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This is a step-by-step guide to configuring and managing a domain, remote server and hosted services, such as VPN, a private and obfuscated Tor bridge, and encrypted chat, using the Debian GNU/Linux operating system and other free software.

I like to set up my servers and services in these ways. This guide is not meant to be a canonical guide on best practices. I am not responsible for anything you do nor break by following any of these steps.

This guide is written for Google Compute Engine (GCE), but will very likely work well on other service providers, such as Linode or Amazon AWS, or any computer which will run GNU/Linux, such as an APU1C in a closet. It uses recommended configuration files from drduh/config.

If you have a suggestion or spot an error, don't hack me, rather please send a pull request or open an issue on GitHub.

Domain

If you are not sure what a domain name is, see the Wikipedia article and decide if you would like to create one at all.

I had decided to purchase duh.to from Tonic, a .to top level domain registrar. A 5 year registration cost $200 - a steep price, but not unreasonable for an esoteric ccTLD with many available short, memorable, three-letter domain names. Tonic.to also does not maintain a public whois database, which is a privacy advantage.

You could instead purchase a less expensive .com, .net or any available domain name from a variety of TLDs and registrars, though be aware of not all offer domain privacy, for instance the .us ccTLD.

After purchasing your domain, configure DNS settings. To use Google Cloud DNS with Tonic:

Wait for DNS records to propagate, which may take several hours. While you wait, feel free to learn more about Tonga.

Eventually, a WHOIS lookup will return the NS record of your hosting provider:

$ whois duh.to
Tonic whoisd V1.1
duh ns-cloud-c1.googledomains.com
duh ns-cloud-c2.googledomains.com

If it doesn't look right, log in to Tonic or your registrar and update DNS information accordingly.

Compute Engine

Create instance

Optional You may want to first Create a network to define firewall rules later, else the default rule set will be used.

Go to VM instances and select Create Instance.

Pick a name, zone and machine type. A "standard" single-vCPU or even shared "micro" or "small" machine with Debian 9 are fine defaults:

A Service account is not necessary and can be disabled.

Select the Networking tab and select your pre-configured network, if any. Apply any desired network tags while here, too.

Select Create to start the instance.

Once you have an External IP assigned, you may want to configure a DNS record. To do so, go to Networking > Cloud DNS and select Create Zone to create a new DNS zone.

Create an A record for the domain by selecting Add Record Set:

Select Create.

After a short while, verify an A record is returned with the correct IPv4 address for your VM instance:

$ dig +short a duh.to
104.197.215.107

If it doesn't work, wait longer for records to propagate, or try specifying the registrar's name severs:

$ dig +short a duh.to @ns-cloud-c1.googledomains.com
104.197.215.107

Likewise, there should be SOA records:

$ dig +short soa duh.to
ns-cloud-c1.googledomains.com. cloud-dns-hostmaster.google.com. 1 21600 3600 1209600 300

Setup access

Use an existing YubiKey or create a new 4096-bit RSA key-pair to use for logging into your instance via SSH (pass-phrase is optional):

$ ssh-keygen -t rsa -b 4096 -C 'sysadm' -f ~/.ssh/duh

Where sysadm is the desired username on the instance.

Copy the public key:

$ cat ~/.ssh/duh.pub
ssh-rsa AAAAB3NzaC1yc2EAAAADAQABAAACAQC/[...] sysadm

Edit your VM instance settings to paste the public key into the SSH Keys section:

Adding an SSH key to an instance

Select Save.

Connect

On a client, edit ~/.ssh/config to use the new key:

Host duh
  User sysadm
  HostName duh.to
  IdentityFile ~/.ssh/duh

The first time you connect, you will see a warning about the host authenticity:

$ ssh duh
[...]
The authenticity of host 'duh' (104.197.215.107)' can't be established.
ECDSA key fingerprint is d6:9a:...:1d:c1.
Are you sure you want to continue connecting (yes/no)?

To verify this fingerprint, you will need to check the instance Serial Console output.

See YubiKey Guide to further secure SSH keys.

Apply updates

Become root:

$ sudo -s

Install any pending updates:

# apt-get update && apt-get -y upgrade

Install any necessary software, for example:

# apt-get -y install zsh vim tmux dnsutils whois git gcc autoconf make lsof tcpdump htop tree

Configure passwords

Set a password for the current user:

$ passwd $USER

If you wish to allow use of sudo without a password for convenience:

$ echo "$USER ALL=(ALL) NOPASSWD:ALL" | sudo tee --append /etc/sudoers

Press Control-D or type exit to logout as root and return to the regular user.

Configure instance

tmux

tmux is a terminal multiplexer. This program will allow you to reconnect to a working terminal session on a remote computer.

Edit the configuration:

$ vim ~/.tmux.conf

Or use my configuration:

$ curl -o ~/.tmux.conf https://raw.githubusercontent.com/drduh/config/master/tmux.conf

Run tmux and open a new tab with `-c or specified keyboard shortcut.

`-1, `-2, `-3 switch to windows 1, 2, 3, etc.

`-d will disconnect from Tmux so you can save your session and log out.

When you reconnect to your instance, simply type tmux attach -t <session name> to select a session to "attach" to (default name is "0"; use `-$ to rename).

Zsh

Z shell is an interactive login shell with many features and improvements over Bourne shell.

