diff --git a/nanobot/agent/tools/shell.py b/nanobot/agent/tools/shell.py
index ce19920..4726e3c 100644
--- a/nanobot/agent/tools/shell.py
+++ b/nanobot/agent/tools/shell.py
@@ -143,7 +143,8 @@ class ExecTool(Tool):
 
             for raw in self._extract_absolute_paths(cmd):
                 try:
-                    p = Path(raw.strip()).resolve()
+                    expanded = os.path.expandvars(raw.strip())
+                    p = Path(expanded).expanduser().resolve()
                 except Exception:
                     continue
                 if p.is_absolute() and cwd_path not in p.parents and p != cwd_path:
@@ -155,4 +156,5 @@ class ExecTool(Tool):
     def _extract_absolute_paths(command: str) -> list[str]:
         win_paths = re.findall(r"[A-Za-z]:\\[^\s\"'|><;]+", command)   # Windows: C:\...
         posix_paths = re.findall(r"(?:^|[\s|>])(/[^\s\"'>]+)", command) # POSIX: /absolute only
-        return win_paths + posix_paths
+        home_paths = re.findall(r"(?:^|[\s|>])(~[^\s\"'>;|<]*)", command) # POSIX/Windows home shortcut: ~
+        return win_paths + posix_paths + home_paths
diff --git a/tests/test_tool_validation.py b/tests/test_tool_validation.py
index c2b4b6a..cf648bf 100644
--- a/tests/test_tool_validation.py
+++ b/tests/test_tool_validation.py
@@ -108,6 +108,19 @@ def test_exec_extract_absolute_paths_captures_posix_absolute_paths() -> None:
     assert "/tmp/out.txt" in paths
 
 
+def test_exec_extract_absolute_paths_captures_home_paths() -> None:
+    cmd = "cat ~/.nanobot/config.json > ~/out.txt"
+    paths = ExecTool._extract_absolute_paths(cmd)
+    assert "~/.nanobot/config.json" in paths
+    assert "~/out.txt" in paths
+
+
+def test_exec_guard_blocks_home_path_outside_workspace(tmp_path) -> None:
+    tool = ExecTool(restrict_to_workspace=True)
+    error = tool._guard_command("cat ~/.nanobot/config.json", str(tmp_path))
+    assert error == "Error: Command blocked by safety guard (path outside working dir)"
+
+
 # --- cast_params tests ---