how to fix never ending password request with homebrew - homebrew

Question

I'm trying to run brew upgrade, and when trying to uninstall a jdk package, it keeps asking for my password, taking it, and then asking for it again and again and never making progress. I am just wondering what's going on here and how to fix it?
(base) user#computer: ~ $
> brew upgrade
==> Casks with `auto_updates` or `version :latest` will not be upgraded
==> Upgrading 1 outdated package:
adoptopenjdk8 8,242:b08 -> 8,272:b10
==> Upgrading adoptopenjdk8
==> Downloading https://github.com/AdoptOpenJDK/openjdk8-binaries/releases/download/jdk8u272-b10/OpenJDK8U-jdk_x64_mac_hotspot_8u272b10.pkg
Already downloaded: /Users/me/Library/Caches/Homebrew/downloads/91154181533f41bf699ae50474345f17a588dd0524ba21698eed51461b2fdcdb--OpenJDK8U-jdk_x64_mac_hotspot_8u272b10.pkg
==> Verifying SHA-256 checksum for Cask 'adoptopenjdk8'.
==> Uninstalling packages:
net.adoptopenjdk.8.jdk
Password: # <- I entered my password here
Password: # <- and here
Password: # <- I tried entering it 10 times, WTF?
DEBUG OUTPUT
after adding the debug options, it looks like a new sudo command is being run at each password request... how many there are I wonder
> HOMEBREW_DEBUG=1 HOMEBREW_VERBOSE=1 brew upgrade
...
# many preamble lines left out, before ending with this:
==> Casks with `auto_updates` or `version :latest` will not be upgraded
==> Upgrading 1 outdated package:
adoptopenjdk8 8,242:b08 -> 8,275:b01
==> Started upgrade process for Cask adoptopenjdk8
==> Upgrading adoptopenjdk8
==> Printing caveats
==> Cask::Installer#fetch
==> Downloading
==> Downloading https://github.com/AdoptOpenJDK/openjdk8-binaries/releases/download/jdk8u275-b01/OpenJDK8U-jdk_x64_mac_hotspot_8u275b01.pkg
/usr/bin/curl --disable --globoff --show-error --user-agent Homebrew/2.5.11\ \(Macintosh\;\ Intel\ Mac\ OS\ X\ 10.15.7\)\ curl/7.64.1 --header Accept-Language:\ en --retry 3 --location --silent --head --request GET https://github.com/AdoptOpenJDK/openjdk8-binaries/releases/download/jdk8u275-b01/OpenJDK8U-jdk_x64_mac_hotspot_8u275b01.pkg
Already downloaded: /Users/user/Library/Caches/Homebrew/downloads/85196e84e33d19d6ed7c43cbeae1e3f26bfe061baf02e3f2802deeb1a4a7c8b4--OpenJDK8U-jdk_x64_mac_hotspot_8u275b01.pkg
==> Checking quarantine support
/usr/bin/xattr
/usr/bin/swift /usr/local/Homebrew/Library/Homebrew/cask/utils/quarantine.swift
==> Quarantine is available.
==> Verifying Gatekeeper status of /Users/user/Library/Caches/Homebrew/downloads/85196e84e33d19d6ed7c43cbeae1e3f26bfe061baf02e3f2802deeb1a4a7c8b4--OpenJDK8U-jdk_x64_mac_hotspot_8u275b01.pkg
/usr/bin/xattr -p com.apple.quarantine /Users/user/Library/Caches/Homebrew/downloads/85196e84e33d19d6ed7c43cbeae1e3f26bfe061baf02e3f2802deeb1a4a7c8b4--OpenJDK8U-jdk_x64_mac_hotspot_8u275b01.pkg
==> /Users/user/Library/Caches/Homebrew/downloads/85196e84e33d19d6ed7c43cbeae1e3f26bfe061baf02e3f2802deeb1a4a7c8b4--OpenJDK8U-jdk_x64_mac_hotspot_8u275b01.pkg is quarantined
==> Downloaded to -> /Users/user/Library/Caches/Homebrew/downloads/85196e84e33d19d6ed7c43cbeae1e3f26bfe061baf02e3f2802deeb1a4a7c8b4--OpenJDK8U-jdk_x64_mac_hotspot_8u275b01.pkg
==> Verifying SHA-256 checksum for Cask 'adoptopenjdk8'.