To set the login shell for the current user to Zsh:

$ sudo chsh -s /usr/bin/zsh $USER

Edit the configuration:

$ vim ~/.zshrc

Or use my configuration:

$ curl -o ~/.zshrc https://raw.githubusercontent.com/drduh/config/master/zshrc

Open a new tmux tab and run zsh or start a new ssh session to make sure the configuration is working to your liking.

Vim

Vim is an excellent open source text editor. Run vimtutor if you have not used Vim before.

Edit the configuration:

$ vim ~/.vimrc

Or use my configuration:

$ curl -o ~/.vimrc https://raw.githubusercontent.com/drduh/config/master/vimrc

$ mkdir -p ~/.vim/{swaps,backups,undo}

Try out Vim:

$ vim ~/.vimrc

Use :q to quit :w to write (save) or :x for both.

SSH

Take a few steps to harden remote access: declare which users are allowed to log in, change the default listening port and generate a new host key. There are many more in-depth guides online on securing SSH (1, 2, 3; these are just basic suggestions:

Create a new host RSA keys (do not use a pass-phrase - else you won't be able to connect remotely after a reboot):

$ ssh-keygen -t rsa -b 4096 -f ssh_host_key -C '' -N ''

Move them into place:

$ sudo mv ssh_host_key{,.pub} /etc/ssh

Lock down file permissions:

$ sudo chown root:root /etc/ssh/ssh_host_key{,.pub}

Edit the ssh server configuration:

$ sudo -E vim /etc/ssh/sshd_config

Or use my configuration:

$ sudo curl -o /etc/ssh/sshd_config https://raw.githubusercontent.com/drduh/config/master/sshd_config

Update Networking firewall rules to allow the new ssh listening port (for example, my sshd configuration uses TCP port 2222).

Do not exit your current ssh session yet; first make sure you can still connect!

Restart ssh server:

$ sudo service ssh restart

On a client, edit ~/.ssh/config to make any modifications, for example by adding Port 2222:

Host duh
  HostName duh.to
  User sysadm
  IdentityFile ~/.ssh/duh
  Port 2222

Start a new ssh session to confirm it still works, then exit the other session.

Note On older versions of OS X, the ssh client may be out of date and may not support newer cipher suites. Either upgrade it using Homebrew, or comment out related lines in the server configuration to connect.

If you had created a new host key, you'll be asked to verify the new RSA key fingerprint:

$ ssh duh
The authenticity of host '[104.197.215.107]:2222 ([104.197.215.107]:2222)' can't be established.
RSA key fingerprint is 19:de:..:fe:58:3a.
Are you sure you want to continue connecting (yes/no)? yes

Check the fingerprint on the server from your previous, existing session:

$ sudo ssh-keygen -lf /etc/ssh/ssh_host_key
4096 19:de:..:fe:58:3a /etc/ssh/ssh_host_key.pub (RSA)

If ssh presents a SHA256 fingerprint:

$ ssh duh
Host key fingerprint is SHA256:47DEQpj8HBSa+/TImW+6JCeuQfRkm5NMpJWZG3hSuFU

Check the fingerprint on the server:

$ awk '{print $2}' /etc/ssh/ssh_host_key.pub | base64 -d | sha256sum -b | awk '{print $1}' | xxd -r -p | base64
47DEQpj8HBSa+/TImW+6JCeuQfRkm5NMpJWZG3hSuFU

Start tmux or reconnect to an existing session.

GPG

GNU Privacy Guard is used to verify signatures for downloaded software, encrypt and decrypt files, text, email, and much more.

Edit the configuration:

$ mkdir ~/.gnupg && vim ~/.gnupg/gpg.conf

Or use my configuration:

$ mkdir ~/.gnupg && curl -o ~/.gnupg/gpg.conf https://raw.githubusercontent.com/drduh/config/master/gpg.conf

Note For older versions of GnuPG, install a keyserver CA certificate:

$ sudo curl -o /etc/sks-keyservers.netCA.pem https://sks-keyservers.net/sks-keyservers.netCA.pem

To use GPG to symmetrically encrypt a directory into a single file:

$ tar zcvf - ~/backup | gpg -c > ~/backup-$(date +%F-%H%M).tar.gz.gpg

To decrypt the file and unpack the directory:

$ gpg -o ~/decrypted-backup.tar.gz -d backup-2016-01-01-0000.tar.gz.gpg && tar zxvf ~/decrypted-backup.tar.gz

See YubiKey Guide to learn more about using GPG.

Services

Dnsmasq

Dnsmasq is a lightweight DNS and DHCP server with many useful features.

