Has anyone had a good experience upgrading an old IMAC so that it can connect with internet?

Upgrade the iMac to Big Sur and get rid of Chrome. Use Firefox or Brave instead. Chrome has a history of being a resource hog and causing problems.

What version of OS X/macOS are you currently running on the 2014 iMac?

The last version of macOS that you can upgrade that 2014 iMac to is Big Sur (11.*). The current version of Chrome browser requires macOS Big Sur 11.* or later.

Web sites are continually upgrading their security protocols and that means that some older browser versions won't meet those evolving security requirements.

If you are already running Big Sur and it is fully updated, then ensure you have the current version of Chrome browser or more appropriately The Brave browser which is based on Chrome but more secure.

If you are on macOS Catalina, then you may wish to upgrade to Big Sur after a last Time Machine backup. To do that you can get Big Sur from How to download and install macOS - Apple Support and I would recommend using Safari for that interaction.

g_wolfman wrote:

OK, if your info is correct - there is only one 2014 iMac model, the iMac14,4 mid-2014 model which would be at Big Sur if you upgraded as far as possible.

There were two 2014 iMacs – a 21.5" Mid 2014 one (iMac14,4), and a 27" Retina 5K Late 2014 one (iMac15,1).

For either, Big Sur is the end of the line.

OK, if your info is correct - there is only one 2014 iMac model, the iMac14,4 mid-2014 model which would be at Big Sur if you upgraded as far as possible.

Firefox 128 ESR will run on your system, as will the current Firefox 130 (https://en.wikipedia.org/wiki/Firefox_version_history#Release_compatibility). Most modern browsers will have a version that should work well (if you prefer Chromium variants or something over Firefox or its various forks).

Ah, my bad - my sources usually list the Retina iMac as a 2015, but there were two 15,1 releases, one in the fall of 2014 (which oddly seems to have had a slightly better CPU than the May 2015 version...)

+1