diff --git a/src/agents/sandbox/sandboxes/docker.py b/src/agents/sandbox/sandboxes/docker.py
index 600aa508bb..0b3d50b066 100644
--- a/src/agents/sandbox/sandboxes/docker.py
+++ b/src/agents/sandbox/sandboxes/docker.py
@@ -1639,7 +1639,9 @@ async def create(
             assert container_id is not None
             service = self._removal_service
             if service is not None:
-                await run_blocking_workspace_io(lambda: service.bind_new(container, manifest))
+                await run_blocking_workspace_io(
+                    lambda: service._bind_new(container, manifest, bootstrap_workspace=True)
+                )
             snapshot_id = str(session_id)
             snapshot_instance = resolve_snapshot(snapshot, snapshot_id)
             state = DockerSandboxSessionState(
@@ -1816,7 +1818,9 @@ async def resume(
                 if service is not None:
                     container.start()
                     await run_blocking_workspace_io(
-                        lambda: service.bind_new(container, state.manifest)
+                        lambda: service._bind_new(
+                            container, state.manifest, bootstrap_workspace=True
+                        )
                     )
 
             inner = DockerSandboxSession(
diff --git a/src/agents/sandbox/sandboxes/docker_removal.py b/src/agents/sandbox/sandboxes/docker_removal.py
index c3c0fe2d8a..5da86dcf4e 100644
--- a/src/agents/sandbox/sandboxes/docker_removal.py
+++ b/src/agents/sandbox/sandboxes/docker_removal.py
@@ -9,9 +9,13 @@
 existing recursive removal and snapshot restoration behavior.
 
 The service requires a trusted image, Docker 26+ with its builtin seccomp profile,
-and the runc runtime. Workspaces and path-only grant roots must exist in the image.
+and the runc runtime. For new client sessions, the service checks container eligibility,
+then creates a missing workspace and its parents using the trusted image's default
+user before binding, as normal session startup does.
+Path-only grant roots must exist at binding time;
+the client does not create unrelated grant directories.
 Read-only host bind mounts are supported outside the private workspace. Writable
-shared mounts, additional capabilities, user namespaces, and missing roots are excluded.
+shared mounts, additional capabilities, user namespaces, and missing grant roots are excluded.
 The application must exclusively own container lifecycle and Docker API access;
 other host administrators are trusted. A service/worker transport failure leaves
 the container paused. Before manually resuming it, stop all service workers.
@@ -269,6 +273,11 @@ def _paused(
 
     def bind_new(self, container: Container, manifest: Manifest) -> None:
         """Bind before a newly created session is returned to its trusted application."""
+        self._bind_new(container, manifest, bootstrap_workspace=False)
+
+    def _bind_new(
+        self, container: Container, manifest: Manifest, *, bootstrap_workspace: bool
+    ) -> None:
         with self._lock:
             if self._closed:
                 raise ValueError("Docker removal service is closed")
@@ -287,6 +296,21 @@ def bind_new(self, container: Container, manifest: Manifest) -> None:
 
         _validate_docker_path_grants(manifest)
         _assert_existing_container_path_grants_match(container, manifest)
+        if bootstrap_workspace:
+            # Reject unsupported mounts and security settings before an image
+            # symlink could redirect mkdir into a shared host directory.
+            self._state(container)
+            # Only the client requests bootstrap, for fresh containers before
+            # application workloads run. Preserve the image's default user.
