diff --git a/home/dot_config/shell/private_private.sh.tmpl b/home/dot_config/shell/private_private.sh.tmpl
index 00611b40..4d507324 100644
--- a/home/dot_config/shell/private_private.sh.tmpl
+++ b/home/dot_config/shell/private_private.sh.tmpl
@@ -49,14 +49,17 @@ export GITLAB_RUNNER_TOKEN="{{ if (stat (joinPath .chezmoi.sourceDir ".chezmoite
 export HEROKU_API_KEY="{{ if (stat (joinPath .chezmoi.sourceDir ".chezmoitemplates" "secrets" "HEROKU_API_KEY")) }}{{ includeTemplate "secrets/HEROKU_API_KEY" | decrypt | trim }}{{ else }}{{ env "HEROKU_API_KEY" }}{{ end }}"
 
 ### Install Doctor
+# TODO: Replace HEADLESS_INSTALL with {{ .host.headless }} data source once headless install detection is implemented
+# export HEADLESS_INSTALL={{ .host.headless }}
 export HEADLESS_INSTALL=true
-export SOFTWARE_GROUP="Full-Desktop"
-export FULL_NAME="Brian Zalewski"
-export PRIMARY_EMAIL="help@megabyte.space"
-export PUBLIC_SERVICES_DOMAIN="megabyte.space"
-export RESTRICTED_ENVIRONMENT=false
-export WORK_ENVIRONMENT=false
-export HOST="$HOST"
+export SOFTWARE_GROUP="{{ .host.softwareGroup }}"
+export FULL_NAME="{{ .user.name }}"
+export PRIMARY_EMAIL="{{ .user.email }}"
+export PUBLIC_SERVICES_DOMAIN="{{ .host.domain }}"
+export RESTRICTED_ENVIRONMENT={{ .host.restricted }}
+export WORK_ENVIRONMENT={{ .host.work }}
+export HOST="{{ .host.hostname }}"
+export KEYID="{{ .user.gpg.id }}"
 
 # Set to work environment if Cisco applications are installed (modify this to your liking)
 if [ -d /Applications/Cisco ]; then
diff --git a/software.yml b/software.yml
index bd954cd0..6a282a4e 100644
--- a/software.yml
+++ b/software.yml
@@ -358,7 +358,7 @@ softwarePackages:
     _bin: graphql-playground
     _github: https://github.com/graphql/graphql-playground
     _name: GraphQL Playground
-    _when:cask: '! test -d "/Applications/GraphQL Playground.app"'
+    _when:cask: '! test -d "/Applications/GraphQL Playground.app" && ! test -d "~/Applications/GraphQL Playground.app"'
     appimage: graphql/graphql-playground
     cask: graphql-playground
     exe: https://github.com/graphql/graphql-playground/releases/download/v1.8.10/graphql-playground-electron-setup-1.8.10.exe
@@ -366,12 +366,12 @@ softwarePackages:
     _bin: kdenlive
     _github: https://github.com/KDE/kdenlive
     _name: Kdenlive
-    _when:cask: '! test -d /Applications/kdenlive.app'
+    _when:cask: '! test -d /Applications/kdenlive.app && ! test -d ~/Applications/kdenlive.app'
     cask: kdenlive
     choco: kdenlive
     flatpak: org.kde.kdenlive
   genymotion:
-    _when:cask: '! test -d /Applications/Genymotion.app'
+    _when:cask: '! test -d /Applications/Genymotion.app && ! test -d ~/Applications/Genymotion.app'
     cask: genymotion
     choco: genymotion
     # TODO: Figure out how to install on Android
@@ -383,7 +383,7 @@ softwarePackages:
     _home: https://pieces.app/
     _name: Pieces
     _post:snap: sudo snap connect pieces-os:dotnet-runtime-aspnetcore
-    _when:script:darwin: '! test -d /Applications/Pieces.app'
+    _when:script:darwin: '! test -d /Applications/Pieces.app && ! test -d ~/Applications/Pieces.app'
     # TODO - Figure out how to deal with appinstaller
     appinstaller: https://builds.pieces.app/stages/production/pieces_suite_windows/appinstaller/download
     script:darwin: cd /tmp && curl -sSL https://builds.pieces.app/stages/production/macos_packaging/pkg/download > Pieces.pkg && sudo installer -pkg Pieces.pkg -target / && rm -f /tmp/Pieces.pkg
@@ -437,7 +437,7 @@ softwarePackages:
     _github: https://github.com/altair-graphql/altair
     _home: https://altairgraphql.dev/
     _name: Altair GraphQL Client
-    _when:cask: '! test -d "/Applications/Altair GraphQL Client.app"'
+    _when:cask: '! test -d "/Applications/Altair GraphQL Client.app" && ! test -d "~/Applications/Altair GraphQL Client.app"'
     cask: altair-graphql-client
     choco: altair-graphql
     snap: altair
@@ -460,7 +460,7 @@ softwarePackages:
     _github: null
     _home: https://developer.android.com/studio
     _name: Android Studio
-    _when:cask: '! test -d "/Applications/Android Studio.app"'
+    _when:cask: '! test -d "/Applications/Android Studio.app" && ! test -d "~/Applications/Android Studio.app"'
     ansible: professormanhattan.androidstudio
     cask: android-studio
     choco: androidstudio
@@ -602,7 +602,7 @@ softwarePackages:
   http-toolkit:
     _github: https://github.com/httptoolkit/httptoolkit
     _name: HTTP Toolkit
-    _when:cask: '! test -d "/Applications/HTTP Toolkit.app"'
+    _when:cask: '! test -d "/Applications/HTTP Toolkit.app" && ! test -d "~/Applications/HTTP Toolkit.app"'
     cask: http-toolkit
     winget: HTTPToolKit.HTTPToolKit
   tart:
@@ -640,7 +640,7 @@ softwarePackages:
   catlight:
     _github: https://github.com/catlightio/CatLight
     _name: Catlight
-    when: '! test -d /Applications/Catlight.app'
+    when: '! test -d /Applications/Catlight.app && ! test -d ~/Applications/Catlight.app'
     cask: catlight
     deb: https://catlight.io/downloads/linux/beta
   d2vm:
@@ -702,7 +702,7 @@ softwarePackages:
     _github: https://github.com/ExistentialAudio/BlackHole
     _name: BlackHole
     _desc: Audio loopback device for macOS (supports sound passthrough to screen recording software on macOS)
-    _when:cask: '! test -d /Library/Audio/Plug-Ins/HAL/BlackHole16ch.driver'
+    _when:cask: '! test -d /Library/Audio/Plug-Ins/HAL/BlackHole16ch.driver && ! test -d ~/Library/Audio/Plug-Ins/HAL/BlackHole16ch.driver'
     cask: blackhole-16ch
   aria2:
     _bin: aria2c
@@ -720,7 +720,7 @@ softwarePackages:
     port: aria2
     scoop: aria2
   ariang:
-    _when:cask: '! test -d "/Applications/AriaNg Native.app"'
+    _when:cask: '! test -d "/Applications/AriaNg Native.app" && ! test -d "~/Applications/AriaNg Native.app"'
     cask: ariang
   iina:
     _bin: null
@@ -729,7 +729,7 @@ softwarePackages:
     _github: https://github.com/iina/iina
     _home: https://iina.io/
     _name: iina macOS Video Player
-    _when:cask: '! test -d /Applications/iina.app'
+    _when:cask: '! test -d /Applications/iina.app && ! test -d ~/Applications/iina.app'
     cask: iina
   asciinema:
     _bin: asciinema
@@ -785,7 +785,7 @@ softwarePackages:
   devtoys:
     _bin: devtoys
     _github: https://github.com/ObuchiYuki/DevToysMac
-    _when:cask: echo '! test -d /Applications/DevToys.app' | bash
+    _when:cask: echo '! test -d /Applications/DevToys.app && ! test -d ~/Applications/DevToys.app' | bash
     cask: devtoys
   devtoys-windows:
     _bin: devtoys
@@ -803,13 +803,13 @@ softwarePackages:
     _bin: codeedit
     _github: https://github.com/CodeEditApp/CodeEdit
     _name: CodeEdit
-    _when:cask: '! test -d /Applications/CodeEdit.app'
+    _when:cask: '! test -d /Applications/CodeEdit.app && ! test -d ~/Applications/CodeEdit.app'
     cask: codeedit
   barrier:
     _bin: barrier
     _github: https://github.com/debauchee/barrier
     _name: Barrier
-    _when:cask: '! test -d /Applications/Barrier.app'
+    _when:cask: '! test -d /Applications/Barrier.app && ! test -d ~/Applications/Barrier.app'
     cask: barrier
     choco: barrier
     flatpak: com.github.debauchee.barrier
@@ -820,7 +820,7 @@ softwarePackages:
     _github: https://github.com/zenangst/Syncalicious
     _home: https://github.com/zenangst/Syncalicious
     _name: Syncalicious
-    _when:cask: '! test -d /Applications/Syncalicious.app'
+    _when:cask: '! test -d /Applications/Syncalicious.app && ! test -d ~/Applications/Syncalicious.app'
