Kindle not receiving emailed documents

Just added a second Kindle (with new email address) to Calibre and I'm not having success sending documents via email. It appears to be successful, but the kindle isn't receiving anything. I sent the same doc to my original email address without any issue. I logged into Amazon and made sure that the Kindle allowed the new email address, and it does...any ideas?

Starting job: Sample to ******@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '220 mx.google.com ESMTP j3sm158617818ibj.1\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP j3sm158617818ibj.1
connect: mx.google.com ESMTP j3sm158617818ibj.1
send: 'ehlo My-PC.gateway.2wire.net\r\n'
reply: '250-mx.google.com at your service, [99.183.227.202]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [99.183.227.202]
SIZE 35882577
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
send: 'ehlo My-PC.gateway.2wire.net\r\n'
reply: '250-mx.google.com at your service, [99.183.227.202]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [99.183.227.202]
SIZE 35882577
8BITMIME
AUTH LOGIN PLAIN XOAUTH
ENHANCEDSTATUSCODES
send: AUTH
reply: '235 2.7.0 Accepted\r\n'
reply: retcode (235); Msg: 2.7.0 Accepted
send: u'mail FROM: size=470971\r\n'
reply: '250 2.1.0 OK j3sm158617818ibj.1\r\n'
reply: retcode (250); Msg: 2.1.0 OK j3sm158617818ibj.1
send: u'rcpt TO:\r\n'
reply: '250 2.1.5 OK j3sm158617818ibj.1\r\n'
reply: retcode (250); Msg: 2.1.5 OK j3sm158617818ibj.1
send: 'data\r\n'
reply: '354 Go ahead j3sm158617818ibj.1\r\n'
reply: retcode (354); Msg: Go ahead j3sm158617818ibj.1
data: (354, 'Go ahead j3sm158617818ibj.1')
send: 'Content-Type: multipart/mixed; boundary="===============0066271408=="\r\nMIME-Version: 1.0\r\nSubje...
reply: '250 2.0.0 OK 1325467512 j3sm158617818ibj.1\r\n'
reply: retcode (250); Msg: 2.0.0 OK 1325467512 j3sm158617818ibj.1
data: (250, '2.0.0 OK 1325467512 j3sm158617818ibj.1')
send: 'quit\r\n'
reply: '221 2.0.0 closing connection j3sm158617818ibj.1\r\n'
reply: retcode (221); Msg: 2.0.0 closing connection j3sm158617818ibj.1
Email successfully sent