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Обновил в офисе одну машину с Ubuntu 16 на 18 и обнаружилось, что с неё теперь невозможно подключиться к WPA2 Enterprise (aka PEAP MSCHAPV2). После недолгого гугленья и ваиршарканья обнаружился такой баг: https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=848982
tl;dr - точка доступа требует TLS_RSA_WITH_3DES_EDE_CBC_SHA, а оно похоже выключено в новом openssl



Ubuntu 18:

# openssl ciphers
ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:DHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-SHA384:ECDHE-RSA-AES256-SHA384:DHE-RSA-AES256-SHA256:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES256-SHA:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES128-SHA:DHE-RSA-AES128-SHA:RSA-PSK-AES256-GCM-SHA384:DHE-PSK-AES256-GCM-SHA384:RSA-PSK-CHACHA20-POLY1305:DHE-PSK-CHACHA20-POLY1305:ECDHE-PSK-CHACHA20-POLY1305:AES256-GCM-SHA384:PSK-AES256-GCM-SHA384:PSK-CHACHA20-POLY1305:RSA-PSK-AES128-GCM-SHA256:DHE-PSK-AES128-GCM-SHA256:AES128-GCM-SHA256:PSK-AES128-GCM-SHA256:AES256-SHA256:AES128-SHA256:ECDHE-PSK-AES256-CBC-SHA384:ECDHE-PSK-AES256-CBC-SHA:SRP-RSA-AES-256-CBC-SHA:SRP-AES-256-CBC-SHA:RSA-PSK-AES256-CBC-SHA384:DHE-PSK-AES256-CBC-SHA384:RSA-PSK-AES256-CBC-SHA:DHE-PSK-AES256-CBC-SHA:AES256-SHA:PSK-AES256-CBC-SHA384:PSK-AES256-CBC-SHA:ECDHE-PSK-AES128-CBC-SHA256:ECDHE-PSK-AES128-CBC-SHA:SRP-RSA-AES-128-CBC-SHA:SRP-AES-128-CBC-SHA:RSA-PSK-AES128-CBC-SHA256:DHE-PSK-AES128-CBC-SHA256:RSA-PSK-AES128-CBC-SHA:DHE-PSK-AES128-CBC-SHA:AES128-SHA:PSK-AES128-CBC-SHA256:PSK-AES128-CBC-SHA

В то же время на Ubuntu 16:

$ openssl ciphers
ECDHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-SHA384:ECDHE-ECDSA-AES256-SHA384:ECDHE-RSA-AES256-SHA:ECDHE-ECDSA-AES256-SHA:SRP-DSS-AES-256-CBC-SHA:SRP-RSA-AES-256-CBC-SHA:SRP-AES-256-CBC-SHA:DH-DSS-AES256-GCM-SHA384:DHE-DSS-AES256-GCM-SHA384:DH-RSA-AES256-GCM-SHA384:DHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES256-SHA256:DHE-DSS-AES256-SHA256:DH-RSA-AES256-SHA256:DH-DSS-AES256-SHA256:DHE-RSA-AES256-SHA:DHE-DSS-AES256-SHA:DH-RSA-AES256-SHA:DH-DSS-AES256-SHA:DHE-RSA-CAMELLIA256-SHA:DHE-DSS-CAMELLIA256-SHA:DH-RSA-CAMELLIA256-SHA:DH-DSS-CAMELLIA256-SHA:ECDH-RSA-AES256-GCM-SHA384:ECDH-ECDSA-AES256-GCM-SHA384:ECDH-RSA-AES256-SHA384:ECDH-ECDSA-AES256-SHA384:ECDH-RSA-AES256-SHA:ECDH-ECDSA-AES256-SHA:AES256-GCM-SHA384:AES256-SHA256:AES256-SHA:CAMELLIA256-SHA:PSK-AES256-CBC-SHA:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA-AES128-SHA:SRP-DSS-AES-128-CBC-SHA:SRP-RSA-AES-128-CBC-SHA:SRP-AES-128-CBC-SHA:DH-DSS-AES128-GCM-SHA256:DHE-DSS-AES128-GCM-SHA256:DH-RSA-AES128-GCM-SHA256:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES128-SHA256:DHE-DSS-AES128-SHA256:DH-RSA-AES128-SHA256:DH-DSS-AES128-SHA256:DHE-RSA-AES128-SHA:DHE-DSS-AES128-SHA:DH-RSA-AES128-SHA:DH-DSS-AES128-SHA:DHE-RSA-SEED-SHA:DHE-DSS-SEED-SHA:DH-RSA-SEED-SHA:DH-DSS-SEED-SHA:DHE-RSA-CAMELLIA128-SHA:DHE-DSS-CAMELLIA128-SHA:DH-RSA-CAMELLIA128-SHA:DH-DSS-CAMELLIA128-SHA:ECDH-RSA-AES128-GCM-SHA256:ECDH-ECDSA-AES128-GCM-SHA256:ECDH-RSA-AES128-SHA256:ECDH-ECDSA-AES128-SHA256:ECDH-RSA-AES128-SHA:ECDH-ECDSA-AES128-SHA:AES128-GCM-SHA256:AES128-SHA256:AES128-SHA:SEED-SHA:CAMELLIA128-SHA:PSK-AES128-CBC-SHA:ECDHE-RSA-RC4-SHA:ECDHE-ECDSA-RC4-SHA:ECDH-RSA-RC4-SHA:ECDH-ECDSA-RC4-SHA:RC4-SHA:RC4-MD5:PSK-RC4-SHA:ECDHE-RSA-DES-CBC3-SHA:ECDHE-ECDSA-DES-CBC3-SHA:SRP-DSS-3DES-EDE-CBC-SHA:SRP-RSA-3DES-EDE-CBC-SHA:SRP-3DES-EDE-CBC-SHA:EDH-RSA-DES-CBC3-SHA:EDH-DSS-DES-CBC3-SHA:DH-RSA-DES-CBC3-SHA:DH-DSS-DES-CBC3-SHA:ECDH-RSA-DES-CBC3-SHA:ECDH-ECDSA-DES-CBC3-SHA:DES-CBC3-SHA:PSK-3DES-EDE-CBC-SHA