     cask: syncalicious
   auto-install:
     _bin: auto-install
@@ -917,7 +917,7 @@ softwarePackages:
     _github: https://github.com/signalapp/Signal-Desktop
     _home: https://signal.org
     _name: Signal Desktop
-    _when:cask: '! test -d "/Applications/Signal.app"'
+    _when:cask: '! test -d "/Applications/Signal.app" && ! test -d "~/Applications/Signal.app"'
     cask: signal
     choco: signal
     flatpak: org.signal.Signal
@@ -955,7 +955,7 @@ softwarePackages:
     _github: https://github.com/balena-io/etcher
     _home: https://www.balena.io/etcher/
     _name: balenaEtcher
-    _when:cask: '! test -d /Applications/balenaEtcher.app'
+    _when:cask: '! test -d /Applications/balenaEtcher.app && ! test -d ~/Applications/balenaEtcher.app'
     ansible:linux: professormanhattan.etcher
     # Waiting for zap to allow headless automation of AppImage Catalog images
     # Currently, it fails because there are multiple versions to select
@@ -1051,7 +1051,7 @@ softwarePackages:
     _github: https://github.com/kdzwinel/betwixt
     _home: https://github.com/kdzwinel/betwixt
     _name: Betwixt
-    _when:cask: '! test -d /Applications/Betwixt.app'
+    _when:cask: '! test -d /Applications/Betwixt.app && ! test -d ~/Applications/Betwixt.app'
     cask: betwixt
   bin:
     _bin: bin
@@ -1077,7 +1077,7 @@ softwarePackages:
     _github: https://github.com/Jintin/Swimat
     _home: https://jintin.github.io/Swimat/
     _name: Swimat
-    _when:cask: '! test -d /Applications/Swimat.app'
+    _when:cask: '! test -d /Applications/Swimat.app && ! test -d ~/Applications/Swimat.app'
     cask: swimat
   textql:
     _bin: textql
@@ -1096,7 +1096,7 @@ softwarePackages:
     _github: https://github.com/brunophilipe/Cakebrew
     _home: http://www.cakebrew.com/
     _name: Cakebrew
-    _when:cask: '! test -d /Applications/Cakebrew.app'
+    _when:cask: '! test -d /Applications/Cakebrew.app && ! test -d ~/Applications/Cakebrew.app'
     cask: cakebrew
   bitwarden:
     _bin: bitwarden
@@ -1105,7 +1105,7 @@ softwarePackages:
     _github: https://github.com/bitwarden/desktop
     _home: null
     _name: BitWarden
-    _when:cask: '! test -d /Applications/Bitwarden.app'
+    _when:cask: '! test -d /Applications/Bitwarden.app && ! test -d ~/Applications/Bitwarden.app'
     cask: bitwarden
     choco: bitwarden
     flatpak: com.bitwarden.desktop
@@ -1179,25 +1179,25 @@ softwarePackages:
     _bin: utm
     _github: https://github.com/utmapp/UTM
     _name: UTM
-    _when:cask: '! test -d /Applications/UTM.app'
+    _when:cask: '! test -d /Applications/UTM.app && ! test -d ~/Applications/UTM.app'
     cask: utm
   amethyst:
     _bin: amethyst
     _github: https://github.com/ianyh/Amethyst
     _name: Amethyst
-    _when:cask: echo '! test -d /Applications/Amethyst.app' | bash
+    _when:cask: echo '! test -d /Applications/Amethyst.app && ! test -d ~/Applications/Amethyst.app' | bash
     cask: amethyst
   alt-tab:
     _bin: alt-tab
     _github: https://github.com/lwouis/alt-tab-macos
     _name: Alt+Tab for macOS that works like alt+tab on Windows
-    _when:cask: echo '! test -d /Applications/AltTab.app' | bash
+    _when:cask: echo '! test -d /Applications/AltTab.app && ! test -d ~/Applications/AltTab.app' | bash
     cask: alt-tab
   fiscript:
     _bin: fiscript
     _github: https://github.com/Mortennn/FiScript
     _name: FiScript
-    _when:cask: echo '! test -d /Applications/FiScript.app' | bash
+    _when:cask: echo '! test -d /Applications/FiScript.app && ! test -d ~/Applications/FiScript.app' | bash
     cask: fiscript
   opencommit:
     _bin: opencommit
@@ -1240,7 +1240,7 @@ softwarePackages:
     _github: https://github.com/Barre/privaxy
     _home: false
     _name: Privaxy
-    _when:script:darwin: '! test -d /Applications/Privaxy.app'
+    _when:script:darwin: '! test -d /Applications/Privaxy.app && ! test -d ~/Applications/Privaxy.app'
     appimage: barre/privaxy
     apt: https://github.com/Barre/privaxy/releases/download/v0.5.2/privaxy_0.5.2_amd64.deb
     script:darwin: curl -sSL https://github.com/Barre/privaxy/releases/download/v0.5.2/Privaxy_0.5.2_universal.dmg > /tmp/Privaxy.dmg && sudo hdiutil attach /tmp/Privaxy.dmg && sudo cp -R /Volumes/Privaxy/Privaxy.app /Applications && sudo hdiutil detach /Volumes/Privaxy && rm -f /tmp/Privaxy.dmg
@@ -1251,7 +1251,7 @@ softwarePackages:
     _github: https://github.com/brave/brave-browser
     _home: https://brave.com/
     _name: Brave Browser
-    _when:cask: '! test -d "/Applications/Brave Browser.app"'
+    _when:cask: '! test -d "/Applications/Brave Browser.app" && ! test -d "~/Applications/Brave Browser.app"'
     ansible: professormanhattan.bravebrowser
     cask: brave-browser
     choco: brave
@@ -1336,7 +1336,7 @@ softwarePackages:
     _bin: lightproxy
     _github: https://github.com/alibaba/lightproxy
     _name: LightProxy
-    _when:cask: echo '! test -d /Applications/LightProxy.app' | bash
+    _when:cask: echo '! test -d /Applications/LightProxy.app && ! test -d ~/Applications/LightProxy.app' | bash
     cask: lightproxy
   carbon-now:
     _bin: carbon-now
@@ -1368,7 +1368,7 @@ softwarePackages:
     _desc: Image compressor that utilizes other applications like ImageOptim under the hood
     _github: https://github.com/ImageOptim/ImageOptim
     _home: https://imageoptim.com/mac
-    _when:cask: '! test -d /Applications/ImageOptim.app'
+    _when:cask: '! test -d /Applications/ImageOptim.app && ! test -d ~/Applications/ImageOptim.app'
     cask: imageoptim
   imageoptim-cli:
     _deps:
@@ -1387,7 +1387,7 @@ softwarePackages:
     _github: https://github.com/cerebroapp/cerebro
     _home: null
     _name: Cerebro
-    _when:cask: '! test -d /Applications/Cerebro.app'
+    _when:cask: '! test -d /Applications/Cerebro.app && ! test -d ~/Applications/Cerebro.app'
     cask: cerebro
     choco: cerebro
     github: github.com/cerebroapp/cerebro
@@ -1482,7 +1482,7 @@ softwarePackages:
     _github: Not open-source
     _home: https://www.google.com/chrome/
     _name: Google Chrome
-    _when:cask: '! test -d "/Applications/Google Chrome.app"'
+    _when:cask: '! test -d "/Applications/Google Chrome.app" && ! test -d "~/Applications/Google Chrome.app"'
     ansible: professormanhattan.chrome
     cask: google-chrome
     choco: googlechrome
@@ -1495,7 +1495,7 @@ softwarePackages:
     _github: false
     _home: https://www.google.com/drive/download/
     _name: Google Drive
-    _when:cask: '! test -d "/Applications/Google Drive.app"'
+    _when:cask: '! test -d "/Applications/Google Drive.app" && ! test -d "~/Applications/Google Drive.app"'
     cask: google-drive
     choco: googledrive
   tor-browser:
@@ -1505,7 +1505,7 @@ softwarePackages:
     _github: https://github.com/TheTorProject/gettorbrowser
     _home: https://www.torproject.org/
     _name: Tor Browser
-    _when:cask: '! test -d "/Applications/Tor Browser.app"'
+    _when:cask: '! test -d "/Applications/Tor Browser.app" && ! test -d "~/Applications/Tor Browser.app"'
     cask: tor-browser
     choco: tor-browser
     flatpak: com.github.micahflee.torbrowser-launcher
@@ -1616,7 +1616,7 @@ softwarePackages:
     pacman: clang
     scoop: llvm
   clocker:
-    _when:cask: '! test -d /Applications/Clocker.app'
+    _when:cask: '! test -d /Applications/Clocker.app && ! test -d ~/Applications/Clocker.app'
     _bin: null
     _desc: Clocker is designed to help you keep track of your friends and colleagues in different time zones.
