Unable to send emails with my VPN running

[The Invincibles 0]

I'm using Thunderbird on an Ubuntu 14.04 Desktop, when I try and send an email from my outlook.com email account I get this message,

Sending of the message failed.
The message could not be sent because the connection to Outgoing server (SMTP) smtp-mail.outlook.com timed out. Try again.

It only seems to happen when I'm connected to the VPN, I'm able to send emails by logging in to the outlook.com web portal regardless of whether I'm connected to the VPN or not.

I found the IP address for the SMTP server by running an nslookup with the server name & I got this output,

Non-authoritative answer:
smtp-mail.outlook.com    canonical name = smtp.live.com.
smtp.live.com    canonical name = smtp.glbdns2.microsoft.com.
Name:    smtp.glbdns2.microsoft.com
Address: 65.55.176.126

So I went in to account settings & changed the server name from the host name to the IP address but I'm still having the same issue.

Any ideas as to what is wrong?
 

[muelli 2]

AFAIK port 25 (smtp)is blocked on the exit servers to prevent spam.

Use port 587 (submission). If MS supports it

[IPiHocYQIGd5ud1 0]

HI All

 

I am a new AirVPN user.   I discovered that while connected I cannot send email via SMTP on port 465 to the GMail smtp server.

I've seen these old threads that imply that port 465 should work.   Is there a workaround here?

Thanks,

Chris

[pseudotimestretch 2]

HI All

 

I am a new AirVPN user.   I discovered that while connected I cannot send email via SMTP on port 465 to the GMail smtp server.

I've seen these old threads that imply that port 465 should work.   Is there a workaround here?

 

Thanks,

Chris

 

Hello,

 

Did you try port 587?

[IPiHocYQIGd5ud1 0]

Yes, no dice.

 

It looks like I was using a server that is blacklisted by the email servers.  Switching to one of the really slow canadian servers fixes the problem, though!

[pcrawford 0]

Today I also see gmail blocking me for POP3/SMTP access using Thunderbird on Ubutnu 14.04 to one of my gmail accounts, but not the other, which is a bit odd.

 

I can log in to the blocked account using the web interface OK and no odd messages (other than a notification of a new sign-on) and tried a password change, but no improvement. I also tried moving from port 465 to 587 for sending and that did not help either. However, if I change from the UK server (I was using 185.103.96.132) to a European one it works again (but generally speeds are slower). Also it seems that Yahoo are doing the same, odd failure to log in today (and maybe yesterday) but OK again on VPN server change.

 

It is really quite annoying as one reason for using a VPN is so I don't get pointless security complaint when travelling and my IP address changes!

[Guest]

Unfortunately I am having the same problem with Mailbox.org, none of the servers tried work for sending SMTP mails via port 465. POP3 works. The web interface works as well, and other mail accounts (other provider) work as well. At the same time, Mailbox.org support insists that the problem is certainly not on their side. Any ideas??

[LZ1 672]

Hello!

 

I just want to warn people regarding Thunderbird or similar email clients + a VPN + a company like Microsoft. If you log into your email from different VPN locations than usual, a company like Microsoft will detect it and possibly lock down your account at some point. The real problem arises if your email client has logged into more than one email address, as it's then possible to be locked out from multiple accounts at once. So either stick to the same VPN locations when logging in or use a company which doesn't discriminate on location, as a security measure .

 

Also, if there's issues with POP3, then trying IMAP is an option. If you're using two-factor authentication, then it might also not be possible to login so easily using a local email client like Thunderbird.

[MrRandom 6]

Starting yesterday I can no longer send emails while connected to AirVPN. I've been using AirVPN for years and never had a problem before, did something just change?

 

I first noticed the problem on my Comcast email account so I thought it was just Comcast. I seem to still be receiving my emails on my Comcast account. At first I thought I could send email with my gmail accounts because I received no errors but then after a few more tests I noticed that I can only send gmail to gmail, when I sent from gmail to a non-gmail account it never arrives.

 

Everything on all my email accounts works fine when I disconnected from AirVPN. If I have to shut down my torrent client and disconnect AirVPN then get everything going again every time I want to send and email that would be a HUGE inconvenience!

 

It's possible that this is Comcast and they are now blocking the use of their SMTP servers on encrypted networks. The fact that I'm receiving email on my Comcast account but can't send an email from one of my gmail accounts to my Comcast account makes me think that SMTP servers are completely blocked now and not just port 25.

 

I'm using Thunderbird (I hate web mail and refuse to use it) and everything is configured correctly. I'm using port 465 and I've tried port 587, gmail wouldn't even connect to it and Comcast just gives me an error.

 

I only use the Canadian servers and I've tried several of them with no luck. Could the Canadian servers be blocking SMTP for some reason?

 

Here's the error message I'm getting when trying to send email on my Comcast account.

An error occurred while sending mail: The mail server sent an incorrect greeting:  resomta-po-06v.sys.comcast.net resomta-po-06v.sys.comcast.net CSI IP ***.***.***.* is not permitted to send messages.  Please contact support if you feel this is in error..

I get no errors when I send and email with gmail but it only seems to be delivered to another gmail account, when I send one to a non-gmail account it just disappears.

[MrRandom 6]

It's been over a month now since my last post, does anyone have any idea what is causing this?

 

I've done all the testing I can with the email accounts I have and I still don't know if this is a problem with AirVPN, Comcast or something else?

 

What ever the problem is it seems to be permanent and it's unbelievably inconvenient to have to shut down my torrent client, disconnect AirVPN then get everything back up again just to send an email.

 

I used to send about 100 emails a month because that's the only way I communicate with some people but I think I've only sent 3 since this problem started.

[debu 4]

I have the same problem from time to time.

 

I also use Canadian servers (UDP 443) and occasionally can only send an email by disconnecting from the VPN.  Receiving is never a problem. 

 

Haven't kept records so can't say if it is server specific or not.

[MrRandom 6]

I'm glad it's not just me.

 

Last night I logged into my Comcast account on their site and turned off their spam filter and I can now send an email from one of my Gmail accounts in Thunderbird to my Comcast account and receive it in Thunderbird all while connected to AirVPN!! I still can't send an email from my Comcast account in Thunderbird while connected to AirVPN.

 

Last night I did some more research and some have suggested that Comcast's spam filter is the problem, that's what gave me the idea to turn off their spam filter. From what I've seen so far it seems to be a Comcast problem so I'm guessing they are blocking the use of their SMTP servers outside of the US or on an encrypted connection. I could easily test the first part of my theory by logging into one of the US servers but I can't think of a way to test the second part.

 

What seems ironic to me is that I first noticed this problem a day or two after I was trying to diagnose my network problems. I removed my router and it turns out my internet connection is now faster than my router and I need a new gigabit router. My router has probably been the cause of all my packet errors and dropped connections since Comcast increased their speed. I just don't see how removing my router from the loop for a few minutes could have caused the email problem? Some people online have suggested changing your routers IP address but every time I try to send an email the IP in the error is the IP of the AirVPN server I'm connected to so I don't see how changing my router's IP could make a difference?