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I am having similar "Email to Kindle" issues with Calibre (v4.2), and am not sure what to do. Tried to check everything I have found on similar threads, but have not been having any success.

Issue: The job fails when trying to email to Kindle

Error Message when Trying with GMX:

Spoiler:

Error Message when Trying with GMail:

Spoiler:

Details and Confirmations:

File type of books was MOBI (two different books used in tests, both actual books).
Kindle address was confirmed, and when I tried to send a file attached to an email from my GMail account, it worked fine. Same initial issue with another Kindle address (my mother's).
The GMX address was created for this, and I enabled the option "Enable access to this account via POP3 and IMAP" in their settings. In Calibre's options, I used the default Hostname (mail.gmx.com), with TLS encryption and port 587. Username (including gmx bit at end) and password were checked, and a test email to some other email addresses works fine.
Used my current GMail address next (after approximately infinite errors). I set up Calibre as an allowed app at security.gmail.com, and got an app-specific password. In Calibre's options, I used the Hostname (smtp.gmx.com), with TLS encryption and port 587. Username (including gmail bit at end) and password were checked, and a test email to some other email addresses works fine.

My apologies for any incorrect terminology, as this is all fairly unfamiliar to me. Any suggestions or help on what to do next would be greatly appreciated - I am not sure what else to do (or what I have done wrong).

Thank you for any help (and thank you even if no help - the answers on previous threads are very good, and I appreciate all the time and effort you guys spend on helping people).