     _docs: null
@@ -1865,7 +1865,7 @@ softwarePackages:
     github: github.com/bcicen/ctop
     yay: ctop-bin
   cumulus:
-    _when:cask: '! test -d /Applications/Cumulus.app'
+    _when:cask: '! test -d /Applications/Cumulus.app && ! test -d ~/Applications/Cumulus.app'
     _bin: null
     _desc: A SoundCloud player that lives in the menubar
     _docs: null
@@ -1977,7 +1977,7 @@ softwarePackages:
     github: github.com/dat-ecosystem-archive/dat
     npm: dat@next
   dat-desktop:
-    _when:cask: '! test -d "/Applications/Dat Desktop.app"'
+    _when:cask: '! test -d "/Applications/Dat Desktop.app" && ! test -d "~/Applications/Dat Desktop.app"'
     _bin: null
     _desc: Peer to peer data syncronization
     _docs: null
@@ -2166,7 +2166,7 @@ softwarePackages:
     _name: Espanso
     _snapClassic: true
     _when:appimage: sudo espanso service register && sudo espanso start
-    _when:cask: '! test -d /Applications/Espanso.app'
+    _when:cask: '! test -d /Applications/Espanso.app && ! test -d ~/Applications/Espanso.app'
     _when:snap: sudo espanso service register && sudo espanso start
     appimage: federico-terzi/espanso
     cask: espanso
@@ -2185,7 +2185,7 @@ softwarePackages:
     _github: https://github.com/docker/compose
     _home: https://www.docker.com/
     _name: Docker Desktop
-    _when:cask: '! test -d /Applications/Docker.app'
+    _when:cask: '! test -d /Applications/Docker.app && ! test -d ~/Applications/Docker.app'
     apt: https://desktop.docker.com/linux/main/amd64/docker-desktop-4.16.2-amd64.deb
     cask: docker
     choco: docker-desktop
@@ -2392,13 +2392,13 @@ softwarePackages:
     _bin: prezi-video
     _github: null
     _name: Prezi Video
-    _when:cask: '! test -d "/Applications/Prezi Video.app"'
+    _when:cask: '! test -d "/Applications/Prezi Video.app" && ! test -d "~/Applications/Prezi Video.app"'
     cask: prezi-video
   orbstack:
     _bin: orb
     _github: 
     _name: OrbStack
-    _when:cask: '! test -d /Applications/OrbStack.app'
+    _when:cask: '! test -d /Applications/OrbStack.app && ! test -d ~/Applications/OrbStack.app'
     cask: orbstack
   gpt-engineer:
     _bin: gpt-engineer
@@ -2409,7 +2409,7 @@ softwarePackages:
     _bin: medis
     _github: https://github.com/luin/medis
     _name: Medis
-    _when:cask: '! test -d /Applications/Medis.app'
+    _when:cask: '! test -d /Applications/Medis.app && ! test -d ~/Applications/Medis.app'
     cask: medis
   ndb:
     _bin: ndb
@@ -2429,7 +2429,7 @@ softwarePackages:
     _home: https://www.electronjs.org/
     _name: Electron
     npm: electron
-    _when:cask: '! test -d /Applications/Electron.app'
+    _when:cask: '! test -d /Applications/Electron.app && ! test -d ~/Applications/Electron.app'
     cask: electron
     choco: electron
   emma:
@@ -2519,7 +2519,7 @@ softwarePackages:
     _bin: mongodb-compass
     _github: https://github.com/mongodb-js/compass
     _name: MongoDB Compass
-    _when:cask: '! test -d "/Applications/MongoDB Compass.app"'
+    _when:cask: '! test -d "/Applications/MongoDB Compass.app" && ! test -d "~/Applications/MongoDB Compass.app"'
     cask: mongodb-compass
     choco: mongodb-compass
     dnf: https://downloads.mongodb.com/compass/mongodb-compass-1.38.0.x86_64.rpm
@@ -2738,7 +2738,7 @@ softwarePackages:
     _github: https://github.com/withfig/autocomplete
     _home: https://fig.io/
     _name: Fig
-    _when:cask: '! test -d "/Applications/Fig.app"'
+    _when:cask: '! test -d "/Applications/Fig.app" && ! test -d "~/Applications/Fig.app"'
     ansible:darwin: professormanhattan.fig
     cask: fig
   steampipe:
@@ -2765,7 +2765,7 @@ softwarePackages:
     github: github.com/filebrowser/filebrowser
   arduino-ide:
     _bin: arduino
-    _when:cask: '! test -d "/Applications/Arduino.app"'
+    _when:cask: '! test -d "/Applications/Arduino.app" && ! test -d "~/Applications/Arduino.app"'
     cask: arduino
     choco: arduino
     flatpak: cc.arduino.IDE2
@@ -2839,7 +2839,7 @@ softwarePackages:
     _github: null
     _home: https://www.mozilla.org/en-US/firefox/new/
     _name: Mozilla Firefox
-    _when:cask: '! test -d "/Applications/Firefox.app"'
+    _when:cask: '! test -d "/Applications/Firefox.app" && ! test -d "~/Applications/Firefox.app"'
     ansible: professormanhattan.firefox
     apt: firefox
     apt:debian: firefox-esr
@@ -2875,7 +2875,7 @@ softwarePackages:
     _github: https://github.com/objective-see/LuLu
     _home: https://objective-see.org/products/lulu.html
     _name: LuLu
-    _when:cask: '! test -d /Applications/LuLu.app'
+    _when:cask: '! test -d /Applications/LuLu.app && ! test -d ~/Applications/LuLu.app'
     cask: lulu
   keycastr:
     _bin: null
@@ -2884,7 +2884,7 @@ softwarePackages:
     _github: https://github.com/keycastr/keycastr
     _home: https://github.com/keycastr/keycastr
     _name: Keycastr
-    _when:cask: '! test -d /Applications/KeyCastr.app'
+    _when:cask: '! test -d /Applications/KeyCastr.app && ! test -d ~/Applications/KeyCastr.app'
     cask: keycastr
   hiddenbar:
     _bin: null
@@ -2893,7 +2893,7 @@ softwarePackages:
     _github: https://github.com/dwarvesf/hidden
     _home: https://dwarves.foundation/opensource/
     _name: Hidden Bar
-    _when:cask: '! test -d "/Applications/Hidden Bar.app"'
+    _when:cask: '! test -d "/Applications/Hidden Bar.app" && ! test -d "~/Applications/Hidden Bar.app"'
     cask: hiddenbar
   flameshot:
     _bin: flameshot
@@ -2903,7 +2903,7 @@ softwarePackages:
     _home: https://flameshot.org/
     _name: Flameshot
     _scoopExtras: true
-    _when:cask: '! test -d "/Applications/flameshot.app"'
+    _when:cask: '! test -d "/Applications/flameshot.app" && ! test -d "~/Applications/flameshot.app"'
     apt: flameshot
     cask: flameshot
     choco: flameshot
@@ -2925,7 +2925,7 @@ softwarePackages:
     _github: https://github.com/jgraph/drawio-desktop
     _home: https://www.diagrams.net/
     _name: DrawIO Desktop
-    _when:cask: '! test -d /Applications/draw.io.app'
+    _when:cask: '! test -d /Applications/draw.io.app && ! test -d ~/Applications/draw.io.app'
     appimage: draw.io
     cask: drawio
     choco: drawio
@@ -2948,7 +2948,7 @@ softwarePackages:
     _github: https://github.com/pock/pock
     _home: https://pock.app/
     _name: Pock
-    _when:cask: '! test -d /Applications/Pock.app'
+    _when:cask: '! test -d /Applications/Pock.app && ! test -d ~/Applications/Pock.app'
     cask: pock
   xcodes:
     _bin: xcodes
@@ -2966,7 +2966,7 @@ softwarePackages:
   swiftbar:
     _github: https://github.com/swiftbar/SwiftBar
     _name: SwiftBar
-    _when:cask: '! test -d /Applications/SwiftBar.app'
+    _when:cask: '! test -d /Applications/SwiftBar.app && ! test -d ~/Applications/SwiftBar.app'
     cask: swiftbar
   crunch:
     _bin: crunch
@@ -2983,7 +2983,7 @@ softwarePackages:
     _github: https://github.com/gao-sun/eul
     _home: https://github.com/gao-sun/eul
     _name: Eul
-    _when:cask: '! test -d /Applications/eul.app'
+    _when:cask: '! test -d /Applications/eul.app && ! test -d ~/Applications/eul.app'
