You should verify, your Mail client is able to do SMTP AUTH. Alexey Melnikov maintains a SASL client list at sendmail.org. It gives an overview on the Mail clients that support SMTP AUTH and their capabilities.
If you plan to use TLS and want to be your own CA authority you should make sure that your Mail clients trust your Mail server. To do this you must add the CA cert that you generated to the root certs that your Mail client should trust.