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I work from home and I VPN into the office. We are a remote team all over the country and we use Google Hangouts to video conference. After I VPN, I then RDP onto my desktop which is a physical machine located in an office across the country. I own a PC and a Mac, but the PC has no built in web cam. So, I end up using my Mac. Microsoft has a Mac RDP client that works well to connect to a Windows machine.

A few weeks ago, a strange thing started to happen. When I hop on the VPN, I am TOTALLY unable to load any website that is owned by Google: Plus, Gmail, Youtube, or the main Google site. ALL other sites load just fine. It's only Google. If I want to use Hangouts, I have to kill the VPN. This makes it impossible to video conference with co-workes and look at my desktop at the same time. As a workaround, I use Hangouts on my phone. That's okay so long as nobody wants to do a screen share.

The thing is, this didn't use to be the case. It just started all at once a few weeks ago.

I have been (when not on VPN obviously) Googling this issue, and I can't find one single other instance of this problem. Lot's of people have the opposite problem... they can't get on Google unless they ARE on VPN.

I'm using a MacBook Pro running iOS 10.9.2. I just updated the OS hoping this would solve the problem. Nope. The VPN is a standard PPTP. Encryption is "Automatic (128 bit or 40 bit). I have it set to not use the VPN for all network traffic.

Below are some trace routes... note the highlights... Why would my machine use a different IP Address for the same domain when I'm on VPN? I tried to flush DNS, but that didn't do the trick.

Any ideas?

WITH NO VPN

traceroute plus.google.com

traceroute: **Warning: plus.google.com has multiple addresses; using 74.125.224.67**

traceroute to plus.google.com (74.125.224.67), 64 hops max, 52 byte packets

 1  192.168.1.1 (192.168.1.1)  2.258 ms  2.461 ms  4.207 ms

 2  10.146.64.1 (10.146.64.1)  7.580 ms  10.589 ms  10.812 ms

 3  dtr01stcdmn-tge-0-5-0-7.stcd.mn.charter.com (96.34.27.120)  12.574 ms  11.454 ms 
 9.959 ms

 4  crr01stcdmn-tge-0-3-0-10.stcd.mn.charter.com (96.34.27.138)  19.980 ms

crr01stcdmn-tge-0-3-0-9.stcd.mn.charter.com (96.34.27.136)  19.069 ms

crr01stcdmn-tge-0-3-0-8.stcd.mn.charter.com (96.34.27.106)  16.332 ms

 5  bbr01stcdmn-bue-2.stcd.mn.charter.com (96.34.2.140)  14.575 ms  14.095 ms  15.967 ms

 6  bbr02chcgil-bue-1.chcg.il.charter.com (96.34.1.149)  36.023 ms  33.109 ms  42.461 ms

 7  prr01chcgil-bue-4.chcg.il.charter.com (96.34.3.11)  33.986 ms  33.072 ms  36.438 ms

 8  96-34-152-30.static.unas.mo.charter.com (96.34.152.30)  31.807 ms  26.556 ms  37.344 ms

 9  209.85.254.128 (209.85.254.128)  27.068 ms

209.85.254.120 (209.85.254.120)  28.014 ms

209.85.254.128 (209.85.254.128)  25.807 ms


10  72.14.237.133 (72.14.237.133)  34.524 ms  29.817 ms

209.85.254.240 (209.85.254.240)  33.913 ms

11  209.85.248.228 (209.85.248.228)  40.783 ms  38.431 ms

72.14.238.104 (72.14.238.104)  40.239 ms

12  216.239.46.52 (216.239.46.52)  60.883 ms  59.278 ms  70.201 ms

13  216.239.46.155 (216.239.46.155)  93.413 ms
216.239.46.153 (216.239.46.153)  80.217 ms  81.843 ms

14  64.233.174.187 (64.233.174.187)  80.163 ms  84.024 ms
64.233.174.191 (64.233.174.191)  82.430 ms

15  209.85.253.185 (209.85.253.185)  86.657 ms  85.792 ms  81.971 ms

16  lax17s02-in-f3.1e100.net (74.125.224.67)  81.444 ms  84.409 ms  84.698 ms

WITH VPN

Caseys-MacBook-Pro:~ ccrookston$ traceroute plus.google.com

traceroute: **Warning: plus.google.com has multiple addresses; using 65.196.188.22**

traceroute to plus.google.com (65.196.188.22), 64 hops max, 52 byte packets

 1  192.168.1.1 (192.168.1.1)  3.176 ms  1.559 ms  1.599 ms

 2  10.146.64.1 (10.146.64.1)  9.344 ms  12.240 ms  8.223 ms

 3  dtr01stcdmn-tge-0-5-0-7.stcd.mn.charter.com (96.34.27.120)  8.854 ms  9.004 ms  7.853 ms

 4  crr01stcdmn-tge-0-3-0-11.stcd.mn.charter.com (96.34.27.140)  16.984 ms

crr01stcdmn-tge-0-3-0-10.stcd.mn.charter.com (96.34.27.138)  12.075 ms

crr01stcdmn-tge-0-3-0-9.stcd.mn.charter.com (96.34.27.136)  17.398 ms

 5  bbr01stcdmn-bue-2.stcd.mn.charter.com (96.34.2.140)  11.178 ms  10.727 ms  14.369 ms

 6  65.46.47.77 (65.46.47.77)  14.132 ms  10.388 ms  12.030 ms

 7  vb1710.rar3.chicago-il.us.xo.net (216.156.0.169)  26.291 ms  31.111 ms  23.546 ms

 8  207.88.14.194.ptr.us.xo.net (207.88.14.194)  20.350 ms  19.322 ms  19.765 ms

 9  0.xe-3-3-0.br3.chi13.alter.net (204.255.168.97)  22.572 ms  59.138 ms  19.948 ms

10  * * *

11  * * *

12  * * *

13  * * *

Figured out a solution. Not sure if it's the best solution, but it's working:

System Preferences > Network > Wi-Fi > Advanced > DNS.

Made a note of the IP Address.

System Preferences > Network > VPN > Advanced > DNS.

Deleted the existing IP Addresses and added the same one that Wi-Fi is using. This seems to have resolved the issue. Found the solution here:

https://apple.stackexchange.com/questions/73076/mac-os-x-mountain-lion-dns-resolving-uses-wrong-order-on-vpn-via-dial-up-conne

3
  • side note: When I trace route 74.125.224.67, it resolves just fine, even when on VPN. Mar 12 '14 at 17:37
  • Your VPN's DNS server is lying. Try nslookup
    – SLaks
    Mar 12 '14 at 17:50
  • Found a solution. As i don't have enough user points, I had to add it to the end of my question. Mar 12 '14 at 17:54

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