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I was curious what this meant, so I looked into it.

They asked Automatic.css to change their name: https://www.reddit.com/r/Wordpress/comments/1omrtrk/automatt...

Automatic.css is a paid CSS framework specifically for WordPress.

Legally speaking I have no opinion here, but I don't think it's as out-of-pocket as it sounds.

The article linked ( https://www.404media.co/automattic-automatic-trademark-matt-... ) is behind a paywall. But reading https://www.searchenginejournal.com/automattic-disputes-use-... it sounds like the claim 'Automattic attempted to claim it owns the word “automatic"' might not be accurate.

Yeah, regardless of other aspects of Automattic's behaviour, flagging that an identically-pronounced single letter variation of their registered company name might be a confusingly similar brand for a third party commercial service specifically designed to customise Automattic's product to adopt seems to be at the reasonable end of trademark disputes...

That's how you can tell the article isn't giving you the full picture.

"Windows", "Word" and "Excel" are just plain English words, but it appears you can trademark them for specific industry. Maybe you have to make it more specific. Like "Microsoft Windows"?