Failed to send mail

[Plurix]

Hi Folks,

I'm new to this forum. Just installed Calibre latest version 5.29.0 in a Windows 10 Pro on a x64-based Processor with latest updates.

I want to share books with my Amazon kindle app. But when trying to test email settings, after a while (couple of minutes) it throws an error "OSerror: Failed do send email: TimeoutError (10060..."

See full error message below:

Spoiler:

Traceback (most recent call last):
File "calibre\gui2\wizard\send_email.py", line 205, in test_email_settings
File "calibre\utils\smtp.py", line 173, in sendmail
File "calibre\utils\smtp.py", line 153, in sendmail_direct
OSError: Failed to send mail: TimeoutError(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', None, 10060, None)

Log:
Find mail exchanger for kindle.com
connect: ('retail-smtp-in.amazon.com.', 25)
connect: to ('retail-smtp-in.amazon.com.', 25) None
Traceback (most recent call last):
File "calibre\utils\smtp.py", line 143, in sendmail_direct
File "smtplib.py", line 339, in connect
File "smtplib.py", line 308, in _get_socket
File "socket.py", line 808, in create_connection
File "socket.py", line 796, in create_connection
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

The sender email is whitelisted on Amazon (Approved Personal Document E-mail List for that Kindle device), and I have no other issues with my system, which is AMD Ryzen 9 5900X 12-Core Processor, 3.70 GHz, Installed RAM 128 GB, 2.5 TB M.2 SSD.

I can send (share) attached books from my google email with no issues at all.

I double checked a few times the Calibre email settings for any incorrection and I found nothing.

Any heads up deeply appreciated, as I'd like to take advantage of this very convenient Calibre feature.

[kovidgoyal]

See https://manual.calibre-ebook.com/faq...-using-calibre

[Plurix]

Yeah... I tried that as well but yet to be fixed... TY!

In fact, I do not want Calibre keep automatically sending my entire ebooks within it, just the ones I want...

So I think I can live without it...

I just want to send the ones I think it's worth sending to Kindle. In this case, I'd rather send them manually... Less of a hassle....

Thank you so much for your kind attention, though!

[theducks]

Calibre only AUTOMATICALLY sends scheduled NEWS (if that option is ticked).
All the rest(books) are MANUALLY selected. Connect-share:email to <....>

Are you sure you have the correct email address for your device??
Mine is of the style of: xyzz_##@kindle.com

[Plurix]

Originally Posted by theducks

Calibre only AUTOMATICALLY sends scheduled NEWS (if that option is ticked).
All the rest(books) are MANUALLY selected. Connect-share:email to <....>

Are you sure you have the correct email address for your device??
Mine is of the style of: xyzz_##@kindle.com

Thank you TheDucks for letting me know about the ticked option for Auto Schedule

I changed the Send-to-Kindle E-Mail Settings for my device to something like Dummy+Kindle1@kindle.com

Also I complied with the Approved Personal Document Email List Amazon requirement to avoid spam, see image below as an example of what I have:

https://www.dropbox.com/s/zhwtzke4p3...EMAIL.jpg?dl=0

Despite those Email settings, no luck for me.

Again, thanks a lot for the heads up.

[DNSB]

Find mail exchanger for kindle.com
connect: ('retail-smtp-in.amazon.com.', 25)
connect: to ('retail-smtp-in.amazon.com.', 25) None

Why are you trying to send directly to Amazon's SMTP server? You should be sending to your email provider whomever they might be (GMail, GMX, etc.).

[Plurix]

Originally Posted by DNSB

Why are you trying to send directly to Amazon's SMTP server? You should be sending to your email provider whomever they might be (GMail, GMX, etc.).

David, thank you so much for your key remarks. I did several tests and copied just the last one as a sample for the posting. But you led me to investigate further, and... Alas!... Issue resolved!...

I will explain in details below, so anybody else running across it can fix it right away...

