Mac attempting to connect to Windows-based server.

[Alienx3]

Recently, I have purchased a Virtual Private Server (for my own personal use, not going to tell why), and it seems as if I cannot connect to it via my iMac(Mac OS X 10.5.8(an 2009/2008 model, can't remember)), but I am able to connect via PC (no, I am not going to use my PC to connect to it at all times). Okay, this is the message that keeps on appearing every single time I attempt to connect on my MAC:

"The Mac cannot connect to the Windows-based computer."
"This problem can occur if:
• The Windows-based computer is not set up to accept remote connections.
• The Windows-based computer is not turned on.
• The Mac, or the Windows-based computer is experiencing network problems.

Try connecting to the Windows-based computer again, or contact your administrator."​

This is a test on pinging to the Windows-based server:

"PING X.XX.XX.XXX (XX.XX.XX.XXX): 56 data bytes // IP is not actually X.XX.XX.XXX, just covered it up.
ping: sendto: No route to host
ping: sendto: Host is down
ping: sendto: Host is down
ping: sendto: Host is down"​

If it helps... the operating system is Windows Server 2008 R2.

 

[mrplow]

Assuming all devices are on the same network and all other network connectivity is working.

OK.
1. How are you trying to connect. Step-by-steps if possible.
2. which protocol are you using ?
3. Do you have a firewall on the server?

 

[Alienx3]

1. I am connecting via Remote Desktop Connection on my Mac. All I do is open it, then connect to the IP. I have even tried the host name.
2. Basically, I am just using Remote Desktop Connection... o.o
3. And no, and I would have problems on my PC if there is. Also, I'm trying to connect to a VPS, not one of my home computers.

 

[mrplow]

The first thing to resolve is the ping issue. Can you ping the VPS from a windows box? (ie. is the VPS allowed to respond to pings?)

If so, use Traceroute in Network Utility to see how far you're getting.

Another thing to check is that the security preferences in RDC on your Mac match those on your successful windows box

 

[Alienx3]

I am able to ping the VPS through a windows computer (not mine though... I have none available atm).

And where do I find Network Utility?

The security is fine.

 

[scathe]

Are both your PC and iMac on the same network? Presumable both at home? Same outer IP?
What about some sort of active VPN connection on the iMac?
If ping is allowed on the server and works from the PC and not from the Mac, check your OSX network settings and firewall as well (even the OSX delivered firewall under Sys pref>Security>firewall).
Check to see if you have the correct port in your RDC URL.

 

[Alienx3]

The PC is not the same network, seeing as it's not mine.
Also, I know how to check my network settings, but what am I looking for in the network settings?

 

[scathe]

I am able to ping the VPS through a windows computer (not mine though... I have none available atm).

And where do I find Network Utility?

The security is fine.

Sounds like you're maybe connecting from a work Windows machine and then from home on an iMac? The virtual server will probably be configured to only accept connections from a certain IP range or specific IP address, but you have to check this with your server provider. It doesn't have to be a setting on the server itself, rather than a setting on the data center firewall.

 

[Alienx3]

One of the staff at the hosting company told me they could connect fine on their Mac.
Also, it does allow any IP address.
I can't even ping the IP, so...

 

[scathe]

One of the staff at the hosting company told me they could connect fine on their Mac.
Also, it does allow any IP address.

Well, if they basically connect on their intranet, then they don't have much of a problem

So you're connecting to a public IP that has absolutely no security setup? All ports open, accepts incoming connections from ANY Ip range? I find that hard to believe.

 

[Alienx3]

Well, perhaps. I will ask them....

 

[scathe]

So what's the difference between the two networks: the windows machine and the network that you iMac is on? Any proxy servers? Other company firewalls and such? VPN?

 

[Alienx3]

Nope. The windows machine is one of my friend's, and my Mac is just a home computer. I don't think there are any company firewalls...

 

[scathe]

Hm, I'd love to help you out further, but from what's been said, all I can guess is a problem with network security somewhere down the line between your home network and the server itself. If you can't even ping the computer, then RDC won't work either (that is unless ping was disabled or only rdc ports were allowed).

Any chance you're using the wrong IP or wrong port? :-D

 

[Alienx3]

Well, all the ports are open, from what I know.
I am not using the wrong IP because my friend is able to connect.

 

[Alienx3]

I am using VNC for it, but I wish to use the VPS (with less lag...).

 

[mrplow]

just search for network utility in spotlight but it's in Applications - Utilities if you want to hunt it down in Finder

 

[Alienx3]

I found it already. I couldn't ping to the IP unfortunately. o.o

 

[mrplow]

But where does it fail?

 

[Alienx3]

I will copy paste it after the whole thing is done. One moment