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microsoft-office Cask with Defender #224555

@samumatic

Description

@samumatic

Verification

Description of issue

I have a microsoft defender installation required by work (non-homebrew), that is preventing the microsoft-office Cask to upgrade. In the upgrade process microsoft-office tries to deinstall the Defender Application, resulting in a Operation not permitted.

Command that failed

brew upgrade microsoft-office

Output of command with --verbose --debug

❯ brew upgrade microsoft-office --verbose --debug
==> Downloading https://formulae.brew.sh/api/formula.jws.json                                    /usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --user-agent Homebrew/4.6.4\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.6\)\ curl/8.7.1 --header Accept-Language:\ en --fail --remote-time --output /Users/smock/Library/Caches/Homebrew/api/formula.jws.json --location --time-cond /Users/smock/Library/Caches/Homebrew/api/formula.jws.json --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.6.4\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.6\)\ curl/8.7.1 --header Accept-Language:\ en --fail --compressed --speed-limit 100 --speed-time 5 https://formulae.brew.sh/api/formula.jws.json
/opt/homebrew/Library/Homebrew/brew.rb (Formulary::NullLoader): loading microsoft-office         /opt/homebrew/Library/Homebrew/brew.rb (Formulary::NullLoader): loading microsoft-office
/opt/homebrew/Library/Homebrew/brew.rb (Formulary::NullLoader): loading microsoft-office         ==> Downloading https://formulae.brew.sh/api/cask.jws.json
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --user-agent Homebrew/4.6.4\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.6\)\ curl/8.7.1 --header Accept-Language:\ en --fail --remote-time --output /Users/smock/Library/Caches/Homebrew/api/cask.jws.json --location --time-cond /Users/smock/Library/Caches/Homebrew/api/cask.jws.json --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.6.4\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.6\)\ curl/8.7.1 --header Accept-Language:\ en --fail --compressed --speed-limit 100 --speed-time 5 https://formulae.brew.sh/api/cask.jws.json                                            /opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading microsoft-office                                                                                                /opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromPathLoader): loading /opt/homebrew/Caskroom/microsoft-office/.metadata/16.99.25071321/20250731065812.680/Casks/microsoft-office.json==> Upgrading 1 outdated package:
microsoft-office 16.99.25071321 -> 16.100.25081015                                               ==> Started upgrade process for Cask microsoft-office
==> Upgrading microsoft-office                                                                   /opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading microsoft-excel
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading microsoft-office-businesspro
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading microsoft-onenote
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading microsoft-outlook
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading microsoft-powerpoint
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading microsoft-word /opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading onedrive
==> Printing caveats                                                                             ==> Cask::Installer#fetch
==> Downloading https://officecdnmac.microsoft.com/pr/C1297A47-86C4-4C1F-97FA-950631F94777/MacAutoupdate/Microsoft_365_and_Office_16.100.25081015_Installer.pkg
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.6.4\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.6\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 -V                                                     /usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.6.4\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.6\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head https://officecdnmac.microsoft.com/pr/C1297A47-86C4-4C1F-97FA-950631F94777/MacAutoupdate/Microsoft_365_and_Office_16.100.25081015_Installer.pkg
Already downloaded: /Users/smock/Library/Caches/Homebrew/downloads/b555c09e44670b8731321a511947f84e5a137ba56ac5e37dd3fec0a23cb6d6ef--Microsoft_365_and_Office_16.100.25081015_Installer.pkg
==> Checking quarantine support
/usr/bin/env /usr/bin/xattr -h                                                                   /usr/bin/env /Library/Developer/CommandLineTools/usr/bin/swift -target arm64-apple-macosx15 /opt/homebrew/Library/Homebrew/cask/utils/quarantine.swift                                            ==> Quarantine is available.
==> Verifying Gatekeeper status of /Users/smock/Library/Caches/Homebrew/downloads/b555c09e44670b8731321a511947f84e5a137ba56ac5e37dd3fec0a23cb6d6ef--Microsoft_365_and_Office_16.100.25081015_Installer.pkg                                                                                         /usr/bin/env /usr/bin/xattr -p com.apple.quarantine /Users/smock/Library/Caches/Homebrew/downloads/b555c09e44670b8731321a511947f84e5a137ba56ac5e37dd3fec0a23cb6d6ef--Microsoft_365_and_Office_16.100.25081015_Installer.pkg
==> /Users/smock/Library/Caches/Homebrew/downloads/b555c09e44670b8731321a511947f84e5a137ba56ac5e37dd3fec0a23cb6d6ef--Microsoft_365_and_Office_16.100.25081015_Installer.pkg is quarantined
