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We are having an issue with our Debian Server, we host several services on it each using several ports (all are open in iptables), all users can connect to these fine, except osx users.

We have got the users to ping / traceroute the server, but it cannot even ping the IP, however pinging from Windows or Linux works fine.

This is really strange, i cannot see what is causing it.

Any ideas?

Updated info:

This is not on a subnet, but over a internet network. result from OSX when traceroute:

traceroute to (, 64 hops max, 52 byte packets
1  * * *
2  * * traceroute: sendto: No route to host
traceroute: wrote 52chars, ret=1
traceroute: sendto: Host is down

Result from unix & windows is a standard sucessful ping at 11ms

When attempting to ping from OSX:

PING ( 56 data bytes
Request timeout for icmp_seq 0
Request timeout for icmp_seq 1
Request timeout for icmp_seq 2
Request timeout for icmp_seq 3
ping: sendto: No route to host
Request timeout for icmp_seq 4

--- ping statistics ---
6 packets transmitted, 0 packets received, 100.0% packet loss
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closed as not a real question by MikeyB, Michael Hampton, HopelessN00b, Scott Pack, MDMarra Oct 5 '12 at 2:16

It's difficult to tell what is being asked here. This question is ambiguous, vague, incomplete, overly broad, or rhetorical and cannot be reasonably answered in its current form. For help clarifying this question so that it can be reopened, visit the help center.If this question can be reworded to fit the rules in the help center, please edit the question.

Redacting IP info makes this especially difficult for us to help you with. Especially if you're using RFC1918 internal addresses. – MDMarra Oct 1 '12 at 17:37

Assuming the boxes are all the same subnet, try pinging the Debian box from the OSX boxes. Then look in the arp table (arp -a) to check that the Debian's MAC address is listed.

If that fails, please provide more details about your network topology and the actual error messages your receive when you ping or try a TCP connection.

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I have updated the above post. – Dan Spiteri Sep 29 '12 at 10:52
Turned out to be the users using Hamachi, and our ip starting with 5. – Dan Spiteri Sep 29 '12 at 10:59
@Dan Spiteri I understand Hamachi is a VPN product. Can you add your resolution as an answer and accept it? – Alastair McCormack Sep 30 '12 at 17:05
I tried at the time but it wouldnt let me due to my reputation. i will add it now. – Dan Spiteri Oct 1 '12 at 17:10
up vote 0 down vote accepted

The solution was that Hamachi was overriding the IP range due to the IP starting with 5.

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Care to elaborate on this a bit more? What you're saying doesn't make any sense to me... – voretaq7 Oct 1 '12 at 17:52
our ip started with 5.*.*.* and that is the network hamachi uses, therefore it caused conflict issues – Dan Spiteri Oct 1 '12 at 20:25

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