Email to Pocketbook Failed with gmx

[Amalthia]

Hello,

Sometimes when I use email to Pocketbook it works and sometimes it does not and this is the error message I see when it fails.

What is odd is at the top it says it's trying to email the title "A Fork in the Road" however by the time you get to the end of the error message "Called with args" I see weird epub file names and nothing at all that looks like the title I'm trying to send to my Pocketbook.

I'm hoping someone may know where that information is coming from? I've tried deleting temp directories but I didn't want to go overboard just in case I broke something.

I'd appreciate any and all help.
Thanks,
Amalthia

calibre, version 9.6.0 (win32, embedded-python: True)
Failed to email book: Failed: Email A Fork in the Road to fake-user-name@pbsync.com

Starting job: Email A Fork in the Road to fake-user-name@pbsync.com 
connect: to ('mail.gmx.com', 587) None 
reply: b'220 gmx.net (mrgmx105) Nemesis ESMTP Service ready\r\n' 
reply: retcode (220); Msg: b'gmx.net (mrgmx105) Nemesis ESMTP Service ready' 
connect: b'gmx.net (mrgmx105) Nemesis ESMTP Service ready' 
send: 'ehlo [10.150.1.18]\r\n' 
reply: b'250-gmx.net Hello [10.150.1.18] [137.229.159.18]\r\n' 
reply: b'250-8BITMIME\r\n' 
reply: b'250-SIZE 141557760\r\n' 
reply: b'250 STARTTLS\r\n' 
reply: retcode (250); Msg: b'gmx.net Hello [10.150.1.18] [137.229.159.18]\n8BITMIME\nSIZE 141557760\nSTARTTLS' 
send: 'STARTTLS\r\n' 
reply: b'220 OK\r\n' 
reply: retcode (220); Msg: b'OK' 

Sending failed...
 
Traceback (most recent call last):
  File "calibre\gui2\email.py", line 44, in run
  File "calibre\gui2\email.py", line 131, in sendmail
  File "calibre\utils\smtp.py", line 184, in sendmail
  File "smtplib.py", line 791, in starttls
  File "ssl.py", line 455, in wrap_socket
  File "ssl.py", line 1076, in _create
  File "ssl.py", line 1372, in do_handshake
TimeoutError: [WinError 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 30 seconds...
 
Waiting 30 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks 
connect: to ('mail.gmx.com', 587) None 
reply: b'220 gmx.net (mrgmx104) Nemesis ESMTP Service ready\r\n' 
reply: retcode (220); Msg: b'gmx.net (mrgmx104) Nemesis ESMTP Service ready' 
connect: b'gmx.net (mrgmx104) Nemesis ESMTP Service ready' 
send: 'ehlo [10.150.1.18]\r\n' 
reply: b'250-gmx.net Hello [10.150.1.18] [137.229.159.18]\r\n' 
reply: b'250-8BITMIME\r\n' 
reply: b'250-SIZE 141557760\r\n' 
reply: b'250 STARTTLS\r\n' 
reply: retcode (250); Msg: b'gmx.net Hello [10.150.1.18] [137.229.159.18]\n8BITMIME\nSIZE 141557760\nSTARTTLS' 
send: 'STARTTLS\r\n' 
reply: b'220 OK\r\n' 
reply: retcode (220); Msg: b'OK' 

Sending failed...
 
Traceback (most recent call last):
  File "calibre\gui2\email.py", line 44, in run
  File "calibre\gui2\email.py", line 131, in sendmail
  File "calibre\utils\smtp.py", line 184, in sendmail
  File "smtplib.py", line 791, in starttls
  File "ssl.py", line 455, in wrap_socket
  File "ssl.py", line 1076, in _create
  File "ssl.py", line 1372, in do_handshake
TimeoutError: [WinError 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 A Fork in the Road to fake-user-name@pbsync.com" failed with error: 
Traceback (most recent call last):
  File "calibre\gui2\threaded_jobs.py", line 85, in start_work
  File "calibre\gui2\email.py", line 99, in __call__
  File "calibre\gui2\email.py", line 44, in run
  File "calibre\gui2\email.py", line 131, in sendmail
  File "calibre\utils\smtp.py", line 184, in sendmail
  File "smtplib.py", line 791, in starttls
  File "ssl.py", line 455, in wrap_socket
  File "ssl.py", line 1076, in _create
  File "ssl.py", line 1372, in do_handshake
TimeoutError: [WinError 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: ('C:\\Users\\fake-user-name\\AppData\\Local\\Temp\\
calibre-_uptf960\\_dyin7q9caltmpfmt.epub', '6lpM8j2ECSZnqc5Dl5zoPB.epub', 
'fake-user-name@pbsync.com', 'Smoke script scope phenomenon ear connection attack 
investment smoke', 'Shock democrat sacred wipe possible may spanish at number sentence
 nonetheless brick rose investigation sure conversation amazing sentence number musical
 make ingredient climb sentence.') {'notifications': <queue.Queue object at 
0x0000020635378C20>, 'abort': <threading.Event at 0x20612c590d0: unset>, 'log': 
<calibre.utils.logging.GUILog object at 0x00000206353A4D70>}

[kovidgoyal]

It's a timeout connecting to the email server. Most likely some security software/firewall on your computer is blocking calibre or you are having network issues.

[Amalthia]

Originally Posted by kovidgoyal

It's a timeout connecting to the email server. Most likely some security software/firewall on your computer is blocking calibre or you are having network issues.

I restarted my computer and when I used "Connect/Share" email to email an ebook to my Pocketbook it worked. However, what stood out to me in the log is the subject of the email.

Why is it listing "Bread chart lawsuit hou..." when the story I sent is titled "Fork in the Road?"

Here is a portion of the log:

send: b'From: myfake-email@gmx.com\r\nTo: fake-name-email@pbsync.com\r\nSubject: Bread chart lawsuit hou...

I thought maybe it's timing out the second time I email a book to my device because maybe the subject heading looks like spam?

Thanks,
Amalthia

[kovidgoyal]

No the time out is before the connection is made and the subject even sent. ANd subject and body are randomised when sending to pocketbook's email service by design because they have major issues with parsing email that contains any non-ascii text, it has been that way for years.

[Amalthia]

Hi,

Okay this is good to know, I was a bit worried about the subject being so random and thought maybe my computer had malware or something.

I'll do some more testing with my VPN turned on and off as I email ebooks to my device in Calibre.

Thanks for your fast response,
Amalthia