Install Dnsmasq:

$ sudo apt-get -y install dnsmasq

Edit the configuration:

$ sudo -E vim /etc/dnsmasq.conf

Or use my configuration:

$ sudo curl -o /etc/dnsmasq.conf https://raw.githubusercontent.com/drduh/config/master/dnsmasq.conf

Pick an upstream name server. To use Google resolvers, add server=169.254.169.254 to /etc/dnsmasq.conf or use a resolv-file:

$ echo "nameserver 169.254.169.254" | sudo tee /etc/resolv.dnsmasq
nameserver 169.254.169.254

Install a DNS blacklist (alternative method), for example:

$ sudo curl https://raw.githubusercontent.com/StevenBlack/hosts/master/hosts -o /etc/blacklist

Optional Append additional lists, for example:

$ curl https://raw.githubusercontent.com/jmdugan/blocklists/master/corporations/facebook/facebook.com | sudo tee --append /etc/blacklist

Check the file length and that no non-localhost addresses were appended:

$ wc -l /etc/blacklist
50741 /etc/blacklist

$ grep -ve "^127.0.0.1\|^0.0.0.0\|^#" /etc/blacklist | sort | uniq
255.255.255.255 broadcasthost
::1 localhost
fe80::1%lo0 localhost

Restart the service:

$ sudo service dnsmasq restart

Check the log to make sure it is running:

$ sudo tail -F /var/log/dnsmasq
started, version 2.72 cachesize 2000
IPv6 GNU-getopt DBus i18n IDN DHCP DHCPv6 no-Lua TFTP conntrack ipset auth DNSSEC loop-detect
using nameserver 127.0.0.1#40
reading /etc/resolv.dnsmasq
using nameserver 169.254.169.254#53
read /etc/hosts - 5 addresses
read /etc/blacklist - 26995 addresses

If it fails to start, try running it manually:

$ sudo dnsmasq -C /etc/dnsmasq.conf -d
dnsmasq: started, version 2.76 cachesize 2000
dnsmasq: compile time options: IPv6 GNU-getopt DBus i18n IDN DHCP DHCPv6 no-Lua TFTP conntrack ipset auth DNSSEC loop-detect inotify
dnsmasq: reading /etc/resolv.dnsmasq
dnsmasq: using nameserver 169.254.169.254#53
dnsmasq: read /etc/hosts - 6 addresses
dnsmasq: read /etc/blacklist - 43638 addresses

Query locally for an A record to confirm dnsmasq is working:

$ dig +short a google.to @127.0.0.1
74.125.202.105
74.125.202.103
74.125.202.104
74.125.202.99
74.125.202.147
74.125.202.106

DNSCrypt

DNSCrypt software can be used as a server and client to encrypt DNS traffic.

If you are running your own private or public recursive DNS server, adding support for the DNSCrypt protocol requires installing DNSCrypt-Wrapper, the server-side DNSCrypt proxy.

To configure a private or public DNSCrypt server, first install libsodium and libevent:

$ sudo apt-get -y install libsodium-dev libevent-dev

Clone the DNSCrypt-Wrapper repository and install the software:

$ git clone --recursive git://github.com/Cofyc/dnscrypt-wrapper.git

$ cd dnscrypt-wrapper

$ make configure

$ ./configure

$ sudo make install

Create keys and certificate (see usage instructions on Cofyc/dnscrypt-wrapper for details):

$ mkdir ~/dnscrypt-keys && cd ~/dnscrypt-keys

$ dnscrypt-wrapper --gen-provider-keypair \
  --provider-name=dnscrypt.cloud --ext-address=$(curl -s https://icanhazip.com/)
Generate provider key pair... ok.
[...]
Keys are stored in public.key & secret.key.

Save the stamp (sdns:\\...) parameter and possibly others for older client versions. To use a port other than 443, use https://dnscrypt.info/stamps to update it.

$ dnscrypt-wrapper --gen-crypt-keypair --crypt-secretkey-file=1.key
Generate crypt key pair... ok.
Secret key stored in 1.key

By default, keys expire after 24 hours - below 30 days are specified.

$ dnscrypt-wrapper --gen-cert-file --crypt-secretkey-file=1.key \
  --provider-cert-file=1.cert --provider-publickey-file=public.key \
  --provider-secretkey-file=secret.key --cert-file-expire-days=30
[20300] 01 May 00:00:00.000 [notice] [main.c:405] Generating pre-signed certificate.
[20300] 01 May 00:00:00.000 [notice] [main.c:412] TXT record for signed-certificate:
[...]
[20300] 01 May 00:00:00.000 [notice] [main.c:566] Certificate stored in 1.cert.

Print the public key fingerprint:

$ dnscrypt-wrapper --show-provider-publickey --provider-publickey-file public.key
Provider public key fingerprint : 390C:...:F93E

Start the server on port 5355:

$ sudo dnscrypt-wrapper --resolver-address=127.0.0.1:53 \
  --listen-address=0.0.0.0:5355 --provider-name=dnscrypt.cloud \
  --crypt-secretkey-file=1.key --provider-cert-file=1.cert -V

Note The provider-name parameter is not encrypted during the connection handshake.

Update Networking firewall rules to allow the new dnscrypt listening port (in this example, UDP port 5355).

Optional Restrict the IP address or range of addresses which can access your VM instance to prevent abuse and DNS attacks.

