Can't seem to get Calibre email settings right

[celinego]

Hi all,

All of a sudden Calibre is having trouble sending to my devices. I'm receiving bounce emails which say "Each of the following recipients was rejected by a remote mail server. The reasons given by the server are included to help you determine why each recipient was rejected.

Recipient: <celineg_iPhone6s@kindle.com>
Reason: 5.7.1 TLS required by recipient"

I'm in the UK and btinternet is my mail provider. Email itself (both webmail and my client, EMClient) are sending and receiving. It's only when I try to send via Calibre I get the bounce back.

I didn't change my Sharing Books by Email settings at all. These WERE
Send email from xxxxxx@btinternet.com (xxxx being my user name)
Hostname: mail.btinternet.com Port 25
Username: xxxxxx@btinternet.com (xxxxx being my user name)
Password: my password and Show is checked so I can see it IS correct
Encryption: None

This WAS working perfectly well till last night but now, it still sends from Calibre but doesn't arrive at my device. Instead I get an immediate bounceback email stating the above 5.7.1 TLS required by recipient" message.

My EMClient settings (I removed the account from EMClient then set it up again and let it autoset everything) to
IMAP
Host: mail.btinternet.com
Port 993
Security Policy: Use SSL/TLS on special port (legacy) (and I think this is how it worked with port 25 above before)
Authentication: Use Identity Credentials (which are input as my username and password)

SMTP
Host: mail.btinternet.com
Port: 587
Security Policy: Use SSL/TLS on special port (legacy)
Authentication: Server requires authentication is checked ...and under that
Use Identity Credentials (input as my username and password same as in IMAP)

I have tried various combination of ports (25, 587, 465) with various combinations of security and just don't seem able to find the right combination to make it work and get the books to get through to my device.

I've also uninstalled and reinstalled both EMClient AND Calibre to see if that would help but nothing has worked yet.

I've also spoken to Tech dept at btinternet. Apart from not using 587 as that's a very old port, they've said use IMAP 993 and SMTP 465 instead. I have tried both those but none of these work either.

When I input to Calibre 465 with Encryption TLS, I get this log in Calibre
"Starting job: Email Stockholm Murders: Broken Mirrors (2) to celineg_iPhone6s@kindle.com
connect: to ('mail.btinternet.com', 465) None

Sending failed...

Traceback (most recent call last):
File "smtplib.py", line 398, in getreply
File "socket.py", line 705, in readinto
ConnectionResetError: [WinError 10054] An existing connection was forcibly closed by the remote host

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
File "calibre\gui2\email.py", line 47, in run
File "calibre\gui2\email.py", line 136, in sendmail
File "calibre\utils\smtp.py", line 171, in sendmail
File "polyglot\smtplib.py", line 36, in __init__
File "smtplib.py", line 255, in __init__
File "smtplib.py", line 343, in connect
File "smtplib.py", line 401, in getreply
smtplib.SMTPServerDisconnected: Connection unexpectedly closed: [WinError 10054] An existing connection was forcibly closed by the remote host


Retrying in 1 seconds...

Waiting 1 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: to ('mail.btinternet.com', 465) None

Sending failed...

Traceback (most recent call last):
File "smtplib.py", line 398, in getreply
File "socket.py", line 705, in readinto
ConnectionResetError: [WinError 10054] An existing connection was forcibly closed by the remote host

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
File "calibre\gui2\email.py", line 47, in run
File "calibre\gui2\email.py", line 136, in sendmail
File "calibre\utils\smtp.py", line 171, in sendmail
File "polyglot\smtplib.py", line 36, in __init__
File "smtplib.py", line 255, in __init__
File "smtplib.py", line 343, in connect
File "smtplib.py", line 401, in getreply
smtplib.SMTPServerDisconnected: Connection unexpectedly closed: [WinError 10054] An existing connection was forcibly closed by the remote host

Job: "Email Stockholm Murders: Broken Mirrors (2) to celineg_iPhone6s@kindle.com" failed with error:
Traceback (most recent call last):
File "smtplib.py", line 398, in getreply
File "socket.py", line 705, in readinto
ConnectionResetError: [WinError 10054] An existing connection was forcibly closed by the remote host