When I first tried to set up "Sharing books by email", I entered the "Email server" settings a couple of times as I presumed it should be done. All the attempts failed, though.

See Email server settings here.

Then I noticed the remark "Calibre can optionally use a server to send mail" just below the "Email server" line... It is not exactly clear to me what it means... It is kind of confusing, misleading... Should I leave blank all the fields and Calibre will take care of it?... Or else, is it mandatory to fill all the blanks?... I didn't know what to do... I can't understand the meaning of this remark...

See the remark notice here.

It didn't work when entering the Email server's information (as I mentioned above). So I decided to give it a try by leaving everything blank, but it didn't work either!...

Because of several variables involved, I spent a few hours trying all possible combinations by trial and error.. Until I gave up and decided to post asking for help using the last error message output I got after leaving everything blank:

See Email server fields blank here.

Find mail exchanger for kindle.com
connect: ('retail-smtp-in.amazon.com.', 25)
connect: to ('retail-smtp-in.amazon.com.', 25) None

Again, folks, keep in mind this message pops up only when you try the connection leaving blank all Email server information... At least for me, in my case...

Moving on, this morning I read your (DNSB's) post about the error message above, and decided to address it once and for all... Which I should have done before anything else anyways...

After googling the errors' output, it all boils down to a google user account security settings. I mean, it all depends on how one sets up her/his google account security. Nothing wrong with Calibre. And neither with my server settings either.

Here below are the steps to resolve the issue. Bear in mind, though, I followed these steps in this order below to no avail until I reached the last one, which gave me the expected result (Email successfully sent) after completing it. So I'm not sure you can attain the same result as mine by completing only the last step.

Go to https://myaccount.google.com/security

1. 2SV/TSV (Two Step Verification): Scroll down to Signing in to Google / 2-Step Verification: If you have activated this feature in your google account, turn it off. Most of us may have this feature set, and for good reasons nowadays. I have one google account, though, created just for simple things, no critical / personal / professional information being kept within it, so this feature is turned off for this google account.

2. Less Secure app access: Scroll a little further down (Just below Your Devices) and turn it off as well. Google might consider Calibre's sign-in process as a less secure sign-in technology, which makes your google account more vulnerable. It (presumably) let Calibre use the smtp.gmail.com connection to send the email to kindle.com.

Applying only these two steps above alone didn't work for me because looks like google also blocks your IP when you try to send an email from an otherwise different, unusual location. So here's the last one step that really did the trick for me:

3. Disable Captcha by going to https://accounts.google.com/DisplayUnlockCaptcha and follow the steps to disable it. Afterwards, go back to Calibre and try sending the email test again using the right credentials. It worked for me, it should for you, too...

Email server settings again: See image here.

Click to see Email successfully sent

These settings may vary if you're using other free (or non free) email accounts (hotmail, outlook, gmx, yahoo and so on), in which case you will need to do your own homework.

Again, David, thanks a lot for pointing me to the right direction to address an issue a lot of rookie members may be facing right now.



I also thank you all who took the time, energy and effort to help me with tips and tricks. It's a privilege to be part of such a great support community of ebooks lovers.



Last but not least, IMHO, I wish the developers of Calibre could change the remark line "Calibre can optionally use a server to send mail" to something more meaningful and clear. BTW, if you want Calibre to send email to Kindle, there's nothing optional in this setting. It is a requirement. Indeed. Again, IMHO.

HTH,

Plurix

P.S.: Not sure why, but the Insert Image url coding did not work for me at this time. Had to use Insert Link instead.

[theducks]

Plurix

P.S.: Not sure why, but the Insert Image url coding did not work for me at this time. Had to use Insert Link instead.

You are to new of a MR user for some things to work (anti-Spam protocol).
As you participate, those will be relaxed automatically

[Plurix]

Originally Posted by theducks

You are too new of a MR user for some things to work (anti-Spam protocol).
As you participate, those will be relaxed automatically

I see. Good to know. Thanks TheDucks!

Is there a way to set this thread as [RESOLVED]?...