     cask: eul
   linkliar:
     _bin: null
@@ -2992,7 +2992,7 @@ softwarePackages:
     _home: https://halo.github.io/LinkLiar/
     _github: https://github.com/halo/LinkLiar
     _name: Link Liar
-    _when:cask: '! test -d /Applications/LinkLiar.app'
+    _when:cask: '! test -d /Applications/LinkLiar.app && ! test -d ~/Applications/LinkLiar.app'
     cask: linkliar
   monitorcontrol:
     _bin: null
@@ -3019,7 +3019,7 @@ softwarePackages:
     _github: https://github.com/chrissimpkins/Crunch
     _home: https://github.com/chrissimpkins/Crunch
     _name: Crunch macOS App
-    _when:cask: '! test -d /Applications/Crunch.app'
+    _when:cask: '! test -d /Applications/Crunch.app && ! test -d ~/Applications/Crunch.app'
     cask: crunch
   xcodes-app:
     _bin: null
@@ -3028,7 +3028,7 @@ softwarePackages:
     _github: https://github.com/XcodesOrg/XcodesApp
     _home: https://github.com/XcodesOrg/XcodesApp
     _name: Xcodes App
-    _when:cask: '! test -d /Applications/Xcodes.app'
+    _when:cask: '! test -d /Applications/Xcodes.app && ! test -d ~/Applications/Xcodes.app'
     cask: xcodes
   nitroshare:
     _bin: nitroshare
@@ -3037,7 +3037,7 @@ softwarePackages:
     _github: https://github.com/nitroshare/nitroshare-desktop
     _home: https://nitroshare.net/
     _name: NitroShare
-    _when:cask: '! test -d /Applications/nitroshare.app'
+    _when:cask: '! test -d /Applications/nitroshare.app && ! test -d ~/Applications/nitroshare.app'
     apt: nitroshare
     cask: nitroshare
     choco: nitroshare
@@ -3154,7 +3154,7 @@ softwarePackages:
     _github: null
     _home: null
     _name: Fuse
-    _when:cask: '! test -d /usr/local/Caskroom/macfuse'
+    _when:cask: '! test -d /usr/local/Caskroom/macfuse && ! test -d ~/usr/local/Caskroom/macfuse'
     ansible:darwin: professormanhattan.fuse
     apt:
       - fuse
@@ -3228,7 +3228,7 @@ softwarePackages:
     _github: https://github.com/standardnotes/app
     _home: https://standardnotes.com/
     _name: Standard Notes
-    _when:cask: '! test -d "/Applications/Standard Notes.app"'
+    _when:cask: '! test -d "/Applications/Standard Notes.app" && ! test -d "~/Applications/Standard Notes.app"'
     cask: standard-notes
     flatpak: org.standardnotes.standardnotes
   deja-dup:
@@ -3237,14 +3237,14 @@ softwarePackages:
   discord:
     _bin: discord
     _name: Discord
-    _when:cask: '! test -d "/Applications/Discord.app"'
+    _when:cask: '! test -d "/Applications/Discord.app" && ! test -d "~/Applications/Discord.app"'
     cask: discord
     choco: discord
     flatpak: com.discordapp.Discord
   telegram:
     _bin: telegram
     _name: Telegram
-    _when:cask: '! test -d "/Applications/Telegram.app"'
+    _when:cask: '! test -d "/Applications/Telegram.app" && ! test -d "~/Applications/Telegram.app"'
     cask: telegram
     choco: telegram
     flatpak: org.telegram.desktop
@@ -3255,7 +3255,7 @@ softwarePackages:
     _github: https://github.com/Melvin-Abraham/Google-Assistant-Unofficial-Desktop-Client
     _home: null
     _name: Google Assistant for Desktop
-    _when:cask: '! test -d "/Applications/Google Assistant.app"'
+    _when:cask: '! test -d "/Applications/Google Assistant.app" && ! test -d "~/Applications/Google Assistant.app"'
     ansible:windows: professormanhattan.googleassistant
     cask: google-assistant
     github: github.com/Melvin-Abraham/Google-Assistant-Unofficial-Desktop-Client
@@ -3354,7 +3354,7 @@ softwarePackages:
     _github: https://github.com/GNOME/gimp
     _home: https://www.gimp.org/
     _name: GIMP
-    _when:cask: '! test -d /Applications/GIMP.app'
+    _when:cask: '! test -d /Applications/GIMP.app && ! test -d ~/Applications/GIMP.app'
     ansible: professormanhattan.gimp
     apt: gimp
     cask: gimp
@@ -3448,13 +3448,13 @@ softwarePackages:
   gitter:
     _bin: gitter
     _name: Gitter
-    _when:cask: '! test -d "/Applications/Gitter.app"'
+    _when:cask: '! test -d "/Applications/Gitter.app" && ! test -d "~/Applications/Gitter.app"'
     cask: gitter
     choco: gitter
     flatpak: im.gitter.Gitter
   github-desktop:
     _bin: github
-    _when:cask: '! test -d "/Applications/GitHub Desktop.app"'
+    _when:cask: '! test -d "/Applications/GitHub Desktop.app" && ! test -d "~/Applications/GitHub Desktop.app"'
     cask: github
     choco: github-desktop
     flatpak: io.github.shiftey.Desktop
@@ -3468,7 +3468,7 @@ softwarePackages:
     _github: https://gitlab.com/mvanremmerden/gitdock
     _home: https://gitlab.com/mvanremmerden/gitdock
     _name: GitDock
-    _when:cask: '! test -d /Applications/GitDock.app'
+    _when:cask: '! test -d /Applications/GitDock.app && ! test -d ~/Applications/GitDock.app'
     ansible:darwin: professormanhattan.gitdock
     cask: gitdock
   zola:
@@ -3524,7 +3524,7 @@ softwarePackages:
     _github: https://github.com/manosim/gitify
     _home: https://github.com/manosim/gitify
     _name: Gitify
-    _when:cask: '! test -d /Applications/Gitify.app'
+    _when:cask: '! test -d /Applications/Gitify.app && ! test -d ~/Applications/Gitify.app'
     cask: gitify
     github: github.com/manosim/gitify
     yay: gitify-bin
@@ -3536,7 +3536,7 @@ softwarePackages:
     _home: https://www.gitkraken.com/
     _name: GitKraken
     _snapClassic: true
-    _when:cask: '! test -d /Applications/GitKraken.app'
+    _when:cask: '! test -d /Applications/GitKraken.app && ! test -d ~/Applications/GitKraken.app'
     ansible: professormanhattan.gitkraken
     cask: gitkraken
     choco: gitkraken
@@ -3586,7 +3586,7 @@ softwarePackages:
     _github: https://github.com/Mudlet/Mudlet
     _home: https://www.mudlet.org/
     _name: Mudlet
-    _when:cask: '! test -d /Applications/mudlet.app'
+    _when:cask: '! test -d /Applications/mudlet.app && ! test -d ~/Applications/mudlet.app'
     cask: mudlet
     choco: mudlet
     snap: mudlet-linux
@@ -3916,7 +3916,7 @@ softwarePackages:
     ansible: professormanhattan.guacamole
   seafile-client:
     _bin: seafile-client
-    _when:cask: '! test -d "/Applications/Seafile Client.app"'
+    _when:cask: '! test -d "/Applications/Seafile Client.app" && ! test -d "~/Applications/Seafile Client.app"'
     cask: seafile-client
     choco: seafile-client
     flatpak: com.seafile.Client
@@ -4040,7 +4040,7 @@ softwarePackages:
     _github: https://github.com/lencx/nofwl
     _home: https://app.nofwl.com/
     _name: ChatGPT Desktop (NoFWL Version)
-    _when:cask: '! test -d /Applications/NoFWL.app'
+    _when:cask: '! test -d /Applications/NoFWL.app && ! test -d ~/Applications/NoFWL.app'
     appimage: lencx/nofwl
     apt: https://github.com/lencx/nofwl/releases/download/v0.1.0/NoFWL_0.1.0_linux_x86_64.deb
     cask: lencx/nofwl/nofwl --no-quarantine
@@ -4061,7 +4061,7 @@ softwarePackages:
     _github: https://github.com/rustdesk/rustdesk
     _home: https://rustdesk.com/
     _name: RustDesk
-    _when:cask: '! test -d /Applications/RustDesk.app'
+    _when:cask: '! test -d /Applications/RustDesk.app && ! test -d ~/Applications/RustDesk.app'
