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Looking to finalize steps needed to upgrade our clients to macOS Catalina.

I have the reset ignored all done.

I have the stub installer in the Applications folder.

When I run the policy to Install I see the following:

Policy Log:

[STEP 1 of 4]
Executing Policy macOS 10.15 Catalina upgrade: Step 3 - Install
[STEP 2 of 4]
[STEP 3 of 4]
Running command /Applications/Install macOS Catalina.app/Contents/Resources/startosinstall --agreetolicense --nointeraction &...
Result of command:<br/>Error: Prepare recovery failed with error: Error Domain=com.apple.OSInstallerSetup.error Code=303 "Installation of macOS could not continue." UserInfo={NSLocalizedDescription=Installation of macOS could not continue., NSLocalizedRecoverySuggestion=Installation requires downloading important content. That content can't be downloaded at this time. Try again later.}<br/>Fetching OS Recovery info from server...
[STEP 4 of 4]

and Install Log

2020-05-12 12:17:20-05 Computernamehere startosinstall[2190]: OSInstallerSetup build: 1
2020-05-12 12:17:20-05 Computernamehere startosinstall[2190]: No compatibility bundle on this version of macOS. Will assume compatible.
2020-05-12 12:17:20-05 Computernamehere osinstallersetupd[2191]: OSISSoftwareUpdateController: Using catalog (source: GM Default): https://swscan.apple.com/content/catalogs/others/index-10.15-10.14-10.13-10.12-10.11-10.10-10.9-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog
2020-05-12 12:17:20-05 Computernamehere osinstallersetupd[2191]: Using product <OSISSharedSupportProduct: 0x7fc914c0c160> at distance 10
2020-05-12 12:17:20-05 Computernamehere osinstallersetupd[2191]: Using product <OSISPredicateUpdateProduct: 0x7fc914e0faf0> at distance 20
2020-05-12 12:17:20-05 Computernamehere osinstallersetupd[2191]: osinstallersetupd registered client
2020-05-12 12:17:20-05 Computernamehere osinstallersetupd[2191]: Using product <OSISPredicateUpdateInstallerProduct: 0x7fc914e141d0> at distance 25
2020-05-12 12:17:20-05 Computernamehere osinstallersetupd[2191]: ROM Features returned: 3775788407
2020-05-12 12:17:27-05 Computernamehere osinstallersetupd[2191]: OSISSoftwareUpdateController: Loaded catalog https://swscan.apple.com/content/catalogs/others/index-10.15-10.14-10.13-10.12-10.11-10.10-10.9-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog (572 products)
2020-05-12 12:17:27-05 Computernamehere osinstallersetupd[2191]: OSISPredicateUpdateProduct: Incompatible Apps List: Evaluating products in catalog
2020-05-12 12:17:27-05 Computernamehere osinstallersetupd[2191]: OSISPredicateUpdateProduct: OS Installation Payload: Evaluating products in catalog
2020-05-12 12:18:01-05 Computernamehere osinstallersetupd[2191]: JS: 10.14.6
2020-05-12 12:18:02-05 Computernamehere osinstallersetupd[2191]: JS: 10.14.6
2020-05-12 12:18:04-05 Computernamehere osinstallersetupd[2191]: JS: No bundle at/Applications/SafeView.app
2020-05-12 12:18:04-05 Computernamehere osinstallersetupd[2191]: JS: No bundle at/Applications/SafeView.app
2020-05-12 12:18:05-05 Computernamehere osinstallersetupd[2191]: JS: No bundle at/Applications/SafeView.app
2020-05-12 12:18:05-05 Computernamehere osinstallersetupd[2191]: ROM Features returned: 3775788407
2020-05-12 12:18:05-05 Computernamehere osinstallersetupd[2191]: OSISPredicateUpdateProduct: OS Installation Payload: Finished evaluating products in catalog (186 installable products)
2020-05-12 12:18:05-05 Computernamehere osinstallersetupd[2191]: OSISPredicateUpdateProduct: OS Installation Payload: No product found
2020-05-12 12:18:05-05 Computernamehere osinstallersetupd[2191]: Predicate update product fetch failed with error: Error Domain=com.apple.OSInstallerSetup.error Code=303 "Installation of macOS could not continue." UserInfo={NSLocalizedDescription=Installation of macOS could not continue., NSLocalizedRecoverySuggestion=Installation requires downloading important content. That content can't be downloaded at this time. Try again later.}

Do you have a clear, unproxied line of site to Apple's macOS Update CDN?
Apple Documentation
In particular, oscdn.apple.com, osrecovery.apple.com, skl.apple.com, swcdn.apple.com, and swdist.apple.com have to be reachable and I believe they also cannot be proxied.

@atomczynski Do you mind sharing what you used/setup to make sure everyone is updated to Catalina? We are finding there are some stragglers and doing the basic prompt to check for updates doesn't seem to work.

The above was on my home network which is pretty simple (it does have a caching server in place).

I was seeing some other weird errors in the install.log and I think I was having download issues.

I did manage to upgrade one computer yesterday after I took out the "-nointeraction" from the command.

@j_allenbrand

This is my approach:
1. Remove the Process Name Install macOS Catalina.app from Restricted Software.
2. Self Service policy to reset ignored macOS updates. The user sees this as Step One

/usr/sbin/softwareupdate --reset-ignored

  1. Self Service Policy to download the Install macOS Catalina stub installer which was previously packaged. with a recon at the end

  2. Self Service Policy to install (upgrade). This is scoped to a smart group that has the Install macOS Catalina in the Applicatoins folder.

/Applications/Install macOS Catalina.app/Contents/Resources/startosinstall --agreetolicense  &

This does work.
Goals to improve in the future. Use Jamf Helper to provide screens with messages and also configure authenticated restart.

Deleted

 

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