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The pineapple from Hak5 is a tasty Wi-Fi security tool. When you first get it, it doesn’t have too many hacks installed, so you have to update it. Here’s how to do that with a Mac:

1. Okay, so the pineapple eth0 is sort of a WAN, and it goes looking for a connection, but that connection has to be on the, which is confusing because eth0 is set to, which is typically a gateway, BUT IT’S NOT really here. So you have to set up your Mac as a non-.1 gateway, then share your Mac Wi-Fi connection with your Mac ethernet port and then do your upgrades…which is friggin’ stupid!

2. Hook your Mac up to its normal wifi connection.

3. Hook up your Mac ethernet to an unmanaged switch.

4. Hook up your Pineapple ethernet to another port on the unmanaged switch.

5. Now reorder your wifi/ethernet preferences in the System Preferences -> Network pop-up box like this. You have to drag the connection upward on the list with your mouse:

6. Notice you also have to set up your Ethernet connection -> Manual to IP:, netmask (don’t need to fill in router) and hit ‘Apply’

7. Now here’s the gotcha, you have to tell your Mac what subnet it should work with, and NOT to use, because the friggin’ Pineapple already used it – Doh! To do this, become root (or okay, sudo/whatever) on your Mac and do:

defaults write /Library/Preferences/SystemConfiguration/com.apple.nat NAT -dict-add SharingNetworkNumberStart
ifconfig en0 down
ifconfig en0 up

8. Now you have to enable sharing on System Preferences -> Sharing -> Share your connection from WI-FI -> To computers using ETHERNET, then check the box that enables Internet Service like this:

9. Now you should be able to:

ssh -p 22 root@
ping yahoo.com

if that worked, it means your pineapple is sharing your Mac’s connection and can get to the Internet to get updates.

10. Now login to the control panel on the Pineapple by clicking: and using the root password you want to set up.

11. Oddly enough, the updates you want are under the: Pineapple Bar -> Pineapple Bar: available. Here you should load stuff up, and also do some updates. After you add stuff, when you go back to the homepage the different hacks will show up there. Also, if you load up cli hacks, you can login as root via ssh and use those as you learn how.

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