     apt: https://github.com/rustdesk/rustdesk/releases/download/1.1.9/rustdesk-1.1.9.deb
     cask: rustdesk
     choco: rustdesk
@@ -4282,7 +4282,7 @@ softwarePackages:
     _github: https://github.com/inkscape/inkscape
     _home: https://inkscape.org
     _name: Inkscape
-    _when:cask: '! test -d "/Applications/Inkscape.app"'
+    _when:cask: '! test -d "/Applications/Inkscape.app" && ! test -d "~/Applications/Inkscape.app"'
     ansible: professormanhattan.inkscape
     apt: inkscape
     cask: inkscape
@@ -4299,7 +4299,7 @@ softwarePackages:
     _home: https://www.jetbrains.com/idea/
     _name: IntelliJ IDEA (CE)
     _snapClassic: true
-    _when:cask: '! test -d "/Applications/IntelliJ IDEA CE.app"'
+    _when:cask: '! test -d "/Applications/IntelliJ IDEA CE.app" && ! test -d "~/Applications/IntelliJ IDEA CE.app"'
     ansible: professormanhattan.intellij
     cask: intellij-idea-ce
     choco: intellijidea-community
@@ -4355,7 +4355,7 @@ softwarePackages:
     _home: https://ipfs.tech/
     _name: IPFS Desktop
     _service:cask: ipfs
-    _when:cask: '! test -d "/Applications/IPFS Desktop.app"'
+    _when:cask: '! test -d "/Applications/IPFS Desktop.app" && ! test -d "~/Applications/IPFS Desktop.app"'
     appimage: https://github.com/ipfs-shipyard/ipfs-desktop/releases/download/v0.28.0/ipfs-desktop-0.28.0-linux-x86_64.AppImage
     cask: ipfs
     choco: ipfs-desktop
@@ -4384,7 +4384,7 @@ softwarePackages:
     _github: https://github.com/gnachman/iTerm2
     _home: https://iterm2.com/
     _name: iTerm2
-    _when:cask: '! test -d /Applications/iTerm.app'
+    _when:cask: '! test -d /Applications/iTerm.app && ! test -d ~/Applications/iTerm.app'
     ansible:darwin: professormanhattan.iterm2
     cask: iterm2
   nativescript:
@@ -4483,7 +4483,7 @@ softwarePackages:
     _github: https://github.com/jitsi/jitsi-meet-electron
     _home: null
     _name: Jitsi Meet Electron
-    _when:cask: '! test -d "/Applications/Jitsi Meet.app"'
+    _when:cask: '! test -d "/Applications/Jitsi Meet.app" && ! test -d "~/Applications/Jitsi Meet.app"'
     cask: jitsi-meet
     choco: jitsi-meet-electron
     flatpak: org.jitsi.jitsi-meet
@@ -4568,7 +4568,7 @@ softwarePackages:
     _home: https://keybase.io/
     _name: Keybase
     _when:ansible: '! test -f /opt/keybase/Keybase'
-    _when:cask: '! test -d /Applications/Keybase.app'
+    _when:cask: '! test -d /Applications/Keybase.app && ! test -d ~/Applications/Keybase.app'
     ansible: professormanhattan.keybase
     cask: keybase
     choco: keybase
@@ -4616,7 +4616,7 @@ softwarePackages:
     go: github.com/weaveworks/footloose@master
   beekeeper-studio:
     _bin: beekeeper-studio
-    _when:cask: '! test -d "/Applications/Beekeeper Studio.app"'
+    _when:cask: '! test -d "/Applications/Beekeeper Studio.app" && ! test -d "~/Applications/Beekeeper Studio.app"'
     cask: beekeeper-studio
     choco: beekeeper-studio
     flatpak: io.beekeeperstudio.Studio
@@ -4627,7 +4627,7 @@ softwarePackages:
     _github: https://github.com/xbmc/xbmc
     _home: https://kodi.tv/
     _name: Kodi
-    _when:cask: '! test -d /Applications/Kodi.app'
+    _when:cask: '! test -d /Applications/Kodi.app && ! test -d ~/Applications/Kodi.app'
     ansible: professormanhattan.kodi
     apt: kodi
     cask: kodi
@@ -4660,7 +4660,7 @@ softwarePackages:
     _github: https://github.com/kubenav/kubenav
     _home: https://kubenav.io/
     _name: kubenav
-    _when:cask: '! test -d /Applications/kubenav.app'
+    _when:cask: '! test -d /Applications/kubenav.app && ! test -d ~/Applications/kubenav.app'
     cask: kubenav
     github: github.com/kubenav/kubenav
     yay: kubenav-bin
@@ -4722,7 +4722,7 @@ softwarePackages:
     _github: https://github.com/GitSquared/edex-ui
     _home: https://github.com/GitSquared/edex-ui
     _name: EDEX UI
-    _when:cask: '! test -d /Applications/eDEX-UI.app'
+    _when:cask: '! test -d /Applications/eDEX-UI.app && ! test -d ~/Applications/eDEX-UI.app'
     appimage: edex-ui
     cask: edex-ui
     port: edex-ui
@@ -4823,7 +4823,7 @@ softwarePackages:
     _github: null
     _home: https://www.ledger.com/ledger-live
     _name: Ledger Live
-    _when:cask: '! test -d "/Applications/Ledger Live.app"'
+    _when:cask: '! test -d "/Applications/Ledger Live.app" && ! test -d "~/Applications/Ledger Live.app"'
     ansible: professormanhattan.ledgerlive
     appimage: ledger-live-desktop
     cask: ledger-live
@@ -4837,7 +4837,7 @@ softwarePackages:
     _home: https://k8slens.dev/
     _name: Lens
     _snapClassic: true
-    _when:cask: '! test -d /Applications/Lens.app'
+    _when:cask: '! test -d /Applications/Lens.app && ! test -d ~/Applications/Lens.app'
     ansible: professormanhattan.lens
     cask: lens
     choco: lens
@@ -4851,7 +4851,7 @@ softwarePackages:
     _github: https://github.com/hackjutsu/Lepton
     _home: https://hackjutsu.com/Lepton/
     _name: lepton
-    _when:cask: '! test -d /Applications/Lepton.app'
+    _when:cask: '! test -d /Applications/Lepton.app && ! test -d ~/Applications/Lepton.app'
     cask: lepton
     snap: lepton
   lexicon:
@@ -4870,7 +4870,7 @@ softwarePackages:
     _github: https://github.com/libimobiledevice/libimobiledevice
     _home: https://libimobiledevice.org/
     _name: null
-    _when: '! test -d /usr/local/Cellar/libimobiledevice'
+    _when: '! test -d /usr/local/Cellar/libimobiledevice && ! test -d ~/usr/local/Cellar/libimobiledevice'
     brew:darwin: libimobiledevice
   kdeplasma-addons:
     apt: kdeplasma-addons
@@ -4885,7 +4885,7 @@ softwarePackages:
     pacman: kde-plasma-desktop
   krita:
     _bin: krita
-    _when:cask: '! test -d "/Applications/krita.app"'
+    _when:cask: '! test -d "/Applications/krita.app" && ! test -d "~/Applications/krita.app"'
     cask: krita
     choco: krita
     flatpak: org.kde.krita
@@ -4896,7 +4896,7 @@ softwarePackages:
     _github: null
     _home: https://www.libreoffice.org/
     _name: LibreOffice
-    _when:cask: '! test -d /Applications/LibreOffice.app'
+    _when:cask: '! test -d /Applications/LibreOffice.app && ! test -d ~/Applications/LibreOffice.app'
     apt: libreoffice
     cask: libreoffice
     choco: libreoffice-fresh
@@ -5080,7 +5080,7 @@ softwarePackages:
     _github: null
     _home: https://www.malwarebytes.com/
     _name: Malwarebytes
-    _when:cask: '! test -d /Applications/Malwarebytes.app'
+    _when:cask: '! test -d /Applications/Malwarebytes.app && ! test -d ~/Applications/Malwarebytes.app'
     cask: malwarebytes
     choco: malwarebytes
   dialect:
@@ -5088,13 +5088,13 @@ softwarePackages:
     flatpak: app.drey.Dialect
   meld:
     _bin: meld
-    _when:cask: '! test -d "/Applications/Meld.app"'
+    _when:cask: '! test -d "/Applications/Meld.app" && ! test -d "~/Applications/Meld.app"'
     cask: meld
     choco: meld
     flatpak: org.gnome.meld
   cryptomator:
     _bin: cryptomator
-    _when:cask: '! test -d "/Applications/Cryptomator.app"'
+    _when:cask: '! test -d "/Applications/Cryptomator.app" && ! test -d "~/Applications/Cryptomator.app"'
     cask: cryptomator
