topic Re: Outlook cant send email when using NordVPN in Tech Help - Software/Hardware etc

Outlook cant send email when using NordVPN

asreilly — Thu, 20 May 2021 09:26:32 GMT

I searched for answers on this issue and can see the same question back in 2018 with lots of replies, but there seemed to be no solution to the problem.

I use Outlook for my email. I'm also running NordVPN. Outlook is able to receive email on my plusnet accounts without any problems but I have to switch off NordVPN to send emails. I simply get that there has been a send/receive error. Once its switched off I can go into the email and send it. I'm also running an exchange email account and that has no issues whilst the NordVPN is running.

Surely PLUSNET must have put some thought into this and resolved the problem which from the previous replies and my findings lies with them not NordVPN.

Thanks

Re: Outlook cant send email when using NordVPN

MisterW — Thu, 20 May 2021 10:16:38 GMT

@asreilly you need to set the outgoing server (relay.plus.net) to use authentiaction with the same username/password that you use for the incoming server. When connected on a PlusNet connection, there is no need to authenticate(but you can) whereas when sending from a non-plusnet connection( as when using a VPN) then you must authenticate

Re: Outlook cant send email when using NordVPN

asreilly — Fri, 21 May 2021 10:53:42 GMT

thanks for the response. When I switch on authentication it pops up the password request for server relay.plus.net. I feed in the correct password but then I'm also getting an error after this for "Send test email message: Your email server rejected your login. Verify your user name and password for this account in Account Settings."

Clearly I'm doing something wrong.

On outgoing server I'm setting 'My outgoing server (SMTP) requires authentication' and then fill in username and password and tick 'require secure password authentication (SPA)' although get similar resuilts whichever are set.

I'm using port 587 for the outgoing server.

Re: Outlook cant send email when using NordVPN

MisterW — Fri, 21 May 2021 15:03:12 GMT

You need to uncheck the 'require secure password authentication (SPA)' box. Then either use STARTTLS with port 587 or SSL/TLS with port 465

Re: Outlook cant send email when using NordVPN

BrianD1 — Tue, 25 Mar 2025 12:57:20 GMT

I have the same problem as the original poster. I have tried the suggested alterations but still get the same 'outlook cannot connect to your outgoing smtp email server. I do not have a proble if I disconnect the vpn. Any other suggestions appreciated!

Re: Outlook cant send email when using NordVPN

MisterW — Tue, 25 Mar 2025 13:05:29 GMT

@BrianD1 with the VPN connected try this from a cmd window

curl.exe -v smtp://relay.plus.net:587 -u userID:password --ssl

post the text from the line begining 235 ( dont post the line after 334 - it contains your username/password and whilst its encrypted it can be decrypted )

Re: Outlook cant send email when using NordVPN

BrianD1 — Tue, 25 Mar 2025 13:15:50 GMT

With vpn off I get:

C:\WINDOWS\system32>curl.exe -v smtp://relay.plus.net:587 -u userID:password --ssl
Warning: --ssl is an insecure option, consider --ssl-reqd instead
* Host relay.plus.net:587 was resolved.
* IPv6: (none)
* IPv4: 212.159.8.107, 212.159.9.107
* Trying 212.159.8.107:587...
* connect to 212.159.8.107 port 587 from 0.0.0.0 port 14583 failed: Address not available
* Trying 212.159.9.107:587...
* connect to 212.159.9.107 port 587 from 0.0.0.0 port 14584 failed: Address not available
* Failed to connect to relay.plus.net port 587 after 1044 ms: Could not connect to server
* closing connection #0
curl: (7) Failed to connect to relay.plus.net port 587 after 1044 ms: Could not connect to server

Re: Outlook cant send email when using NordVPN

Dan_the_Van — Tue, 25 Mar 2025 13:50:15 GMT

Deleted unwanted post text

Looking at the error message there looks to be an issue with your IP address

connect to 212.159.8.107 port 587 from 0.0.0.0 port 14583 failed: Address not available * Trying 212.159.9.107:587... * connect to 212.159.9.107 port 587 from 0.0.0.0 port 14584 failed: Address not available

I see

curl.exe -v smtp://relay.plus.net:587 -u userID:password -ssl * Host relay.plus.net:587 was resolved. * IPv6: (none) * IPv4: 212.159.8.107, 212.159.9.107 * Trying 212.159.8.107:587... * Connected to relay.plus.net (212.159.8.107) port 587 < 220 avasout-peh-002 smtp relay.plus.net > EHLO DESKTOP-QADN989 < 250-avasout-peh-002 hello [my public IP Address], pleased to meet you

Re: Outlook cant send email when using NordVPN

MisterW — Tue, 25 Mar 2025 13:50:54 GMT

There is a typo in the command

Oops!

