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I'm not really an IT Pro, but this seemed like the best place to ask this question... I have setup VPN networks in the past, for fun, and everything was great, but now I've set one up for my boss, and while my computers all work great, his Mac machines are almost too slow to work with. Its pretty much vanilla configs all around, anyone have any ideas? Its a TUN routing setup over UDP.

Back Story: My boss travels a lot, and wants to be able to access all his files from the road, and is also pretty paranoid about security (even though knows almost nothing about computers). SO i figured a VPN would be the answer. I went with OpenVPN, but there are some other issues. The only ISP we can get in our area besides Dial-UP is a crappy Satellite provider, that doesn't offer public IPs unless your willing to pay, so while the computers and VPN setup are pretty vanilla, the routing and structure is strange to get around this limitation.

Specs: Its OpenVPN2, and there are six machines using it (only three actually use it, the rest are my test machines), one Windows 7 laptop, two XP Desktops, one OS X 10.5 Desktop, one 10.6 Desktop, and one 10.6 Laptop. One XP Desktop sits at my house and acts as the server (6Mbs/2Mbs FIOS connection). One XP desktop sits at the office and hosts a webpage that will wake up the Main Mac Desktop from sleep, and also ping all the machines on the VPN and show their status. The main office mac (10.6) stays in sleep mode until it gets the Wake-On-Lan packet from the Office XP, and then it auto connects to the VPN and opens itself up. The reason for all this is the Satellite private IP crap means i cant directly access the office machines outside of the LAN, so everyone connects to my house first, then they talk to each other from there. The Wake On Lan weirdness is because my boss doesn't want to leave the main Mac on all the time, and making a quick and dirty webpage was the easiest way to send a Magic Packet from inside the LAN without confusing my boss. The VPN uses Client Config files to make static IPs for the client. The only thing i found in google was some changes to the VPN MTU settings (down to 1400) but no real help. Oh, and i forgot...all the windows machines just have OpenVPN start as a service. The Mac laptop uses tunnelblick (an OpenVPN GUI) and the Mac Desktops use OpenVPN in normal command line mode.

Server Config:

tun-mtu 1500
fragment 1450
mssfix 1450
management localhost ####
port ####
proto udp
dev tun
ca #######
cert #######
key ######
dh ######
server 10.8.0.0 255.255.255.0
ifconfig-pool-persist ipp.txt
client-config-dir ccd
route 10.8.0.0 255.255.255.252
client-to-client
keepalive 10 120
comp-lzo
persist-key
persist-tun
status openvpn-status log

Client Configs (all are simple variations on this)

tun-mtu 1500
fragment 1450
mssfix 1450
client
dev  tun
proto udp
remote ######## ####
resolv-retry infinite
nobind
persist-key
presist-tun
ca #####
cert #####
key #####
ns-cert-type server
comp-lzo
verb 3
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1 Answer 1

Have you tried to use Viscosity VPN instead of Tunnelblick on your Mac?

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2  
+1 Viscosity is amazing. –  Antoine Benkemoun May 27 '10 at 6:50
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