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I've been digging around YouTube and Google in general for reasons why my macbook isn't able to get into contact with my Windows server.

At the moment my server is running a basic DNS and DHCP server role.

My Macbook, my girlfriends Windows laptop and my Windows gaming computer are recieving IP configurations from the DHCP server with no problem at all.

Where the bad part started is when I configured the DNS role on my server. To test my configuration, I created a record which pointed "printer" to an IP address. (It doesn't matter if it's there or not because I don't even own a network printer)

Point is, I pinged this "printer" on the Windows laptop and it worked perfectly. Asside from the fact that it isn't there, the console acknowledged the printer being bound to an IP address I specified on my server.

This however didn't work on my macbook. So I checked out the DNS servers in my network settings. As soon as I removed the 192.168.1.1 entry and only left in 192.168.1.100 (my server), I couldn't navigate to any webpage and so proved that my macbook once again wasn't able to make use of the DNS services of my server.

Thinking of the most basic way to test all my devices and if they were able to reach each other, I performed these ping tests:

  • [X] Macbook pings Windows server
  • [X] Windows server pings macbook
  • [✓] Windows laptop pings Windows server

So basically, my macbook is the culprit and I should move my focus to this machine instead of planting my foot into the casing of my Windows server, right?

  • I am running macOS Sierra on a late 2013 Retina Macbook Pro
  • My girlfriends laptop has Windows 8.1 installed
  • and my gaming rig is running Windows 10

Also, here is the output of my console:

Creedence:etc ackoujens$ ping 192.168.1.100
PING 192.168.1.100 (192.168.1.100): 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
Request timeout for icmp_seq 4
Request timeout for icmp_seq 5

Misc information:

  • all my devices exist under the same subnet
  • all my devices are directly connected to my ISP's modem
    • laptops by WiFi
    • gaming rig by ethernet cable
  • local IP's set up in 192.168.1.x format
  • DHCP leases IP's starting from 192.168.1.200 -> 192.168.1.250
  • I installed a fresh version of Windows Server only a few days ago, this is not a server that has been running and tinkered on for a long time
  • I tried turning off the firewall of my server completely, also on the mac
  • The macbook is able to ping www.google.com
  • The macbook is able to ping my router at 192.168.1.1
  • The macbook is able to ping the Windows laptop at 192.168.1.203
  • Windows laptop is able to ping the macbook at 192.168.1.200

If you have to know how to solve this issue or any other suggestions for possible tests, please share them below.

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    Make sure its not something network related. Can the Macbook ping any other device, such as the windows laptop, and visa versa? – LPChip Jan 31 '17 at 20:42
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    Macbook has pings blocked in it's firewall? Can it ping www.google.com? – DavidPostill Jan 31 '17 at 21:05
  • @DavidPostill Yes I can ping www.google.com – Jens Ackou Feb 1 '17 at 16:12
  • @LPChip Yes I can ping the windows laptop. Checked ipconfig and reported that the laptop has the IP address 192.168.1.203, which I can ping. I am also able to ping the router (192.168.1.1) which my macbook is connected to. – Jens Ackou Feb 1 '17 at 16:16
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    Almost sounds like there is an IP block specifically on either devices that causes this. Does other kind of traffic than pinging work? for example, on the windows server, download paping and ping a specific open port on the mac – LPChip Feb 1 '17 at 16:30

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