==> Verifying checksum for 'b555c09e44670b8731321a511947f84e5a137ba56ac5e37dd3fec0a23cb6d6ef--Microsoft_365_and_Office_16.100.25081015_Installer.pkg'
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading microsoft-auto-update
/usr/bin/env hdiutil imageinfo -format /Users/smock/Library/Caches/Homebrew/downloads/b555c09e44670b8731321a511947f84e5a137ba56ac5e37dd3fec0a23cb6d6ef--Microsoft_365_and_Office_16.100.25081015_Installer.pkg                                                                                     All dependencies satisfied.
==> Uninstalling artifacts                                                                       ==> 3 artifacts defined
#<Cask::ArtifactSet: {#<Cask::Artifact::Uninstall:0x00000001586fd7a0 @cask=#<Cask microsoft-office /opt/homebrew/Caskroom/microsoft-office/.metadata/16.99.25071321/20250731065812.680/Casks/microsoft-office.json>, @dirmethod=nil, @dsl_args=[{launchctl: ["com.microsoft.office.licensing.helper", "com.microsoft.office.licensingV2.helper", "com.microsoft.OneDriveStandaloneUpdater", "com.microsoft.OneDriveStandaloneUpdaterDaemon", "com.microsoft.OneDriveUpdaterDaemon", "com.microsoft.SyncReporter"], quit: "com.microsoft.autoupdate2", pkgutil: ["com.microsoft.OneDrive", "com.microsoft.package.DFonts", "com.microsoft.package.Frameworks", "com.microsoft.package.Microsoft_Excel.app", "com.microsoft.package.Microsoft_OneNote.app", "com.microsoft.package.Microsoft_Outlook.app", "com.microsoft.package.Microsoft_PowerPoint.app", "com.microsoft.package.Microsoft_Word.app", "com.microsoft.package.Proofing_Tools", "com.microsoft.pkg.licensing", "com.microsoft.wdav", "com.microsoft.wdav.shim"], delete: ["/Applications/Microsoft Excel.app", "/Applications/Microsoft OneNote.app", "/Applications/Microsoft Outlook.app", "/Applications/Microsoft PowerPoint.app", "/Applications/Microsoft Word.app", "/Applications/OneDrive.app"]}], @dsl_key=nil, @english_article=nil, @english_name=nil, @directives={launchctl: ["com.microsoft.office.licensing.helper", "com.microsoft.office.licensingV2.helper", "com.microsoft.OneDriveStandaloneUpdater", "com.microsoft.OneDriveStandaloneUpdaterDaemon", "com.microsoft.OneDriveUpdaterDaemon", "com.microsoft.SyncReporter"], quit: "com.microsoft.autoupdate2", pkgutil: ["com.microsoft.OneDrive", "com.microsoft.package.DFonts", "com.microsoft.package.Frameworks", "com.microsoft.package.Microsoft_Excel.app", "com.microsoft.package.Microsoft_OneNote.app", "com.microsoft.package.Microsoft_Outlook.app", "com.microsoft.package.Microsoft_PowerPoint.app", "com.microsoft.package.Microsoft_Word.app", "com.microsoft.package.Proofing_Tools", "com.microsoft.pkg.licensing", "com.microsoft.wdav", "com.microsoft.wdav.shim"], delete: ["/Applications/Microsoft Excel.app", "/Applications/Microsoft OneNote.app", "/Applications/Microsoft Outlook.app", "/Applications/Microsoft PowerPoint.app", "/Applications/Microsoft Word.app", "/Applications/OneDrive.app"], signal: []}>, #<Cask::Artifact::Pkg:0x00000001586fcc60 @cask=#<Cask microsoft-office /opt/homebrew/Caskroom/microsoft-office/.metadata/16.99.25071321/20250731065812.680/Casks/microsoft-office.json>, @dirmethod=nil, @dsl_args=["Microsoft_365_and_Office_16.99.25071321_Installer.pkg", {choices: [{choiceIdentifier: "com.microsoft.autoupdate", choiceAttribute: "selected", attributeSetting: 0}]}], @dsl_key=nil, @english_article=nil, @english_name=nil, @path=#<Pathname:/opt/homebrew/Caskroom/microsoft-office/16.99.25071321/Microsoft_365_and_Office_16.99.25071321_Installer.pkg>, @stanza_options={choices: [{choiceIdentifier: "com.microsoft.autoupdate", choiceAttribute: "selected", attributeSetting: 0}]}>, #<Cask::Artifact::Zap:0x00000001586fac30 @cask=#<Cask microsoft-office /opt/homebrew/Caskroom/microsoft-office/.metadata/16.99.25071321/20250731065812.680/Casks/microsoft-office.json>, @dirmethod=nil, @dsl_args=[{trash: ["~/Library/Application Scripts/com.microsoft.errorreporting", "~/Library/Application Scripts/com.microsoft.Excel", "~/Library/Application Scripts/com.microsoft.Office365ServiceV2", "~/Library/Application Scripts/com.microsoft.OneDrive.FileProvider", "~/Library/Application Scripts/com.microsoft.OneDrive.FinderSync", "~/Library/Application Scripts/com.microsoft.OneDriveLauncher", "~/Library/Application Scripts/com.microsoft.onenote.mac", "~/Library/Application Scripts/com.microsoft.onenote.mac.shareextension", "~/Library/Application Scripts/com.microsoft.openxml.excel.app", "~/Library/Application Scripts/com.microsoft.Outlook", "~/Library/Application Scripts/com.microsoft.outlook.profilemanager", "~/Library/Application Scripts/com.microsoft.Powerpoint", "~/Library/Application Scripts/com.microsoft.Word", "~/Library/Application Support/com.apple.sharedfilelist/com.apple.LSSharedFileList.ApplicationRecentDocuments/com.microsoft.excel.sfl*", "~/Library/Application Support/com.apple.sharedfilelist/com.apple.LSSharedFileList.ApplicationRecentDocuments/com.microsoft.powerpoint.sfl*", "~/Library/Application Support/com.apple.sharedfilelist/com.apple.LSSharedFileList.ApplicationRecentDocuments/com.microsoft.word.sfl*", "~/Library/Application Support/CrashReporter/Microsoft Error Reporting_*.plist", "~/Library/Application Support/Microsoft Update