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
File "calibre\gui2\threaded_jobs.py", line 82, in start_work
File "calibre\gui2\email.py", line 104, in __call__
File "calibre\gui2\email.py", line 47, in run
File "calibre\gui2\email.py", line 136, in sendmail
File "calibre\utils\smtp.py", line 171, in sendmail
File "polyglot\smtplib.py", line 36, in __init__
File "smtplib.py", line 255, in __init__
File "smtplib.py", line 343, in connect
File "smtplib.py", line 401, in getreply
smtplib.SMTPServerDisconnected: Connection unexpectedly closed: [WinError 10054] An existing connection was forcibly closed by the remote host

Called with args: ('C:\\Users\\celin\\AppData\\Local\\Temp\\calibre_ 2oap0qwk\\gxnqwhpacaltmpfmt.epub', 'Stockholm Murders_ Broken Mirrors (2).epub', 'celineg_iPhone6s@kindle.com', 'Q5rXTgQKDf9l7qNtYgEo64', '6ISOC5574mesGKQotr2a53') {'notifications': <queue.Queue object at 0x000002C9189F2950>, 'abort': <threading.Event object at 0x000002C9189F30A0>, 'log': <calibre.utils.logging.GUILog object at 0x000002C9189F3E20>}

When I input port 465 with Encryption SSL I don't get a Calibre log error, it sends but then I instantly get the bounce email saying 5.7.1 TLS required recipient, the recipient being my iphone 6's kindle email address.

I don't really know what to try next. Last night was all working with port 25 and Encryption None! Please help as this is above my tech knowledge level and I'm pretty desperate now.

Many thanks..... Celine


"

[Quoth]

IMAP vs POP3 really is more for reading and if email reading is on one PC then POP3 makes more sense.

SMTP is for sending.

Make sure the same settings work in a regular email program like Thunderbird.

You have added your own email address to the Kindle Web page management? Not your own Kindle email.
Amazon only accepts sending addresses you have added.

Go Amazon -> Manage Content and Devices -> Preferences
Bottom of page: Personal Document Settings
Add any email address allowed to send to your Kindle.

Elephant in room!
Send To Kindle messes up the format compared to Calibre & convert to AZW3 and USB transfer
USB Transfer is faster and Kindle is charging. No Internet needed.
Send To Kindle gives Amazon a free copy of of whatever it is.

So multiple issues.

[celinego]

Originally Posted by Quoth

IMAP vs POP3 really is more for reading and if email reading is on one PC then POP3 makes more sense.

SMTP is for sending.

Make sure the same settings work in a regular email program like Thunderbird.

You have added your own email address to the Kindle Web page management? Not your own Kindle email.
Amazon only accepts sending addresses you have added.

Go Amazon -> Manage Content and Devices -> Preferences
Bottom of page: Personal Document Settings
Add any email address allowed to send to your Kindle.

Elephant in room!
Send To Kindle messes up the format compared to Calibre & convert to AZW3 and USB transfer
USB Transfer is faster and Kindle is charging. No Internet needed.
Send To Kindle gives Amazon a free copy of of whatever it is.

So multiple issues.

My Amazon account IS set to receive PDOCS from my own email address, not my kindle address. My kindle address is the address I sent to from my calibre library. It's not because I have the wrong or missing addresses, but the wrong mail port settings and suffixes.

That said .... you triggered me to change the settings to the smtp suffix, input port 465 and checked SSL encryption .... and it's working again!!!! So I think my ISP changed the settings again without telling me!. I also checked through historic posts (mine) when it happened before and that was saying they told me THEN they'd changed from the aforesaid to the mail. suffix instead of smtp and changed the port from 587 to 25.
When I actually spoke to a technician on the phone this week, she told me that it doesn't matter if it's incoming or outgoing mail, the suffix will always be mail. for both! I'm still IMAP ... as I prefer that. But thankfully, now all working again. Something so simple can make such a big difference. So, thank you Quoth for the trigger on smtp.

[Quoth]

I tried to cover everything I could think of. Glad you are sorted.

[celinego]

Originally Posted by Quoth

I tried to cover everything I could think of. Glad you are sorted.

very much