Sending News While Connected to VPN

Loosheesh · 04-28-2022, 02:47 PM

When I'm connected to the VPN, Calibre can't send news to my Kindle; I get an error message ("Failed to email book") with these details:

Spoiler:

Is there a way around this?

DNSB · 04-28-2022, 03:21 PM

Looking at your posted log, you are not able to use DNS to resolve the smtp server address when connected to the VPN. You might want to check what DNS servers are in use when you are connected to the VPN and if you can ping the smtp server when connected to the VPN.

Also I'm not certain you can email directly to a kindle.com address. The only time I've tried it, I have used a gmx.com SMTP server to forward the email to my kindle.com address.

Loosheesh · 04-28-2022, 08:21 PM

Quote:

Originally Posted by DNSB

You might want to check what DNS servers are in use when you are connected to the VPN and if you can ping the smtp server when connected to the VPN.

How would I do that? Thanks in advance.

Quote:

Originally Posted by DNSB

Also I'm not certain you can email directly to a kindle.com address. The only time I've tried it, I have used a gmx.com SMTP server to forward the email to my kindle.com address.

Well, not quite directly; I get the usual verification request email from Amazon and then I get the news in my Kindle library after I confirm.

DNSB · 04-28-2022, 09:26 PM

Quote:

Originally Posted by DNSB

You might want to check what DNS servers are in use when you are connected to the VPN and if you can ping the smtp server when connected to the VPN.

Quote:

Originally Posted by Loosheesh

How would I do that? Thanks in advance.

You would connect to the VPN and then open a command line interface (cmd for Windows, terminal for MacOS and Linux). You should then be able to display the network settings (ipconfig /all for Windows, nmcli or ifconfig or whatever for Linux (there are quite a few options), for MacOS, ipconfig getiflist will return the network adapter list then ipconfig getoption (network adapter name from list) domain_server_name will return the DNS servers in use).

The easy part is the basic ping command on all 3 would be ping kindle.com though using ping -c 4 kindle.com on MacOS and Linus to set the ping count to 4 times is what I generally do so ping -c 4 kindle.com would work.

SUSE Linux Tumbleweed

Code:

localhost:~ # nmcli
ens33: connected to Wired connection 1
        "Intel 82545EM"
        ethernet (e1000), 00:0C:29:55:FA:CE, hw, mtu 1500
        ip4 default
        inet4 192.168.232.132/24
        route4 192.168.232.0/24 metric 100
        route4 default via 192.168.232.2 metric 100
        inet6 fe80::497d:7a5e:2d0f:2f02/64
        route6 fe80::/64 metric 1024

lo: unmanaged
        "lo"
        loopback (unknown), 00:00:00:00:00:00, sw, mtu 65536

DNS configuration:
        servers: 192.168.232.2
        domains: localdomain
        interface: ens33

MacOS Monterey 12.3.1

Code:

davidb@Davids-VMMac ~ % ipconfig getiflist                       
en0
davidb@Davids-VMMac ~ % ipconfig getifaddr en0                   
10.0.0.128
davidb@Davids-VMMac ~ % ipconfig getoption en0 domain_name_server
1.1.1.1

Windows 11 (just the relevant chunk)

Code:

   Description . . . . . . . . . . . : Intel(R) Dual Band Wireless-AC 8265
   Physical Address. . . . . . . . . : 30-24-32-46-CE-FD
   DHCP Enabled. . . . . . . . . . . : Yes
   Autoconfiguration Enabled . . . . : Yes
   IPv4 Address. . . . . . . . . . . : 192.168.127.59(Preferred)
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Lease Obtained. . . . . . . . . . : April 28, 2022 5:50:39 PM
   Lease Expires . . . . . . . . . . : April 30, 2022 5:50:39 PM
   Default Gateway . . . . . . . . . : 10.0.0.1
   DHCP Server . . . . . . . . . . . : 10.0.0.1
   DNS Servers . . . . . . . . . . . : 1.1.1.1
                                       8.8.4.4

Loosheesh · 04-29-2022, 01:14 PM

I checked it based on your instructions and I can't figure what's wrong; everything looks normal

Anyway, I've decided to simply let the news stay in my library and temporarily turn off the VPN to send it manually.

