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).

CVE-2026-81690 affects the openssl-encrypt pip package before version 1.4.9, exposing a symlink-following vulnerability in its verify-usb v2 added-file allowlist scan. The flaw arises because rglob() in CPython does not descend into symlinked directories, while O_NOFOLLOW only guards the final path component during hashing. An evil-maid attacker with physical access to a removable drive can replace a tool-tree directory with a symlink pointing to a copy containing byte-identical files plus a malicious __pycache__/*.pyc file. Since the planted file is never enumerated, the verify-usb check reports PASSED despite the tampering. When the victim subsequently runs the portable install, the planted bytecode is executed, achieving arbitrary code execution. Both the 1.4.x and 1.5.x lines are affected, and the issue is fixed in version 1.4.9.