To connect from a client, edit dnscrypt-proxy.toml to include the static server stamp, like:

listen_addresses = ['127.0.0.1:40']
server_names = ['abc']
[static]
  [static.'abc']
  stamp = 'sdns://AQAAAAAAAAAAEj...ZA'

Then start the client manually:

$ sudo ./dnscrypt-proxy
[NOTICE] dnscrypt-proxy 2.0.11
[NOTICE] Now listening to 127.0.0.1:5355 [UDP]
[NOTICE] Now listening to 127.0.0.1:5355 [TCP]
[NOTICE] [abc] OK (crypto v1) - rtt: 10ms
[NOTICE] Server with the lowest initial latency: abc (rtt: 10ms)
[NOTICE] dnscrypt-proxy is ready - live servers: 1

Or install it as a service:

$ sudo ./dnscrypt-proxy -service install

Or on older versions of dnscrypt-proxy:

$ sudo dnscrypt-proxy \
  -a 127.0.0.1:40 -r 104.197.215.107:5355 \
  -k 390C:...:F93E -N 2.dnscrypt-cert.duh.to
[NOTICE] Starting dnscrypt-proxy 1.9.4
[INFO] Generating a new session key pair
[INFO] Done
[INFO] Server certificate #808441433 received
[INFO] This certificate looks valid
[INFO] Chosen certificate #808441433 is valid from [2016-05-08] to [2017-05-08]
[INFO] Server key fingerprint is 9147:...:212E
[NOTICE] Proxying from 127.0.0.1:40 to 104.197.215.107:5355

Outgoing DNS packets will now be encrypted from the client.

For example, take a packet capture on the client while running dig a google.to @127.0.0.1 -p 40 in another terminal:

$ sudo tcpdump -As80 -tni eth0 "udp port 5355"
listening on eth0, link-type EN10MB (Ethernet), capture size 80 bytes
IP 10.8.4.2.55555 > 104.197.215.107:5355: UDP, length 512
E...    [email protected]
..%h.x}._.......G.....%.....0......bOF.".#%...ZA.T...

IP 104.197.215.107.5355 > 10.8.4.2.55555: UDP, length 304
E..L.E..)...h.x}
..%..._.8..r6fnvWj84'TQ.&.. O....&..>
.P|y.%.....
^C

Compare with querying Google Public DNS directly with dig a google.to @8.8.8.8 while listening on UDP port 53:

$ sudo tcpdump -As80 -tni eth0 "udp port 53"
listening on eth0, link-type EN10MB (Ethernet), capture size 80 bytes
IP 10.8.4.2.55555 > 8.8.8.8.53: 45279+ [1au] A? google.to. (38)
[email protected]
..%.....t.5...|... .........google.to.......)........
IP 8.8.8.8.53 > 10.8.4.2.55555: 45279 1/0/1 (54)
E..R*...4.=.....
..%.5.t.>...............google.to..............+.
^C

Once DNSCrypt is configured on the client, edit /etc/dnsmasq.conf and append server=127.0.0.1#40 to use the local port for DNSCrypt.

Privoxy

Privoxy is a non-caching web proxy with advanced filtering capabilities for enhancing privacy, modifying web page data and HTTP headers, controlling access, and removing ads and other obnoxious Internet junk.

Install Privoxy on the server:

$ sudo apt-get -y install privoxy

Edit the configuration:

$ sudo -E vim /etc/privoxy/config

Or use my configuration:

$ sudo curl -o /etc/privoxy/config https://raw.githubusercontent.com/drduh/config/master/privoxy

Restart Privoxy:

$ sudo service privoxy restart

Test Privoxy locally on the server:

$ ALL_PROXY=127.0.0.1:8000 curl -I http://p.p/
HTTP/1.1 200 OK
Content-Length: 3312
Content-Type: text/html
Cache-Control: no-cache
Date: Sun, 01 May 2016 00:00:00 GMT
Last-Modified: Sun, 01 May 2016 00:00:00 GMT
Expires: Sat, 17 Jun 2000 12:00:00 GMT
Pragma: no-cache

Clients can use the remote proxy with Secure Shell tunneling, also known as a "poor man's VPN" (Note AllowTcpForwarding yes must be enabled in /etc/ssh/sshd_config on the server to use these features, followed by sudo service ssh restart).

$ ssh -NCL 5555:127.0.0.1:8000 duh

In another client terminal:

$ ALL_PROXY='127.0.0.1:5555' curl https://icanhazip.com/
104.197.215.107

Or to use ssh as a SOCKS proxy:

$ ssh -NCD 7000 duh

In another client terminal:

$ curl --proxy socks5h://127.0.0.1:7000 https://icanhazip.com/
104.197.215.107

Watch Privoxy logs (you may wish to disable logging by removing debug lines in /etc/privoxy/config):

$ sudo tail -F /var/log/privoxy/logfile

Tor

Tor can be used as a public relay or as a private bridge for you and your friends.

Install Tor on the server:

$ sudo apt-get -y install tor

Optional Install and configure anonymizing relay monitor (arm), a terminal-based status monitor for Tor.

DNS over Tor

Tor can listen locally to resolve DNS A, AAAA and PTR records anonymously. To use, add a local address to /etc/tor/torrc:

DNSPort 127.26.255.1:53

Then append server=127.26.255.1 to /etc/dnsmasq.conf and restart both services.

Obfuscation

Additionally, obfuscate Tor traffic by using obfsproxy or some other Tor pluggable transport.

To install the latest version of obfs4proxy, first install Golang:

$ sudo apt-get -y install golang

Create a temporary download and build directory:

$ export GOPATH=$(mktemp -d) ; echo $GOPATH
/tmp/tmp.u40VUD66nP

Download and build obfs4proxy:

$ go get git.torproject.org/pluggable-transports/obfs4.git/obfs4proxy

Note If this fails for any reason, you likely need a more recent version of Go.