     choco: cryptomator
     flatpak: org.cryptomator.Cryptomator
@@ -5103,13 +5103,13 @@ softwarePackages:
     flatpak: org.gnome.Connections
   ferdium:
     _bin: ferdium
-    _when:cask: '! test -d "/Applications/Ferdium.app"'
+    _when:cask: '! test -d "/Applications/Ferdium.app" && ! test -d "~/Applications/Ferdium.app"'
     cask: ferdium
     choco: ferdium
     flatpak: org.ferdium.Ferdium
   thunderbird:
     _bin: thunderbird
-    _when:cask: '! test -d "/Applications/Thunderbird.app"'
+    _when:cask: '! test -d "/Applications/Thunderbird.app" && ! test -d "~/Applications/Thunderbird.app"'
     cask: thunderbird
     choco: thunderbird
     flatpak: org.mozilla.Thunderbird
@@ -5138,7 +5138,7 @@ softwarePackages:
     _github: https://github.com/Foundry376/Mailspring
     _home: https://getmailspring.com/
     _name: Mailspring
-    _when:cask: '! test -d /Applications/Mailspring.app'
+    _when:cask: '! test -d /Applications/Mailspring.app && ! test -d ~/Applications/Mailspring.app'
     ansible: professormanhattan.mailspring
     cask: mailspring
     choco: mailspring
@@ -5152,7 +5152,7 @@ softwarePackages:
     _github: https://github.com/hql287/Manta
     _home: null
     _name: Manta
-    _when:cask: '! test -d /Applications/Manta.app'
+    _when:cask: '! test -d /Applications/Manta.app && ! test -d ~/Applications/Manta.app'
     appimage: https://github.com/hql287/Manta/releases/download/v1.1.4/Manta-1.1.4-x86_64.AppImage
     cask: manta
     exe: https://github.com/hql287/Manta/releases/download/v1.1.4/Manta.Setup.1.1.4.exe
@@ -5164,7 +5164,7 @@ softwarePackages:
     _github: https://github.com/marktext/marktext
     _home: null
     _name: MarkText
-    _when:cask: '! test -d /Applications/MarkText.app'
+    _when:cask: '! test -d /Applications/MarkText.app && ! test -d ~/Applications/MarkText.app'
     cask: mark-text
     choco: marktext
     github: github.com/marktext/marktext
@@ -5196,7 +5196,7 @@ softwarePackages:
     _github: https://github.com/antonreshetov/massCode
     _home: null
     _name: MassCode
-    _when:cask: '! test -d /Applications/massCode.app'
+    _when:cask: '! test -d /Applications/massCode.app && ! test -d ~/Applications/massCode.app'
     cask: masscode
     github: github.com/antonreshetov/massCode
   mc:
@@ -5234,7 +5234,7 @@ softwarePackages:
     _github: false
     _home: https://www.microsoft.com/en-us/edge
     _name: Microsoft Edge
-    _when:cask: '! test -d "/Applications/Microsoft Edge.app"'
+    _when:cask: '! test -d "/Applications/Microsoft Edge.app" && ! test -d "~/Applications/Microsoft Edge.app"'
     ansible: professormanhattan.microsoftedge
     cask: microsoft-edge
     choco: microsoft-edge
@@ -5263,7 +5263,7 @@ softwarePackages:
     _bin: swifty
     _github: https://github.com/swiftyapp/swifty
     _name: Swifty
-    _when:cask: '! test -d /Applications/Swifty.app'
+    _when:cask: '! test -d /Applications/Swifty.app && ! test -d ~/Applications/Swifty.app'
     appimage: swiftyapp/swifty
     cask: swifty
     exe: https://github.com/swiftyapp/swifty/releases/download/v0.6.13/Swifty-Setup-0.6.13.exe
@@ -5274,7 +5274,7 @@ softwarePackages:
     _github: null
     _home: https://www.office.com/
     _name: Office
-    _when:cask: '! test -d "/Applications/Microsoft Word.app"'
+    _when:cask: '! test -d "/Applications/Microsoft Word.app" && ! test -d "~/Applications/Microsoft Word.app"'
     cask: microsoft-office
     choco: office365business
   microsoft-todo:
@@ -5284,7 +5284,7 @@ softwarePackages:
     _github: false
     _home: https://todo.microsoft.com/tasks/
     _name: Microsoft To-Do
-    _when:cask: '! test -d /Applications/Ao.app'
+    _when:cask: '! test -d /Applications/Ao.app && ! test -d ~/Applications/Ao.app'
     ansible: professormanhattan.microsofttodo
     cask: ao
     snap: microsoft-todo-unofficial
@@ -5320,7 +5320,7 @@ softwarePackages:
     _github: https://github.com/mjmlio/mjml-app
     _home: https://mjmlio.github.io/mjml-app/
     _name: MJML App
-    _when:cask: '! test -d /Applications/MJML.app'
+    _when:cask: '! test -d /Applications/MJML.app && ! test -d ~/Applications/MJML.app'
     cask: mjml
     github: github.com/mjmlio/mjml-app
     npm: mjml
@@ -5343,7 +5343,7 @@ softwarePackages:
     _github: https://github.com/mockoon/mockoon
     _home: null
     _name: Mockoon
-    _when:cask: '! test -d /Applications/Mockoon.app'
+    _when:cask: '! test -d /Applications/Mockoon.app && ! test -d ~/Applications/Mockoon.app'
     cask: mockoon
     choco: mockoon
     github: github.com/mockoon/mockoon
@@ -5367,7 +5367,7 @@ softwarePackages:
     brew: dotenv-org/brew/dotenv-vault
   privileges:
     _name: Privileges
-    _when:cask: '! test -d /Applications/Privileges.app'
+    _when:cask: '! test -d /Applications/Privileges.app && ! test -d ~/Applications/Privileges.app'
     cask: privileges
   hss:
     _bin: hss
@@ -5410,7 +5410,7 @@ softwarePackages:
     _name: Monero
     _restricted: true
     _service: monero
-    _when:cask: '! test -d /Applications/monero-wallet-gui.app'
+    _when:cask: '! test -d /Applications/monero-wallet-gui.app && ! test -d ~/Applications/monero-wallet-gui.app'
     ansible: professormanhattan.monero
     cask: monero-wallet
     choco: monero
@@ -5436,7 +5436,7 @@ softwarePackages:
     _github: https://github.com/mymonero/mymonero-app-js
     _docs: https://github.com/mymonero/mymonero-app-js
     _home: https://mymonero.com/
-    _when:cask: '! test -d /Applications/MyMonero.app'
+    _when:cask: '! test -d /Applications/MyMonero.app && ! test -d ~/Applications/MyMonero.app'
     cask: mymonero
     choco: mymonero
   motrix:
@@ -5446,7 +5446,7 @@ softwarePackages:
     _github: https://github.com/agalwood/Motrix
     _home: https://motrix.app/
     _name: Motrix
-    _when:cask: '! test -d /Applications/Motrix.app'
+    _when:cask: '! test -d /Applications/Motrix.app && ! test -d ~/Applications/Motrix.app'
     ansible: professormanhattan.motrix
     cask: motrix
     choco: motrix
@@ -5475,7 +5475,7 @@ softwarePackages:
     _github: https://github.com/emqx/MQTTX
     _home: null
     _name: MQTT X
-    _when:cask: '! test -d /Applications/MQTTX.app'
+    _when:cask: '! test -d /Applications/MQTTX.app && ! test -d ~/Applications/MQTTX.app'
     cask: mqttx
     flatpak: com.emqx.MQTTX
     github: github.com/emqx/MQTTX
@@ -5520,7 +5520,7 @@ softwarePackages:
     _github: https://github.com/hschmidt/EnvPane
     _home: https://github.com/hschmidt/EnvPane
     _name: EnvPane
-    _when:script: '! test -d "$HOME/Library/PreferencePanes/EnvPane.prefPane"'
+    _when:script: '! test -d "$HOME/Library/PreferencePanes/EnvPane.prefPane" && ! test -d "~$HOME/Library/PreferencePanes/EnvPane.prefPane"'
     script:darwin: '(cd ~/Library/PreferencePanes && rm -rf EnvPane.prefPane && curl -sL https://github.com/hschmidt/EnvPane/releases/download/releases%2F0.8/EnvPane-0.8.tar.bz2 | tar -xjf -)'
   skhd:
     _bin: skhd
@@ -5538,7 +5538,7 @@ softwarePackages:
     _github: https://github.com/ProfileCreator/ProfileCreator