+            result = container.exec_run(
+                cmd=["mkdir", "-p", "--", manifest.root],
+                user="",
+                workdir="/",
+                stdout=False,
+                stderr=False,
+            )
+            if result.exit_code != 0:
+                raise RuntimeError("Unable to create Docker workspace before removal binding")
         worker: _Worker | None = None
         with self._paused(
             container, lambda: worker is not None and worker.uncertain
diff --git a/tests/sandbox/_docker_removal_helpers.py b/tests/sandbox/_docker_removal_helpers.py
index 91330b4068..8e2251b531 100644
--- a/tests/sandbox/_docker_removal_helpers.py
+++ b/tests/sandbox/_docker_removal_helpers.py
@@ -79,6 +79,9 @@ def service(
     limits.update(getattr(request, "param", {}))
     instance = DockerRemovalService(**limits)
     container = RecordingContainer()
+    monkeypatch.setattr(
+        container, "exec_run", Mock(return_value=SimpleNamespace(exit_code=0)), raising=False
+    )
     worker = RecordingWorker(container)
     monkeypatch.setattr(instance, "_state", lambda _: (123, "incarnation"))
     monkeypatch.setattr(docker_removal, "_Worker", lambda _: worker)
diff --git a/tests/sandbox/test_docker_removal_client.py b/tests/sandbox/test_docker_removal_client.py
new file mode 100644
index 0000000000..becc9df0a2
--- /dev/null
+++ b/tests/sandbox/test_docker_removal_client.py
@@ -0,0 +1,277 @@
+"""Docker client lifecycle tests with simulated transport and real filesystem binding."""
+
+from __future__ import annotations
+
+import os
+from collections.abc import Iterator
+from contextlib import ExitStack
+from pathlib import Path
+from types import SimpleNamespace
+from typing import Any
+from unittest.mock import Mock
+
+import pytest
+
+from agents.sandbox import Manifest, SandboxPathGrant
+from agents.sandbox.errors import WorkspaceArchiveWriteError
+from agents.sandbox.sandboxes.docker import DockerSandboxClient, DockerSandboxClientOptions
+from agents.sandbox.sandboxes.docker_removal import DockerRemovalService
+
+from . import _docker_removal_helpers as removal_helpers
+from ._docker_removal_helpers import RecordingContainer, RecordingWorker, session
+
+service = removal_helpers.service
+worker_code = pytest.importorskip(
+    "agents.sandbox.sandboxes._docker_removal_worker", exc_type=ImportError
+)
+
+
+@pytest.fixture
+def client_lifecycle(
+    service: tuple[DockerRemovalService, RecordingContainer, RecordingWorker],
+    monkeypatch: pytest.MonkeyPatch,
+    tmp_path: Path,
+) -> Iterator[tuple[DockerSandboxClient, DockerRemovalService, Any, RecordingWorker]]:
+    manager, container, worker = service
+    client = DockerSandboxClient(manager.docker_client, removal_service=manager)
+    monkeypatch.setattr(client, "get_container", lambda _: None)
+    monkeypatch.setattr(container, "start", lambda: None, raising=False)
+    monkeypatch.setattr(container, "remove", Mock(), raising=False)
+    owners: dict[Path, str] = {}
+
+    def create_container(**kwargs: Any) -> RecordingContainer:
+        # Docker's daemon creates its working directory before startup.
+        if workdir := kwargs.get("working_dir"):
+            root = Path(workdir)
+            if not root.exists():
+                root.mkdir(parents=True)
+                owners[root] = "0:0"
+        return container
+
+    manager.docker_client.containers.create.side_effect = create_container
+
+    def exec_run(
+        cmd: list[str], *, user: str = "", demux: bool = False, **kwargs: Any
+    ) -> SimpleNamespace:
+        effective_user = user or container.attrs["Config"]["User"]
+        target = Path(cmd[-1])
+        exit_code = 0
+        if cmd[:3] == ["mkdir", "-p", "--"]:
+            if not target.exists():
+                target.mkdir(parents=True)
+                owners[target] = effective_user
+        elif cmd[:2] == ["test", "-d"]:
+            exit_code = 0 if target.is_dir() else 1
+        elif cmd[0] == "touch":
+            # A daemon-created 0755 workspace is not writable by the image user.
+            if owners.get(target.parent, effective_user) != effective_user:
+                exit_code = 1
+            else:
+                target.touch()
+        else:
+            raise AssertionError(f"Unexpected test command: {cmd}")
+        return SimpleNamespace(exit_code=exit_code, output=(b"", b"") if demux else b"")
+
+    monkeypatch.setattr(container, "exec_run", exec_run)
+    # The real worker enters the container root. Model that root on tmp_path's
+    # filesystem, which may differ from the host root (for example, tmpfs /tmp).
