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  • Tailscale
  • OpenVPN
  • Infrastructure Overview
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  • Setup OpenVPN
  1. Cloud Tooling

VPN

Setup virtual private network (VPN)

PreviousInfrastructure as Code

Last updated 3 years ago

Tailscale

A secure network that just works. Zero config VPN. Installs on any device in minutes, manages firewall rules for you, and works from anywhere. Setup and configuration has been extremely easy compared to OpenVPN.

OpenVPN

OpenVPN is a virtual private network (VPN) system that implements techniques to create secure point-to-point or site-to-site connections in routed or bridged configurations and remote access facilities. It implements both client and server applications.

Infrastructure Overview

The following diagram shows a typical setup for a SAAS environment that is using OpenVPN. All critical systems run in private subnets. Only the OpenVPN bastion host is accessible from the public Internet. Thats how SRE / OPS / DEVS can connect to the environment using secure VPN clients (like or )

  1. Setup VPC

  2. Setup Public Subnet

    1. used for anything that needs to be accessible from the public internet, i.e. a OpenVPN bastion host, loadbalancer, ...

  3. Setup Private Subnet

    1. thats where critical systems get installed, i.e. datastores, kubernetes cluster, ...

  4. Setup NAT Gateway

    1. NAT Gateway will be used by all hosts that need to talk to the public internet

  5. Setup OpenVPN Bastion host

    1. This server is only accessible from the public Internet via port 1194

OpenVPN with 2FA

For additional level of security OpenVPN can be configured with 2-Factor-Authentication

  1. Users installs DUO App on Mobile Phone

  2. Once a user has authenticated using user/password, openvpn makes a request to duo.com to push a message to the Mobile Phone for the user. This process can be seen in the second diagram

  1. Open VPN connection initiated

  2. Primary authentication

  3. Open VPN connection established to Duo Security over TCP port 443

  4. Secondary authentication via Duo Security’s service

  5. Open VPN receives authentication response

  6. Open VPN session logged in

Setup OpenVPN

Step 1. Generate the CA key

openssl genrsa 4096 > vpn-ca-key.pem

Step 2. Using the CA key, generate the CA certificate (10 years)

openssl req -new -x509 -nodes -days 365000 -key vpn-ca-key.pem -out vpn-ca.pem
openssl x509 -noout -text -in vpn-ca.pem

Step 3: Generate Intermediate CA key

openssl genrsa 4096 > intermediate.cakey.pem

Step 4: Create intermediate CA Certificate Signing Request (CSR)

openssl req -new -sha256 -config intermediate/openssl.cnf \
   -key intermediate/private/intermediate.cakey.pem \
   -out intermediate/csr/intermediate.csr.pem

Step 5: Sign and generate intermediate CA certificate

openssl ca -config openssl.cnf -extensions v3_intermediate_ca -days 2650 \
   -notext -batch -in intermediate/csr/intermediate.csr.pem \
   -out intermediate/certs/intermediate.cacert.pem

Links

https://www.golinuxcloud.com/openssl-create-certificate-chain-linux/

Source:

https://tailscale.com/
Tunnelblick on MacOS
openvpn client on Linux
https://duo.com/docs/openvpn