     _home: https://github.com/ProfileCreator/ProfileCreator
     _name: Profile Creator
-    _when:cask: '! test -d /Applications/ProfileCreator.app'
+    _when:cask: '! test -d /Applications/ProfileCreator.app && ! test -d ~/Applications/ProfileCreator.app'
     cask: profilecreator
   vagrant-manager:
     _bin: null
@@ -5547,7 +5547,7 @@ softwarePackages:
     _github: https://github.com/lanayotech/vagrant-manager
     _home: https://www.vagrantmanager.com/
     _name: Vagrant Manager
-    _when:cask: '! test -d "/Applications/Vagrant Manager.app"'
+    _when:cask: '! test -d "/Applications/Vagrant Manager.app" && ! test -d "~/Applications/Vagrant Manager.app"'
     cask: vagrant-manager
     choco: vagrant-manager
   openinterminal:
@@ -5557,14 +5557,14 @@ softwarePackages:
     _github: https://github.com/Ji4n1ng/OpenInTerminal
     _home: https://github.com/Ji4n1ng/OpenInTerminal
     _name: OpenInTerminal
-    _when:cask: '! test -d /Applications/OpenInTerminal.app'
+    _when:cask: '! test -d /Applications/OpenInTerminal.app && ! test -d ~/Applications/OpenInTerminal.app'
     cask: openinterminal
   youtube-music:
     _desc: YouTube Music desktop app bundled with custom plugins (and built-in ad blocker / downloader)
     _docs: null
     _github: https://github.com/th-ch/youtube-music
     _home: https://th-ch.github.io/youtube-music/
-    _when:script:darwin: '! test -d "/Applications/YouTube Music.app"'
+    _when:script:darwin: '! test -d "/Applications/YouTube Music.app" && ! test -d "~/Applications/YouTube Music.app"'
     appimage: th-ch/youtube-music
     apt: https://github.com/th-ch/youtube-music/releases/download/v1.19.0/youtube-music_1.19.0_amd64.deb
     exe: https://github.com/th-ch/youtube-music/releases/download/v1.19.0/YouTube-Music-Setup-1.19.0.exe
@@ -5579,7 +5579,7 @@ softwarePackages:
     _github: https://github.com/meowtec/Imagine
     _home: https://github.com/meowtec/Imagine
     _name: Imagine
-    _when:script:darwin: '! test -d /Applications/Imagine.app'
+    _when:script:darwin: '! test -d /Applications/Imagine.app && ! test -d ~/Applications/Imagine.app'
     appimage: meowtec/Imagine
     exe: https://github.com/meowtec/Imagine/releases/download/v0.7.4/Imagine-Setup-0.7.4.exe
     script:darwin: curl -sSL https://github.com/meowtec/Imagine/releases/download/v0.7.4/Imagine-0.7.4.dmg > /tmp/Imagine.dmg && sudo hdiutil attach /tmp/Imagine.dmg && sudo cp -R "/Volumes/Imagine 0.7.4/Imagine.app" /Applications && sudo hdiutil detach "/Volumes/Imagine 0.7.4" && rm -f /tmp/Imagine.dmg
@@ -5590,7 +5590,7 @@ softwarePackages:
     _github: https://github.com/mullvad/mullvadvpn-app
     _home: null
     _name: Mullvad VPN
-    _when:cask: '! test -d "/Applications/Mullvad VPN.app"'
+    _when:cask: '! test -d "/Applications/Mullvad VPN.app" && ! test -d "~/Applications/Mullvad VPN.app"'
     apt: https://github.com/mullvad/mullvadvpn-app/releases/download/2022.5/MullvadVPN-2022.5_amd64.deb
     cask: mullvadvpn
     exe: https://github.com/mullvad/mullvadvpn-app/releases/download/2022.5/MullvadVPN-2022.5.exe
@@ -5606,7 +5606,7 @@ softwarePackages:
     _name: Multipass
     _post:cask: multipass set local.driver=virtualbox
     _post:choco: multipass set local.driver=virtualbox
-    _when:cask: '! test -d /Applications/Multipass.app'
+    _when:cask: '! test -d /Applications/Multipass.app && ! test -d ~/Applications/Multipass.app'
     ansible: professormanhattan.multipass
     cask: multipass
     choco: multipass
@@ -5861,7 +5861,7 @@ softwarePackages:
     _github: https://github.com/nextcloud/desktop
     _home: https://nextcloud.com
     _name: Nextcloud Client
-    _when:cask: '! test -d /Applications/Nextcloud.app'
+    _when:cask: '! test -d /Applications/Nextcloud.app && ! test -d ~/Applications/Nextcloud.app'
     cask: nextcloud
     choco: nextcloud-client
     flatpak: com.nextcloud.desktopclient.nextcloud
@@ -5986,7 +5986,7 @@ softwarePackages:
     _home: https://www.notion.so/
     _name: Notion AI
     _note: Waiting on Linux install alternative.
-    _when:cask: '! test -d /Applications/Notion.app'
+    _when:cask: '! test -d /Applications/Notion.app && ! test -d ~/Applications/Notion.app'
     cask: notion
     choco: notion
   zaproxy:
@@ -5997,7 +5997,7 @@ softwarePackages:
     _home: https://www.zaproxy.org/
     _name: OWASP ZAP
     _snapClassic: true
-    _when:cask: '! test -d "/Applications/OWASP ZAP.app"'
+    _when:cask: '! test -d "/Applications/OWASP ZAP.app" && ! test -d "~/Applications/OWASP ZAP.app"'
     cask: owasp-zap
     choco: zap
     flatpak: org.zaproxy.ZAP
@@ -6011,7 +6011,7 @@ softwarePackages:
     _github: https://github.com/superhighfives/pika
     _home: https://superhighfives.com/pika
     _name: Pika
-    _when:cask: '! test -d /Applications/Pika.app'
+    _when:cask: '! test -d /Applications/Pika.app && ! test -d ~/Applications/Pika.app'
     cask: pika
   obsidian:
     _bin: null
@@ -6020,7 +6020,7 @@ softwarePackages:
     _github: false
     _home: https://obsidian.md/
     _name: Obsidian
-    _when:cask: '! test -d /Applications/Obsidian.app'
+    _when:cask: '! test -d /Applications/Obsidian.app && ! test -d ~/Applications/Obsidian.app'
     appimage: Obsidian
     cask: obsidian
     choco: obsidian
@@ -6034,7 +6034,7 @@ softwarePackages:
     _github: https://github.com/raycast/extensions
     _home: https://www.raycast.com/
     _name: Raycast
-    _when:cask: '! test -d /Applications/Raycast.app'
+    _when:cask: '! test -d /Applications/Raycast.app && ! test -d ~/Applications/Raycast.app'
     cask: raycast
   mage-ai:
     _bin: mage
@@ -6051,7 +6051,7 @@ softwarePackages:
     _github: https://github.com/warpdotdev/Warp
     _home: https://www.warp.dev/
     _name: Warp Terminal
-    _when:cask: '! test -d /Applications/Warp.app'
+    _when:cask: '! test -d /Applications/Warp.app && ! test -d ~/Applications/Warp.app'
     cask: warp
   figma:
     _bin: null
@@ -6060,7 +6060,7 @@ softwarePackages:
     _github: false
     _home: https://www.figma.com/
     _name: Figma
-    _when:cask: '! test -d /Applications/Figma.app'
+    _when:cask: '! test -d /Applications/Figma.app && ! test -d ~/Applications/Figma.app'
     appimage: Figma-Linux/figma-linux
     cask: figma
     choco: figma
@@ -6073,7 +6073,7 @@ softwarePackages:
     _github: https://github.com/teaxyz/gui
     _home: https://tea.xyz/
     _name: Tea GUI
-    _when:cask: '! test -d /Applications/tea.app'
+    _when:cask: '! test -d /Applications/tea.app && ! test -d ~/Applications/tea.app'
     cask: tea
   node-prune:
     _bin: node-prune
@@ -6147,7 +6147,7 @@ softwarePackages:
     _github: https://github.com/nukeop/nuclear
     _home: https://nuclear.js.org/
     _name: Nuclear
-    _when:cask: '! test -d /Applications/nuclear.app'
+    _when:cask: '! test -d /Applications/nuclear.app && ! test -d ~/Applications/nuclear.app'
     cask: nuclear
     choco: nuclear
     flatpak: org.js.nuclear.Nuclear
@@ -6201,7 +6201,7 @@ softwarePackages:
       sudo chmod 644 /etc/udev/rules.d/49-onlykey.rules