Re: Outlook cant send email when using NordVPN

Dan_the_Van — Tue, 25 Mar 2025 13:53:06 GMT

@MisterW

I deleted some of the text as it was not needed, it seems to work with --ssl as well. Looks to be an IP issue

Re: Outlook cant send email when using NordVPN

MisterW — Tue, 25 Mar 2025 13:55:17 GMT

@Dan_the_Van Looks to be an IP issue

That was my conclusion but you beat me to it!. Looks like no public IP allocated...

Re: Outlook cant send email when using NordVPN

Champnet — Tue, 25 Mar 2025 15:04:35 GMT

I’ve only setup and used site to site VPNs but logically it look’s like the email system is correctly denying access.

Apart from Company email systems or having the option to bypass the VPN security has anyone got this type of setup working ?

Re: Outlook cant send email when using NordVPN

dvorak — Tue, 25 Mar 2025 15:32:47 GMT

ProtonVPN works fine when set to UK:

~$ curl -v smtp://relay.plus.net:587 -u userID:password -ssl * Host relay.plus.net:587 was resolved. * IPv6: (none) * IPv4: 212.159.8.107, 212.159.9.107 * Trying 212.159.8.107:587... * Connected to relay.plus.net (212.159.8.107) port 587 < 220 avasout-peh-002 smtp relay.plus.net > EHLO ubuntu-linux-2404 < 250-avasout-peh-002 hello [79.127.146.184], pleased to meet you < 250-HELP < 250-AUTH LOGIN PLAIN < 250-SIZE 104857600 < 250-PIPELINING < 250-8BITMIME < 250-STARTTLS

Re: Outlook cant send email when using NordVPN

Champnet — Tue, 25 Mar 2025 15:48:58 GMT

Thanks @dvorak that eliminates a VPN problem unless it’s specific to Nord.

Re: Outlook cant send email when using NordVPN

Champnet — Tue, 25 Mar 2025 19:07:58 GMT

@asreilly Take a look here, this may be of help : : Why can't I send email messages? | Nordlayer Help

Re: Outlook cant send email when using NordVPN

BrianD1 — Tue, 25 Mar 2025 19:33:40 GMT

Thank you all for your suggestions. I did change the IP address but did not solve the problem. I ended up findung a setting in 'AVG, basic protection, email shield' and unchecked 'Scan outbound emails smtp' which cured the problem. Sorry if I should have mentioned I used free AVG which I assume was causing the problem in the first place? Thank you anyway!

Re: Outlook cant send email when using NordVPN

erazered — Tue, 25 Mar 2025 19:34:23 GMT

I am having the same issue. When I turn NORD off on my phone I can send the emails out.

But when it's on get the authentification error.

Anyone tried changing their port settings to see if that solves the problem?

Re: Outlook cant send email when using NordVPN

paul_blitz — Fri, 28 Mar 2025 11:12:28 GMT

We know for a fact that the current plusnet email system DOES do checks on the "Source address" when sending email. This is done as an anti-spam measure.

It appears to be driven by externally purchased "address lists" (quite normal).

One way a spam originator will send emails is via a VPN (to make it difficult to track who is sending the spam!), thus these lists will often block email sent via a VPN (technical note: when you send an email from home, it will originate from your broadband IP, when you send it over a VPN, it will originate from one of the VPN provider's IP's. It's therefore easy for the email provider to see who is trying to connect!)

Blocking connections from VPNs generally is quite common: one of the the main reasons people will use a VPN is to pretend to be in the UK, when they are actually in, say, China. As a web site, maybe I only wish to deal with ACTUAL UK users, who live in the UK (I don't wish to export my product)... so I block users accessing via known VPNs (I used to provide training for a product that included this ability)

There's 2 solutions:

1) don't use the VPN to send email;

2) move your email service to someone who DOES allow connections via a VPN.

(And yes, I know the latter is a PITA, I have a personal email address - so won't need to change it - and moving THAT has enough issues. For most users, they are still using an "@plus.net" email address (or similar), so that's ALSO gonna need a change of email address. But you'd need to do that anyway, if you changed your broadband supplier!)