11-02-2019, 04:08 PM	#27
sajfsajf Junior Member Posts: 1 Karma: 10 Join Date: Nov 2019 Device: None	Calibre Email to Kindle Issue I am having similar "Email to Kindle" issues with Calibre (v4.2), and am not sure what to do. Tried to check everything I have found on similar threads, but have not been having any success. Issue: The job fails when trying to email to Kindle Error Message when Trying with GMX: Spoiler: Starting job: Email TestBook to censoreduser@kindle.com connect: (u'mail.gmx.com', 587) connect: (u'mail.gmx.com', 587) reply: '220 gmx.com (mrgmx004) Nemesis ESMTP Service ready\r\n' reply: retcode (220); Msg: gmx.com (mrgmx004) Nemesis ESMTP Service ready connect: gmx.com (mrgmx004) Nemesis ESMTP Service ready send: u'ehlo CensoredComp.domain.actdsltmp\r\n' reply: '250-gmx.com Hello CensoredComp.domain.actdsltmp [CensoredIP]\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 CensoredComp.domain.actdsltmp [CensoredIP] 8BITMIME AUTH LOGIN PLAIN SIZE 69920427 STARTTLS send: 'STARTTLS\r\n' reply: '220 OK\r\n' reply: retcode (220); Msg: OK send: u'ehlo CensoredComp.domain.actdsltmp\r\n' reply: '250-gmx.com Hello CensoredComp.domain.actdsltmp [CensoredIP]\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 CensoredComp.domain.actdsltmp [CensoredIP] 8BITMIME AUTH LOGIN PLAIN SIZE 69920427 send: AUTH <censored> reply: '235 Authentication succeeded\r\n' reply: retcode (235); Msg: Authentication succeeded send: u'mail FROM:<censoreduser@gmx.com> size=3477720\r\n' reply: '250 Requested mail action okay, completed\r\n' reply: retcode (250); Msg: Requested mail action okay, completed send: u'rcpt TO:<censoreduser@kindle.com>\r\n' reply: '250 OK\r\n' reply: retcode (250); Msg: OK send: 'data\r\n' reply: '354 Start mail input; end with <CRLF>.<CRLF>\r\n' reply: retcode (354); Msg: Start mail input; end with <CRLF>.<CRLF> data: (354, 'Start mail input; end with <CRLF>.<CRLF>') send: 'Content-Type: multipart/mixed; boundary="===============1444180317=="\r\nMIME-Version: 1.0\r\nSubje... send: 'quit\r\n' Sending failed... Traceback (most recent call last): File "site-packages\calibre\gui2\email.py", line 45, in run File "site-packages\calibre\gui2\email.py", line 135, in sendmail File "site-packages\calibre\utils\smtp.py", line 185, in sendmail File "site-packages\calibre\utils\smtplib.py", line 774, in sendmail File "site-packages\calibre\utils\smtplib.py", line 532, in data File "site-packages\calibre\utils\smtplib.py", line 354, in send SMTPServerDisconnected: Server not connected Retrying in 1 seconds... Waiting 1 seconds before sending, to avoid being marked as spam. You can control this delay via Preferences->Tweaks connect: (u'mail.gmx.com', 587) connect: (u'mail.gmx.com', 587) reply: '220 gmx.com (mrgmx004) Nemesis ESMTP Service ready\r\n' reply: retcode (220); Msg: gmx.com (mrgmx004) Nemesis ESMTP Service ready connect: gmx.com (mrgmx004) Nemesis ESMTP Service ready send: u'ehlo CensoredComp.domain.actdsltmp\r\n' reply: '250-gmx.com Hello CensoredComp.domain.actdsltmp [CensoredIP]\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 CensoredComp.domain.actdsltmp [CensoredIP] 8BITMIME AUTH LOGIN PLAIN SIZE 69920427 STARTTLS send: 'STARTTLS\r\n' reply: '220 OK\r\n' reply: retcode (220); Msg: OK send: u'ehlo CensoredComp.domain.actdsltmp\r\n' reply: '250-gmx.com Hello CensoredComp.domain.actdsltmp [CensoredIP]\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 CensoredComp.domain.actdsltmp [CensoredIP] 8BITMIME AUTH LOGIN PLAIN SIZE 69920427 send: AUTH <censored> reply: '235 Authentication succeeded\r\n' reply: retcode (235); Msg: Authentication succeeded send: u'mail FROM:<censoreduser@gmx.com> size=3477720\r\n' reply: '250 Requested mail action okay, completed\r\n' reply: retcode (250); Msg: Requested mail action okay, completed send: u'rcpt TO:<censoreduser@kindle.com>\r\n' reply: '250 OK\r\n' reply: retcode (250); Msg: OK send: 'data\r\n' reply: '354 Start mail input; end with <CRLF>.<CRLF>\r\n' reply: retcode (354); Msg: Start mail input; end with <CRLF>.<CRLF> data: (354, 'Start mail input; end with <CRLF>.