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.