==> Uninstalling artifacts
==> 2 artifact/s defined
#<SortedSet: {#<Cask::Artifact::Uninstall:0x00007fa30a2a3780 #cask=#<Cask::Cask:0x00007fa30a29ab08 #token="adoptopenjdk8", #sourcefile_path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8/.metadata/8,242:b08/20200414143743.728/Casks/adoptopenjdk8.rb>, #tap=nil, #block=#<Proc:0x00007fa30a29aa68#/usr/local/Caskroom/adoptopenjdk8/.metadata/8,242:b08/20200414143743.728/Casks/adoptopenjdk8.rb:1>, #default_config=#<Cask::Config:0x00007fa30a29aa40 #explicit={}>, #caskroom_path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8>, #metadata_master_container_path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8/.metadata>, #config=#<Cask::Config:0x00007fa30a298e98 #explicit={}, #default={:languages=>["en-US"], :appdir=>#<Pathname:/Applications>, :colorpickerdir=>#<Pathname:/Users/user/Library/ColorPickers>, :prefpanedir=>#<Pathname:/Users/user/Library/PreferencePanes>, :qlplugindir=>#<Pathname:/Users/user/Library/QuickLook>, :mdimporterdir=>#<Pathname:/Users/user/Library/Spotlight>, :dictionarydir=>#<Pathname:/Users/user/Library/Dictionaries>, :fontdir=>#<Pathname:/Users/user/Library/Fonts>, :servicedir=>#<Pathname:/Users/user/Library/Services>, :input_methoddir=>#<Pathname:/Users/user/Library/Input Methods>, :internet_plugindir=>#<Pathname:/Users/user/Library/Internet Plug-Ins>, :audio_unit_plugindir=>#<Pathname:/Users/user/Library/Audio/Plug-Ins/Components>, :vst_plugindir=>#<Pathname:/Users/user/Library/Audio/Plug-Ins/VST>, :vst3_plugindir=>#<Pathname:/Users/user/Library/Audio/Plug-Ins/VST3>, :screen_saverdir=>#<Pathname:/Users/user/Library/Screen Savers>}, #env={}>, #dsl=#<Cask::DSL:0x00007fa30897e6d8 #cask=#<Cask::Cask:0x00007fa30a29ab08 ...>, #token="adoptopenjdk8", #version="8,242:b08", #sha256="b24754532fdefc3ae03c56dce972803fc78fd2243bbab12fb412a93aabf05adc", #url=#<URL:0x00007fa30897d828 #uri=#<URI::HTTPS https://github.com/AdoptOpenJDK/openjdk8-binaries/releases/download/jdk8u242-b08/OpenJDK8U-jdk_x64_mac_hotspot_8u242b08.pkg>, #using=nil, #tag=nil, #branch=nil, #revisions=nil, #revision=nil, #trust_cert=nil, #cookies=nil, #referer=nil, #header=nil, #user_agent=:default, #data=nil, #specs={:user_agent=>:default}>, #appcast=#<Cask::DSL::Appcast:0x00007fa30897d3a0 #uri=#<URI::HTTPS https://github.com/adoptopenjdk/openjdk8-binaries/releases.atom>, #parameters={}>, #name=["AdoptOpenJDK 8"], #homepage="https://adoptopenjdk.net/", #artifacts=#<SortedSet: {...}>, #staged_path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8/8,242:b08>, #language_eval=nil>>, #directives={:pkgutil=>"net.adoptopenjdk.8.jdk", :signal=>[]}>, #<Cask::Artifact::Pkg:0x00007fa30897c630 #cask=#<Cask::Cask:0x00007fa30a29ab08 #token="adoptopenjdk8", #sourcefile_path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8/.metadata/8,242:b08/20200414143743.728/Casks/adoptopenjdk8.rb>, #tap=nil, #block=#<Proc:0x00007fa30a29aa68#/usr/local/Caskroom/adoptopenjdk8/.metadata/8,242:b08/20200414143743.728/Casks/adoptopenjdk8.rb:1>, #default_config=#<Cask::Config:0x00007fa30a29aa40 #explicit={}>, #caskroom_path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8>, #metadata_master_container_path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8/.metadata>, #config=#<Cask::Config:0x00007fa30a298e98 #explicit={}, #default={:languages=>["en-US"], :appdir=>#<Pathname:/Applications>, :colorpickerdir=>#<Pathname:/Users/user/Library/ColorPickers>, :prefpanedir=>#<Pathname:/Users/user/Library/PreferencePanes>, :qlplugindir=>#<Pathname:/Users/user/Library/QuickLook>, :mdimporterdir=>#<Pathname:/Users/user/Library/Spotlight>, :dictionarydir=>#<Pathname:/Users/user/Library/Dictionaries>, :fontdir=>#<Pathname:/Users/user/Library/Fonts>, :servicedir=>#<Pathname:/Users/user/Library/Services>, :input_methoddir=>#<Pathname:/Users/user/Library/Input Methods>, :internet_plugindir=>#<Pathname:/Users/user/Library/Internet Plug-Ins>, :audio_unit_plugindir=>#<Pathname:/Users/user/Library/Audio/Plug-Ins/Components>, :vst_plugindir=>#<Pathname:/Users/user/Library/Audio/Plug-Ins/VST>, :vst3_plugindir=>#<Pathname:/Users/user/Library/Audio/Plug-Ins/VST3>, :screen_saverdir=>#<Pathname:/Users/user/Library/Screen Savers>}, #env={}>, #dsl=#<Cask::DSL:0x00007fa30897e6d8 #cask=#<Cask::Cask:0x00007fa30a29ab08 ...