diff --git a/tests/tools/test_ssh_remote_cwd.py b/tests/tools/test_ssh_remote_cwd.py
new file mode 100644
index 0000000000..2152e05436
--- /dev/null
+++ b/tests/tools/test_ssh_remote_cwd.py
@@ -0,0 +1,46 @@
+"""SSH file paths must not land on the Hermes host's subprocess home.
+
+Docker sets that home to ``/opt/data/home``. Expanding ``~`` or a relative
+path against it, then sending the result to an SSH backend, writes on a
+directory the remote machine does not have.
+"""
+
+from unittest.mock import patch
+
+import tools.file_tools_paths as paths
+import tools.terminal_tool as terminal_tool
+
+
+def test_ssh_relative_path_stays_off_container_home(monkeypatch):
+    monkeypatch.setattr(paths, "_terminal_env_type_for_task", lambda task_id="default": "ssh")
+    monkeypatch.setattr(terminal_tool, "_session_cwd", {"sess": "/opt/data/home"})
+    with patch("hermes_constants.get_subprocess_home", return_value="/opt/data/home"):
+        resolved = paths._resolve_path_for_task("cwd_probe.txt", task_id="sess")
+    assert str(resolved) == "~/cwd_probe.txt"
+    assert "/opt/data/home" not in str(resolved)
+
+
+def test_ssh_tilde_is_not_rewritten_to_the_host_home(monkeypatch):
+    monkeypatch.setattr(paths, "_terminal_env_type_for_task", lambda task_id="default": "ssh")
+    monkeypatch.setattr(terminal_tool, "_session_cwd", {})
+    with patch("hermes_constants.get_subprocess_home", return_value="/opt/data/home"):
+        resolved = paths._resolve_path_for_task("~/cwd_probe.txt", task_id="sess")
+    assert str(resolved) == "~/cwd_probe.txt"
+
+
+def test_ssh_keeps_a_real_remote_directory(monkeypatch):
+    monkeypatch.setattr(paths, "_terminal_env_type_for_task", lambda task_id="default": "ssh")
+    monkeypatch.setattr(terminal_tool, "_session_cwd", {"sess": "/home/ubuntu/COMPRESS"})
+    with patch("hermes_constants.get_subprocess_home", return_value="/opt/data/home"):
+        resolved = paths._resolve_path_for_task("cwd_probe.txt", task_id="sess")
+    assert str(resolved) == "/home/ubuntu/COMPRESS/cwd_probe.txt"
+
+
+def test_local_tilde_still_uses_subprocess_home(monkeypatch, tmp_path):
+    home = tmp_path / "profile_home"
+    home.mkdir()
+    monkeypatch.setattr(paths, "_terminal_env_type_for_task", lambda task_id="default": "local")
+    monkeypatch.setattr(terminal_tool, "_session_cwd", {})
+    with patch("hermes_constants.get_subprocess_home", return_value=str(home)):
+        resolved = paths._resolve_path_for_task("~/cwd_probe.txt", task_id="sess")
+    assert str(resolved).startswith(str(home))
diff --git a/tools/file_tools_paths.py b/tools/file_tools_paths.py
index 45bc5ad434..8c4a2cb657 100644
--- a/tools/file_tools_paths.py
+++ b/tools/file_tools_paths.py
@@ -163,10 +163,56 @@ def _anchor(text: str, base, container_paths: bool) -> Path | PurePosixPath:
     return p.resolve()
 
 
+def _ssh_remote_anchor(task_id: str) -> str:
+    """Working directory on the SSH target, never the Hermes host's home.
+
+    A recorded ``~`` stays ``~``. A recorded copy of the container subprocess
+    home (the host path ``get_subprocess_home()`` returns) is the same idea
+    written out by mistake, so it collapses back to ``~`` for the remote shell.
+    """
+    from tools.terminal_tool_config import coerce_ssh_remote_cwd
+
+    raw = _authoritative_workspace_root(task_id) or "~"
+    return coerce_ssh_remote_cwd(raw, "ssh") or "~"
+
+
+def _resolve_ssh_path(filepath: str, task_id: str) -> PurePosixPath:
+    """Resolve *filepath* in the SSH target's namespace.
