Using Openvpn with Outlook 2010

helloworld

Hi

I have setup an internet email account in Outlook 2010 on the client side using the openvpn server's ip as the outgoing mail server(SMTP).

Any ideas why only the first email can be sent succesfully but subsequent emails will be stuck in the outbox of the Outlook email account?

Note: Server and client can connect to each other on openvpn with no problem.

Any help will be greatly appreciated.

maikcat

if other services (smb,ftp) have problem maybe its an MTU issue..

Michael.

milan

helloworld wroteHi

I have setup an internet email account in Outlook 2010 on the client side using the openvpn server's ip as the outgoing mail server(SMTP).

Any ideas why only the first email can be sent succesfully but subsequent emails will be stuck in the outbox of the Outlook email account?

Note: Server and client can connect to each other on openvpn with no problem.

Any help will be greatly appreciated.

Hello

I have same problem. Im using Thunderbird, SMTP is configured on SSl/TSL port 465.

First email is outgoing OK, but other have problem with connection on SMTP server.

Please HELP 😐

maikcat

other services (scp,ftp,http) work ok if you trasnfer big files?

Michael.

milan

maikcat wroteother services (scp,ftp,http) work ok if you trasnfer big files?

Michael.

Hello

yes, problem is in outgoing emails through email client only, FTP, http and other works very fine

can it be blocked, sending emails?

I am very happy with openVPN, but can not send emails through email client :-(

maikcat

do you have antivirus software which scans mail traffic?
if yes can you disable it ?

which ip do you use for smtp server in your thunderbird?

Michael.

milan

maikcat wrotedo you have antivirus software which scans mail traffic?
if yes can you disable it ?

which ip do you use for smtp server in your thunderbird?

Michael.

I have OSX, no need antivirus :twisted:

my smtp is: host218.hostmonster.com on port 465

maikcat

I have OSX, no need antivirus :twisted:

so you are sure that you dont need AV uh? :mrgreen:

my smtp is: host218.hostmonster.com on port 465

your smtp is a public ip ,are you sure that traffic to smtp passes though your vpn?
what your SMTP logs show?

Michael.

milan

maikcat wrote
I have OSX, no need antivirus :twisted:
so you are sure that you dont need AV uh? :mrgreen:
my smtp is: host218.hostmonster.com on port 465
your smtp is a public ip ,are you sure that traffic to smtp passes though your vpn?
what your SMTP logs show?
Michael.

Hello Michael

"your smtp is a public ip ,are you sure that traffic to smtp passes though your vpn?"

I dont understand, SMTP server must be set as public IP?

maikcat

hello milan,

I dont understand, SMTP server must be set as public IP?

you are using a hostname which resolves to a public ip address not a private one,
without knowing your current config (you didnt post it and you hijacked another users thread)
i am asking you if traffic destined to this server passes via vpn tunnel?
also what your smtp logs show when you facing this problem?

also posting full vpn configs used would help...

Michael.

milan

maikcat wrotehello milan,

I dont understand, SMTP server must be set as public IP?
you are using a hostname which resolves to a public ip address not a private one,
without knowing your current config (you didnt post it and you hijacked another users thread)
i am asking you if traffic destined to this server passes via vpn tunnel?
also what your smtp logs show when you facing this problem?

also posting full vpn configs used would help...

Michael.

VPN config:

client
dev tun3
proto tcp
remote 93.115.84.195 80
resolv-retry infinite
nobind
persist-key
persist-tun
auth-user-pass
comp-lzo
verb 3
cipher AES-128-CBC
fast-io
pull
route-delay 2
redirect-gateway
<ca>

-----BEGIN CERTIFICATE-----

SMTP log:

milan

I cannt post smtp log, bacause TBTracer is not function in my osx 10.8.4
cannt set "environment variables", dosnt work oh god :evil:

milan

few days and I will be programmer :ugeek:

here is TB log, only for SMTP:

1930715520[100560110]: SMTP Connecting to: host218.hostmonster.com
1930715520[100560110]: SMTP Connecting to: host218.hostmonster.com
1930715520[100560110]: SMTP Connecting to: smtp.gmail.com

I sent 3 emails and connect to SMTP server was not established

maikcat

do you control your SMTP SERVER?

Michael.

milan

maikcat wrotedo you control your SMTP SERVER?

Michael.

no, they are not my SMTP servers.

maikcat

do you control your VPN server?

Michael.

milan

maikcat wrotedo you control your VPN server?

Michael.

:cry: NO

I can control only my PC and router. Cannt be problem on FW? or VPN server?

maikcat

if your vpn servers redirects ALL traffic via it and its
configured to block certain outgoing traffic (fe SMTP)
you will never send mail while connected....

Michael.