<CRLF>') send: 'Content-Type: multipart/mixed; boundary="===============1051987160=="\r\nMIME-Version: 1.0\r\nSubje... send: 'quit\r\n' Sending failed... Traceback (most recent call last): File "site-packages\calibre\gui2\email.py", line 45, in run File "site-packages\calibre\gui2\email.py", line 135, in sendmail File "site-packages\calibre\utils\smtp.py", line 185, in sendmail File "site-packages\calibre\utils\smtplib.py", line 774, in sendmail File "site-packages\calibre\utils\smtplib.py", line 532, in data File "site-packages\calibre\utils\smtplib.py", line 354, in send SMTPServerDisconnected: Server not connected Job: "Email TestBook1 to censoreduser@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 102, in __call__ SMTPServerDisconnected: Server not connected Called with args: (u'C:\\Users\\censoreduser\\AppData\\Local\\Temp\\ calibre_jpl6v6\\wsagyocaltmpfmt.mobi', u'TestBook1 - TestAuthor.mobi', u'censoreduser@kindle.com', u'E-book: TestBook1', u'Attached, you will find the e-book\n\nTestBook1\n\tby TestAuthor\n\nin the MOBI format.') {u'notifications': <Queue.Queue instance at 0x0000023EA38AEBC8>, u'log': <calibre.utils.logging.GUILog object at 0x0000023EA38AE9C8>, u'abort': <threading._Event object at 0x0000023EA38AE888>} Error Message when Trying with GMail: Spoiler: Starting job: Email TestBook2 to censoreduser@kindle.com connect: (u'smtp.gmail.com', 587) connect: (u'smtp.gmail.com', 587) reply: '220 smtp.gmail.com ESMTP l14sm3270311qkj.61 - gsmtp\r\n' reply: retcode (220); Msg: smtp.gmail.com ESMTP l14sm3270311qkj.61 - gsmtp connect: smtp.gmail.com ESMTP l14sm3270311qkj.61 - gsmtp send: u'ehlo CensoredComp.domain.actdsltmp\r\n' reply: '250-smtp.gmail.com at your service, [CensoredIP]\r\n' reply: '250-SIZE 35882577\r\n' reply: '250-8BITMIME\r\n' reply: '250-STARTTLS\r\n' reply: '250-ENHANCEDSTATUSCODES\r\n' reply: '250-PIPELINING\r\n' reply: '250-CHUNKING\r\n' reply: '250 SMTPUTF8\r\n' reply: retcode (250); Msg: smtp.gmail.com at your service, [CensoredIP] SIZE 35882577 8BITMIME STARTTLS ENHANCEDSTATUSCODES PIPELINING CHUNKING SMTPUTF8 send: 'STARTTLS\r\n' reply: '220 2.0.0 Ready to start TLS\r\n' reply: retcode (220); Msg: 2.0.0 Ready to start TLS send: u'ehlo CensoredComp.domain.actdsltmp\r\n' reply: '250-smtp.gmail.com at your service, [CensoredIP]\r\n' reply: '250-SIZE 35882577\r\n' reply: '250-8BITMIME\r\n' reply: '250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n' reply: '250-ENHANCEDSTATUSCODES\r\n' reply: '250-PIPELINING\r\n' reply: '250-CHUNKING\r\n' reply: '250 SMTPUTF8\r\n' reply: retcode (250); Msg: smtp.gmail.com at your service, [CensoredIP] SIZE 35882577 8BITMIME AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH ENHANCEDSTATUSCODES PIPELINING CHUNKING SMTPUTF8 send: AUTH <censored> reply: '235 2.7.0 Accepted\r\n' reply: retcode (235); Msg: 2.7.0 Accepted send: u'mail FROM:<censoreduser@gmail.com> size=6800036\r\n' reply: '250 2.1.0 OK l14sm3270311qkj.61 - gsmtp\r\n' reply: retcode (250); Msg: 2.1.0 OK l14sm3270311qkj.61 - gsmtp send: u'rcpt TO:<censoreduser@kindle.com>\r\n' reply: '250 2.1.5 OK l14sm3270311qkj.61 - gsmtp\r\n' reply: retcode (250); Msg: 2.1.5 OK l14sm3270311qkj.61 - gsmtp send: 'data\r\n' reply: '354 Go ahead l14sm3270311qkj.61 - gsmtp\r\n' reply: retcode (354); Msg: Go ahead l14sm3270311qkj.61 - gsmtp data: (354, 'Go ahead l14sm3270311qkj.61 - gsmtp') send: 'Content-Type: multipart/mixed; boundary="===============0775040686=="\r\nMIME-Version: 1.0\r\nSubje... send: 'quit\r\n' Sending failed... Traceback (most recent call last): File "site-packages\calibre\gui2\email.py", line 45, in run File "site-packages\calibre\gui2\email.py", line 135, in sendmail File "site-packages\calibre\utils\smtp.py", line 185, in sendmail File "site-packages\calibre\utils\smtplib.py", line 774, in sendmail File "site-packages\calibre\utils\smtplib.py", line 532, in data File "site-packages\calibre\utils\smtplib.py", line 354, in send SMTPServerDisconnected: Server not connected Retrying in 1 seconds... Waiting 1 seconds before sending, to avoid being marked as spam. You can control this delay via Preferences->Tweaks connect: (u'smtp.gmail.com', 587) connect: (u'smtp.gmail.com', 587) reply: '220 smtp.gmail.com ESMTP z70sm6137007qkb.60 - gsmtp\r\n' reply: retcode (220); Msg: smtp.gmail.com ESMTP z70sm6137007qkb.60 - gsmtp connect: smtp.gmail.com ESMTP z70sm6137007qkb.60 - gsmtp send: u'ehlo CensoredComp.domain.actdsltmp\r\n' reply: '250-smtp.gmail.com at your service, [CensoredIP]\r\n' reply: '250-SIZE 35882577\r\n' reply: '250-8BITMIME\r\n' reply: '250-STARTTLS\r\n' reply: '250-ENHANCEDSTATUSCODES\r\n' reply: '250-PIPELINING\r\n' reply: '250-CHUNKING\r\n' reply: '250 SMTPUTF8\r\n' reply: retcode (250); Msg: smtp.gmail.com at your service, [CensoredIP] SIZE 35882577 8BITMIME STARTTLS ENHANCEDSTATUSCODES PIPELINING CHUNKING SMTPUTF8 send: 'STARTTLS\r\n' reply: '220 2.0.0 Ready to start TLS\r\n' reply: retcode (220); Msg: 2.0.0 Ready to start TLS send: u'ehlo CensoredComp.domain.actdsltmp\r\n' reply: '250-smtp.gmail.com at your service, [CensoredIP]\r\n' reply: '250-SIZE 35882577\r\n' reply: '250-8BITMIME\r\n' reply: '250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n' reply: '250-ENHANCEDSTATUSCODES\r\n' reply: '250-PIPELINING\r\n' reply: '250-CHUNKING\r\n' reply: '250 SMTPUTF8\r\n' reply: retcode (250); Msg: smtp.gmail.com at your service, [CensoredIP] SIZE 35882577 8BITMIME AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH ENHANCEDSTATUSCODES PIPELINING CHUNKING SMTPUTF8 send: AUTH <censored> reply: '235 2.7.0 Accepted\r\n' reply: retcode (235); Msg: 2.7.0 Accepted send: u'mail FROM:<censoreduser@gmail.com> size=6800036\r\n' reply: '250 2.1.0 OK z70sm6137007qkb.60 - gsmtp\r\n' reply: retcode (250); Msg: 2.1.0 OK z70sm6137007qkb.60 - gsmtp send: u'rcpt TO:<censoreduser@kindle.com>\r\n' reply: '250 2.1.5 OK z70sm6137007qkb.60 - gsmtp\r\n' reply: retcode (250); Msg: 2.1.5 OK z70sm6137007qkb.60 - gsmtp send: 'data\r\n' reply: '354 Go ahead z70sm6137007qkb.60 - gsmtp\r\n' reply: retcode (354); Msg: Go ahead z70sm6137007qkb.60 - gsmtp data: (354, 'Go ahead z70sm6137007qkb.60 - gsmtp') send: 'Content-Type: multipart/mixed; boundary="===============1347068378=="\r\nMIME-Version: 1.0\r\nSubje... send: 'quit\r\n' Sending failed... Traceback (most recent call last): File "site-packages\calibre\gui2\email.py", line 45, in run File "site-packages\calibre\gui2\email.py", line 135, in sendmail File "site-packages\calibre\utils\smtp.py", line 185, in sendmail File "site-packages\calibre\utils\smtplib.py", line 774, in sendmail File "site-packages\calibre\utils\smtplib.py", line 532, in data File "site-packages\calibre\utils\smtplib.py", line 354, in send SMTPServerDisconnected: Server not connected Job: "Email TestBook2 to censoreduser@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 102, in __call__ SMTPServerDisconnected: Server not connected Called with args: (u'C:\\Users\\censored\\AppData\\Local\\Temp\\cali bre_jpl6v6\\bulclbcaltmpfmt.mobi', u'TestBook2 - TestAuthor.mobi', u'censoreduser@kindle.com', u'E-book: TestBook2', u'Attached, you will find the e-book\n\nTestBook2\n\tby TestAuthor\n\nin the MOBI format.') {u'notifications': <Queue.Queue instance at 0x0000023EA0C37B08>, u'log': <calibre.utils.logging.GUILog object at 0x0000023EA0AEF748>, u'abort': <threading._Event object at 0x0000023EA0AEF188>} Details and Confirmations: File type of books was MOBI (two different books used in tests, both actual books). Kindle address was confirmed, and when I tried to send a file attached to an email from my GMail account, it worked fine. Same initial issue with another Kindle address (my mother's). The GMX address was created for this, and I enabled the option "Enable access to this account via POP3 and IMAP" in their settings. In Calibre's options, I used the default Hostname (mail.gmx.com), with TLS encryption and port 587. Username (including gmx bit at end) and password were checked, and a test email to some other email addresses works fine. Used my current GMail address next (after approximately infinite errors). I set up Calibre as an allowed app at security.gmail.com, and got an app-specific password. In Calibre's options, I used the Hostname (smtp.gmx.com), with TLS encryption and port 587. Username (including gmail bit at end) and password were checked, and a test email to some other email addresses works fine. My apologies for any incorrect terminology, as this is all fairly unfamiliar to me. Any suggestions or help on what to do next would be greatly appreciated - I am not sure what else to do (or what I have done wrong). Thank you for any help (and thank you even if no help - the answers on previous threads are very good, and I appreciate all the time and effort you guys spend on helping people).