diff --git a/src/agent_tools/filesystem_tools.py b/src/agent_tools/filesystem_tools.py
index d1180d53b..b0f5b6a89 100644
--- a/src/agent_tools/filesystem_tools.py
+++ b/src/agent_tools/filesystem_tools.py
@@ -303,11 +303,26 @@ class GlobTool:
             base = os.path.abspath(root)
             if not os.path.isdir(base):
                 return None, f"glob: {root}: not a directory"
+            rbase = os.path.realpath(base)
             norm_pat = pattern.replace("\\", "/")
             # Fast path: literal pattern (no wildcards) → direct path lookup.
             if not any(c in norm_pat for c in "*?["):
-                cand = os.path.normpath(os.path.join(base, norm_pat))
-                if os.path.exists(cand):
+                cand = os.path.realpath(os.path.join(base, norm_pat))
+                # Keep the literal lookup inside the search root. os.path.join
+                # lets an absolute pattern (or one containing ../) escape `base`,
+                # which would turn glob into an existence/path oracle for
+                # arbitrary host files — bypassing the workspace/allowlist
+                # confinement that _resolve_search_root applies to the root.
+                # An escaping literal falls through to the walk, which only ever
+                # yields paths under base.
+                nbase = os.path.normcase(rbase)
+                try:
+                    inside = cand == rbase or os.path.commonpath(
+                        [os.path.normcase(cand), nbase]
+                    ) == nbase
+                except ValueError:
+                    inside = False
+                if inside and os.path.exists(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).
diff --git a/tests/test_workspace_confine.py b/tests/test_workspace_confine.py
index 81bc7235c..ca0819cc7 100644
--- a/tests/test_workspace_confine.py
+++ b/tests/test_workspace_confine.py
@@ -140,6 +140,33 @@ async def test_grep_and_ls_confined_e2e(ws, admin):
     assert r["exit_code"] == 1 and "outside the workspace" in r["error"]
 
 
+@pytest.mark.asyncio
+async def test_glob_confined_e2e(ws, admin):
+    """glob's literal fast-path must stay inside the workspace. A pattern with
+    ../ or an absolute path outside the root would otherwise leak the existence
+    and full path of arbitrary host files (an oracle), even though read_file
+    blocks reading them."""
+    with open(os.path.join(ws, "found.py"), "w") as f:
+        f.write("x")
+    _, r = await execute_tool_block(_block("glob", json.dumps({"pattern": "found.py"})), owner="a", workspace=ws)
+    assert r["exit_code"] == 0 and "found.py" in r["output"]
+
+    # a secret outside the workspace must not be discoverable via glob
+    outside = tempfile.mkdtemp()
+    secret = os.path.join(outside, "secret.txt")
+    with open(secret, "w") as f:
+        f.write("nope")
+    # An escaping pattern must come back as "No files" (the not-found message),
+    # not as a match that returns the file's path. The not-found message echoes
+    # the pattern the model supplied, so the signal is the absence of a match,
+    # not the absence of the path string.
+    rel = os.path.relpath(secret, os.path.realpath(ws))
+    _, r = await execute_tool_block(_block("glob", json.dumps({"pattern": rel})), owner="a", workspace=ws)
+    assert r["exit_code"] == 0 and "No files" in r["output"] and secret not in r["output"]
+    _, r = await execute_tool_block(_block("glob", json.dumps({"pattern": secret})), 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)."""