Confirm it's built:

$ $GOPATH/bin/obfs4proxy -version
obfs4proxy-0.0.8-dev

Install it:

$ sudo cp $GOPATH/bin/obfs4proxy /usr/local/bin

Secure it:

$ sudo chown root:root /usr/local/bin/obfs4proxy

Edit /etc/tor/torrc to include:

ORPort 9993
ExtORPort auto
BridgeRelay 1
ServerTransportPlugin obfs4 exec /usr/local/bin/obfs4proxy
ServerTransportListenAddr obfs4 0.0.0.0:10022

Restart Tor:

$ sudo service tor restart

Ensure obfs4proxy is accepting connections:

$ sudo lsof -Pni | grep 10022
obfs4prox 6685     debiant-tor    4u  IPv6  44617      0t0  TCP *:10022 (LISTEN)

Update Networking firewall rules to allow the new proxy listening port (in this case, TCP port 10022).

If Tor did not start, try starting it manually (sudo may be required to bind to privileged ports):

$ tor -f /etc/tor/torrc
[notice] Opening Socks listener on 127.0.0.1:9050
[notice] Opening OR listener on 0.0.0.0:9993
[notice] Opening Extended OR listener on 127.0.0.1:0
Extended OR listener listening on port 50161.
[...]
Bootstrapped 0%: Starting
Bootstrapped 5%: Connecting to directory server
Bootstrapped 45%: Asking for relay descriptors
Bootstrapped 78%: Loading relay descriptors
Registered server transport 'obfs4' at '[::]:10022'
Guessed our IP address as 104.197.215.107 (source: 62.210.222.166).
We now have enough directory information to build circuits.
Bootstrapped 80%: Connecting to the Tor network
Bootstrapped 90%: Establishing a Tor circuit
Tor has successfully opened a circuit. Looks like client functionality is working.
Bootstrapped 100%: Done

Copy the bridgeline, filling in the IP address and port:

$ sudo tail -n1 /var/lib/tor/pt_state/obfs4_bridgeline.txt
Bridge obfs4 <IP ADDRESS>:<PORT> <FINGERPRINT> cert=4ar[...]8FA iat-mode=0

To connect from a Mac or Linux client, edit torrc to use the IP address and assigned port, for example:

UseBridges 1
Bridge obfs4 104.197.215.107:10022 cert=4ar[...]8FA iat-mode=0

Using Tor Browser, select Configure and Enter custom bridges:

To connect from Android, download Orbot and Orfox applications and configure a custom bridge in Orbot settings.

Hidden Service

Optional To host a hidden service, append something like this to /etc/tor/torrc on the server (for example, to use with a Web server):

HiddenServiceDir /var/lib/tor/hidden_service/
HiddenServicePort 80 127.0.0.1:80

Restart Tor:

$ sudo service tor restart

Get the hidden service hostname:

$ sudo cat /var/lib/tor/hidden_service/hostname
pqccxgxxxxxxxl5h.onion

You can also host services like ssh as a hidden service.

To generate a specific .onion hostname, some software exists.

Certificates

Create your own public-key infrastructure, so that you may use your own keys and certificates for VPN, HTTPS, etc.

To create a certificate authority, intermediate authority, server and client certificates, download my script (run on a trusted client machine, preferably air-gapped):

$ mkdir ~/pki && cd ~/pki

$ curl -o ~/pki/pki.sh https://raw.githubusercontent.com/drduh/config/master/pki.sh

Read through and edit the script and variables, especially CN_ ones, to your suit your needs:

$ vim pki.sh

Make the script executable:

$ chmod +x pki.sh

Optional Disable default OpenSSL certificate requirements, like mandatory location:

$ sudo sed -i.bak "s/= match/= optional/g" /usr/lib/ssl/openssl.cnf

Run the script, accepting prompts with y to sign certificates and commit changes:

$ ./pki.sh
Generating RSA private key, 4096 bit long modulus
........................................................................++
.....................................++
[...]
Sign the certificate? [y/n]:y

If successful, the script created private and public keys for a certificate authority, intemediate authority, server and one client:

$ ls ~/pki
ca.key      client.csr  demoCA            intermediate.pem  server.cnf  server.pem
ca.pem      client.key  intermediate.csr  intermediate.srl  server.csr
client.cnf  client.pem  intermediate.key  pki.sh            server.key

Check any of the certificate files (.pem extension) with OpenSSL:

$ openssl x509 -in ca.pem -noout -subject -issuer -enddate
subject=CN = Example Authority
issuer=CN = Example Authority
notAfter=Dec 1 00:00:00 2018 GMT

You could also use OpenVPN/easy-rsa.

You could also purchase trusted certificates from a variety of online vendors. There are also free options available from public certificate authorities. Use these if you can't install your own certificate authority on clients.

OpenVPN

OpenVPN is free, open source TLS-based VPN server and client software.

Install OpenVPN:

$ sudo apt-get -y install openvpn

Edit the configuration:

$ sudo -E vim /etc/openvpn/openvpn.conf

Or use my configuration:

$ sudo curl -o /etc/openvpn/openvpn.conf https://raw.githubusercontent.com/drduh/config/master/openvpn.conf

Generate a static key so that only trusted clients can attempt connections (extra authentication on top of TLS):

$ cd ~/pki

$ sudo openvpn --genkey --secret ta.key

Create Diffie-Hellman key exchange parameters:

$ openssl dhparam -dsaparam -out ~/pki/dh.pem 4096

Configure certificates from the previous section, or install your own:

$ sudo mkdir /etc/pki

$ cd ~/pki

$ cat ca.pem intermediate.pem > chain.pem

$ sudo cp chain.pem server.pem server.key dh.pem ta.key /etc/pki

Enable IP forwarding:

$ sudo sysctl -w net.ipv4.ip_forward=1

To make the change permanent:

$ echo "net.ipv4.ip_forward = 1" | sudo tee --append /etc/sysctl.conf

Create a NAT for VPN clients:

$ sudo iptables -t nat -A POSTROUTING -o eth0 -s 10.8.0.0/16 -j MASQUERADE

Optional Route all HTTP (TCP port 80) traffic through Privoxy.

