Project Overview
One of my first major system upgrade projects was converting a Terminal Server system setup to one that was more conducive to the business’s current needs. A Terminal Server system requires a main server each user can remote into and then systems for each of the employees. Usually the client systems are not powerful and are locked down to prevent misuse.
I had not done a project like this before, and required some research to find the best method to deploy a new system like this without disrupting work.
Approach & Plan
Current System
I had to understand what systems they had in place at the time.
It included the following:
Host Server
Exchange 2012
Windows Server 2012
File server
Dedicated IP
Client Devices
These systems were likely costing in tens of thousands to maintain each year due to their age and system setup. I had asked management what their most recent HIPAA audit had shown and their vulnerability list was showing a bunch of vulnerabilities that had patches available for them. This was disconcerting, but allowed me to propose a better system that could still be maintained easily.
New System
I had asked the stakeholders what they wanted to upgrade to and their main requirements were stability and flexibility.
I came up with a plan to shift them to a less costly system and shared the details, including technical plan, impact, change management, cost, opportunity loss, pros/cons, and migration schedule.
We would remove the client desktops and move them to a managed laptop & docking station system, so we could take advantage of mobile work if needed and use some of the existing hardware infrastructure to reduce downtime.
We would migrate their email to O365 to improve downtime issues with email and make management easier.
We would move the file server to a cloud storage solution using a NAS to cloud storage syncing tool. The cloud would also take care of backups, file syncing and offline/online work requests.
We would move system management to Azure Active Directory (at the time that was what it was called). AAD would allow system management, app deployment and other tools to manage the system.
We would use a remote desktop connection tool so I could remote into the systems in case I needed to work on any of the systems remotely.
We would have on-prem hardware warranty from the laptop manufacturer to maintain any hardware failures. This was important because we didn’t want to have a failure take too long to repair.
I also insisted on maintaining a backup laptop that could be used if a system failed. Hardware system failures did happen 4 times in the time I was there and all times the warranty proved its worth, and the system was repaired within 48 hours, and the user was able to pivot to the backup machine with little friction.
We would use a Sophos on-prem wireless & firewall system to maintain wireless connectivity in the office (until the office was closed down).
Deployment
Deployment would require me to maintain current office productivity while transitioning all systems to the new infrastructure.
Email was the trickiest because it would require me to use migration tools to move the system from Exchange 2012 to O365 cloud servers. Because the server was not updated it took several service pack upgrades on both Windows Server and Exchange sever and a late Friday night to transition the emails for access on Monday morning.
The transition was successful and maintain minimal downtime as Monday morning I could continue to have users access their email using the new username & password provided to them.
File Server
Before switching, I needed to find a file service provider that would be easy for the users to understand as well as something that would require minimal setup from whatever system they needed to work from.
After I found something that fit the profile, I used a NAS sync app to complete the initial sync and maintain sync between the cloud and the NAS server while I transitioned users.
Password Manager
Passwords were being saved to an Excel spreadsheet, so to make password management easier, I created a password management system that each user could save their passwords and access shared passwords as necessary. It also improved security by allowing logs on used passwords. I was able to import the passwords and assign the passwords and users to groups to maintain least privilege.
To improve security I created technical and administrative policies to require passwords to be saved to the password manager and shared with the team to ensure the policies were being followed.
Hardware
After purchasing the hardware, (we were not remote at the time), I set up each users system in the conference room and prepared their computers with little interaction from the users. After each system was setup, I planned to switch them over in a 30 minute session throughout the day, switching the client devices to the new laptops, showing them how to access their folders (set up and synced from the original NAS file server), their email and other items that may have changed.
Change Management
I coordinated change management with the users by sending a document with what would be impacting them, the timeline of the change, what to expect that was different, as well as a Q&A. I made sure I communicated any difficulties or timeline changes so there was no surprises.
Test and Validation
After each system transition, I would test to make sure that the old system was still working as expected and make sure the new system data and transfers didn’t fail and included all expected information.
With products that had cut-offs, like email and laptop deployment, I made sure a backup solution was still working in case I had to roll back to resolve an issue. Luckily, all system deployments went as expected.
After the transition was completed, I would turn off the old system for 30 days to confirm no one had data or other information they needed that may have been stored in a non-standard location, then would shut the system down completely.
Collaboration & Continuous Changes
The only thing that I needed to follow up on was training and further education. I completed this by writing a wiki with the most common questions asked by users and shared with everyone. The wiki helped reduce my time with each user and focus on the final transition details and shut down of the old system.
Final Results
The final result was a successful shut down of the terminal server system and prepared workers for hybrid work which began several months later. The owner and manager was extremely satisfied with the end result and the disruption to work was minimal and established my ability to provide results (as it was one of my first projects I worked on).
The best part, was when COVID required all employees to work from home, the transition was simple and did not require any system change to satisfy that requirement.
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