diff --git a/openedx/core/lib/extract_archive.py b/openedx/core/lib/extract_archive.py
index 4706e0caffb7..ce59574b6ffe 100644
--- a/openedx/core/lib/extract_archive.py
+++ b/openedx/core/lib/extract_archive.py
@@ -7,7 +7,7 @@
 """
 
 import logging
-from os.path import abspath, dirname
+from os.path import abspath, commonpath, dirname
 from os.path import join as joinpath
 from os.path import realpath
 from typing import List, Union
@@ -30,8 +30,18 @@ def resolved(rpath):
 def _is_bad_path(path, base):
     """
     Is (the canonical absolute path of) `path` outside `base`?
+
+    Uses ``os.path.commonpath`` for a segment-aware containment check so that
+    sibling directories whose names happen to extend ``base`` as a string
+    prefix (e.g. ``<base>evil/...``) are correctly classified as outside.
     """
-    return not resolved(joinpath(base, path)).startswith(base)
+    target = resolved(joinpath(base, path))
+    try:
+        return commonpath([target, base]) != base
+    except ValueError:
+        # commonpath raises when paths are incomparable (e.g. mixed absolute
+        # and relative, or different drives on Windows). Treat as bad.
+        return True
 
 
 def _is_bad_link(info, base):
diff --git a/openedx/core/lib/tests/test_extract_archive.py b/openedx/core/lib/tests/test_extract_archive.py
new file mode 100644
index 000000000000..6b999586eae3
--- /dev/null
+++ b/openedx/core/lib/tests/test_extract_archive.py
@@ -0,0 +1,93 @@
+"""
+Tests for openedx.core.lib.extract_archive.
+
+The path-containment helpers must treat ``base`` as a directory boundary, not
+a raw string prefix: a sibling whose name extends ``base`` as a string prefix
+(e.g. ``<parent>/foo_evil/x`` next to ``<parent>/foo``) is *outside* ``base``.
+These tests pin that boundary down at the helper level and end-to-end through
+``safe_extractall``.
+"""
+
+import io
+import os
+import tarfile
+import tempfile
+
+import pytest
+from django.core.exceptions import SuspiciousOperation
+from django.test import override_settings
+
+from openedx.core.lib.extract_archive import _is_bad_path, safe_extractall
+
+# Direct tests of the path-containment helper. No Django settings needed.
+
+def test_is_bad_path_prefix_bypass_is_rejected():
+    """
+    A sibling path whose name extends the base's name as a raw string prefix
+    (e.g. ``<parent>/Y29evil/file`` vs base ``<parent>/Y29``) is outside
+    ``base`` and must be flagged as bad.
+    """
+    with tempfile.TemporaryDirectory() as parent:
+        base = os.path.join(parent, "Y29")
+        os.mkdir(base)
+        assert _is_bad_path("../Y29evil/file", base) is True
+
+
+def test_is_bad_path_inside_base_is_accepted():
+    with tempfile.TemporaryDirectory() as parent:
+        base = os.path.join(parent, "Y29")
+        os.mkdir(base)
+        assert _is_bad_path("nested/file.txt", base) is False
+
+
+def test_is_bad_path_traversal_outside_base_is_rejected():
+    with tempfile.TemporaryDirectory() as parent:
+        base = os.path.join(parent, "Y29")
+        os.mkdir(base)
+        assert _is_bad_path("../../etc/passwd", base) is True
+
+
+# End-to-end tests of safe_extractall against crafted .tar.gz archives.
+
+def _add_file(tar, name, content=b""):
+    info = tarfile.TarInfo(name=name)
+    info.size = len(content)
+    tar.addfile(info, io.BytesIO(content))
+
+
+def _add_symlink(tar, name, linkname):
+    info = tarfile.TarInfo(name=name)
+    info.type = tarfile.SYMTYPE
+    info.linkname = linkname
+    tar.addfile(info)
+
+
+def test_safe_extractall_blocks_file_entry_with_prefix_bypass(tmp_path):
+    root = str(tmp_path)
+    extract_dir = os.path.join(root, "Y29")
+    os.mkdir(extract_dir)
+    archive = os.path.join(root, "malicious.tar.gz")
+    with tarfile.open(archive, "w:gz") as tar:
+        _add_file(tar, "../Y29evil/sentinel.txt", b"owned")
+
+    with override_settings(GITHUB_REPO_ROOT=root):
+        with pytest.raises(SuspiciousOperation):
+            safe_extractall(archive, extract_dir)
+
+    escape_target = os.path.join(root, "Y29evil", "sentinel.txt")
+    assert not os.path.exists(escape_target)
+
+
+def test_safe_extractall_blocks_symlink_target_with_prefix_bypass(tmp_path):
+    root = str(tmp_path)
+    extract_dir = os.path.join(root, "Y29")
+    os.mkdir(extract_dir)
+    archive = os.path.join(root, "malicious.tar.gz")
+    # symlink inside extract_dir pointing at a sibling whose name extends
+    # extract_dir's basename as a string prefix.
+    with tarfile.open(archive, "w:gz") as tar:
+        _add_symlink(tar, name="link", linkname="../Y29evil/secret")
+
+    with override_settings(GITHUB_REPO_ROOT=root):
+        with pytest.raises(SuspiciousOperation):
+            safe_extractall(archive, extract_dir)