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Homebrew / homebrew-cask

🍻 A CLI workflow for the administration of macOS applications distributed as binaries
https://brew.sh
BSD 2-Clause "Simplified" License
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session-manager-plugin: macOS unable to verify developer/malware status; removes after each update #109290

Closed bleachbyte closed 3 years ago

bleachbyte commented 3 years ago

Description of issue

The AWS Session Manager plugin (https://formulae.brew.sh/cask/session-manager-plugin) will not run on macOS Catalina 10.15.7, as it is stopped by Gatekeeper: Screen Shot 2021-07-29 at 1 04 41 PM

This comes up every time the plugin is updated, which is frequent enough that it becomes a bit tedious to reinstall with --no-quarantine any time it's updated.

This was originally raised in #90637 ; the solution offered was the above doc (although that link is broken). I'm raising this issue to ask:

  1. Is/can there be a better/more elegant solution to this process?
  2. Given the scope of this error/issue, is this something that can be addressed in Homebrew, or will it ultimately be up to AWS to update their plugin permissions?

Command that failed

aws ssm start-session

Output of command with --verbose --debug

aws ssm start-session --document-name AWS-StartInteractiveCommand --parameters command='sudo su - bleachbyte' --target [REDACTED-InstanceID] 


Command '['session-manager-plugin', '{"SessionId": "bleachbyte-0123456789abcdefg", "TokenValue": "[REDACTED]", "StreamUrl": "wss://ssmmessages.us-west-2.amazonaws.com/v1/data-channel/bleachbyte-0123456789abcdefg?role=publish_subscribe", "ResponseMetadata": {"RequestId": "[REDACTED]", "HTTPStatusCode": 200, "HTTPHeaders": {"server": "Server", "date": "Thu, 29 Jul 2021 17:59:34 GMT", "content-type": "application/x-amz-json-1.1", "content-length": "680", "connection": "keep-alive", "x-amzn-requestid": "[REDACTED]"}, "RetryAttempts": 0}}', 'us-west-2', 'StartSession', '', '{"Target": "[REDACTED]", "DocumentName": "AWS-StartInteractiveCommand", "Parameters": {"command": ["sudo su - bleachbyte"]}}', 'https://ssm.us-west-2.amazonaws.com']' died with .
brew reinstall --cask session-manager-plugin --verbose --debug


