In brief: You would hope that electronic systems used in elections would be some of the most secure machines on the planet. But old software and even more outdated regulatory systems mean that even newly bought hardware may be highly vulnerable to attacks and interference, come November 2020.
Any level of doubt as to the freeness and fairness of an election is a bad thing for a democratic country, which is why the adoption of secure and trusted electronic voting systems has been so slow. You might expect newly discovered loopholes or cutting-edge attacks would be the main issues for such systems, but for much of the hardware purchased by US states and cities the problem is more basic: the operating system.
A new analysis by the Associated Press has revealed that hardware used by most election jurisdictions across the US to create ballots, tally votes, and report final counts, actually runs on Windows 7 or sometimes even older operating systems. The problem with this is that Windows 7 will reach its "end of life" (EOL) stage on January 14 2020, eleven months prior to the next Presidential election.
EOL for the OS means that Microsoft will no longer provide patches or tech support, as they encourage users to upgrade to a newer version. Given that Windows 7 launched in 2009, it's no bad thing to get people upgrading.
While it seems like quite a while between now and the November 2020 election, there's also the primaries to consider which will happen sooner. And there's no guarantee that the vendors who operate the electronic electoral hardware will get new, Windows 10-based systems in place before the election. The accreditation process is understandably arduous and costly.
Associated Press surveyed every US state and discovered that "multiple battleground states [are] affected by the end of Windows 7 support, including Pennsylvania, Wisconsin, Florida, Iowa, Indiana, Arizona and North Carolina."
It remains to be seen whether secure systems will be in place ahead of the primaries starting February next year.