Trouble sending file from Calibre to Kindle

[mcykindle]

I converted my files to mobi and trying to send to my kindle. It has worked in the past but is no longer working. This is the error message I receive:

Sending failed...

Traceback (most recent call last):
File "site-packages/calibre/gui2/email.py", line 43, in run
File "site-packages/calibre/gui2/email.py", line 124, in sendmail
File "site-packages/calibre/utils/smtp.py", line 116, in sendmail
File "site-packages/calibre/utils/smtp.py", line 108, in sendmail_direct
IOError: Failed to send mail: IOError(32, 'Broken pipe')

Job: "Email Dancing Girls and Other Stories to ZZZZZ@free.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 98, in __call__
IOError: Failed to send mail: IOError(32, 'Broken pipe')

Called with args: (u'/var/folders/nj/sk2rpyc94gvfr8vm2wq0_61c0000gn/T/calibre_2.10.0_tmp_4kUXnv/H4fpo8caltmpfmt.mobi', u'Dancing Girls and Other Stories - Margaret Atwood.mobi', u'ZZZZ@free.kindle.com', u'E-book: Dancing Girls and Other Stories', u'Attached, you will find the e-book\n\nDancing Girls and Other Stories\n\tby Margaret Atwood\n\nin the MOBI format.') {u'log': , u'abort': , u'notifications': }

Any ideas how to help? THANKS!

[theducks]

Moderator Notice
Be very careful when posting logs to obscure email and like id's in the content (I replaced your account name with ZZZ's) while not changing anything else that might hide your issue.

[kovidgoyal]

http://manual.calibre-ebook.com/faq....-using-calibre

[groovysaur]

I am having the same problem as mcykindle - I get the same error message when I try to email converted MOBI files to my Kindle. I have a macbook and used to have an old iOS installed (not sure which one). I used to email files to my Kindle all the time w/o a problem. My HD died, so I had it replaced and my iOS is now OS X Yosemite 10.10.1. I tried using an older version of Calibre, but that didn't help. I even signed up for a GMX account (per the suggestion in the FAQ), but still can't seem to email anything from Calibre...to my Kindle or a general email account. Any other advice?

[groovysaur]

oh, thanks!