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I have had a similar problem periodically (not always) in the last two weeks. I use a GMail account for sending and it has worked fine for months. But recently I have been getting this error every once in a while: (How do I run 'CONNECT'?)
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ERROR: Failed to email books: Failed to email the following books:
New York Times
please run connect() first
Traceback (most recent call last):
File "site-packages\calibre\gui2\device.py", line 645, in _send_mails
File "site-packages\calibre\utils\smtp.py", line 108, in sendmail
File "smtplib.py", line 730, in quit
File "smtplib.py", line 362, in docmd
File "smtplib.py", line 318, in putcmd
File "smtplib.py", line 310, in send
SMTPServerDisconnected: please run connect() first
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