+
+    Do not ``Path.resolve()`` or expand ``~`` with ``get_subprocess_home()``:
+    both name directories on the Hermes host (``/opt/data/home`` in Docker),
+    which the remote ``cd`` then rejects.
+    """
+    text = str(filepath or "").strip()
+    if text == "~" or text.startswith("~/"):
+        return PurePosixPath(text)
+    if posixpath.isabs(text):
+        return _normalize_without_host_deref(text)
+    anchor = _ssh_remote_anchor(task_id)
+    if anchor == "~":
+        joined = f"~/{text}"
+    elif anchor.startswith("~/"):
+        joined = f"{anchor.rstrip('/')}/{text}"
+    else:
+        joined = posixpath.normpath(posixpath.join(anchor, text))
+    if joined == "~" or joined.startswith("~/"):
+        return PurePosixPath(joined)
+    return _normalize_without_host_deref(joined)
+
+
 def _resolve_base_dir(
     task_id: str = "default", *, container_paths: bool | None = None) -> Path | PurePosixPath:
     """Return the ABSOLUTE base directory for resolving relative paths:
-    ``_authoritative_workspace_root``, else the process cwd as a last resort."""
+    ``_authoritative_workspace_root``, else the process cwd as a last resort.
+
+    SSH is the exception: the anchor is a remote path (often ``~``), and the
+    process cwd is the Hermes host.
+    """
+    if _terminal_env_type_for_task(task_id) == "ssh":
+        anchor = _ssh_remote_anchor(task_id)
+        if anchor == "~" or anchor.startswith("~/"):
+            return PurePosixPath(anchor)
+        return _normalize_without_host_deref(anchor)
     root = _authoritative_workspace_root(task_id)
     if container_paths is None:
         container_paths = _uses_container_paths(task_id)
@@ -177,6 +223,8 @@ def _resolve_base_dir(
 def _resolve_path_for_task(filepath: str, task_id: str = "default") -> Path | PurePosixPath:
     """Resolve *filepath* against the task's absolute base directory
     (absolute inputs are returned resolved-but-unanchored)."""
+    if _terminal_env_type_for_task(task_id) == "ssh":
+        return _resolve_ssh_path(filepath, task_id)
     container_paths = _uses_container_paths(task_id)
     return _anchor(_host_text(filepath, container_paths),
                    lambda: _resolve_base_dir(task_id, container_paths=container_paths), container_paths)
diff --git a/tools/terminal_tool_config.py b/tools/terminal_tool_config.py
index 9bb017040d..58d12f2b6a 100644
--- a/tools/terminal_tool_config.py
+++ b/tools/terminal_tool_config.py
@@ -95,6 +95,32 @@ def _get_plugin_env_provider(env_type: str):
     return _plugin_registry_lookup(env_type, "get_provider", None)
 
 
+def coerce_ssh_remote_cwd(cwd: str | None, env_type: str | None) -> str | None:
+    """Cwd to send to an SSH backend.
+
+    ``~`` and ``~/...`` stay literal so the remote shell expands them to the
+    SSH user's home. The Hermes process's subprocess home (``/opt/data/home``
+    in the official Docker image) is a directory on the machine running
+    Hermes. Using it as the remote working directory makes ``cd`` exit 126
+    and anchors relative writes on a path that does not exist on the target.
+    Other backends are unchanged.
+    """
+    if not isinstance(cwd, str) or (env_type or "").strip().lower() != "ssh":
+        return cwd
+    text = cwd.strip()
+    if not text or text == "~" or text.startswith("~/"):
+        return text or "~"
+    try:
+        from hermes_constants import get_subprocess_home
+
+        home = get_subprocess_home()
+    except Exception:
+        home = None
+    if home and os.path.normpath(text) == os.path.normpath(home):
+        return "~"
+    return text
+
+
 def _is_unusable_container_cwd(cwd: str) -> bool:
     """True if *cwd* is a host or relative path that can't be a container
     workdir: ``docker run -w`` needs an absolute in-sandbox path, otherwise the