I'm in charge of rolling out a time tracking tool, Monitask, to over 500 company machines for remote and hybrid employees. The rollout is already planned by HR, so I just need to make sure the deployment goes smoothly and doesn't lead to a technical mess. I'm preparing for the basics like using GPO/Intune for scripting the deployment, checking for conflicts with our endpoint detection and response system, and testing how the software performs on older laptops. For those who have experience deploying similar software at this scale, what unexpected issues have you encountered? Any insights from your previous experiences would really help me out!
5 Answers
Make sure to test the deployment on various machines, especially the older, slower ones. You might end up with a lot of complaints about slow performance if it's too resource-intensive. Document everything!
If possible, try rolling it out in waves. This way, you can iron out any quirks before a full deployment. Communication is key; make sure employees know when they're getting the update. Also, invest in logging to track any issues that come up during the rollout.
It's crucial to build a rollback feature into your deployment script. If things go wrong, you want the ability to revert to the previous state without leaving users in a bind.
Definitely focus on whitelisting. Your EDR might go haywire seeing an app that takes screenshots and logs activity. Get those hashes from the vendor and add them to your exception policies before anything else!
One major issue you'll face is not the rollout itself, but the aftermath. Employees might claim they were working, but the software may misreport their activities. Be ready for disputes!
Absolutely! Testing on different specs can save you a lot of headaches later. You'll know what to expect.