I'm having issues with routing / DNS and need help, please

[loopy]

Hello, I've never used a VPN network (successfully) before, I'm just going to try to explain my problem and my goals and I'll do my best to provide the most information I can.

I'm running on Windows Vista 32 bit and I am attempting to get OpenVPN-GUI v4 running. I have turned off windows firewall completely. I have made the application run as administrator (as is the overwhelming majority of answers to peoples problems upon a search for help).

I get no errors whatsoever when connecting to my VPN; tray icon is green, logs look ok, status window looks good. (Being new...I'm uncertain and might as well as ask as long as I'm looking newbish with this post anyway... it would be stupid to paste/show pictures of the actual IP my VPN is showing, right [even thought I know it changes]?).

Now - only sometimes does it actually seem to start routing my internet through the VPN, and that's after I restart completely and BEFORE I run any other applications. Only do I know that it seems to work is because I can then no longer ping any web address or visit any url (e.g. google.com) in my browser; my first thought was DNS (actually it was static routing.. I'm getting there) -- and so I try to ping googles IP address 74.125.239.37 and voila, it works! Just to test things, I try visiting the ip address of ipchicken.com 209.68.27.16 to see what it's giving me, and it's still my same old ISP address!

So, information:

1. The main adapter used to regularly connect to the internet
   
2. Once open VPN successfully connects (which it always does), it comes up on 'Ethernet adapter Local Area Connection 2'. Under the network and sharing center(man I hate Microsoft), It always shows me as connected to Local Area Connection, regardless of if I have OpenVPN connected or not -- http://i.imgur.com/hIKPBIV.png

My physical setup is as such:

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my_computer (192.168.0.102) -> DD-WRT router (192.168.0.101) -> internet

Honestly I've been reading up on subnets, and I guess I'm just not in a mode where I can absorb information right now. I'm apparently in the subnet 255.255.255.0. My VPN is trying to go on 255.255.252.0 - I thought that this is where I need static routing, but I don't know for sure, and I'm definitely uncertain how.

The only information I have from 'Local Area Connection 2' from ipconfig is the subnet (255.255.252.0) and the IPv4 Address which is the IP address that OpenVPN says I was assigned. I cannot for the life of me recall the command to get the routing tables on windows right now and a cursory google turned up nothing, but I can tell you that the routing table did indeed update once the VPN was connected, from when I checked earlier.

I'm not really sure what to do from here, and any help or advice is greatly appreciated -- I've been trying to get this working for an embarrassing amount of time.

edit:
I have also forwarded port 1194 as I understand that is the default port OpenVPN uses.

[loopy]

I'm sorry about the missing image, here it is.

[mwandelaar]

I saw some things which raise questions:
* What is your local (i mean normal lan) address-range?
If it's 192.168.0.0, this ain't gonna work, as the vpn-address and local-addres are the same

* I think you wat to redirect your gateway via the openvpn-instance on your dd-wrt router. If you are in your local lan (which i think you are), your external ip-address will never change, as you still use the same internet-connection.

And can you post your client+server configs, so we can read along what you are doing?

[loopy]

Hello mwandelaar, thanks for response. In the interim, I posted a related thread to the subreddit /r/VPN that answers some questions, and I just (as of ~30 minutes ago) resolved the issue.

The problem was solved by changing from a TAP to TUN in my config file, that is:

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dev tap

->

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dev tun

From my readings on wikipedia:

TAP (as in network tap) simulates a link layer device and it operates with layer 2 packets such as Ethernet frames. TUN (as in network TUNnel) simulates a network layer device ...

TAP is used to create a network bridge, while TUN is used with routing.

I'm ashamed it took me so long to realize, but relieved I can finally use my VPN.