+    # Keep canonicalization, open/fstat, and descriptor identity checks real.
+    root_stat = tmp_path.stat()
+
+    def container_stat(path: Any, *args: Any, **kwargs: Any) -> os.stat_result:
+        return root_stat if path == "/" else os.stat(path, *args, **kwargs)
+
+    worker_os = SimpleNamespace(**vars(os))
+    worker_os.stat = container_stat
+    # Exercise real O_PATH on Linux; other Unix hosts use read-only descriptors.
+    worker_os.O_PATH = getattr(os, "O_PATH", os.O_RDONLY)
+    monkeypatch.setattr(worker_code, "os", worker_os)
+    with ExitStack() as bindings:
+        original_request = worker.request
+
+        def request(**data: Any) -> dict[str, Any]:
+            response = original_request(**data)
+            if data["operation"] == "bind":
+                bound = bindings.enter_context(worker_code._bind_paths(data["paths"]))
+                response["paths"] = bound.paths
+            return response
+
+        monkeypatch.setattr(worker, "request", request)
+        try:
+            yield client, manager, container, worker
+        finally:
+            manager.close()
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("resume", [False, True])
+@pytest.mark.parametrize("workspace_setup", ["missing", "existing", "ancestor_grant"])
+async def test_client_bootstraps_workspace_before_strict_binding(
+    client_lifecycle: tuple[DockerSandboxClient, DockerRemovalService, Any, RecordingWorker],
+    tmp_path: Path,
+    resume: bool,
+    workspace_setup: str,
+) -> None:
+    client, manager, container, worker = client_lifecycle
+    root = tmp_path / "nested" / "workspace"
+    if workspace_setup == "existing":
+        root.mkdir(parents=True)
+        (root / "keep.txt").write_text("existing contents")
+    grants = (
+        (SandboxPathGrant(path=str(root.parent), read_only=True),)
+        if workspace_setup == "ancestor_grant"
+        else ()
+    )
+    configured = Manifest(root=str(root), extra_path_grants=grants)
+    state = session(manager, container, configured).state
+    state.container_id = "missing-container"
+    if resume:
+        wrapped = await client.resume(state)
+    else:
+        wrapped = await client.create(
+            manifest=configured, options=DockerSandboxClientOptions(image="trusted-image")
+        )
+    assert root.is_dir()
+    manager.assert_bound(container, configured)
+    assert not wrapped._inner.state.workspace_root_ready
+    result = await wrapped.exec("touch", str(root / "created.txt"), shell=False)
+    assert result.ok()
+    assert (root / "created.txt").is_file()
+    if workspace_setup == "existing":
+        assert (root / "keep.txt").read_text() == "existing contents"
+    with pytest.raises(WorkspaceArchiveWriteError):
+        await wrapped.rm(str(root), recursive=True)
+    if grants:
+        with pytest.raises(WorkspaceArchiveWriteError):
+            await wrapped.rm(str(root.parent), recursive=True)
+    assert not worker.removed
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("resume", [False, True])
+async def test_client_bootstrap_does_not_create_missing_grant_roots(
+    client_lifecycle: tuple[DockerSandboxClient, DockerRemovalService, Any, RecordingWorker],
+    tmp_path: Path,
+    resume: bool,
+) -> None:
+    client, manager, container, worker = client_lifecycle
+    root = tmp_path / "workspace"
+    grant = tmp_path / "external"
+    configured = Manifest(root=str(root), extra_path_grants=(SandboxPathGrant(path=str(grant)),))
+    state = session(manager, container, configured).state
+    state.container_id = "missing-container"
+    state.workspace_root_ready = True
+    original_session_id = state.session_id
+    with pytest.raises(FileNotFoundError):
+        if resume:
+            await client.resume(state)
+        else:
+            await client.create(
+                manifest=configured, options=DockerSandboxClientOptions(image="trusted-image")
+            )
+    assert root.is_dir()
+    assert not grant.exists()
+    assert not manager._bindings
+    container.remove.assert_called_once_with(force=True)
+    assert "close" in container.events
+    if resume:
