<http://stackoverflow.com/questions/35838822/trying-to-set-up-freeradius-in-eap-tls-mode-using-wpa-supplicant#> I am trying to setup freeraadius in eap-tls mode. I am using freeradius as a server and wpa-supplicant as a client. I have installed both packages in Ubuntu-14.04.3. I am using the sample certificates provided along with freeradius package. I use the script bootstrap provided in */freerad/raddb/cert* . I donot know if this script properly signs the certificate or not as i am not an expert in this area. I simply provide the paths to these certificates in client.conf to freeradius and configuration file in wpa-supplicant. Following is the wpa-supplicant configuration i am using network={ ssid="YOUR-SSID" scan_ssid=1 key_mgmt=WPA-EAP eap=TLS identity="alice" ca_cert="/home/areh/freeradius-server-3.0.11/raddb/certs/ca.pem" client_cert="/home/areh/freeradius-server-3.0.11/raddb/certs/client.pem" private_key="/home/areh/freeradius-server-3.0.11/raddb/certs/client.key" } I am running freeradius using *Freeradius -X* command and *eapol_test -c eap-tls.conf -s testing123* for wpa-supplicant command. I receive the following error on wpa-supplicant terminal: OpenSSL: tls_connection_client_cert - SSL_use_certificate_file (DER) failed error:0D0680A8:asn1 encoding routines:ASN1_CHECK_TLEN:wrong tag OpenSSL: pending error: error:0D07803A:asn1 encoding routines:ASN1_ITEM_EX_D2I:nested asn1 error OpenSSL: pending error: error:140C800D:SSL routines:SSL_use_certificate_file:ASN1 lib OpenSSL: SSL_use_certificate_file (PEM) --> OK OpenSSL: tls_connection_private_key - SSL_use_PrivateKey_File (DER) failed error:0D0680A8:asn1 encoding routines:ASN1_CHECK_TLEN:wrong tag OpenSSL: pending error: error:0D08303A:asn1 encoding routines:ASN1_TEMPLATE_NOEXP_D2I:nested asn1 error OpenSSL: pending error: error:0D0680A8:asn1 encoding routines:ASN1_CHECK_TLEN:wrong tag OpenSSL: pending error: error:0D07803A:asn1 encoding routines:ASN1_ITEM_EX_D2I:nested asn1 error OpenSSL: pending error: error:04093004:rsa routines:OLD_RSA_PRIV_DECODE:RSA lib OpenSSL: pending error: error:0D0680A8:asn1 encoding routines:ASN1_CHECK_TLEN:wrong tag OpenSSL: pending error: error:0D07803A:asn1 encoding routines:ASN1_ITEM_EX_D2I:nested asn1 error OpenSSL: pending error: error:140CB00D:SSL routines:SSL_use_PrivateKey_file:ASN1 lib OpenSSL: tls_connection_private_key - SSL_use_PrivateKey_File (PEM) failed error:0907B068:PEM routines:PEM_READ_BIO_PRIVATEKEY:bad password read OpenSSL: pending error: error:140CB009:SSL routines:SSL_use_PrivateKey_file:PEM lib OpenSSL: tls_read_pkcs12 - Failed to use PKCS#12 file error:0D0680A8:asn1 encoding routines:ASN1_CHECK_TLEN:wrong tag OpenSSL: pending error: error:0D07803A:asn1 encoding routines:ASN1_ITEM_EX_D2I:nested asn1 error OpenSSL: Failed to load private key TLS: Failed to load private key '/home/areh/freeradius-server-3.0.11/raddb/certs/client.key' TLS: Failed to set TLS connection parameters I am using wpa_supplicant-0.7.3 and also tried with 2.5 version, freeradius version is freeradius-server-3.0.11. I would really appreciate any clue or help. I am debugging using wireshark and I can see access-challenge and access-request packets being exchanged but never reach the next message stage. Kindly help with this problem. Any help will be appreciated. Ammad Rehmat