diff --git a/src/agent_tools/filesystem_tools.py b/src/agent_tools/filesystem_tools.py
index b0f5b6a89..573d30db3 100644
--- a/src/agent_tools/filesystem_tools.py
+++ b/src/agent_tools/filesystem_tools.py
@@ -281,7 +281,13 @@ class LsTool:
 
 class GlobTool:
     async def execute(self, content: str, ctx: dict) -> dict:
-        from src.tool_execution import _resolve_tool_path, _resolve_search_root, _truncate
+        from src.tool_execution import (
+            _SENSITIVE_BASENAMES,
+            _is_sensitive_path,
+            _resolve_tool_path,
+            _resolve_search_root,
+            _truncate,
+        )
         args = {}
         _s = (content or "").strip()
         if _s.startswith("{"):
@@ -322,7 +328,11 @@ class GlobTool:
                     ) == nbase
                 except ValueError:
                     inside = False
-                if inside and os.path.exists(cand):
+                # A literal that names a deny-listed sensitive file (.env,
+                # .ssh/id_rsa, …) falls through to the walk, which skips it —
+                # otherwise glob would surface secret paths that read_file /
+                # grep already refuse to touch.
+                if inside and os.path.exists(cand) and not _is_sensitive_path(cand):
                     return [cand], None
                 # Literal not at exact path — fall through to walk so
                 # e.g. "foo.py" still matches at any depth (like rglob).
@@ -334,11 +344,20 @@ class GlobTool:
                 for dp, dns, fns in os.walk(base):
                     # Prune skipped dirs before descending (unlike rglob which
                     # descends first then filters — fatal on large node_modules).
-                    dns[:] = [d for d in dns if d not in _CODENAV_SKIP_DIRS]
+                    # Sensitive dirs (.ssh, .gnupg, …) are pruned too so glob
+                    # never enumerates the keys/tokens inside them.
+                    dns[:] = [
+                        d for d in dns
+                        if d not in _CODENAV_SKIP_DIRS and d not in _SENSITIVE_BASENAMES
+                    ]
                     for name in fns + dns:
                         full = os.path.join(dp, name)
                         rel = os.path.relpath(full, base).replace(os.sep, "/")
                         if regex.fullmatch(rel) or regex.fullmatch(name):
+                            # Skip deny-listed sensitive files (.env, id_rsa,
+                            # known_hosts, …) the same way grep does.
+                            if _is_sensitive_path(os.path.realpath(full)):
+                                continue
                             try:
                                 mtime = os.stat(full).st_mtime
                             except OSError:
diff --git a/tests/test_workspace_confine.py b/tests/test_workspace_confine.py
index ca0819cc7..6d90789c9 100644
--- a/tests/test_workspace_confine.py
+++ b/tests/test_workspace_confine.py
@@ -167,6 +167,38 @@ async def test_glob_confined_e2e(ws, admin):
     assert r["exit_code"] == 0 and "No files" in r["output"]
 
 
+@pytest.mark.asyncio
+async def test_glob_skips_sensitive_files_in_workspace(ws, admin):
+    """glob must not enumerate deny-listed sensitive files that live inside the
+    workspace. read_file/write_file/edit_file refuse them and grep skips them,
+    so glob surfacing their paths is an enumeration oracle for prompt-injection.
+    """
+    with open(os.path.join(ws, "keep.py"), "w") as f:
+        f.write("x")
+    with open(os.path.join(ws, ".env"), "w") as f:
+        f.write("AWS_SECRET=xxx")
+    with open(os.path.join(ws, "id_rsa"), "w") as f:  # non-dotfile key at root
+        f.write("KEY")
+    os.makedirs(os.path.join(ws, ".ssh"), exist_ok=True)
+    with open(os.path.join(ws, ".ssh", "authorized_keys"), "w") as f:
+        f.write("ssh-rsa AAAA")
+
+    # A recursive wildcard returns ordinary files but none of the sensitive
+    # ones. The pattern "**/*" contains no secret names, so a secret basename
+    # appearing in the output is a real leak (not the echoed not-found pattern).
+    _, r = await execute_tool_block(_block("glob", json.dumps({"pattern": "**/*"})), owner="a", workspace=ws)
+    assert r["exit_code"] == 0
+    assert "keep.py" in r["output"]
+    for leak in (".env", "id_rsa", "authorized_keys"):
+        assert leak not in r["output"], f"glob leaked sensitive file: {leak}"
+
+    # Directly targeting a sensitive file (literal fast-path and wildcard) must
+    # come back as the not-found message, never a match with the file's path.
+    for pat in (".env", "**/id_rsa", "**/authorized_keys"):
+        _, r = await execute_tool_block(_block("glob", json.dumps({"pattern": pat})), owner="a", workspace=ws)
+        assert r["exit_code"] == 0 and "No files" in r["output"]
+
+
 @pytest.mark.asyncio
 async def test_subprocess_cwd_is_workspace_e2e(ws, admin):
     """python tool runs with cwd = workspace (OS-agnostic probe)."""