DNSB · 04-29-2022, 10:59 PM

Quote:

Originally Posted by Loosheesh

I checked it based on your instructions and I can't figure what's wrong; everything looks normal

Anyway, I've decided to simply let the news stay in my library and temporarily turn off the VPN to send it manually.

One last question. What VPN are you using?

Loosheesh · 04-30-2022, 09:24 AM

Quote:

Originally Posted by DNSB

One last question. What VPN are you using?

I'm now using ExpressVPN but I had the same issue with another VPN.

SquiddOhio · 04-30-2022, 10:08 AM

I noticed quite a while ago that I cannot send items to a Kindle via email from Calibre when my computer is using VPN (ExpressVPN). My solution was simply to turn off the VPN, and then send the books.
PATIENT: "Doctor, it hurts when I do this."
DOCTOR: "Well, don't do that."

DNSB · 04-30-2022, 04:00 PM

I took a quick look at ExpressVPN. There were several items on issues with email. See Unable to send email while connected to VPN for one example.

Loosheesh · 04-30-2022, 05:55 PM

Quote:

Originally Posted by DNSB

I took a quick look at ExpressVPN. There were several items on issues with email. See Unable to send email while connected to VPN for one example.

The first option is already set. How would the second option work with Calibre, as the book isn't sent through an email app ... or is it? I have no idea how that works. I use Outlook on my laptop and I'm able to both send and receive emails with the VPN on.

I also tried excluding Calibre with the split tunneling but that didn't work either.

DNSB · 05-01-2022, 01:09 AM

Quote:

Originally Posted by Loosheesh

The first option is already set. How would the second option work with Calibre, as the book isn't sent through an email app ... or is it? I have no idea how that works. I use Outlook on my laptop and I'm able to both send and receive emails with the VPN on.

In your use case, calibre would be the email app.

Quote:

Originally Posted by Loosheesh

I also tried excluding Calibre with the split tunneling but that didn't work either.

Given that ExpressVPN states that even with split tunneling, ExpressVPN's DNS servers are still used, I would not have expected split tunnelling to help.

Quote:

What happens to my DNS queries when I use split tunneling?

As long as you are connected to ExpressVPN, all of your DNS queries will go through ExpressVPN’s servers, no matter how you configure your split-tunneling settings.

Loosheesh · 05-01-2022, 08:32 AM

Quote:

Originally Posted by DNSB

Given that ExpressVPN states that even with split tunneling, ExpressVPN's DNS servers are still used, I would not have expected split tunnelling to help.

Thanks for the help. I've quite given up and accepted that it'll no longer be a fully automated process