Assistant", "~/Library/Caches/com.microsoft.OneDriveStandaloneUpdater", "~/Library/Caches/com.plausiblelabs.crashreporter.data/com.microsoft.OneDriveStandaloneUpdater", "~/Library/Containers/com.microsoft.com.microsoft.RMS-XPCService", "~/Library/Containers/com.microsoft.errorreporting", "~/Library/Containers/com.microsoft.Excel", "~/Library/Containers/com.microsoft.netlib.shipassertprocess", "~/Library/Containers/com.microsoft.Office365ServiceV2", "~/Library/Containers/com.microsoft.onenote.mac", "~/Library/Containers/com.microsoft.onenote.mac.shareextension", "~/Library/Containers/com.microsoft.openxml.excel.app", "~/Library/Containers/com.microsoft.Outlook", "~/Library/Containers/com.microsoft.outlook.profilemanager", "~/Library/Containers/com.microsoft.Powerpoint", "~/Library/Containers/com.microsoft.Word", "~/Library/Group Containers/UBF8T346G9.ms", "~/Library/Group Containers/UBF8T346G9.Office", "~/Library/Group Containers/UBF8T346G9.OfficeOneDriveSyncIntegration", "~/Library/Group Containers/UBF8T346G9.OfficeOsfWebHost", "~/Library/HTTPStorages/com.microsoft.OneDriveStandaloneUpdater", "~/Library/HTTPStorages/com.microsoft.OneDriveStandaloneUpdater.binarycookies", "~/Library/Preferences/com.microsoft.Excel.plist", "~/Library/Preferences/com.microsoft.Outlook.plist", "~/Library/Preferences/com.microsoft.Powerpoint.plist", "~/Library/Preferences/com.microsoft.Word.plist", "~/Library/Saved Application State/com.microsoft.office.setupassistant.savedState", "~/Library/Saved Application State/com.microsoft.Word.savedState"]}], @dsl_key=nil, @english_article=nil, @english_name=nil, @directives={trash: ["~/Library/Application Scripts/com.microsoft.errorreporting", "~/Library/Application Scripts/com.microsoft.Excel", "~/Library/Application Scripts/com.microsoft.Office365ServiceV2", "~/Library/Application Scripts/com.microsoft.OneDrive.FileProvider", "~/Library/Application Scripts/com.microsoft.OneDrive.FinderSync", "~/Library/Application Scripts/com.microsoft.OneDriveLauncher", "~/Library/Application Scripts/com.microsoft.onenote.mac", "~/Library/Application Scripts/com.microsoft.onenote.mac.shareextension", "~/Library/Application Scripts/com.microsoft.openxml.excel.app", "~/Library/Application Scripts/com.microsoft.Outlook", "~/Library/Application Scripts/com.microsoft.outlook.profilemanager", "~/Library/Application Scripts/com.microsoft.Powerpoint", "~/Library/Application Scripts/com.microsoft.Word", "~/Library/Application Support/com.apple.sharedfilelist/com.apple.LSSharedFileList.ApplicationRecentDocuments/com.microsoft.excel.sfl*", "~/Library/Application Support/com.apple.sharedfilelist/com.apple.LSSharedFileList.ApplicationRecentDocuments/com.microsoft.powerpoint.sfl*", "~/Library/Application Support/com.apple.sharedfilelist/com.apple.LSSharedFileList.ApplicationRecentDocuments/com.microsoft.word.sfl*", "~/Library/Application Support/CrashReporter/Microsoft Error Reporting_*.plist", "~/Library/Application Support/Microsoft Update Assistant", "~/Library/Caches/com.microsoft.OneDriveStandaloneUpdater", "~/Library/Caches/com.plausiblelabs.crashreporter.data/com.microsoft.OneDriveStandaloneUpdater", "~/Library/Containers/com.microsoft.com.microsoft.RMS-XPCService", "~/Library/Containers/com.microsoft.errorreporting", "~/Library/Containers/com.microsoft.Excel", "~/Library/Containers/com.microsoft.netlib.shipassertprocess", "~/Library/Containers/com.microsoft.Office365ServiceV2", "~/Library/Containers/com.microsoft.onenote.mac", "~/Library/Containers/com.microsoft.onenote.mac.shareextension", "~/Library/Containers/com.microsoft.openxml.excel.app", "~/Library/Containers/com.microsoft.Outlook", "~/Library/Containers/com.microsoft.outlook.profilemanager", "~/Library/Containers/com.microsoft.Powerpoint", "~/Library/Containers/com.microsoft.Word", "~/Library/Group Containers/UBF8T346G9.ms", "~/Library/Group Containers/UBF8T346G9.Office", "~/Library/Group Containers/UBF8T346G9.OfficeOneDriveSyncIntegration", "~/Library/Group Containers/UBF8T346G9.OfficeOsfWebHost", "~/Library/HTTPStorages/com.microsoft.OneDriveStandaloneUpdater", "~/Library/HTTPStorages/com.microsoft.OneDriveStandaloneUpdater.binarycookies", "~/Library/Preferences/com.microsoft.Excel.plist", "~/Library/Preferences/com.microsoft.Outlook.plist", "~/Library/Preferences/com.microsoft.Powerpoint.plist", "~/Library/Preferences/com.microsoft.Word.plist", "~/Library/Saved Application State/com.microsoft.office.setupassistant.savedState", "~/Library/Saved Application State/com.microsoft.Word.savedState"], signal: []}>}>
==> Uninstalling artifact of class Cask::Artifact::Uninstall                                     ==> Removing launchctl service com.microsoft.office.licensing.helper
/usr/bin/env /bin/launchctl list com.microsoft.office.licensing.helper                           /usr/bin/sudo -u root -E -- /bin/launchctl list com.microsoft.office.licensing.helper
==> Removing launchctl service com.microsoft.office.licensingV2.helper                           /usr/bin/env /bin/launchctl list com.microsoft.office.licensingV2.helper
/usr/bin/sudo -u root -E -- /bin/launchctl list com.microsoft.office.licensingV2.helper          ==> Removing launchctl service com.microsoft.OneDriveStandaloneUpdater
/usr/bin/env /bin/launchctl list com.microsoft.OneDriveStandaloneUpdater                         /usr/bin/sudo -u root -E -- /bin/launchctl list com.microsoft.OneDriveStandaloneUpdater
==> Removing launchctl service com.microsoft.OneDriveStandaloneUpdaterDaemon                     /usr/bin/env /bin/launchctl list com.microsoft.OneDriveStandaloneUpdaterDaemon
/usr/bin/sudo -u root -E -- /bin/launchctl list com.microsoft.OneDriveStandaloneUpdaterDaemon    ==> Removing launchctl service com.microsoft.OneDriveUpdaterDaemon
/usr/bin/env /bin/launchctl list com.microsoft.OneDriveUpdaterDaemon                             /usr/bin/sudo -u root -E -- /bin/launchctl list com.microsoft.OneDriveUpdaterDaemon
