Send to Kindle email not functioning

ellie0303 · 12-20-2018, 08:46 AM

I am running MacOS Mohave 10.14.2 with no antivirus software. Looking for any insights on how to fix the the following error when running a test:

Traceback (most recent call last):
File "site-packages/calibre/gui2/wizard/send_email.py", line 207, in test_email_settings
File "site-packages/calibre/utils/smtp.py", line 136, in sendmail
File "site-packages/calibre/utils/smtp.py", line 128, in sendmail_direct
IOError: Failed to send mail: error(60, 'Operation timed out')

Log:
Find mail exchanger for kindle.com
Traceback (most recent call last):
File "site-packages/calibre/utils/smtp.py", line 121, in sendmail_direct
File "site-packages/calibre/utils/smtplib.py", line 336, in connect
File "site-packages/calibre/utils/smtplib.py", line 310, in _get_socket
File "lib/python2.7/socket.py", line 575, in create_connection
error: [Errno 60] Operation timed out

kovidgoyal · 12-20-2018, 10:04 AM

Follow the steps here: https://manual.calibre-ebook.com/faq...-using-calibre

NSILMike · 12-20-2018, 11:46 AM

Quote:

Originally Posted by ellie0303

I am running MacOS Mohave 10.14.2 with no antivirus software.[snipped]

Just FYI, you're crazy not to run antivirus even on a Mac. There are several highly rated free antivirus apps... so no need to pay. https://download.cnet.com/security-antivirus/mac/

ellie0303 · 12-20-2018, 05:14 PM

Thanks. I had actually followed those instructions and posted because they don't seem to be working for me. I am sure I am doing something wrong. I have a gmx account, set to allow SMTP, have the email address set up on Amazon, and don't have anti-virus. I was hoping the error message revealed something I am missing.

kovidgoyal · 12-20-2018, 09:57 PM

According to the error message you are not using an email relay such as GMX, but sending email directly.

Bola de Fogo · 12-22-2018, 07:24 PM

Sudenlly I started to have problems with email sending too. Using GMX. Someone knows what to do?

connect: (u'mail.gmx.com', 587)
connect: (u'mail.gmx.com', 587)
reply: '220 gmx.com (mrgmx101) Nemesis ESMTP Service ready\r\n'
reply: retcode (220); Msg: gmx.com (mrgmx101) Nemesis ESMTP Service ready
connect: gmx.com (mrgmx101) Nemesis ESMTP Service ready
send: 'ehlo [192.168.0.11]\r\n'
reply: '250-gmx.com Hello [192.168.0.11] [191.180.209.108]\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN\r\n'
reply: '250-SIZE 69920427\r\n'
reply: '250 STARTTLS\r\n'
reply: retcode (250); Msg: gmx.com Hello [192.168.0.11] [191.180.209.108]
8BITMIME
AUTH LOGIN PLAIN
SIZE 69920427
STARTTLS
send: 'STARTTLS\r\n'
reply: '220 OK\r\n'
reply: retcode (220); Msg: OK
send: 'ehlo [192.168.0.11]\r\n'
reply: '250-gmx.com Hello [192.168.0.11] [191.180.209.108]\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN\r\n'
reply: '250 SIZE 69920427\r\n'
reply: retcode (250); Msg: gmx.com Hello [192.168.0.11] [191.180.209.108]
8BITMIME
AUTH LOGIN PLAIN
SIZE 69920427
send: AUTH
reply: '535 Authentication credentials invalid\r\n'
reply: retcode (535); Msg: Authentication credentials invalid

kovidgoyal · 12-22-2018, 10:01 PM

reply: '535 Authentication credentials invalid\r\n'

that line means gmx is saying your username/password are incorrect. Rememberthat gmx user names are full email addresses.

Bola de Fogo · 12-23-2018, 11:49 AM

It seems that GMX deleted my account (cant create a new one either).

Changed to Hotmail and it worked fine.

Leilani · 01-10-2019, 12:00 AM

Quote:

Originally Posted by Bola de Fogo

It seems that GMX deleted my account (cant create a new one either).

Changed to Hotmail and it worked fine.

I was able to mail books last wee, but I tried now and the send is failing and I tried to login to my gmx account and mine appears to be deleted as well.

ovillo · 01-10-2019, 03:21 AM

Same thing happening to me. Seems gmx has deleted our accounts. :/

BdBaldy · 01-11-2019, 01:01 AM

I don't understand GMX, but how do you restore or correct the information in order for the email to work again. Something happened without me doing anything and now it won't work.

ovillo · 01-18-2019, 02:48 AM

Quote:

Originally Posted by BdBaldy

I don't understand GMX, but how do you restore or correct the information in order for the email to work again. Something happened without me doing anything and now it won't work.

Try logging in to gmx.com. Likely, as happened to others , your account has been deleted, and you need to use another one to send to your kindle.

tomwitt · 04-18-2021, 02:08 PM

I know this message is kind of old but it's one of the first Google hits to come up when using Google to search for a specific error message when attempting to setup email sending of ebooks in Calibre.

Trying to setup Calibre on a chromebook and was testing the sending of ebooks using a kindle email account through GMX.com and got the "invalid credentials" message.

Upon looking at my GMX inbox, I had received a message from GMX that an email program was trying to interact with their servers but that functionality was currently turned off for my account.

I had to specifically enable POP/IMAP access for my GMX account. After enabling, I was able to successfully send a test email in Calibre using my GMX.com credentials.

