Unfortunately, Google has killed their Cloud Print service (like many of their projects) at the end of 2020. Other products like directprint.io and PaperCut are possible alternatives. But see if your printer is still compatible by going into your Chromebook's advanced settings, click "printers" under "printing", and check if the printer can be added. Both devices must be on the same WiFi network in your home. If things aren't working out wirelessly, use a USB cable to connect to the printer.
John wants to know if a Chromebook will work with a printer/scanner. Leo says they will work wirelessly through Google Cloud Print. Most new printer models support the Cloud Print standard. Chromebooks probably don't have drivers for peripherals, so the wireless Cloud Print setting is the way to go. John should look in his printer settings for how to set it up. Then he can set it up through his Google account. He'll just print and then it sends it to his printer via the internet. A laser printer is probably best for John since he's a trucker.
Doug has a Toshiba Laptop running Windows 8. After a recent update, it broke connectivity to his HP printer. Leo says Doug should go to HP's driver site to get the latest drivers for his printer. It may be that HP doesn't have a recent driver anymore for Doug's old printer. But that's the first place to start.