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Everytime I activate iCloud on my old macPro (OS 10.11.6) it erases all my local Calendar entries and I have to spend the day restoring from Time Machine. I have never put my Keychain data into the cloud or upgraded my Notes for fear of losing critical data in the process and of losing control of that data. Unfortunately it looks like there is no way to migrate certain Keychains to a new machine (OS 11.4) without using the iCloud service.

I figured there would be a way to clear the already uploaded iCloud Calendars so there would be nothing on the cloud side to replace the local data as it syncs, but cannot find a way to do that.

How do you activate iCloud and migrate critical data (specifically local keychains and calendars) to a new machine in a way that assures the data on the original machine is in no way threatened or lost in the process?

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This is a little too obvious, but...

Export the local data first, then if necessary, import again after connecting to iCloud.

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  • That is not something I can do with the Login/Local keychains that I can see and I cannot take a chance of losing that data.
    – rebusB
    Jul 6 at 22:21
  • Confirmed: I cannot export entries from the login keychain to a newly created keychain and there is no option to send it anywhere else. It first asks for permission to unlock the entry (for each item) and then reports it cannot add an item because it already exists in the keychain. The keychain is empty btw...
    – rebusB
    Jul 6 at 22:40
  • fwiw - the Calendar is syncing properly after the last round of restorations. Did archive it first this time, so maybe that is the key... having a fix fixes the issue. ;-)
    – rebusB
    Jul 6 at 22:44
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    Or just... don't use iCloud. Apple has yet to really get a handle on Internet services. Re your notes... yeah, since that's an opaque database with no way to back it up save for exporting the notes one at a time, I wouldn't use it either. Since you can't take a chance of losing the keychain data, how are you backing it up now? Jul 7 at 0:43
  • @MarcWilson - Time Machine... and it looks like that is the way to go, just like with the Calendars... I am not going to export hundreds of entries one at a time, and it doesn't seem to work anyway so, hope that if things go wrong the TM backup will restore them. So far that appears to be the only way.
    – rebusB
    Jul 7 at 18:38
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Found way to skip the cloud all together thus keeping its hands off my sensitive bits.

In the case of the "login keychain" it was simply a matter of copying the Keychains folder (~/Library/Keychains) over to the new machine, then adding the contained login keychain from within Keychain Access on the new machine (File>Add Keychain...). Be sure to wipe the file off your transfer medium since it is all your passwords.

This probably would have worked with the Calendar archive file, but since it eventually moved via iCloud I did not test.

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