes: int | None | NotGiven = not_given
     max_image_base64_bytes: int | None | NotGiven = not_given
     max_pdf_bytes: int | None | NotGiven = not_given
+    # Whether to keep skill directories on disk after the context exits.
+    # When True, ``_cleanup_skills`` is a no-op, allowing the workdir to
+    # serve as a persistent skills cache across sessions.
+    keep_skills: bool = False
     # Resolved directories the write and edit tools refuse to modify. The
     # worker sets this to the roots of read-only memory stores so the agent
     # sees the error at write time instead of the change silently never
@@ -316,6 +320,8 @@ async def _cleanup_skills(self) -> None:
         Only the directories this context created are removed — a pre-existing
         ``{workdir}/skills`` tree is left untouched.
         """
+        if self.keep_skills:
+            return
         for skill_dir in self._skill_dirs:
             try:
                 # ``shutil.rmtree`` is blocking; keep it off the event loop.