When you open your web browser pop - ups are showing to enter login password and you are not able to connect to iCloud .
For I cloud issues use this article : Get help using iCloud Keychain - Apple Support
On your Mac:
- Choose Apple menu > System Preferences. Click iCloud, then select Keychain.
- When asked to enter your iCloud Security Code, click Forgot Code.
- Click Reset Keychain to replace your iCloud Keychain in the cloud with the iCloud Keychain items on your Mac.
- Click Reset to confirm. You'll be asked to create a new iCloud Security Code.
And regarding your the prompt of entering login password multiple times .
If keychain is prompting to enter password multiple times , & pop - up is not going away when safari is opened .
In user library click on go to go folder & type ~/Library then find a folder > keychains > remove first folder ( alfa numeric folder ) to trash . Restart & empty the trash , go to internet accounts & once again configure web mail account , I cloud mail account by entering their passwords .
Open air port utility via spotlight > enter your base station password .
And , also system preferences is not responding open activity monitor via spotlight , take the cursor on top menu bar > view > click on windowed processes > if you see system preferences ( written in red colour , system preferences not responding ) , select it > go to force quit > quit system preferences .
Also it , is recommended enter in your user library ( click on go > to go folder and type ~/Library , find a folder preferences right click on com.apple.systempreferences.plist to the desktop .
Restart the machine , open safari and browse for few minutes , then again go to the user library , new plist of system preferences , is created - just monitor , then you can delete the system preferences plist that is on the desktop into the trash , again restart the system and empty the trash .
As corrupted plist must not be in the trash .