$ sudo iptables -t nat -A PREROUTING --source 10.8.0.0/16 -p tcp -m tcp --dport 80 -j DNAT --to 10.8.0.1:8000

$ echo "listen-address 10.8.0.1:8000" | sudo tee --append /etc/privoxy/config

$ sudo service privoxy restart

To make it permanent:

$ sudo apt-get -y install iptables-persistent

$ sudo iptables-save | sudo tee /etc/iptables/rules.v4

If using Dnsmasq, append 10.8.0.1 as a listening address:

$ sudo sed -i.bak "s/listen-address=127.0.0.1/listen-address=127.0.0.1,10.8.0.1/g" /etc/dnsmasq.conf

$ sudo service dnsmasq restart

Restart the service:

$ sudo service openvpn restart

Watch the log:

$ sudo tail -F /var/log/openvpn.log
TUN/TAP device tun0 opened
TUN/TAP TX queue length set to 100
do_ifconfig, tt->ipv6=0, tt->did_ifconfig_ipv6_setup=0
/sbin/ip link set dev tun0 up mtu 1500
/sbin/ip addr add dev tun0 10.8.0.1/24 broadcast 10.8.0.255
UDPv4 link local (bound): [undef]
UDPv4 link remote: [undef]
v=256
IFCONFIG POOL: base=10.8.0.2 size=252, ipv6=0
Initialization Sequence Completed

If it fails, try to start OpenVPN server manually:

$ sudo openvpn --config /etc/openvpn/openvpn.conf --verb 3 --suppress-timestamps
OpenVPN 2.4.0 x86_64-pc-linux-gnu [SSL (OpenSSL)] [LZO] [LZ4] [EPOLL] [PKCS11] [MH/PKTINFO] [AEAD] built on Jul 18 2017
library versions: OpenSSL 1.0.2l  25 May 2017, LZO 2.08
Diffie-Hellman initialized with 4096 bit key
Control Channel Authentication: using '/etc/pki/ta.key' as a OpenVPN static key file
Outgoing Control Channel Authentication: Using 256 bit message hash 'SHA256' for HMAC authentication
Incoming Control Channel Authentication: Using 256 bit message hash 'SHA256' for HMAC authentication
ROUTE_GATEWAY 10.240.0.1
TUN/TAP device tun0 opened
TUN/TAP TX queue length set to 100
do_ifconfig, tt->did_ifconfig_ipv6_setup=1
/sbin/ip link set dev tun0 up mtu 1500
/sbin/ip addr add dev tun0 10.8.0.1/24 broadcast 10.8.0.255
/sbin/ip -6 addr add 2001:db8:123::1/64 dev tun0
/sbin/ip route add 10.8.0.0/24 via 10.8.0.2
[...]
Initialization Sequence Completed

Update Networking firewall rules to allow the new VPN listening port (in this case, UDP port 443)

For each connecting device, edit a client configuration:

$ mkdir ~/vpn

$ vim ~/vpn/client.ovpn

Or use my configuration:

$ curl -o ~/vpn/client.ovpn https://raw.githubusercontent.com/drduh/config/master/client.ovpn

Add the CA certificate, client certificate and client key material to the configuration:

$ (echo "<ca>" ; cat ~/pki/ca.pem ; echo "</ca>\n<cert>" ; cat ~/pki/client.pem; echo "</cert>\n<key>" ; cat ~/pki/client.key ; echo "</key>") >> client.ovpn

From a client, copy ta.key from your server:

$ scp duh:~/pki/ta.key ~/vpn

To connect from Linux, install OpenVPN and start it:

$ sudo apt-get -y install openvpn

$ cd ~/vpn

$ sudo openvpn --config client.ovpn
[...]
TLS: Initial packet from [AF_INET]104.197.215.107:443, sid=6901c819 3e11276e
VERIFY OK: depth=2, CN=Duh Authority
VERIFY OK: depth=1, CN=Duh Intermediate Authority
Validating certificate key usage
++ Certificate has key usage  00a0, expects 00a0
VERIFY KU OK
Validating certificate extended key usage
++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
VERIFY EKU OK
VERIFY OK: depth=0, CN=duh.to
[...]

Verify your local IP address is the same as your server:

$ curl -4 https://icanhazip.com/
104.197.215.107

Note If IPv6 is disabled, the connection may fail - you'll need to disable these options on the server to connect:

#server-ipv6 2001:db8:123::/64
#push "route-ipv6 2000::/3"

To connect from Android, install OpenVPN Connect.

Copy client.ovpn and ta.key to a folder on the Android device, using a USB cable or by sharing the files through Google Drive, for example.

Select Import > Import Profile from SD card and select client.ovpn, perhaps in the Download folder.

