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I used the "Software Update" to update MacOS to the latest 13.3 (22E252) version.

Unfortunately, the WireGuard app (installed through App Store) did not take it well, and all of my tunnel (configuration) disappeared.

Now, I do have Time Machine backup; however, I can't imagine myself rolling back OS updates due to WireGuard vanished tunnels; there gotta be another way...

Please advise.

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2 Answers 2

Reset to default
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I reached out to Apple for support, and of course, Apple suggested I contact WireGuard for help (no surprise here).

While holding for an Apple representative and using "Google," I discovered that WireGuard stores tunnel configuration inside Keychain.

Back to my TimeMachine backup ;-)

% pwd
/Volumes/G-DRIVE mobile SSD R-Series/Backups.backupdb/mbp/2023-03-15-160527/APPLE SSD - Data/Users/user/Library/Keychains
% file login.keychain-db
login.keychain-db: Mac OS X Keychain File
%

I opened login.keychain-db with Keychain Access, then searched for WireGuard and voila!

Then, use "copy password to clipboard," to copy each tunnel configuration into clipboard, then paste it into WireGuard and the rest is history!

ALWAYS make a backup!

To be fair to Apple, the representative did share following document with me that help me find the right file and resolve my issue)

Copy keychains to another Mac - Apple Support

Thanks to everyone (including Apple)!

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    Software Update removed items from Keychain ?!?!? SMH
    – WGroleau
    Mar 31 at 17:41
  • It certainly appears that way, or something happened during the software update and then (at least parts of it) end up disappear.. i also asked representative to document and pass this feedback along to appropriate department.
    – alexus
    Mar 31 at 20:08
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Since the question is "please advise," the only advice I can give is to complain via Feedback Assistant.  Sadly, MacOS updates have often changed some of my Preferences*

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  • * Oh, sorry, now they're called Settings (another gratuitous change with NO functional value).
    – WGroleau
    Mar 31 at 16:19

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