>, #token="adoptopenjdk8", #version="8,242:b08", #sha256="b24754532fdefc3ae03c56dce972803fc78fd2243bbab12fb412a93aabf05adc", #url=#<URL:0x00007fa30897d828 #uri=#<URI::HTTPS https://github.com/AdoptOpenJDK/openjdk8-binaries/releases/download/jdk8u242-b08/OpenJDK8U-jdk_x64_mac_hotspot_8u242b08.pkg>, #using=nil, #tag=nil, #branch=nil, #revisions=nil, #revision=nil, #trust_cert=nil, #cookies=nil, #referer=nil, #header=nil, #user_agent=:default, #data=nil, #specs={:user_agent=>:default}>, #appcast=#<Cask::DSL::Appcast:0x00007fa30897d3a0 #uri=#<URI::HTTPS https://github.com/adoptopenjdk/openjdk8-binaries/releases.atom>, #parameters={}>, #name=["AdoptOpenJDK 8"], #homepage="https://adoptopenjdk.net/", #artifacts=#<SortedSet: {...}>, #staged_path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8/8,242:b08>, #language_eval=nil>>, #path=#<Pathname:/usr/local/Caskroom/adoptopenjdk8/8,242:b08/OpenJDK8U-jdk_x64_mac_hotspot_8u242b08.pkg>, #stanza_options={}>}>
==> Uninstalling artifact of class Cask::Artifact::Uninstall
==> Uninstalling packages:
/usr/sbin/pkgutil --pkgs=net.adoptopenjdk.8.jdk
net.adoptopenjdk.8.jdk
/usr/sbin/pkgutil --files net.adoptopenjdk.8.jdk
/usr/sbin/pkgutil --pkg-info-plist net.adoptopenjdk.8.jdk
==> Deleting pkg directories
/usr/bin/stat -f \%Of -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/jmx/jmx-scandir/test/com/sun
/usr/bin/sudo -E -- /bin/chmod -- 777 /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/jmx/jmx-scandir/test/com/sun
Password:
Sorry, try again.
Password:
/usr/bin/sudo -E -- /bin/rmdir -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/jmx/jmx-scandir/test/com/sun
Password:
/usr/bin/stat -f \%Of -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/jmx/jmx-scandir/src/com/sun
/usr/bin/sudo -E -- /bin/chmod -- 777 /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/jmx/jmx-scandir/src/com/sun
Password:
Sorry, try again.
Password:
/usr/bin/sudo -E -- /bin/rmdir -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/jmx/jmx-scandir/src/com/sun
Password:
/usr/bin/stat -f \%Of -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/demo/jpda/com/sun/tools/example
/usr/bin/sudo -E -- /bin/chmod -- 777 /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/demo/jpda/com/sun/tools/example
Password:
/usr/bin/sudo -E -- /bin/rmdir -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/demo/jpda/com/sun/tools/example
Password:
/usr/bin/stat -f \%Of -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/annotations/DependencyChecker/Plugins/src/plugins
/usr/bin/sudo -E -- /bin/chmod -- 777 /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/annotations/DependencyChecker/Plugins/src/plugins
Password:
/usr/bin/sudo -E -- /bin/rmdir -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/annotations/DependencyChecker/Plugins/src/plugins
Password:
/usr/bin/stat -f \%Of -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/scripting/scriptpad/src/com
/usr/bin/sudo -E -- /bin/chmod -- 777 /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/scripting/scriptpad/src/com
Password:
/usr/bin/sudo -E -- /bin/rmdir -- /Library/Java/JavaVirtualMachines/adoptopenjdk-8.jdk/Contents/Home/sample/scripting/scriptpad/src/com

Answer 1

After adding the debug options it seemed as though all of the password required operations were changing permissions and deleting folders in the adoptopenjdk directory. I quit homebrew, deleted the adoptopenjdk directory, again ran brew upgrade and it proceeded with the upgrade of adoptopenjdk successfully, but did ask for my password two more times