Can someone tell me what I am doing wrong?

[Sydney's Mom]

I used to be able to send books to my PW, my Fire, my husband's Fire. But I had to refresh Windows yesterday. I got everything working the way I like it, but went to send a book, and got and error message

Spoiler:

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: error(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 1 seconds...

Waiting 1 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks

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: error(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 Fierce Urgency of Now: Lyndon Johnson, Congress, and the Battle for the Great Society to dlraymer@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: error(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\\Debra\\AppData\\Local\\Temp\\calibre _gzgzua\\tpimw7caltmpfmt.mobi', u'The Fierce Urgency of Now_ Lyndon Johnson, Congress, and the Battle for the Great Society - Julian E. Zelizer.mobi', u'dlraymer@kindle.com', u'E-book: The Fierce Urgency of Now: Lyndon Johnson, Congress, and the Battle for the Great Society', u'Attached, you will find the e-book\n\nThe Fierce Urgency of Now: Lyndon Johnson, Congress, and the Battle for the Great Society\n\tby Julian E. Zelizer\n\nin the MOBI format.') {u'abort': <threading._Event object at 0x0CFA3870>, u'notifications': <Queue.Queue instance at 0x0AE06E90>, u'log': <calibre.utils.logging.GUILog object at 0x0CFA33F0>}

I am using my gmail address to send from. Any ideas would be greatly appreciated

[eschwartz]

Is calibre being blocked by a firewall?

[Sydney's Mom]

Turned off the firewall. Same messages

This is like a brand new computer, and brand new Calibre. I am checking to see if I might have changed something else. I wasn't getting metadata downloads of the book summary, but I had turned off downloading comments. I will report back if I find anything. I really love sending by email, but sideloading is effective, as well.

[Sydney's Mom]

Tried to set up a proxy server. Still getting:

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

[Sydney's Mom]

same result on port 80

[BetterRed]

@Sydney's Mom - Have you read this since your upgrade ==>> I cannot send emails using calibre?

FWIW : I send all mail via my ISP's mail server, if that's not there then I've probably lost my internet connect. And if there's a problem at least there's someone I can call who has skin in the game.

BR

[eschwartz]

Yeah, firewall plus antivirus is the common culprit.

I venture to say your GMail settings are fine, if it worked before.

[PeterT]

For what it's worth here are my gMail settings:

Send eMail from: me@gmail.com
Mail Server:
Hostname: smtp.gmail.com 
Port: 587
Username: me@gmail.com
Password: Application specific gMail password 
Encryption: TLS

[gbm]

Originally Posted by PeterT

For what it's worth here are my gMail settings:

Send eMail from: me@gmail.com
Mail Server:
Hostname: smtp.gmail.com 
Port: 587
Username: me@gmail.com
Password: Application specific gMail password 
Encryption: TLS

The Application specific gMail password, I have run into that with other programs.

Also increase your wait time to 15 seconds, that was in a post sometime ago.

bernie

[eschwartz]

I simply enabled "less secure" apps. (Scare quotes deliberate.)

That email address isn't important enough to care about.

[kovidgoyal]

I recommend not using gmail. In the last year or so, gmail has introduced various "security" features that make using it from anything other than the web interface *cough*ad delivery interface*cough* much harder.

Instead, create a free account at gmx or hotmail and use that. Don't forget to add the new email address to the allowed email address in your amazon manage kindle page.

Personally, I use a throwaway account at GMX I created for just this purpose.

[Sydney's Mom]

Originally Posted by kovidgoyal

I recommend not using gmail. In the last year or so, gmail has introduced various "security" features that make using it from anything other than the web interface *cough*ad delivery interface*cough* much harder.

Instead, create a free account at gmx or hotmail and use that. Don't forget to add the new email address to the allowed email address in your amazon manage kindle page.

Personally, I use a throwaway account at GMX I created for just this purpose.

Thanks, but GMX was not working for me. Kept getting a page not found-I couldn't sign up! I turned off my darn firewall, and I still couldn't sign up.

[eschwartz]

Well, I suspect the problem isn't GMail anyway, not if it used to work mere days ago.

Anyway, you can always make sure as I said in the other thread, by checking the settings for "Less Secure" Apps.

It does seem that calibre cannot connect to the internet.
Does metadata download work?

Have you checked your antivirus in addition to the firewall?

[Sydney's Mom]

Originally Posted by PeterT

For what it's worth here are my gMail settings:

Send eMail from: me@gmail.com
Mail Server:
Hostname: smtp.gmail.com 
Port: 587
Username: me@gmail.com
Password: Application specific gMail password 
Encryption: TLS

This did it! Thanks everyone-K for you!

[Sydney's Mom]

Originally Posted by gbm

Also increase your wait time to 15 seconds, that was in a post sometime ago.

bernie

Can you please tell me where to do this?