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CISS-125 Project 2 – SSH and Certificates

Posted on January 26, 2019January 28, 2019 By William Jojo
CISS-125-Project

In this project we will use some secure connections with a terminal protocol called SSH. We will also create some certificates that will be used in another project.


Learning outcomes

  • Planning and design.
  • Enhancing existing virtualization and networking skills.
  • VMware guest modifications.
  • Installing application software.
  • Public Key Infrastcture.
  • Secure Communications and Protocols.
  • Generate key and certificate signing request (CSR).

Ubuntu SSH daemon (server)

To install the SSH server, we will use the following as root:

apt install openssh-server

Once installed the program will run in the background servicing connection requests. Your instructor will explain the details of the protocol and how this will be used in later projects.


Windows 10 SSH PuTTY client

Now, go to the Windows 10 VM. Download & install the PuTTY MSI 64-bit installer from Putty Programs

Once installed, your instructor will give you more details on how you will use this product.


NOTE: Wait for the all-clear before moving to this next step. This involves some complexity that needs further explanation.


Ubuntu SSL

Note: Read this whole section before you begin!

At this point we will be creating certificate signing requests (CSR) for the Ubuntu server. It is recommended that you create a new directory and do your work there.

mkdir cert
cd cert

This way anything we do is captured in one directory and allows for easy maintenance and/or cleanup, if we make a mistake.

DigiCert has some very helpful tools when it comes to creating certificate components. Use the tool for creating a key and CSR command. Once all the fields are filled in, the tool will generate a command that you will run in a terminal window.

Paste the command generated by the wizard into a terminal window to create the private key and CSR.

Alternatively, if you are accustomed to doing this sort of work, you can use the following command in Ubuntu and fill in the values when prompted.

openssl req –new –newkey rsa:2048 –nodes –keyout server.key –out server.csr

Send the CSR to your instructor via Blackboard. You will received a signed certificate as a reply. This will be used in a later project.


Windows Server IIS

You will need to install the IIS server for Windows Server 2016. This is done by using Server Manager.

Within Server Manager, select Manage, select Add Roles and Features, select Next three times, select Web Server IIS, select Add Features, select Next four times, select Install.

Follow the instructions for creating a CSR for IIS 10. Only follow the first step for creating the CSR.

Send the CSR to your instructor via email. You will received a signed certificate as a reply. This will be used in a later project.

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