04-28-2022, 02:47 PM	#1
Loosheesh Wizard Posts: 1,680 Karma: 3137505 Join Date: Dec 2010 Location: Jianghu Device: PW1, PW5, iPhone SE 2016, iPhone 13 Pro, iPad Pro 9.7, iPad Pro 2021	Sending News While Connected to VPN When I'm connected to the VPN, Calibre can't send news to my Kindle; I get an error message ("Failed to email book") with these details: Spoiler: Starting job: Email Local News1 [Thu, 28 Apr 2022] to blank@kindle.com 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 162, in sendmail File "calibre\utils\smtp.py", line 120, in sendmail_direct File "calibre\utils\smtp.py", line 111, in get_mx File "dns\resolver.py", line 1221, in query File "dns\resolver.py", line 1205, in resolve File "dns\resolver.py", line 1043, in resolve File "dns\resolver.py", line 950, in _compute_timeout dns.exception.Timeout: The DNS operation timed out after 5.1015238761901855 seconds Retrying in 1 seconds... Waiting 1 seconds before sending, to avoid being marked as spam. You can control this delay via Preferences->Tweaks 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 162, in sendmail File "calibre\utils\smtp.py", line 120, in sendmail_direct File "calibre\utils\smtp.py", line 111, in get_mx File "dns\resolver.py", line 1221, in query File "dns\resolver.py", line 1205, in resolve File "dns\resolver.py", line 1043, in resolve File "dns\resolver.py", line 950, in _compute_timeout dns.exception.Timeout: The DNS operation timed out after 5.102790117263794 seconds Job: "Email Local News1 [Thu, 28 Apr 2022] to blank@kindle.com" failed with error: Traceback (most recent call last): File "calibre\gui2\threaded_jobs.py", line 82, in start_work File "calibre\gui2\email.py", line 105, in __call__ File "calibre\gui2\email.py", line 48, in run File "calibre\gui2\email.py", line 137, in sendmail File "calibre\utils\smtp.py", line 162, in sendmail File "calibre\utils\smtp.py", line 120, in sendmail_direct File "calibre\utils\smtp.py", line 111, in get_mx File "dns\resolver.py", line 1221, in query File "dns\resolver.py", line 1205, in resolve File "dns\resolver.py", line 1043, in resolve File "dns\resolver.py", line 950, in _compute_timeout dns.exception.Timeout: The DNS operation timed out after 5.102790117263794 seconds Called with args: ('C:\\Users\\Blank\\AppData\\Local\\Temp\\calibre_ n1m8j5mq\\nw4u5jt7caltmpfmt.mobi', 'Local News1 [Thu, 28 Apr 2022] - calibre.mobi', 'blank@kindle.com', 'E-book: Local News1 [Thu, 28 Apr 2022]', 'Attached, you will find the e-book\n\nLocal News1 [Thu, 28 Apr 2022]\n\tby calibre\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x00000220868A7F70>, 'abort': <threading.Event object at 0x00000220868A73D0>, 'log': <calibre.utils.logging.GUILog object at 0x00000220868A7250>} Is there a way around this?

Similar Threads
Thread	Thread Starter	Forum	Replies	Last Post
Can only download Amazon metadata while connected to VPN	josephyw	Library Management	5	03-20-2021 12:24 PM
How to prevent sending news to one of my devices?	yurkennis	Library Management	1	01-20-2018 09:54 PM
Auto Convert News Feeds from EPUB to MOBI before Device is Connected	SunLight	Calibre	4	08-04-2015 11:48 PM
sending plaintext news to email	alexquick	General Discussions	0	04-05-2011 03:05 AM

04-28-2022, 03:21 PM	#2
DNSB Bibliophagist Posts: 46,168 Karma: 168983734 Join Date: Jul 2010 Location: Vancouver Device: Kobo Sage, Libra Colour, Lenovo M8 FHD, Paperwhite 4, Tolino epos	Looking at your posted log, you are not able to use DNS to resolve the smtp server address when connected to the VPN. You might want to check what DNS servers are in use when you are connected to the VPN and if you can ping the smtp server when connected to the VPN. Also I'm not certain you can email directly to a kindle.com address. The only time I've tried it, I have used a gmx.com SMTP server to forward the email to my kindle.com address.

04-29-2022, 01:14 PM	#5
Loosheesh Wizard Posts: 1,680 Karma: 3137505 Join Date: Dec 2010 Location: Jianghu Device: PW1, PW5, iPhone SE 2016, iPhone 13 Pro, iPad Pro 9.7, iPad Pro 2021	I checked it based on your instructions and I can't figure what's wrong; everything looks normal Anyway, I've decided to simply let the news stay in my library and temporarily turn off the VPN to send it manually.

04-30-2022, 10:08 AM	#8
SquiddOhio Connoisseur Posts: 61 Karma: 151030 Join Date: May 2012 Device: Kindle Touch	I noticed quite a while ago that I cannot send items to a Kindle via email from Calibre when my computer is using VPN (ExpressVPN). My solution was simply to turn off the VPN, and then send the books. PATIENT: "Doctor, it hurts when I do this." DOCTOR: "Well, don't do that."

04-30-2022, 04:00 PM	#9
DNSB Bibliophagist Posts: 46,168 Karma: 168983734 Join Date: Jul 2010 Location: Vancouver Device: Kobo Sage, Libra Colour, Lenovo M8 FHD, Paperwhite 4, Tolino epos	I took a quick look at ExpressVPN. There were several items on issues with email. See Unable to send email while connected to VPN for one example.

Advert

Advert