O.K. here are my logs, I also took out of relay-domains my domain, should I put it back in access? anyways I am so very confused and am very grateful for your help thus far. When I first click send with authentication turned on: Jul 24 18:42:04 localhostname sendmail[5030]: i6OMfx2N005030: <-- AUTH PLAIN some wierd characters are hear, think its my passwrd. Jul 24 18:42:04 localhostname sendmail[5030]: i6OMfx2N005030: --- 535 5.7.0 authentication failed Jul 24 18:42:04 localhostname sendmail[5030]: i6OMfx2N005030: AUTH failure (PLAIN): no mechanism available (-4) SASL(-4): no mechanism available: Password verification failed Jul 24 18:42:04 localhostname sendmail[5030]: i6OMfx2N005030: <-- AUTH LOGIN Jul 24 18:42:04 localhostname sendmail[5030]: i6OMfx2N005030: --- 334 VXNlcm5hbWU6 Jul 24 18:42:04 localhostname sendmail[5030]: i6OMfx2N005030: --- 334 UGFzc3dvcmQ6 Jul 24 18:42:04 localhostname sendmail[5030]: i6OMfx2N005030: --- 535 5.7.0 authentication failed Jul 24 18:42:04 localhostname sendmail[5030]: i6OMfx2N005030: AUTH failure (LOGIN): no mechanism available (-4) SASL(-4): no mechanism available: checkpass failed After I abort attempt to enter password (press cancel) Jul 24 18:42:37 localhostname sendmail[5030]: i6OMfx2N005030: --- 421 4.4.1 localhostname.dyndns.org Lost input channel from [192.168.2.4] Jul 24 18:42:37 localhostname sendmail[5030]: i6OMfx2N005030: [192.168.2.4] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA Anyways I can still sendmail without authentication, it works fine.