While trying to update to macOS Monterey, I received an error that said “Download failed: HTTPSConnectionPool(host=‘swcdn.apple.com’, port=443): Read timed out.” How do I get around this?
The error “Download failed: HTTPSConnectionPool(host=‘swcdn.apple.com’, port=443): Read timed out.” seems to be related to the Apple server. I suggest you take a look at the current status of the server that’s responsible for software download. If it’s down, you’ll have to wait until Apple fixes it.
Open the link below and check if “macOS Software Update” is available.
Are you trying to update from Software Update? Maybe you can try a different way to download macOS Monterey. For instance, you can download it from the Mac App Store by searching for macOS Monterey and following the instructions to get it. Or, you can download it directly from a reliable third-party source.
Check the article below for more info:
macOS Monterey Download Center: Full Installer, DMG, ISO