diff --git a/nanobot/agent/tools/shell.py b/nanobot/agent/tools/shell.py
index ce19920..b4a4044 100644
--- a/nanobot/agent/tools/shell.py
+++ b/nanobot/agent/tools/shell.py
@@ -143,10 +143,10 @@ class ExecTool(Tool):
 
             for raw in self._extract_absolute_paths(cmd):
                 try:
-                    p = Path(raw.strip()).resolve()
+                    p = Path(raw.strip()).expanduser().resolve()
                 except Exception:
                     continue
-                if p.is_absolute() and cwd_path not in p.parents and p != cwd_path:
+                if not p.is_relative_to(cwd_path):
                     return "Error: Command blocked by safety guard (path outside working dir)"
 
         return None
@@ -155,4 +155,5 @@ 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
+        tilde_paths = re.findall(r"(?:^|[\s|>])(~[^\s\"'>]*)", command) # Tilde: ~/...
+        return win_paths + posix_paths + tilde_paths