server 2008 VPN

Hi All

I have set-up the VPN on my server 2008, I can connect remotely using and PC based machine. I can ping the server by IP, by name and map network drives  but when I connect a MAC to the VPN which is successful I cant map a drive either by IP or by the server name, any help would be appreciated.
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Rich WeisslerProfessional Troublemaker^h^h^h^h^hshooterCommented:
Any chance your MAC is running Lion (10.7)?  Apparently Apple re-wrote their own version of SMB for that version of the OS, and there are/were a lot of incompatibilities with Windows Vista+/2008+.  (Or is there any chance you've had this MAC connected to that samba share without the vpn successfully?)
AJ1978Author Commented:
I would need to check the version of MAC OS and revert back to you. Internal everything is fine it is only over the VON that I encounter issues but my MAC is running the latests version and would need to check the clients version.
Rich WeisslerProfessional Troublemaker^h^h^h^h^hshooterCommented:
Sounds like a different problem... assuming a version more recent than Lion...
If you traceroute to the remote server IP address... can you see whether the traffic is going through the VPN?  (And I think you said you could ping the server from a PC when connected to the VPN... do you get the same ping response from the Mac?)
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AJ1978Author Commented:
Hi Rich

I am running OS X Yosemite, I cant ping the server but I can Ping the MAC from the server when connected. I can connect to a drive mapping when on the local network!  I need to try to ping from the MAC while on the LAN that is the only this I haven't done! AS I say windows 7 & 8 are just fine.
Rich WeisslerProfessional Troublemaker^h^h^h^h^hshooterCommented:
Is the windows firewall on the server configured to authenticate connections?  (Could check ICMP or fileshare connection rules.)

Can the MAC ping other devices on the LAN when connected via VPN?
AJ1978Author Commented:
Windows firewall is turned off, I cant ping anything on the network over the VPN.
Kash2nd Line EngineerCommented:
what is your Office Network IP range and what is your home/remote network range.

If they are same then thats what the problem is?

if not then what kind of router are you using to connect to ?

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AJ1978Author Commented:
Its on the same range I will try this but if a PC work on the same range why not MAC?
AJ1978Author Commented:
My office network is 192.168.1.***  I have changed the IP range where I am testing to 192.168.10.*** and I still see the same issue.
AJ1978Author Commented:
Routers both side are Asus AC68U
Kash2nd Line EngineerCommented:
are you using wireless on your mac ?

Also, as a test, can you change the priority on the network on your mac so the once VPN connects, its right on the top.

Connect and try to ping.

Also, for a test, disable the firewall on both routers and also disable on MAC.
Kash2nd Line EngineerCommented:
also is that mac a laptop and if taken on site, is it able to connect to the network shares at all?
AJ1978Author Commented:
The MAC is hard cabled not on wireless, whilst the MAC is in the office it connects to all the drive shares fine!
Kash2nd Line EngineerCommented:
do you by any chance have another mac or may be an ipad handy so you can test on that.

once connected to the VPN, what results does trace route dish out?
AJ1978Author Commented:
I will give that a go and revert back to you, Thanks for the help.
AJ1978Author Commented:
Very strange, I tried in the IPAD first then I tied on the same IP range same issue, tried again on a different and both are working! Thank you so much, I am going to split the point with Rich as he was supper helpful also, I hope your cool with that.
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Windows Server 2008

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