==> Removing launchctl service com.microsoft.SyncReporter                                        /usr/bin/env /bin/launchctl list com.microsoft.SyncReporter
/usr/bin/sudo -u root -E -- /bin/launchctl list com.microsoft.SyncReporter                       ==> Uninstalling packages with `sudo` (which may request your password)...
/usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.OneDrive                                     /usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.package.DFonts
/usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.package.Frameworks                           /usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.package.Microsoft_Excel.app
/usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.package.Microsoft_OneNote.app                /usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.package.Microsoft_Outlook.app
/usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.package.Microsoft_PowerPoint.app             /usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.package.Microsoft_Word.app
/usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.package.Proofing_Tools                       /usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.pkg.licensing
/usr/bin/env /usr/sbin/pkgutil --pkgs=com.microsoft.wdav                                         com.microsoft.wdav
/usr/bin/env /usr/sbin/pkgutil --files com.microsoft.wdav                                        /usr/bin/env /usr/sbin/pkgutil --pkg-info-plist com.microsoft.wdav
==> Deleting pkg files                                                                           /usr/bin/sudo -u root -E -- /usr/bin/xargs -0 -- /bin/rm --
rm: /Applications/Microsoft Defender.app/Contents/CodeResources: Operation not permitted         rm: /Applications/Microsoft Defender.app/Contents/Frameworks/OneAuth.framework/Versions/A/OneAuth: Operation not permitted                                                                        rm: /Applications/Microsoft Defender.app/Contents/Frameworks/OneAuth.framework/Versions/A/Resources/Info.plist: Operation not permitted                                                           rm: /Applications/Microsoft Defender.app/Contents/Frameworks/OneAuth.framework/Versions/A/Resources/PrivacyInfo.xcprivacy: Operation not permitted                                                rm: /Applications/Microsoft Defender.app/Contents/Frameworks/OneAuth.framework/Versions/A/_CodeSignature/CodeResources: Operation not permitted                                                   rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libazure-storage-lite.dylib: Operation not permitted                                                                                 rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_atomic.dylib: Operation not permitted                                                                                       rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_chrono.dylib: Operation not permitted                                                                                       rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_container.dylib: Operation not permitted                                                                                    rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_context.dylib: Operation not permitted                                                                                      rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_date_time.dylib: Operation not permitted                                                                                    rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_filesystem.dylib: Operation not permitted                                                                                   rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_iostreams.dylib: Operation not permitted                                                                                    rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_json.dylib: Operation not permitted                                                                                         rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_log.dylib: Operation not permitted                                                                                          rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_log_setup.dylib: Operation not permitted                                                                                    rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_prg_exec_monitor.dylib: Operation not permitted                                                                             rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_program_options.dylib: Operation not permitted                                                                              rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_random.dylib: Operation not permitted                                                                                       rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_regex.dylib: Operation not permitted                                                                                        rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_serialization.dylib: Operation not permitted                                                                                rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_system.dylib: Operation not