icloud data isnt syncing

I am sure that you can log in to your MacBook Pro and use it. If so, double-check that you are using the correct Apple ID on both your iPhone and MacBook Pro. Sometimes, using different Apple IDs can cause syncing problems.

Visit Apple - Support - System Status to see if there are any known outages or issues with iCloud services. If there are, you'll need to wait for Apple to resolve them before you can continue.

On both your iPhone and MacBook Pro, sign out of iCloud completely and then sign back in. This can refresh the connection and resolve syncing issues.

In short:

• Make sure that both your iPhone and MacBook Pro are connected to the internet.
• Make sure that you are using the same Apple ID on both devices.
• Make sure that both devices have the latest software updates installed.

I’ve just started seeing this repeatedly the last few hours on all my devices. At first, I thought it was because I resurrected a beloved MacBook Pro with a cracked screen and signed in/put it on the internet for the first time in a while. Thus, I expected to get the nagware everywhere that a new device had signed in. Several different devices on the same iCloud account keep having me sign back in, requesting device passwords. I, too would see it reject a known good password as incorrect. Also annoying is that I have several MacBook Pros, so having it tell me to supply the “MacBook Pro password” wasn’t very helpful. I recommend clicking on the “I don’t know the password for the device” link. It’s weird, I know.

My successful workaround was to choose the “I don’t know this device’s password” link. This link gives you an icon of each available device along with its host name (a necessity!). I finally ended up having luck choosing any of my mobile device’s PINs (my MacBook passwords are multilingual and I imagine there may be an issue with the language encoding that is being expected/used).

Despite repeatedly successfully authenticating, devices NOT on the VPN network still got these issues. I thought that perhaps there was an issue on the reauthenticated device. However, I’m thinking it’s of asomething else entirely, and me joining the device was a coincidence.

I recently signed up for a Proton VPN service utilising Wireguard, and set it up in such a way that all of my traffic on my WiFi router is “tunnelled” in via the VPN. This differs from a normal on-device VPN configuration in tthe Apple world.

• On-Device VPN: Most traffic is protected. When you install / configure an VPN of any protocol (IPSEC, OpenVPN, Cisco, Wireguard, etc) you can configure most of your user data to go through the VPN. However, some OS data is exempted. It seems Apple allows data specific to its services to “leak” outside a given VPN (see the following Proton knowledge base article discussing this. My guess is that this is an effort to prevent fraud and misuse of their notification services, iCloud, etc. It allows them to perform a sort of KYC.
• Whole Router VPN: All traffic is encrypted for any device connected to the router. This way, there is no data leakage at all. However, I think that Apple then cannot perform KYC as your “OS traffic” now seems to come in from a common VPN address. This can throw a red flag to services who cannot perform KYC. Similar can happen when logging into banking accounts or other systems. I would guess maybe the system performs a check, sees that the system doesn’t appear to be running a VPN, yet has traffic suddenly coming in from a VPN. Depending on how rules are configured for this behaviour this can throw flags and block functionality.

This is just a wild guess, but aside from reattaching my still-updated MacBook Pro M1 (up to date, secured), I can’t see any other issue except my securing my traffic with a VPN. I would suggest reviewing if any of your systems or router is secured by a VPN, or if it’s going through some kind of proxy server or other caching or anonymising service.

I was having the same issue.

signed into iCloud on my iPhone with my MacBook open. I think I also had to put in password for my MacBook. I got the prompt on MacBook to approve or disapprove. With MacBook still open I went to iPad and had the same issue. Asked for all the same information and it finally cleared. What a hassle but it is finally resolved.