Calibre will not send e-mails to Kindle

[AvocadoRivalry]

I've set up Calibre to send books wirelessly using the instructions I've read in various places on the website using my G-mail address, but have had no luck. Every time I try and send a book (either to my @kindle or @free.kindle account), Calibre does nothing and then finally after about six minutes, gives me this error message:

calibre, version 0.8.21
ERROR: Failed to email book: <b>Failed</b>: Email The Great Hunt to jonathan.warrick@kindle.com

Starting job: Email The Great Hunt to jonathan.warrick@kindle.com
connect: (u'smtp.gmail.com', 25)
connect: (25, u'smtp.gmail.com')

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 37, in run
File "site-packages\calibre\gui2\email.py", line 112, in sendmail
File "site-packages\calibre\utils\smtp.py", line 103, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 281, in _get_socket
File "socket.py", line 571, in create_connection
error: [Errno 10060] A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond


Retrying in 301 seconds...

connect: (u'smtp.gmail.com', 25)
connect: (25, u'smtp.gmail.com')

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 37, in run
File "site-packages\calibre\gui2\email.py", line 112, in sendmail
File "site-packages\calibre\utils\smtp.py", line 103, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 281, in _get_socket
File "socket.py", line 571, in create_connection
error: [Errno 10060] A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond

Job: "Email The Great Hunt to jonathan.warrick@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 92, in __call__
error: [Errno 10060] A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond

Called with args: (u'c:\\users\\jonathan\\appdata\\local\\temp\\cali bre_0.8.21_tmp_pdyvj8\\nymtdecaltmpfmt.mobi', u'The Great Hunt - Robert Jordan.mobi', u'jonathan.warrick@kindle.com', u'E-book: The Great Hunt', u'Attached, you will find the e-book\n\nThe Great Hunt\n\tby Robert Jordan\n\nin the MOBI format.') {u'notifications': <Queue.Queue instance at 0x098C0F08>, u'abort': <threading._Event object at 0x09643D10>, u'log': <calibre.utils.logging.GUILog object at 0x09643D90>}

I'm using a Kindle 3 with Windows 7 and the most up-to-date version of Calibre. I can e-mail books just fine by attaching them to e-mails sent from my G-mail account. Any idea what could be the probleM?

[Motomaggot]

Having the same issues, did you ever find a solution yet? Do you by any chance run pyTivo on your computer? This one has everyone confused.

matthew