permitted                                                                                       rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_thread.dylib: Operation not permitted                                                                                       rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libboost_wserialization.dylib: Operation not permitted                                                                               rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libcpprest.2.10.dylib: Operation not permitted                                                                                       rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libcrypto.3.dylib: Operation not permitted                                                                                           rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libcurl.4.dylib: Operation not permitted                                                                                             rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libmagic.1.dylib: Operation not permitted                                                                                            rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libmagic.dylib: Operation not permitted                                                                                              rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libminizip.2.5.dylib: Operation not permitted                                                                                        rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libmpengine.dylib: Operation not permitted                                                                                           rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libsqlite3.0.dylib: Operation not permitted                                                                                          rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libsqlite3.dylib: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libssl.3.dylib: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libwdavdaemon_core.dylib: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libwdavdaemon_edr_dylib.dylib: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Frameworks/libwdavdaemon_sysextctrl.dylib: Operation not permitted                                                                              rm: /Applications/Microsoft Defender.app/Contents/Info.plist: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.epsext.systemextension/Contents/Frameworks/libboost_regex.dylib: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.epsext.systemextension/Contents/Info.plist: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.epsext.systemextension/Contents/MacOS/epsext: Operation not permitted                               rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.epsext.systemextension/Contents/_CodeSignature/CodeResources: Operation not permitted               rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.epsext.systemextension/Contents/embedded.provisionprofile: Operation not permitted                  rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libazure-storage-lite.dylib: Operation not permitted     rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_atomic.dylib: Operation not permitted           rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_chrono.dylib: Operation not permitted           rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_context.dylib: Operation not permitted          rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_date_time.dylib: Operation not permitted        rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_filesystem.dylib: Operation not permitted       rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_locale.dylib: Operation not permitted           rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_log.dylib: Operation not permitted              rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_random.dylib: Operation not permitted           rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_regex.dylib: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_system.dylib: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/Library/SystemExtensions/com.microsoft.wdav.netext.systemextension/Contents/Frameworks/libboost_thread.dylib: Operation not permitted
[...]
==> Purging files for version 16.100.25081015 of Cask microsoft-office
Error: microsoft-office: Failure while executing; `/usr/bin/sudo -u root -E -- /usr/bin/xargs -0 -- /bin/rm --` exited with 1. Here's the output:
[...]
rm: /Applications/Microsoft Defender.app/Contents/CodeResources: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/MacOS/wdavdaemon_enterprise.app/Contents/Resources/Scripts/tvm/no_unowned_files_and_directories.sh: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/MacOS/wdavdaemon_enterprise.app/Contents/Resources/Scripts/tvm/root_path.sh: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/MacOS/wdavdaemon_enterprise.app/Contents/Resources/Scripts/tvm/service_enabled_running.sh: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/MacOS/wdavdaemon_enterprise.app/Contents/Resources/Scripts/tvm/service_masked_stopped.sh: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/MacOS/wdavdaemon_enterprise.app/Contents/Resources/Scripts/tvm/sestatus_check.sh: Operation not permitted
rm: /Applications/Microsoft Defender.app/Contents/MacOS/wdavdaemon_enterprise.app/

