Hi, I hope my question is not off topic. I try to create a self signed certificate, which is signed by my own CA. I have created a pkcs12 file, which includes cert, key, and CA:
openssl pkcs12 -export -in newcert.pem -inkey newkey.pem -CAfile cacert.pem -chain -out croessner.p12 I have imported this file on Mac OS X. I explicitly have given a full trust to the CA certificate and hav moved it to „System“. My certificate is listed and the key chain app tells me that it trusts this certificate. I also created a SHA256 fingerprint and modified main.cf to accept mail from this certificate. 1.) Thunderbird I imported the same p12 file in Thunderbird. Did a test mail and a dialog asked me to use the imported certificate. I chose yes and I could successfully send mail. On my test account I verified the headers and saw that the user was verified. 2.) Apple Mail I entered settings and selected my account. I clicked on the certificate selector and found my certificate. Under SMTP servers I chose „External (TLS-Certificate)“. Trying to deliver a test mail with this application, I directly get an error that the remote mail server would not support TLS certificates. So now I wonder what is wrong. Because Thunderbird is working, I guess there is not a configuration problem in Postfix, could it? I have not very much knowledge about the openssl.cnf stuff. This here is what I used: cat openssl_client.cnf | grep -ve ^.*#.* -ve ^$ HOME = . RANDFILE = $ENV::HOME/.rnd oid_section = new_oids [ new_oids ] tsa_policy1 = 1.2.3.4.1 tsa_policy2 = 1.2.3.4.5.6 tsa_policy3 = 1.2.3.4.5.7 [ ca ] [ CA_default ] policy = policy_match [ policy_match ] domainComponent = match stateOrProvinceName = match organizationName = match organizationalUnitName = optional commonName = supplied emailAddress = optional [ policy_anything ] domainComponent = optional stateOrProvinceName = optional localityName = optional organizationName = optional organizationalUnitName = optional commonName = supplied emailAddress = optional [ req ] default_bits = 2048 default_md = sha1 default_keyfile = privkey.pem distinguished_name = req_distinguished_name attributes = req_attributes string_mask = utf8only [ req_distinguished_name ] 0.domainComponent = TLD domain component 0.domainComponent_default = de 1.domainComponent = 2nd domain component 1.domainComponent_default = roessner-net stateOrProvinceName = State or Province Name (full name) stateOrProvinceName_default = Deutschland localityName = Locality Name (eg, city) localityName_default = Alsfeld 0.organizationName = Organization Name (eg, company) 0.organizationName_default = roessner-network-solutions.com organizationalUnitName = Organizational Unit Name (eg, section) commonName = Common Name (eg, your name or your server\'s hostname) commonName_max = 64 emailAddress = Email Address emailAddress_max = 64 emailAddress_default = c...@roessner-network-solutions.com [ req_attributes ] challengePassword = A challenge password challengePassword_min = 4 challengePassword_max = 20 unstructuredName = An optional company name [ usr_cert ] basicConstraints=CA:FALSE nsCertType = client, email nsComment = "OpenSSL Generated Certificate" subjectKeyIdentifier=hash authorityKeyIdentifier=keyid,issuer [ v3_req ] basicConstraints = CA:FALSE keyUsage = nonRepudiation, digitalSignature, keyEncipherment [ v3_ca ] subjectKeyIdentifier=hash authorityKeyIdentifier=keyid:always,issuer basicConstraints = CA:true [ crl_ext ] authorityKeyIdentifier=keyid:always [ proxy_cert_ext ] basicConstraints=CA:FALSE nsCertType = client, email nsComment = "OpenSSL Generated Certificate" subjectKeyIdentifier=hash authorityKeyIdentifier=keyid,issuer proxyCertInfo=critical,language:id-ppl-anyLanguage,pathlen:3,policy:foo [ tsa ] [ tsa_config1 ] Is it possible that Apple Mail requires something special? Or do I have to do something else with the certificate? It would be great, if I could use Apple Mail with Postfix and TLS certs. postconf -c /etc/postfix-submission/ -n alias_database = alias_maps = amavisd_milter = inet:[::1]:10024 anvil_rate_time_unit = 30s anvil_status_update_time = 600s broken_sasl_auth_clients = yes command_directory = /usr/sbin config_directory = /etc/postfix-submission/ daemon_directory = /usr/libexec/postfix data_directory = /var/lib/postfix-submission default_database_type = lmdb enable_long_queue_ids = yes html_directory = no inet_interfaces = ${mail_roessner_net_de} inet_protocols = ipv4, ipv6 ldap = proxy:ldap:${config_directory}/ldap local_recipient_maps = local_transport = error:5.1.1 Mailbox unavailable mail_owner = postfix mail_roessner_net_de = 193.239.107.42 mailbox_size_limit = 0 mailq_path = /usr/bin/mailq manpage_directory = /usr/man map = ${config_directory}/maps mapidx = ${default_database_type}:${map} message_size_limit = 31457280 meta_directory = /etc/postfix milter_connect_macros = j, v, {daemon_name}, {client_ptr} milter_macro_daemon_name = ORIGINATING milter_mail_macros = i, {auth_type}, {auth_authen}, {auth_author}, {mail_addr}, {mail_host}, {mail_mailer}, {client_name} multi_instance_enable = yes multi_instance_name = postfix-submission mydestination = mydomain = roessner-net.de myhostname = mail.${mydomain} mynetworks = newaliases_path = /usr/bin/newaliases odkim_sign = inet:[::1]:8892 proxy_read_maps = proxy:unix:passwd.byname, ${ldap}/smtpd_sender_login_maps.cf queue_directory = /var/spool/postfix-submission queue_minfree = 47185920 readme_directory = no relay_clientcerts = ${mapidx}/relay_clientcerts relayhost = [mx0.roessner-net.de]:10025 sample_directory = /etc/postfix sendmail_path = /usr/sbin/sendmail setgid_group = postdrop shlib_directory = /usr/lib64/postfix/${mail_version} smtp_bind_address = ${mail_roessner_net_de} smtp_dns_support_level = dnssec smtp_host_lookup = dns smtp_send_xforward_command = yes smtp_tls_CAfile = /etc/ssl/certs/ca-certificates.crt smtp_tls_cert_file = /etc/ssl/certs/mail.roessner-net.de.pem smtp_tls_exclude_ciphers = RC4, aNULL smtp_tls_key_file = /etc/ssl/private/mail.roessner-net.de.key.pem smtp_tls_loglevel = 1 smtp_tls_mandatory_ciphers = high smtp_tls_mandatory_protocols = !SSLv2, !SSLv3 smtp_tls_note_starttls_offer = yes smtp_tls_protocols = !SSLv2, !SSLv3 smtp_tls_security_level = dane-only smtp_tls_session_cache_database = btree:${data_directory}/smtp_session_cache smtpd_banner = ${myhostname} ESMTP Submission smtpd_client_connection_rate_limit = 8 smtpd_client_message_rate_limit = 20 smtpd_client_new_tls_session_rate_limit = 5 smtpd_client_port_logging = yes smtpd_client_recipient_rate_limit = 0 smtpd_delay_reject = yes smtpd_helo_required = yes smtpd_milters = ${amavisd_milter}, ${odkim_sign} smtpd_recipient_restrictions = permit_sasl_authenticated, reject smtpd_relay_restrictions = check_sender_access pcre:${map}/sender_access.pcre, check_recipient_access ${mapidx}/reject_srvint_net, reject_non_fqdn_recipient, permit_tls_clientcerts, permit_sasl_authenticated, reject_unauthenticated_sender_login_mismatch, reject smtpd_sasl_auth_enable = yes smtpd_sasl_authenticated_header = yes smtpd_sasl_local_domain = ${mydomain} smtpd_sasl_security_options = noanonymous, noplaintext smtpd_sasl_tls_security_options = noanonymous smtpd_sasl_type = cyrus smtpd_sender_login_maps = ${ldap}/smtpd_sender_login_maps.cf smtpd_tls_CAfile = /etc/ssl/certs/ca-certificates.crt smtpd_tls_ask_ccert = yes smtpd_tls_cert_file = /etc/ssl/certs/mail.roessner-net.de.pem smtpd_tls_dh1024_param_file = ${config_directory}/ssl/dh_2048.pem smtpd_tls_dh512_param_file = ${config_directory}/ssl/dh_512.pem smtpd_tls_eecdh_grade = strong smtpd_tls_exclude_ciphers = RC4, aNULL, SEED-SHA, EXPORT smtpd_tls_fingerprint_digest = sha256 smtpd_tls_key_file = /etc/ssl/private/mail.roessner-net.de.key.pem smtpd_tls_loglevel = 1 smtpd_tls_mandatory_ciphers = high smtpd_tls_mandatory_protocols = !SSLv2, !SSLv3 smtpd_tls_received_header = yes smtpd_tls_security_level = encrypt smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_session_cache sogo_roessner_net_de = 193.239.107.43 syslog_name = postfix-submission tls_preempt_cipherlist = yes tls_ssl_options = no_ticket, no_compression Thanks in advance -Christian Rößner -- Bachelor of Science Informatik Erlenwiese 14, 36304 Alsfeld T: +49 6631 78823400, F: +49 6631 78823409, M: +49 171 9905345 USt-IdNr.: DE225643613, http://www.roessner-network-solutions.com
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