E-mail to Kindle fails

[mazinho]

Sending ebooks in MOBI format from Calibre to my Kindle fails. Can anyone spot anything in the error log to guide me towards a solution? Which part of the error log would you need (it is long) to spot the issue?

Update: Amazon sent me an e-mail with the following text. It surprises me as I am sending MOBI format. Maybe it helps:

Dear Customer,

Your message to masked@kindle.com, sent at 12:53 PM on Thu, Jul 28, 2022 GMT did not include any attached documents or image files.

The Kindle Personal Document Service can convert and deliver the following types of documents:
Microsoft Word (.doc, .docx)
Rich Text Format (.rtf)
HTML (.htm, .html)
Text (.txt) documents
Archived documents (zip , x-zip) and compressed archived documents
Mobi book

Images that are of type JPEGs (.jpg), GIFs (.gif), Bitmaps (.bmp), and PNG images (.png).
Adobe PDF (.pdf) documents are delivered without conversion to Kindle DX, Second Generation and Latest Generation Kindles.

Conversion of Adobe PDF (.pdf) to Kindle format is done on experimental basis.

If the document(s) that failed belonged to one of the above document types, please ensure the document is not password protected or encrypted. Note that the Latest Generation Kindles support password protected PDFs.

[kovidgoyal]

https://manual.calibre-ebook.com/faq...-of-mobi-files

[koray]

Originally Posted by kovidgoyal

https://manual.calibre-ebook.com/faq...-of-mobi-files

Thanks for the answer! I also have a question on Kindle and epub files. I have set my calibre to send epub format to Kindle, and it works great. Except for the cover images and ability to browse between chapters by swiping up and down. Is this a limitation of Kindle? With mobi files I was able to see covers and browse between chapters by swiping up and down. Another issue is that now covers appear on sleep screen (which didn't happen with mobi files).

Thanks for the great work Kovid Goyal!

K.

[kovidgoyal]

yes its a limitation of amazon. Any issues you have with epubs mailed to kindles can only be because of amazon. Amazon actually converts epub to something else using their own substandard conversion software. And then delivers the end result of that conversion to your kindle.

[bugmen00t]

What's the maximal size of the file that Calibre could sent to email? I've been experimenting with files of different size a while ago and got this error at some point:

Spoiler:

PHP Code:

connect: ('mail.gmx.com', 587) 
connect: to ('mail.gmx.com', 587) None 
reply: b'220 gmx.net (mrgmx004) Nemesis ESMTP Service ready\r\n' 
reply: retcode (220); Msg: b'gmx.net (mrgmx004) Nemesis ESMTP Service ready' 
connect: b'gmx.net (mrgmx004) Nemesis ESMTP Service ready' 
send: 'ehlo [10.8.3.9]\r\n' 
reply: b'250-gmx.net Hello [10.8.3.9] [***.***.***.***]\r\n' 
reply: b'250-8BITMIME\r\n' 
reply: b'250-SIZE 69920427\r\n' 
reply: b'250 STARTTLS\r\n' 
reply: retcode (250); Msg: b'gmx.net Hello [10.8.3.9] [***.***.***.***]\n8BITMIME\nSIZE 69920427\nSTARTTLS' 
send: 'STARTTLS\r\n' 
reply: b'220 OK\r\n' 
reply: retcode (220); Msg: b'OK' 
send: 'ehlo [10.8.3.9]\r\n' 
reply: b'250-gmx.net Hello [10.8.3.9] [***.***.***.***]\r\n' 
reply: b'250-8BITMIME\r\n' 
reply: b'250-AUTH LOGIN PLAIN\r\n' 
reply: b'250 SIZE 69920427\r\n' 
reply: retcode (250); Msg: b'gmx.net Hello [***.***.***.***] [***.***.***.***]\n8BITMIME\nAUTH LOGIN PLAIN\nSIZE 69920427' 
send: AUTH  
reply: b'235 Authentication succeeded\r\n' 
reply: retcode (235); Msg: b'Authentication succeeded' 
send: 'quit\r\n' 
reply: b'221 gmx.net Service closing transmission channel\r\n' 
reply: retcode (221); Msg: b'gmx.net Service closing transmission channel' 

Sending failed...
 
