Just an update, after 15 minutes of waiting for the book to send through Calibre, using the new email address i got this message:
Starting job: Email Beautiful Disaster to
TarraAnn85@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
Sending timed out
Job: "Email Beautiful Disaster to
TarraAnn85@kindle.com" failed with error:
Traceback (most recent call last):
File "site-packages\calibre\gui2\threaded_jobs.py", line 83, in start_work
File "site-packages\calibre\gui2\email.py", line 84, in __call__
Exception: Sending email u'E-book: Beautiful Disaster' to u'TarraAnn85@kindle.com' timed out, aborting
Called with args: (u'C:\\Users\\Tarra\\AppData\\Local\\Temp\\calibre _0.9.6_tmp_x91uh3\\3g7nkbcaltmpfmt.mobi', u'Beautiful Disaster - Jamie McGuire.mobi', u'TarraAnn85@kindle.com', u'E-book: Beautiful Disaster', u'Attached, you will find the e-book\n\nBeautiful Disaster\n\tby Jamie McGuire\n\nin the MOBI format.') {u'notifications': , u'abort': , u'log': }