[iMore Question]

We recently hooked up an iMac to the same wifi system. Does this have anything to do with this? The iPad asks for me to sign in to the cloud as much as a few times in five minutes..... Can be annoying

[Just_Me_D]

It'll ask until you sign in. It's more than likely for security purposes.

[HankAZ]

We recently hooked up an iMac to the same wifi system. Does this have anything to do with this? The iPad asks for me to sign in to the cloud as much as a few times in five minutes..... Can be annoying

Are you using two-factor authentication with you iCloud account / AppleID?

Apple started requiring application specific passwords/keys for iCloud access for apps that use iCloud data when 2 factor authentication is active. I first encountered this issue with Fantastical.

If you see this prompt, log into your iCloud account and create an app-specific password. Enter that new password in the prompt, and everything seems to be good now.

Using app-specific passwords

Thank you for using two-step verification to protect your Apple ID and the data you store with iCloud.

This is a reminder that starting tomorrow, app-specific passwords will be required to access your iCloud data using third party apps such as Microsoft Outlook, Mozilla Thunderbird, or other mail, contacts, and calendar apps.

If you are currently signed in to a third party app using your primary Apple ID password, you will be signed out automatically when this change takes effect. You will need to generate an app-specific password and sign in again.

To generate an app-specific password:
1. Sign in to My Apple ID (https://appleid.apple.com)
2. Go to Password & Security
3. Click Generate App-Specific Password