Пытаюсь перекомпилить openssl:

./config --prefix=/root/openssl-1.1.0h/out shared enable-weak-ssl-ciphers
make
make install_sw

# LD_LIBRARY_PATH=/root/openssl-1.1.0h/out/lib out/bin/openssl ciphers
ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:DHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-SHA384:ECDHE-RSA-AES256-SHA384:DHE-RSA-AES256-SHA256:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES256-SHA:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES128-SHA:DHE-RSA-AES128-SHA:RSA-PSK-AES256-GCM-SHA384:DHE-PSK-AES256-GCM-SHA384:RSA-PSK-CHACHA20-POLY1305:DHE-PSK-CHACHA20-POLY1305:ECDHE-PSK-CHACHA20-POLY1305:AES256-GCM-SHA384:PSK-AES256-GCM-SHA384:PSK-CHACHA20-POLY1305:RSA-PSK-AES128-GCM-SHA256:DHE-PSK-AES128-GCM-SHA256:AES128-GCM-SHA256:PSK-AES128-GCM-SHA256:AES256-SHA256:AES128-SHA256:ECDHE-PSK-AES256-CBC-SHA384:ECDHE-PSK-AES256-CBC-SHA:SRP-RSA-AES-256-CBC-SHA:SRP-AES-256-CBC-SHA:RSA-PSK-AES256-CBC-SHA384:DHE-PSK-AES256-CBC-SHA384:RSA-PSK-AES256-CBC-SHA:DHE-PSK-AES256-CBC-SHA:AES256-SHA:PSK-AES256-CBC-SHA384:PSK-AES256-CBC-SHA:ECDHE-PSK-AES128-CBC-SHA256:ECDHE-PSK-AES128-CBC-SHA:SRP-RSA-AES-128-CBC-SHA:SRP-AES-128-CBC-SHA:RSA-PSK-AES128-CBC-SHA256:DHE-PSK-AES128-CBC-SHA256:RSA-PSK-AES128-CBC-SHA:DHE-PSK-AES128-CBC-SHA:AES128-SHA:PSK-AES128-CBC-SHA256:PSK-AES128-CBC-SHA

Список не изменился - нету DES

ЧЯДНТ?

UPD
После перекомпиляции openssl надо также явно указать шифр в конфиге wpa_supplicant:

openssl_ciphers="SYSTEM:3DES"

https://ru-linux.livejournal.com/3066107.html