12-20-2018, 08:46 AM	#1
ellie0303 Junior Member Posts: 6 Karma: 10 Join Date: Dec 2018 Device: Kindle	Send to Kindle email not functioning I am running MacOS Mohave 10.14.2 with no antivirus software. Looking for any insights on how to fix the the following error when running a test: Traceback (most recent call last): File "site-packages/calibre/gui2/wizard/send_email.py", line 207, in test_email_settings File "site-packages/calibre/utils/smtp.py", line 136, in sendmail File "site-packages/calibre/utils/smtp.py", line 128, in sendmail_direct IOError: Failed to send mail: error(60, 'Operation timed out') Log: Find mail exchanger for kindle.com Traceback (most recent call last): File "site-packages/calibre/utils/smtp.py", line 121, in sendmail_direct File "site-packages/calibre/utils/smtplib.py", line 336, in connect File "site-packages/calibre/utils/smtplib.py", line 310, in _get_socket File "lib/python2.7/socket.py", line 575, in create_connection error: [Errno 60] Operation timed out

12-20-2018, 05:14 PM	#4
ellie0303 Junior Member Posts: 6 Karma: 10 Join Date: Dec 2018 Device: Kindle	Thanks, @kovidgoyal Thanks. I had actually followed those instructions and posted because they don't seem to be working for me. I am sure I am doing something wrong. I have a gmx account, set to allow SMTP, have the email address set up on Amazon, and don't have anti-virus. I was hoping the error message revealed something I am missing.

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12-20-2018, 10:04 AM	#2
kovidgoyal creator of calibre Posts: 43,858 Karma: 22666666 Join Date: Oct 2006 Location: Mumbai, India Device: Various	Follow the steps here: https://manual.calibre-ebook.com/faq...-using-calibre

12-20-2018, 09:57 PM	#5
kovidgoyal creator of calibre Posts: 43,858 Karma: 22666666 Join Date: Oct 2006 Location: Mumbai, India Device: Various	According to the error message you are not using an email relay such as GMX, but sending email directly.

12-22-2018, 07:24 PM	#6
Bola de Fogo Member Posts: 21 Karma: 10 Join Date: May 2016 Device: Kindle Paper White	Sudenlly I started to have problems with email sending too. Using GMX. Someone knows what to do? connect: (u'mail.gmx.com', 587) connect: (u'mail.gmx.com', 587) reply: '220 gmx.com (mrgmx101) Nemesis ESMTP Service ready\r\n' reply: retcode (220); Msg: gmx.com (mrgmx101) Nemesis ESMTP Service ready connect: gmx.com (mrgmx101) Nemesis ESMTP Service ready send: 'ehlo [192.168.0.11]\r\n' reply: '250-gmx.com Hello [192.168.0.11] [191.180.209.108]\r\n' reply: '250-8BITMIME\r\n' reply: '250-AUTH LOGIN PLAIN\r\n' reply: '250-SIZE 69920427\r\n' reply: '250 STARTTLS\r\n' reply: retcode (250); Msg: gmx.com Hello [192.168.0.11] [191.180.209.108] 8BITMIME AUTH LOGIN PLAIN SIZE 69920427 STARTTLS send: 'STARTTLS\r\n' reply: '220 OK\r\n' reply: retcode (220); Msg: OK send: 'ehlo [192.168.0.11]\r\n' reply: '250-gmx.com Hello [192.168.0.11] [191.180.209.108]\r\n' reply: '250-8BITMIME\r\n' reply: '250-AUTH LOGIN PLAIN\r\n' reply: '250 SIZE 69920427\r\n' reply: retcode (250); Msg: gmx.com Hello [192.168.0.11] [191.180.209.108] 8BITMIME AUTH LOGIN PLAIN SIZE 69920427 send: AUTH reply: '535 Authentication credentials invalid\r\n' reply: retcode (535); Msg: Authentication credentials invalid

12-22-2018, 10:01 PM	#7
kovidgoyal creator of calibre Posts: 43,858 Karma: 22666666 Join Date: Oct 2006 Location: Mumbai, India Device: Various	reply: '535 Authentication credentials invalid\r\n' that line means gmx is saying your username/password are incorrect. Rememberthat gmx user names are full email addresses.

12-23-2018, 11:49 AM	#8
Bola de Fogo Member Posts: 21 Karma: 10 Join Date: May 2016 Device: Kindle Paper White	It seems that GMX deleted my account (cant create a new one either). Changed to Hotmail and it worked fine.

01-10-2019, 03:21 AM	#10
ovillo Junior Member Posts: 2 Karma: 10 Join Date: Jan 2019 Device: Kindle paperwhite	Same thing happening to me. Seems gmx has deleted our accounts. :/

01-11-2019, 01:01 AM	#11
BdBaldy Junior Member Posts: 1 Karma: 10 Join Date: Jan 2019 Device: kindle	I don't understand GMX, but how do you restore or correct the information in order for the email to work again. Something happened without me doing anything and now it won't work.

04-18-2021, 02:08 PM	#13
tomwitt Junior Member Posts: 5 Karma: 80 Join Date: Apr 2011 Device: nook color	I know this message is kind of old but it's one of the first Google hits to come up when using Google to search for a specific error message when attempting to setup email sending of ebooks in Calibre. Trying to setup Calibre on a chromebook and was testing the sending of ebooks using a kindle email account through GMX.com and got the "invalid credentials" message. Upon looking at my GMX inbox, I had received a message from GMX that an email program was trying to interact with their servers but that functionality was currently turned off for my account. I had to specifically enable POP/IMAP access for my GMX account. After enabling, I was able to successfully send a test email in Calibre using my GMX.com credentials.