vpn blocking outgoing mail?

[Rahh]

Having a weird problem with our VPN connection where it will block outgoing mail for my alltell.net e-mail. If the vpn connection is off it sends fine but once the vpn is connected it will not send any outgoing but will still receive incoming. The VPN is a connection for a piece of software and thats all it's used for. It connects to an external ip then shoots to the server on a reg. 192.168.0.1 ip address.

Any clue why it would block my alltell.net outgoing mail? By the way, it does not affect any other outgoing mail i have setup just the alltell one. Oh, and I did contact their tech support and they could pretty much only tell me what i knew already.

 

[YeOldeStonecat]

What error messages pop up?
Can you ping your SMTP mail host by name, and get resolution/replies?
Are you VPN'ing into another bandwidth host...so that your outgoing mail might be trying to go outbound on bandwidth other than alltell.net Because in the battle of SPAM, many ISPs now block port 25 from entering/leaving their bandwidth.

 

[0ldman]

I'm betting Outlook is using the VPN for internet access. If the other side is with a different ISP, try enabling authentication for outgoing mail.

 

[Rahh]

port 25 is not blocked by the ISP and I get error 550 in outlook 2000. Tried the authentication for outgoing and put that info. in to no avail.

 

[Malk-a-mite]

YeOldeStonecat is almost on it, sounds like the mail client is trying to send via the same method it normally does but is now connecting from a different IP than the mail server is expecting.

Rahh - did you even look up the error? It's a simple relay error message. Recieving but not being able to send is a common problem in that situation, prevents (well, limits) spamming.

 

[YeOldeStonecat]

550...yeah, betting your VPN host is on different bandwidth (outside of your SMTP host).

Can you verify this? Port 25 outbound might not be blocked by the ISP of your VPN host location, but alltell (if your VPN host does not reside on their bandwidth) might not accept incoming SMTP from outside their bandwidth...or IF they do......require authentication. 550 error usually points to those 2x things.