$ brew reinstall --cask session-manager-plugin --verbose --debug
==> Cask::Installer#reinstall
==> Cask::Installer#install
==> Printing caveats
==> Cask::Installer#fetch
==> Downloading https://session-manager-downloads.s3.amazonaws.com/plugin/1.2.234.0/mac/sessionmanager-bundle.zip
/usr/bin/curl --disable --globoff --show-error --user-agent Homebrew/3.2.5-17-g689c1fd\ \(Macintosh\;\ Intel\ Mac\ OS\ X\ 10.15.7\)\ curl/7.64.1 --header Accept-Language:\ en --retry 3 --location --silent --head --request GET https://session-manager-downloads.s3.amazonaws.com/plugin/1.2.234.0/mac/sessionmanager-bundle.zip
Already downloaded: /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
==> Checking quarantine support
/usr/bin/xattr -h
/usr/bin/swift /usr/local/Homebrew/Library/Homebrew/cask/utils/quarantine.swift
==> Quarantine is available.
==> Verifying Gatekeeper status of /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
/usr/bin/xattr -p com.apple.quarantine /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
==> /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip is quarantined
==> Verifying checksum for cask 'session-manager-plugin'
hdiutil imageinfo -format /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
zipinfo -1 /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
==> Uninstalling Cask session-manager-plugin
==> Uninstalling artifacts
==> 1 artifact defined
#, @tap=nil, @block=#, @default_config=#, @caskroom_path=#, @metadata_main_container_path=#, @config=#["en-US"], :appdir=>#, :colorpickerdir=>#, :prefpanedir=>#, :qlplugindir=>#, :mdimporterdir=>#, :dictionarydir=>#, :fontdir=>#, :servicedir=>#, :input_methoddir=>#, :internet_plugindir=>#, :audio_unit_plugindir=>#, :vst_plugindir=>#, :vst3_plugindir=>#, :screen_saverdir=>#}, @env={}, @binarydir=#>, @dsl=#, @token="session-manager-plugin", @version="1.2.234.0", @sha256=#, @url=#, @verified="session-manager-downloads.s3.amazonaws.com/", @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={:verified=>"session-manager-downloads.s3.amazonaws.com/", :user_agent=>:default}>, @name=["Session Manager Plugin for the AWS CLI"], @desc="Plugin for AWS CLI to start and end sessions that connect to managed instances", @homepage="https://docs.aws.amazon.com/systems-manager/latest/userguide/session-manager-working-with-install-plugin.html", @livecheck=#, @regex=/\s*v?(\d+(?:\.\d+)+)\s*<\/td>/i, @skip=false, @skip_msg=nil, @strategy=nil, @url=:homepage>, @livecheckable=true, @artifacts=#, @staged_path=#, @language_eval=nil>>, @source_string="sessionmanager-bundle/bin/session-manager-plugin", @target_string="", @source=#, @target=#>}>
==> Uninstalling artifact of class Cask::Artifact::Binary
==> Unlinking Binary '/usr/local/bin/session-manager-plugin'
==> Purging files for version 1.2.234.0 of Cask session-manager-plugin
==> Purging all staged versions of Cask session-manager-plugin
==> Installing Cask session-manager-plugin
==> Cask::Installer#stage
==> Extracting primary container
==> Using container class UnpackStrategy::Zip for /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
zipinfo -1 /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
unzip -o /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip -d /private/tmp/d20210729-70927-16jvfdo
cp -pR /private/tmp/d20210729-70927-16jvfdo/sessionmanager-bundle/. /usr/local/Caskroom/session-manager-plugin/1.2.234.0/sessionmanager-bundle
chmod -Rf +w /private/tmp/d20210729-70927-16jvfdo
==> Verifying Gatekeeper status of /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
/usr/bin/xattr -p com.apple.quarantine /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
==> /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip is quarantined
==> Propagating quarantine from /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip to /usr/local/Caskroom/session-manager-plugin/1.2.234.0
/usr/bin/xattr -p com.apple.quarantine /Users/bleachbyte/Library/Caches/Homebrew/downloads/ac45872cb4cfc1ade1e091a61176b819bf70cfa466cabeeafe02afefba4ff5ae--sessionmanager-bundle.zip
/usr/bin/xargs -0 -- /bin/chmod -h u\+w
/usr/bin/xargs -0 -- /usr/bin/xattr -w com.apple.quarantine 0181\;6101a111\;Homebrew\\x20Cask\;FE526EEE-6B66-45FA-A2AE-EB8367CC553A
==> Creating metadata directory: /usr/local/Caskroom/session-manager-plugin/.metadata/1.2.234.0/20210729182720.499
==> Creating metadata subdirectory: /usr/local/Caskroom/session-manager-plugin/.metadata/1.2.234.0/20210729182720.499/Casks
==> Installing artifacts
==> 1 artifact defined
#, @tap=#, @alias_table=nil, @alias_reverse_table=nil, @formula_renames={}, @cask_dir=#>, @block=#, @default_config=#, @caskroom_path=#, @metadata_main_container_path=#, @config=#>, @dsl=#, @token="session-manager-plugin", @version="1.2.234.0", @sha256=#, @url=#, @verified="session-manager-downloads.s3.amazonaws.com/", @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={:verified=>"session-manager-downloads.s3.amazonaws.com/", :user_agent=>:default}>, @name=["Session Manager Plugin for the AWS CLI"], @desc="Plugin for AWS CLI to start and end sessions that connect to managed instances", @homepage="https://docs.aws.amazon.com/systems-manager/latest/userguide/session-manager-working-with-install-plugin.html", @livecheck=#, @regex=/\s*v?(\d+(?:\.\d+)+)\s*<\/td>/i, @skip=false, @skip_msg=nil, @strategy=nil, @url=:homepage>, @livecheckable=true, @artifacts=#, @staged_path=#, @language_eval=nil>>, @source_string="sessionmanager-bundle/bin/session-manager-plugin", @target_string="", @source=#, @target=#>}>
==> Installing artifact of class Cask::Artifact::Binary
==> Linking Binary 'session-manager-plugin' to '/usr/local/bin/session-manager-plugin'
/bin/ln -h -f -s -- /usr/local/Caskroom/session-manager-plugin/1.2.234.0/sessionmanager-bundle/bin/session-manager-plugin /usr/local/bin/session-manager-plugin
/usr/local/Homebrew/Library/Homebrew/shims/scm/git --version
🍺  session-manager-plugin was successfully installed!

Output of brew doctor --verbose

Click to expand


==> Cask Environment Variables:
BUNDLE_PATH
CHRUBY_VERSION
GEM_HOME
GEM_PATH
HOMEBREW_CASK_OPTS
LC_ALL
PATH
RBENV_VERSION
RUBYLIB
RUBYOPT
RUBYPATH
SHELL
==> $LOAD_PATHS
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/usr/local/Homebrew/Library/Homebrew/vendor/portable-ruby/2.6.3_2/lib/ruby/2.6.0
/usr/local/Homebrew/Library/Homebrew/vendor/portable-ruby/2.6.3_2/lib/ruby/2.6.0/x86_64-darwin14
/usr/local/Homebrew/Library/Homebrew
==> Homebrew Version
3.2.5-17-g689c1fd
==> macOS
10.15.7
==> SIP
Enabled
==> Homebrew Cask Staging Location
/usr/local/Caskroom
==> Homebrew Cask Taps:
/usr/local/Homebrew/Library/Taps/homebrew/homebrew-cask (3958 casks)
/usr/local/Homebrew/Library/Taps/chef/homebrew-chef (4 casks)
/usr/local/Homebrew/Library/Taps/homebrew/homebrew-cask-versions (195 casks)
Your system is ready to brew.

Output of brew tap

Click to expand


chef/chef
cloudfoundry/tap
domt4/autoupdate
homebrew/bundle
homebrew/cask
homebrew/cask-versions
homebrew/core
homebrew/services
lucagrulla/tap
mikhailai/misc
miccal commented 3 years ago

Unfortunately there is not way around this without using the --no-quarantine flag, as we are not able to remove the quarantine protection via Cask as explained in https://github.com/Homebrew/homebrew-cask/pull/98525.

Another way is to set HOMEBREW_CASK_OPTS="--no-quarantine" as an environment variable.