There is no excuse to still be using Windows 7 after today. I don't care who you are, or what you do. Poor horizon scanning.
Remember the NHS wannacry fiasco.
If my team of three can move 4,000 machines from 7 to 10 which contains huge amounts of old software and/or legacy hardware devices anyone can! Hell, whilst we were at it, we also moved over to part zero terminals and VDI/AppV where possible so that in 18 months when Windows 10 version xxxx goes end of life we can easily and quickly upgrade.
The technology exists to make life easy. Most of our PCs were 10 years old and all kind of makes and models. We managed.
My comment may seem a bit harsh, but it's more for the senior leadership team not the IT dept. In very special cases, you can pay Microsoft for extended support but my take on it, is that they've had years of warning so what's going to change now which could not have done years ago?
I hear excuses like 'special software', ok...fair enough, but they should have been looking/researching/developing years ago if they intend to stick with Windows. It was the same excuse with XP. Microsoft made it very clear when the support ran out. Amazingly our local university hasn't even started a windows 10 upgrade project! Then again, most of their servers are 2008 and unpatched lol
Unless cyber threats isn't high on the priority list for a company, they can't cry when they get hacked.
Anything can be achieved with the right amount of resources.
The problem with this software is will only run on Windows 7 32 bit. Its no longer made and their isn't an affordable alternative. basically it was a few hundred pounds. The equivalent now is a few thousand pounds and subscription based and doesn't do as much as the old software (in the same situation). So there has never been a real reason to upgrade.
.. I will add that I have already warned him if the PCs die hardware wise I wont be able to re-build windows 7 on a newer PC. I also wont be able to install the older software anyway as it wont activate. At some point will have to bite the bullet. I will do the processes I mentioned about AV and Backups. and Re-iterate that he needs to find viable alternative product asap
oh and office365 will give up at some point too as that wont be supported. eventually his hand will be forced
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