Traceback (most recent call last):
  File "calibre\gui2\email.py", line 48, in run
  File "calibre\gui2\email.py", line 137, in sendmail
  File "calibre\utils\smtp.py", line 184, in sendmail
  File "smtplib.py", line 968, in send_message
  File "email\generator.py", line 116, in flatten
  File "email\generator.py", line 181, in _write
  File "email\generator.py", line 214, in _dispatch
  File "email\generator.py", line 272, in _handle_multipart
  File "email\generator.py", line 116, in flatten
  File "email\generator.py", line 181, in _write
  File "email\generator.py", line 214, in _dispatch
  File "email\generator.py", line 432, in _handle_text
  File "email\generator.py", line 249, in _handle_text
  File "email\generator.py", line 155, in _write_lines
  File "email\generator.py", line 406, in write
MemoryError
 

Retrying in 301 seconds...
 
Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks 


Not sure if it was software error of my FrankenCalibre (portable 5.44 on Windows 7 x64) or my ancient laptop just ran out of RAM.

[jhowell]

Originally Posted by bugmen00t

Not sure if it was software error of my FrankenCalibre (portable 5.44 on Windows 7 x64) or my ancient laptop just ran out of RAM.

Portable builds of calibre prior to version 6 are 32-bit and prone to running out of memory.

[Quoth]

There are four common limits:
The max size the SMTP server will accept.
The max size the local email program (in this case Calibre) will send.
The space free in the receiving Internet server mailbox (and total space).
The max size a client using POP3 or IMAP will retrieve.

I'd normally limit to 20 M byte. You seem to be testing with 69 M Byte?

[bugmen00t]

Originally Posted by jhowell

Portable builds of calibre prior to version 6 are 32-bit and prone to running out of memory.

I didn't knew that portables were 32 bit (or just didn't noticed) because I always just have been unpacking MSI installer and than copy/replace files to "./Calibre Portable/Calibre/" folder.
Highly likely this was the main reason of "MemoryError" message as conversion/sending process is quite RAM-hungry:

Spoiler:

Also as I mentioned it was version 5.44 running on officially unsupported Windows 7 (the last supported version is 3.48 IIRC), so there could be incompatibility problems.

Originally Posted by Quoth

There are four common limits

Originally Posted by Quoth

I'd normally limit to 20 M byte. You seem to be testing with 69 M Byte?

I managed to send 7, 14, 21, 28, 35 and 42 Mb EPUB files to my Kindle via GMX Mail without problems. However when I tried to push 128 Mb monstrosity, I instantly got error message "smtplib.SMTPSenderRefused: (552, b'Requested mail action aborted: exceeded storage allocation', '********************@gmx.com')".

I'd like to run more experiments to find out the maximal limit but have concerns that in the end Amazon will ban my account for such shenanigans.

[CathyA]

Originally Posted by bugmen00t

... I managed to send 7, 14, 21, 28, 35 and 42 Mb EPUB files to my Kindle via GMX Mail without problems. However when I tried to push 128 Mb monstrosity, I instantly got error message "smtplib.SMTPSenderRefused: (552, b'Requested mail action aborted: exceeded storage allocation', '********************@gmx.com')".

I'd like to run more experiments to find out the maximal limit but have concerns that in the end Amazon will ban my account for such shenanigans.

Email services publish the max size for messages. It's trivially easy to find out this info, no need to send many emails to calculate it yourself.

GMX's limit is 50M: https://www.gmx.com/mail/attachment/

Amazon's limit is 50M: https://www.amazon.com/gp/help/custo...NECT4B4ZWHQ8WV

So this is why a 42M file works and 128M file doesn't.

Amazon isn't going to ban your account for sending them files (unless you're doing it in a way that seems like an attack, which this does not). Emailing of documents is a service they provide as part of the Kindle product, and you're allowed to use it. They will just reject any inbound message that's over 50M in size. But in your case, GMX will actually reject it first because their max is also 50M.

[bugmen00t]

Originally Posted by CathyA

So this is why a 42M file works and 128M file doesn't.

Thanks for clarification. Different Kindle models were in my possesion for more than decade but it seems that I never used send-to-email functionality until a couple weeks ago.

My experiments weren't only aimed to calculate maximal possible attachment size, I also used different ebook file formats, image file formats, high- and even absurd image resolutions etc. and to see if Kindles could manage the resulting files Looks like I had had too much free time recently...

[mazinho]

Originally Posted by kovidgoyal

https://manual.calibre-ebook.com/faq...-of-mobi-files

Thank you, this totally answered my question and fixed my issue.