+        assert state.container_id == "missing-container"
+        assert state.session_id == original_session_id
+        assert state.workspace_root_ready
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("resume", [False, True])
+async def test_failed_workspace_bootstrap_cleans_up_before_binding(
+    client_lifecycle: tuple[DockerSandboxClient, DockerRemovalService, Any, RecordingWorker],
+    monkeypatch: pytest.MonkeyPatch,
+    tmp_path: Path,
+    resume: bool,
+) -> None:
+    client, manager, container, worker = client_lifecycle
+    configured = Manifest(root=str(tmp_path / "workspace"))
+    state = session(manager, container, configured).state
+    state.container_id = "missing-container"
+    state.workspace_root_ready = True
+    original_session_id = state.session_id
+    monkeypatch.setattr(container, "exec_run", Mock(return_value=SimpleNamespace(exit_code=1)))
+    with pytest.raises(RuntimeError, match="Unable to create Docker workspace"):
+        if resume:
+            await client.resume(state)
+        else:
+            await client.create(
+                manifest=configured, options=DockerSandboxClientOptions(image="trusted-image")
+            )
+    assert not manager._bindings
+    assert not worker.calls
+    container.remove.assert_called_once_with(force=True)
+    if resume:
+        assert state.container_id == "missing-container"
+        assert state.session_id == original_session_id
+        assert state.workspace_root_ready
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("resume", [False, True])
+@pytest.mark.parametrize("mount_kind", ["host_grant", "image_volume"])
+async def test_ineligible_mount_is_rejected_before_bootstrap_writes(
+    client_lifecycle: tuple[DockerSandboxClient, DockerRemovalService, Any, RecordingWorker],
+    monkeypatch: pytest.MonkeyPatch,
+    tmp_path: Path,
+    resume: bool,
+    mount_kind: str,
+) -> None:
+    client, manager, container, worker = client_lifecycle
+    shared = tmp_path / "shared"
+    shared.mkdir()
+    (shared / "keep.txt").write_text("host contents")
+    alias = tmp_path / "image-workspace"
+    alias.symlink_to(shared, target_is_directory=True)
+    configured = Manifest(
+        root=str(alias / "build"),
+        extra_path_grants=(
+            (SandboxPathGrant(path=str(shared), host_path=str(shared)),)
+            if mount_kind == "host_grant"
+            else ()
+        ),
+    )
+    container.attrs["Mounts"] = [
+        {
+            "Type": "bind" if mount_kind == "host_grant" else "volume",
+            "Destination": str(shared),
+            "Source": str(shared),
+            "RW": True,
+            "Propagation": "rprivate",
+        }
+    ]
+    container.attrs["HostConfig"] = {}
+    container.attrs["State"].update(Running=True, Pid=123, StartedAt="incarnation")
+    manager.docker_client.info.return_value = {
+        "SecurityOptions": ["name=seccomp,profile=builtin"],
+        "DefaultRuntime": "runc",
+    }
+    manager.docker_client.version.return_value = {"Version": "26.0.0"}
+    monkeypatch.setattr(manager, "_state", DockerRemovalService._state.__get__(manager))
+    execute = Mock(wraps=container.exec_run)
+    monkeypatch.setattr(container, "exec_run", execute)
+    state = session(manager, container, configured).state
+    state.container_id = "missing-container"
+    state.workspace_root_ready = True
+    original_session_id = state.session_id
+    with pytest.raises(ValueError, match="shared host paths|private container"):
+        if resume:
+            await client.resume(state)
+        else:
+            await client.create(
+                manifest=configured, options=DockerSandboxClientOptions(image="trusted-image")
+            )
+    assert sorted(path.name for path in shared.iterdir()) == ["keep.txt"]
+    assert (shared / "keep.txt").read_text() == "host contents"
+    execute.assert_not_called()
+    assert not worker.calls
+    assert not manager._bindings
+    container.remove.assert_called_once_with(force=True)
+    if resume:
+        assert state.container_id == "missing-container"
+        assert state.session_id == original_session_id
+        assert state.workspace_root_ready