Problem sending email to my Kindle account

[Simsky]

Hello everybody,

I am getting some problems to send ebooks from my Calibre library to the mail of my Kindle account. On my Amazon account, I added the sending mail in the list of approved emails to send ebooks. When I send a book attached directly from that email, the book is being received on my kindle.

Yet, when I try to send it via Calibre, there is a time-out.
The sending and receiving emails on Calibre both seem good.
Also, in the preferences, when I try to make the test of the mailing configuration, I am getting that message:

Traceback (most recent call last):
File "site-packages/calibre/gui2/wizard/send_email.py", line 209, in test_email_settings
File "site-packages/calibre/utils/smtp.py", line 162, in sendmail
File "site-packages/calibre/utils/smtp.py", line 143, in sendmail_direct
IOError: Failed to send mail: error(60, 'Operation timed out')


Log:
Find mail exchanger for kindle.com
connect: (u'retail-smtp-in.amazon.com.', 25)
connect: (u'retail-smtp-in.amazon.com.', 25)
Traceback (most recent call last):
File "site-packages/calibre/utils/smtp.py", line 136, in sendmail_direct
File "site-packages/calibre/utils/smtplib.py", line 338, in connect
File "site-packages/calibre/utils/smtplib.py", line 312, in _get_socket
File "lib/python2.7/socket.py", line 575, in create_connection
error: [Errno 60] Operation timed out

I am on Calibre 4.23 running on macOS Catalina 10.15.7.
I think I got it working in the past, but no idea why it is not working now.
I installed the last version but got back to the 4.23 to be able to use DEDRM plugin.

Would someone be able to help me with that issue?

Thank you,
Best Regards,
Simsky

[DNSB]

Trying a connection to retail-smtp-in.amazon.com does not appear to be responding with an expected message similar to "220 retail-smtp-in.amazon.com ESMTP server ready". That address may have worked a few years back but not it does not appear to be working now.

If you use your ISP's SMTP server address with your username/password, what results do you see?

[kovidgoyal]

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

[Simsky]

Thank you, I got it to work filling the smtp server information and all and activating on my gmail account the connections from outside.

Regards,
Julien

[dunhill]

Originally Posted by Simsky

Thank you, I got it to work filling the smtp server information and all and activating on my gmail account the connections from outside.

Regards,
Julien

If you could make a hotmail account it works better than gmail to send mail

[JSWolf]

Originally Posted by dunhill

If you could make a hotmail account it works better than gmail to send mail

Hotmail is for when you absolutely want to lose your email in the blink of an eye. Use Outlook instead.

[ownedbycats]

Originally Posted by JSWolf

Hotmail is for when you absolutely want to lose your email in the blink of an eye. Use Outlook instead.

Question: When was the last time you put hotmail.com into your address bar...?

[BetterRed]

Originally Posted by JSWolf

Hotmail is for when you absolutely want to lose your email in the blink of an eye. Use Outlook instead.

I still use the hotmail account I signed up for when Sabeer Bhatia and Jack Smith owned it. That was in late 1995, when it was called HoTMaiL and the client ran on Solaris. And through its various incarnations I have never lost anything from it -- unlike GMail and Lavabit.

Originally Posted by ownedbycats

Question: When was the last time you put hotmail.com into your address bar...?

Don't think I ever did, before now

BR

[dunhill]

Originally Posted by JSWolf

Hotmail is for when you absolutely want to lose your email in the blink of an eye. Use Outlook instead.

Is not the same?

[JSWolf]

Originally Posted by ownedbycats

Question: When was the last time you put hotmail.com into your address bar...?

Do that and you end up at Outlook. So really, Hotmail is dead.

[Rellwood]

FYI, just so you know that Amazon has stopped showing the author names when emailing to Kindle and just shows the email address it comes from. Unless the fixed it. As of October it was doing that. The only way around this is to use the send to kindle for PC and manually change the author when it shows the books it's about to upload. It only works for one author at a time. So multiple authors need to be singled out. If you just let it go as normal it will show your name or the name the Kindle for PC is registered to as the author.

[binaryhermit]

At least on eInk kindles, it shows the actual author name once you download it.

[Rellwood]

Off topic for the thread, but for this discussion, my parents still use Hotmail from when it first came out, and I still have my 1997 account, they still use the @hotmail.com in their email address, should it be @outlook.com now?

[BetterRed]

Originally Posted by Rellwood

Off topic for the thread, but for this discussion, my parents still use Hotmail from when it first came out, and I still have my 1997 account, they still use the @hotmail.com in their email address, should it be @outlook.com now?

N-O No

I have used my @hotmail account as my primary email account since I created it when it was known as HoTMaiL and was owned by Sabeer Bhatia and Jack Smith before they sold it to Microsoft. It has continued to work through Redmond's frequent renames - MSN Hotmail, Windows Live Mail and Outlook. No point in you changing it, one day they will probably revert to calling it HoTMaiL again. Rellwood@hotmail.com and Rellwood@outlook.com are aliases to the same account on the same service.

I have never never lost anything from my hotmail account. Unlike Gmail, a UK ISP mail account which both lost mail, and I lost everything I had at Lavabit when the NSA shut it down (because Snowden used it).

BR