Passwords not shared between IOS and OS/X despite both having iCloud Keychain turned on

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Passwords not shared between IOS and OS/X despite both having iCloud Keychain turned on

For quite some time, I've been noticing that password changes between my mac and iPhone are not picked up between each other, despite iCloud keychain being turned on for both. Both have autofill turned on in Safari. As a test (and yes, I kind of hate myself for having done this ;) ), I turned iCloud keychain off for the mac and did not save passwords local. All my passwords for sites disappeared. I turned it back on and... still no passwords. Now, if I need one, I have to use airdrop to send it from my phone to my mac.

When I open Keychain on the mac and look at iCloud, I DO see passwords going back to 2018. It's a bit harder to tell on IOS, but I see passwords as far back as at least 2020.

I am wondering if this might be a trust issue between the phone and mac. I can't connect my phone to the mac by usb right now, as it says I need a software update when I do, and that update always fails, even since I upgraded to IOS 15.7 (I'm on OS/X 10.15.7).

If there is no obvious answer, anyone know how to airdrop all the passwords from my phone to my mac? I'm not going to go through one by one... Thanks!

Mac mini, macOS 10.15

Posted on Sep 28, 2022 9:36 AM

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Answer 1

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tygb

Level 9

64,610 points

Sep 28, 2022 9:58 AM in response to bee61

See the articles If iCloud Keychain won't turn on or sync - Apple Support

Make your passwords available on all your devices with iPhone and iCloud Keychain - Apple Support

Share passwords securely with AirDrop on iPhone - Apple Support ( multiple passwords can't be selected and shared ) .

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Answer 2

tygb

Level 9

64,610 points

Sep 29, 2022 1:11 AM in response to bee61

See a thread Keychain certificate password lock / cann… - Apple Community

How can I delete Key Chain Certificates? - Apple Community

Determine if a certificate is valid using Keychain Access on Mac - Apple Support

Get information about a certificate in Keychain Access on Mac - Apple Support

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Answer 3

tygb

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64,610 points

Sep 29, 2022 10:01 AM in response to bee61

If you chane Apple ID password from Mac , it has to be updated on iPhone https://support.apple.com/en-in/HT204071 , if you are talking about Mac admin password it will never update on iPhone .

Note : when 2FA is turned as on in Mac / iPhone the function of keychain is over , the box of keychain is checked or not it doesn't matter after 14 days the account is permanent .

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Answer 4

tygb

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64,610 points

Sep 30, 2022 6:41 PM in response to bee61

The website is browsed from Mac so its password will be saved in safari preferences Change Passwords preferences in Safari on Mac - Apple Support

Share a password .

Send the password for the selected website to someone in your contacts list (in the Contacts app) using AirDrop.

To send to a Mac, the person must allow themselves to be discovered in AirDrop in the Finder. To send to an iPhone, iPad, or iPod touch, ask the person to open Control Center and turn on AirDrop.

iCloud Keychain must be set up on iPhone or iPod touch (iOS 6 or later), or iPad.

Automatic syncing of passwords will not occur .

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Answer 5

bee61 Author

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Oct 1, 2022 8:31 AM in response to bee61

Checking this... it seems like iCloud keychain should allow passwords to be shared in cloud between trusted devices. So, I think I hear you saying that 2fa ruins that. So, maybe I need to get rid of 2fa.

Use iCloud Keychain to keep information secure on Mac - Apple Support

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Answer 6

tygb

Level 9

64,610 points

Oct 2, 2022 12:24 AM in response to bee61

See a thread How can I turn off two-factor authenticat… - Apple Community

Intro to syncing your Mac and your devices - Apple Support

Sync content between your Mac and iPhone or iPad - Apple Support

The passwords are to be exported from Mac Use iCloud Keychain to keep information secure on Mac - Apple Support

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Answer 7

tygb

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64,610 points

Sep 28, 2022 10:31 AM in response to bee61

You can't select multiple passwords from iPhone , and share using air drop , however from Mac safari preferences they can be selected for different websites and exported .

You must not turn off iCloud Keychain on Mac / iPhone .

In your Mac , is iCloud Keychain box tuned on , in front of option button > can you see your country and trusted number , or the account is set with 2FA ( for it the option button will not be shown ) , this is a major difference between secondary authentication and 2FA .

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Answer 8

bee61 Author

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Sep 28, 2022 10:16 AM in response to tygb

Yes, this is actually a question on the article you mention first. The second article doesn't really relate much, unless you are suggesting I turn off iCloud keychain on both devices and then turn it back on?

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Answer 9

bee61 Author

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Sep 29, 2022 8:27 AM in response to tygb

So... I think then that you were saying to just delete the expired certs, which I did. No help though, I tried changing a password on my mac and the change does not show up on phone. Either one of them is not using cloud OR there is a differentiation based on lack of a trust?

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Answer 10

bee61 Author

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Sep 30, 2022 8:01 AM in response to tygb

Yes, my Mac and iPhone are both properly connected to cloud with the same account and password. So, you are saying that since I've had 2FA on for at least a year or two that the Keychain settings don't matter, OK. So, as a test, I changed a password on a site on my Mac yesterday. The phone still has the old password. Any ideas?

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Answer 11

bee61 Author

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Oct 1, 2022 8:28 AM in response to tygb

Whaaaaa-aaaaa-aaaat?!!! Syncing of passwords will not occur?

It used to, maybe that was before I put 2fa in place. Maybe I should turn that off? Yes, I'm using Airdrop, but that is only useful when you are at home. When you are out on the road with only your phone and the password does not work, you are out of luck. This is especially bad if you are using the Apple generated passwords, as you can use auto-fill on those from one device, but these are not passwords you can remember if you are out of reach of your other devices.

Are you absolutely sure? This is a horrible loss of functionality vs. what I had under.... Mavericks?

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Answer 12

bee61 Author

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Oct 1, 2022 11:10 AM in response to tygb

Riii-i-iiight. But, what I'm looking for is to either have both devices share the same keychain in cloud, secured by a trust... or at least to sync passwords when connected by usb or wifi. My question now is... can I achieve one of these if I turn off 2fa?

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Answer 13

bee61 Author

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Sep 28, 2022 11:37 AM in response to tygb

Yes to both, I have 2fa turned on. I noticed this in keychain as I was looking around at trusts:

Not sure if this relates... or how to fix if so...

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Answer 14

tygb

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64,610 points

Oct 1, 2022 10:06 AM in response to bee61

When iPhone is not in home network range , only hot spot can be created from it , the Mac or other devices are not in network range , so syncing of two devices will not occur .

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Passwords not shared between IOS and OS/X despite both having iCloud Keychain turned on

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