If the profile was was successfully imported, select Connect.

To connect from a Mac, install OpenVPN from Homebrew:

$ brew install openvpn

Start OpenVPN:

$ sudo ~/homebrew/sbin/openvpn --config client.ovpn
OpenVPN 2.4.4 x86_64-apple-darwin16.7.0 [SSL (OpenSSL)] [LZO] [LZ4] [PKCS11] [MH/RECVDA] [AEAD] built on Oct  2 2017
[...]
TLS: Initial packet from [AF_INET]104.197.215.107:443, sid=db4ecf82 4e4e4c5b
VERIFY OK: depth=2, CN=Duh Authority
VERIFY OK: depth=1, CN=Duh Intermediate Authority
Validating certificate key usage
++ Certificate has key usage  00a0, expects 00a0
VERIFY KU OK
Validating certificate extended key usage
++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
VERIFY EKU OK
VERIFY OK: depth=0, CN=duh.to
[...]
Initialization Sequence Completed

Verify:

$ curl https://icanhazip.com/
104.197.215.107

Or use a GUI-based VPN client like Tunnelblick.

See also OS-X-Security-and-Privacy-Guide#vpn.

Web Server

You may wish to run a Web server to serve static or dynamic pages.

Install Lighttpd with ModMagnet (optional):

$ sudo apt-get -y install lighttpd lighttpd-mod-magnet

Edit the configuration:

$ sudo -E vim /etc/lighttpd/lighttpd.conf

Or use my configuration:

$ sudo curl -o /etc/lighttpd/lighttpd.conf https://raw.githubusercontent.com/drduh/config/master/lighttpd.conf

$ sudo curl -o /etc/lighttpd/magnet.luau https://raw.githubusercontent.com/drduh/config/master/magnet.luau

Note Lighttpd expects the server private key and certificate to be stored in one file as the ssl.pemfile argument:

$ sudo cat /etc/pki/server.key /etc/pki/server.pem | sudo tee /etc/pki/lighttpd.pem

You may need to comment out the following line in /etc/lighttpd/lighttpd.conf in order to accept requests on Internet-facing interfaces:

#server.bind = "127.0.0.1"

Restart Lighttpd:

$ sudo service lighttpd restart

Check that it's running - look for the process listening on TCP ports 80 or 443:

$ sudo lsof -Pni | grep lighttpd
lighttpd  3291   www-data    4u  IPv4  18206      0t0  TCP *:80 (LISTEN)
lighttpd  3291   www-data    5u  IPv4  18207      0t0  TCP *:443 (LISTEN)

If it failed to start, try running it directly to check for errors:

$ sudo lighttpd -f /etc/lighttpd/lighttpd.conf -D

Update Networking firewall rules to allow the new HTTP/HTTPS listening port(s) (in this example, TCP port 80 and 443).

Create some content:

$ echo "Hello, World" | sudo tee /var/www/index.html

Once Lighttpd is running, request a page from your server in a Web browser or by using cURL:

$ curl -vv http://duh.to/
Hello, World

You can use client certificates as a means of authentication and authorization, rather than relying on user-provided passwords. See my Lighttpd configuration for an example.

See also ioerror/duraconf/configs/lighttpd/lighttpd.conf.

XMPP

Run your own XMPP chat server with Prosody. Client can use Off The Record (OTR) messaging, a form of secure messaging which includes encryption, authentication, deniability and perfect forward secrecy, to communicate privately.

Install Prosody:

$ sudo apt-get -y install prosody

Edit the configuration:

$ sudo -E vim /etc/prosody/prosody.cfg.lua

Or use my configuration and edit it to suit your needs:

$ sudo curl -o /etc/prosody/prosody.cfg.lua https://raw.githubusercontent.com/drduh/config/master/prosody.cfg.lua

See also Advanced ssl config.

Use Diffie-Hellman key exchange parameters from the Certificate steps:

$ sudo cp ~/pki/dh.pem /etc/pki/dh.pem

Or create new parameters:

$ sudo openssl dhparam -out /etc/pki/dh.pem 4096

Copy the server certificate and key from the Certificate steps:

$ sudo cp ~/pki/server.pem /etc/pki/xmpp-cert.pem

$ sudo cp ~/pki/server.key /etc/pki/xmpp-key.pem

If using a custom CA or intermediate certificate, append it to the server certificate, for example:

$ cd ~/pki && cat server.pem intermediate.pem ca.pem | sudo tee /etc/pki/xmpp-cert.pem

Or generate a new self-signed certificate:

$ openssl req -x509 -newkey rsa:4096 -days 365 -sha256 -subj "/CN=duh.to" \
  -keyout /etc/pki/xmpp-key.pem -nodes -out /etc/pki/xmpp-cert.pem

Set file ownership:

$ sudo chown prosody:prosody /etc/pki/xmpp-*pem

Restart Prosody:

$ sudo service prosody restart

Ensure it's running:

$ sudo tail -n1 /var/log/prosody/prosody.log
mod_posix       info    Successfully daemonized to PID 1831

Ensure it's listening:

$ sudo lsof -Pni | grep prosody
lua5.1     1831    prosody    6u  IPv6 317986      0t0  TCP *:5269 (LISTEN)
lua5.1     1831    prosody    7u  IPv4 317987      0t0  TCP *:5269 (LISTEN)
lua5.1     1831    prosody    8u  IPv6 317990      0t0  TCP *:5222 (LISTEN)
lua5.1     1831    prosody    9u  IPv4 317991      0t0  TCP *:5222 (LISTEN)

Update Networking firewall rules to allow the new prosody listening ports (in this example, TCP ports 5222 and 5269).

