Outlook cant send email when using NordVPN

[#1]

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

[#2]

@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

[#3]

Hi

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.

[#4]

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

[#5]

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!

[#6]

@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 )

[#7]

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

[#8]

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

[#9]

There is a typo in the command

Oops!

[#10]

@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 

[#11]

@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...

[#12]

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 ?

[#13]

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

[#14]

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

[#15]

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