openssl-encrypt (pip package) before 1.4.9 contains a symlink-following flaw in its verify-usb v2 added-file allowlist scan. The scan enumerated the drive with rglob(), which in CPython does not descend into symlinked directories and treats the symlink as an ordinary directory, while O_NOFOLLOW on the hash side binds only the final path component. An evil-maid attacker with physical access to the removable drive could replace a tool-tree directory with a symlink to a copy containing byte-identical files plus a planted __pycache__/*.pyc file (which CPython loads in preference to recompiling the clean .py). The planted file is never enumerated, added_files stays 0, and verify-usb reports PASSED, resulting in code execution when the victim runs the portable install. Fixed in 1.4.9 (affects both 1.4.x and 1.5.x lines).