Create a new user:

$ sudo prosodyctl adduser [email protected]

Note The domain must match the server certificate common name (CN_SERVER in pki.sh) - check with openssl x509 -in /etc/pki/xmpp-cert.pem -noout -subject

Federating

Optional For other XMPP servers to communicate with yours, you must configure DNS records for interdomain federation:

_xmpp-client._tcp of type SRV with data 0 5 5222 duh.to.

_xmpp-server._tcp of type SRV with data 0 5 5269 duh.to.

After a little while, check your records:

$ dig +short srv _xmpp-server._tcp.duh.to
0 5 5269 duh.to.

$ dig +short srv _xmpp-client._tcp.duh.to
0 5 5222 duh.to.

Using

To connect from a Linux client, use an XMPP client like Profanity or agl/xmpp-client:

$ sudo apt-get -y install profanity

Start Profanity:

$ profanity

Log in by typing /connect [email protected] and entering the password when prompted.

Generate OTR keys by typing /otr gen - this part may take a while.

Send a message to a contact by typing /msg [email protected] - to navigate tabs, use /win 1, /win 2, etc.

To start OTR, type /otr start - Profanity will show OTR session started (untrusted).

To authenticate your chat partner, type /otr question foo? bar where bar is an answer to foo? which only the person you assume to be speaking with can answer. If the person answers correctly, Profanity will show Authentication successful followed by OTR session trusted - now you can be sure the connection is encrypted and authenticated.

To connect from an Android client, use an XMPP client like Conversations (do not use the Conversations app - its quality is dubious and author's intentions are questionable) or Chat Secure.

Start the app and sign in. If you receive a warning that the certificate is not signed by a known authority, verify it using the step below.

To start a chat, select the + icon and select New Chat.

Start OTR by selecting the lock icon and verifying your contact with a secret question and answer, or out of band (e.g., in person).

To connect from a Mac client, use an XMPP client like Profanity, agl/xmpp-client, or Adium.

If you can't connect, check for errors in /var/log/prosody/prosody.err on the server.

Verify the SHA-256 fingerprint matches the certificate you see on the server:

$ openssl x509 -in /etc/pki/xmpp-cert.pem -fingerprint -noout -sha256

If it matches the fingerprint in the presented certificate prompt, trust it and connect.

To view and verify the XMPP server's certificate fingerprint remotely, use the openssl command:

$ echo -e | openssl s_client -connect duh.to:5222 -starttls xmpp | openssl x509 -noout -fingerprint -sha256 | tr -d ':'
[...]
SHA256 Fingerprint=9B759D41E3DE30F9D2F902027D792B65D950A98BBB6D6D56BE7F2528453BF8E9

Note If using agl/xmpp-client and custom certificates (i.e., not signed by a trusted root CA), you will need to manually add the server's SHA256 fingerprint to ~/.xmpp-client, like:

"ServerCertificateSHA256": "9B759D41E3DE30F9D2F902027D792B65D950A98BBB6D6D56BE7F2528453BF8E9"

If an error occurs while attempting to connect, ssh to the server and check /var/log/prosody/prosody.err.

Mail

Configuring and running a mail server is an enormous hassle and maintaining one is a time-consuming task. Moreover, many service providers do not allow outbound SMTP.

It is much easier to simply run something like Google Apps for Work to get Gmail for your custom domain. If going down this route, simply follow instructions to configure MX records to point to Google's mail servers.

Visit https://admin.google.com/ to get started. To verify your domain, simply download and host an HTML file or edit your DNS TXT records, per the instructions.

The MX records for your domain should look something like this:

$ dig mx +short duh.to
1 aspmx.l.google.com.
5 alt1.aspmx.l.google.com.
5 alt2.aspmx.l.google.com.
10 alt3.aspmx.l.google.com.
10 alt4.aspmx.l.google.com.

Warning Google Apps appears to add X-Originating-IP headers to emails sent from newly registered domains. This may reveal information about the location and computer used to send your mail, so wait a little while (first N days? during free trial period?) before using Google Apps mail. Alternatively, only send mail from your instance by connecting through a proxy or using a text-based e-mail client, like Mutt.

To install Mutt:

$ sudo apt-get -y install mutt

Edit the configuration:

$ vim ~/.muttrc

Note You will need to turn on 2-Step Verification and create an App password to use Mutt.

Lock it down:

$ chmod 0600 ~/.muttrc

Start Mutt:

$ mutt

Type ? to see available commands, or read online guides to using Mutt.

Conclusion

Reboot the instance and make sure everything still works. If not, you'll need to automate certain programs to start up on their own (for example, Privoxy will fail to start if OpenVPN does not first create a tunnel interface to bind to).

With this guide, one can set up a fairly secure server with several privacy- and security-enchancing services. The server can be used to circumvent firewalls, provide strong encryption and overall improve your online experience, all for a low monthly cost (average ~$35 per month for a "standard" instance.) A domain name also lets you receive email and assign DNS records, which is convenient, but totally optional.

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Guide to using a remote Debian server for security and privacy services

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