Output of brew doctor and brew config

❯ brew doctor
Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
working fine: please don't worry or file an issue; just ignore this. Thanks!

Warning: Some installed casks are deprecated or disabled.
You should find replacements for the following casks:
  darktable
  displaylink
  vmware-fusion

Warning: The following casks have the same name as core casks:
  localsend/localsend/localsend
Some of these can be resolved with:
  brew untap localsend/localsend

Warning: The following formulae have the same name as core formulae:
  samtay/tui/so
Their taps are in use, so you must use these full names throughout Homebrew.

Warning: Unbrewed dylibs were found in /usr/local/lib.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae and may need to be deleted.                                                                                                                                            Unexpected dylibs:
  /usr/local/lib/libAPI_DYN.dylib                                                                                                                                                                 Warning: You have unlinked kegs in your Cellar.
Leaving kegs unlinked can lead to build-trouble and cause formulae that depend on                those kegs to fail to run properly once built. Run `brew link` on these:                           docker
  docker-completion
❯ brew config
HOMEBREW_VERSION: 4.6.4                                                                          ORIGIN: https://github.com/Homebrew/brew
HEAD: 160af073a53fcb23331d70d79785d17d13da41e7                                                   Last commit: 2 days ago                                                                          Branch: stable
Core tap JSON: 19 Aug 18:25 UTC                                                                  Core cask tap JSON: 19 Aug 18:25 UTC
HOMEBREW_PREFIX: /opt/homebrew                                                                   HOMEBREW_CASK_OPTS: []
HOMEBREW_FORBID_PACKAGES_FROM_PATHS: set                                                         HOMEBREW_MAKE_JOBS: 8
Homebrew Ruby: 3.4.5 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.5/bin/ruby       CPU: octa-core 64-bit arm_ibiza                                                                  Clang: 17.0.0 build 1700
Git: 2.51.0 => /opt/homebrew/bin/git                                                             Curl: 8.7.1 => /usr/bin/curl                                                                     macOS: 15.6-arm64
CLT: 16.4.0.0.1.1747106510                                                                       Xcode: N/A
Rosetta 2: false

Output of brew tap

❯ brew tap
domt4/autoupdate
gcenx/wine                                                                                       grishka/grishka                                                                                  gromgit/fuse
iina/mpv-iina                                                                                    jzaleski/jzaleski
lihaoyun6/tap                                                                                    localsend/localsend
oven-sh/bun                                                                                      powershell/tap
real-aazam/aazam                                                                                 samtay/tui
xpipe-io/tap

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