Cannot VPN to Windows work machine from Mac mini/Airport Extreme at home

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Cannot VPN to Windows work machine from Mac mini/Airport Extreme at home

I am trying to VPN to my PC work computer (running windows 7) from the Macmini (running OS X 10.9.1). The Mac mini is connected to my modem via an Airport Extreme Time Capsule.

It appears that I can VPN to the server at work (they can ping me), but when I try to ping my work desktop, I get a 'request timeout' message. Obviously none of the remote desktop apps work, giving me error messages ranging from "timeout" to "check firewall settings"

Other remote Mac users seem to have no trouble connecting, but none of them use the Airport Extreme, so I suspect the problem has something to do with the router.

I've made a DHCP reservation and opened port 3389 through the airport utility, but this doesn't seem to have worked. Can anyone confirm the methodology behind this?

Any suggestions on what my next steps are?

Thanks in advance for any help you may offer!

iPad mini Wi-Fi, OS X Mavericks (10.9.1)

Posted on Jan 9, 2014 10:16 PM

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Answer 1

Jan 10, 2014 12:09 AM in response to norteoeste

So you are using remote desktop not vpn then.. port 3389 is not for any vpn.

Can you please bypass the apple router and plug the computer directly into the modem.. and test if it works.. this stops you wasting a whole lot of time on what turns out to be the wrong thing.

Mostly you should not need to open the port from the client end.. only from the server end.

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Answer 2

norteoeste Author

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Jan 19, 2014 9:48 PM in response to LaPastenague

I connected the modem to my computer and my attempt to use remote desktop still fails. Still unable to ping the work server even though the VPN connection appears to be functioning and they can ping me.

What would you suggest I try next?

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Answer 3

Jan 19, 2014 11:01 PM in response to norteoeste

norteoeste wrote:

I connected the modem to my computer and my attempt to use remote desktop still fails.

I am confused about what software exactly you are using..

Are you using a vpn software .. if so which one? The office should be running a server and you run a client.

Or your using some sort of remote desktop software.. tell me exactly which one. Version and everything.

If the computer still fails with the Mini connected directly to the modem then the AE is not the problem.

It could be your ISP.

It could be the firewall on your computer.. although the ping response suggests things are fine at your end if work can ping you.. it is your connection to work that is the problem.

If you do a traceroute in terminal to the work server.. how does that go? Particularly is the ISP giving you a public or private IP address.

This is out of the area of AE now.. you should post under Mavericks since the issue is more related to setting of the OS I suspect.

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Answer 4

norteoeste Author

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Jan 20, 2014 9:56 PM in response to LaPastenague

I have tried Jump Desktop, Microsoft Remote Desktop, and CoRD. A friend using CoRD through the same ISP from a macbook pro, is able to connect. He isn't running mavericks though, an older os, i'm unsure of the version

when I run traceroute to my work machine IP, I get this

1 10.0.1.1 (10.0.1.1) 0.475 ms 0.196 ms 0.199 ms

2 * * *

3 *

We've eliminated the AE as the problem, through the bypass.

Should I try post under mavericks? Thanks very much for your help

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Answer 5

Jan 21, 2014 2:12 AM in response to norteoeste

I think that is good idea..

What about picking up the mini and going to your work collegues place and trying it there.

That will give you a final proof of Mavericks.

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