       sudo udevadm control --reload-rules
       sudo udevadm trigger
-    _when:script:darwin: '! test -d "/Applications/OnlyKey App.app"'
+    _when:script:darwin: '! test -d "/Applications/OnlyKey App.app" && ! test -d "~/Applications/OnlyKey App.app"'
     ansible:darwin: professormanhattan.onlykey
     script:darwin: cd /tmp && curl -sSL https://github.com/trustcrypto/OnlyKey-App/releases/download/v5.3.6/OnlyKey.App.5.3.6.dmg > OnlyKey.dmg  && hdiutil attach "/tmp/OnlyKey.dmg" &&  sudo cp -R "/Volumes/OnlyKey App/OnlyKey App.app" /Applications && sudo hdiutil detach "/Volumes/OnlyKey App" && rm -f "/tmp/OnlyKey.dmg"
     choco: onlykey
@@ -6370,7 +6370,7 @@ softwarePackages:
     _github: https://github.com/neovide/neovide
     _home: https://neovide.dev/
     _name: Neovide
-    _when:cask: '! test -d /Applications/Neovide.app'
+    _when:cask: '! test -d /Applications/Neovide.app && ! test -d ~/Applications/Neovide.app'
     cask: neovide
     pacman: neovide
     scoop: neovide
@@ -6434,7 +6434,7 @@ softwarePackages:
     _github: null
     _home: https://www.parallels.com/
     _name: Parallels
-    _when: '! test -d "/Applications/Parallels Desktop.app"'
+    _when: '! test -d "/Applications/Parallels Desktop.app" && ! test -d "~/Applications/Parallels Desktop.app"'
     ansible:darwin: professormanhattan.parallels
   gnome-passwords-keys:
     _bin: seahorse
@@ -6653,7 +6653,7 @@ softwarePackages:
     _github: false
     _home: https://www.plex.tv/
     _name: Plex
-    _when:cask: '! test -d /Applications/Plex.app'
+    _when:cask: '! test -d /Applications/Plex.app && ! test -d ~/Applications/Plex.app'
     ansible: professormanhattan.plex
     cask: plex
     choco: plex
@@ -6688,7 +6688,7 @@ softwarePackages:
     _bin: plex-media-server
     _github: false
     _name: Plex Media Server
-    _when:cask: '! test -d "/Applications/Plex Media Server.app"'
+    _when:cask: '! test -d "/Applications/Plex Media Server.app" && ! test -d "~/Applications/Plex Media Server.app"'
     _ports:
       - port: 32400
         proto: tcp
@@ -6713,7 +6713,7 @@ softwarePackages:
     _github: false
     _home: https://www.plex.tv/
     _name: Plex HTPC
-    _when:cask: '! test -d "/Applications/Plex HTPC.app"'
+    _when:cask: '! test -d "/Applications/Plex HTPC.app" && ! test -d "~/Applications/Plex HTPC.app"'
     cask: plex-htpc
     choco: plex-home-theater
     flatpak: tv.plex.PlexHTPC
@@ -6827,7 +6827,7 @@ softwarePackages:
     _github: null
     _home: https://www.postman.com/
     _name: Postman
-    _when:cask: '! test -d /Applications/Postman.app'
+    _when:cask: '! test -d /Applications/Postman.app && ! test -d ~/Applications/Postman.app'
     ansible: professormanhattan.postman
     cask: postman
     choco: postman
@@ -6842,7 +6842,7 @@ softwarePackages:
     _home: null
     _name: Powershell
     _snapClassic: true
-    _when:cask: '! test -d /Applications/PowerShell.app'
+    _when:cask: '! test -d /Applications/PowerShell.app && ! test -d ~/Applications/PowerShell.app'
     ansible: professormanhattan.powershell
     cask: powershell
     snap: powershell
@@ -6909,7 +6909,7 @@ softwarePackages:
     _home: https://github.com/amiechen/pretzel
     _name: Pretzel
     _todo: Waiting for SHASUM error on Homebrew cask to resolve
-    _when:cask: '! test -d /Applications/Pretzel.app'
+    _when:cask: '! test -d /Applications/Pretzel.app && ! test -d ~/Applications/Pretzel.app'
     # cask: pretzel
   procs:
     _bin: procs
@@ -6945,7 +6945,7 @@ softwarePackages:
     _post:yay: sudo pacman -Syu libappindicator-gtk3 gnome-shell-extension-appindicator
     _pre:apt: sudo apt-get install -y https://repo.protonvpn.com/debian/dists/stable/main/binary-all/protonvpn-stable-release_1.0.3_all.deb && sudo apt-get update
     _pre:dnf: sudo dnf install -y https://repo.protonvpn.com/fedora-36-stable/release-packages/protonvpn-stable-release-1.0.1-1.noarch.rpm && sudo dnf update
-    _when:cask: '! test -d /Applications/ProtonVPN.app'
+    _when:cask: '! test -d /Applications/ProtonVPN.app && ! test -d ~/Applications/ProtonVPN.app'
     # ansible: professormanhattan.proton
     apt:
       - gir1.2-appindicator3-0.1
@@ -6974,14 +6974,14 @@ softwarePackages:
     script:darwin: brew install openvpn dialog python3 || true && sudo rm -rf /usr/local/src/protonvpn-cli && sudo git clone https://github.com/phx/protonvpn-cli-macos /usr/local/src/protonvpn-cli && cd /usr/local/src/protonvpn-cli && pip3 install -r requirements.txt && sudo python3 setup.py install
   protonmail-bridge:
     _bin: protonmail-bridge
-    _when:cask: '! test -d "/Applications/Proton Mail Bridge.app"'
+    _when:cask: '! test -d "/Applications/Proton Mail Bridge.app" && ! test -d "~/Applications/Proton Mail Bridge.app"'
     cask: protonmail-bridge
     choco: protonmailbridge
     flatpak: ch.protonmail.protonmail-bridge
     yay: protonmail-bridge
   protonmail-import-export:
     _bin: protonmail-import-export
-    _when:cask: '! test -d "/Applications/ProtonMail Import-Export app.app"'
+    _when:cask: '! test -d "/Applications/ProtonMail Import-Export app.app" && ! test -d "~/Applications/ProtonMail Import-Export app.app"'
     cask: protonmail-import-export
     flatpak: ch.protonmail.protonmail-import-export-app
   bottles:
@@ -7059,7 +7059,7 @@ softwarePackages:
     _github: https://github.com/qbittorrent/qBittorrent
     _home: https://www.qbittorrent.org/
     _name: qBittorrent
-    _when:cask: '! test -d /Applications/qBittorrent.app'
+    _when:cask: '! test -d /Applications/qBittorrent.app && ! test -d ~/Applications/qBittorrent.app'
     ansible: professormanhattan.qbittorrent
     apt: qbittorrent
     cask: qbittorrent
@@ -7157,7 +7157,7 @@ softwarePackages:
     _github: https://github.com/raspberrypi/rpi-imager
     _home: https://www.raspberrypi.com/software/
     _name: Raspberry Pi Imager
-    _when:cask: '! test -d "/Applications/Raspberry Pi Imager.app"'
+    _when:cask: '! test -d "/Applications/Raspberry Pi Imager.app" && ! test -d "~/Applications/Raspberry Pi Imager.app"'
     ansible: professormanhattan.raspberryimager
     cask: raspberry-pi-imager
     choco: rpi-imager
@@ -7200,7 +7200,7 @@ softwarePackages:
     _github: https://github.com/RedisInsight/RedisInsight
     _name: Redis Insight
     _post:cask: if [ -d ~/Applications/RedisInsight.app ]; then mv ~/Applications/RedisInsight.app /Applications/RedisInsight.app; fi
-    _when:cask: '! test -d /Applications/RedisInsight.app'
+    _when:cask: '! test -d /Applications/RedisInsight.app && ! test -d ~/Applications/RedisInsight.app'
     cask: redisinsight
     flatpak: com.redis.RedisInsight
   recoverpy:
@@ -7270,7 +7270,7 @@ softwarePackages:
     _github: null
     _home: null
     _name: Microsoft Remote Desktop
-    _when:cask: '! test -d "/Applications/Microsoft Remote Desktop.app"'
+    _when:cask: '! test -d "/Applications/Microsoft Remote Desktop.app" && ! test -d "~/Applications/Microsoft Remote Desktop.app"'
     cask: microsoft-remote-desktop
   aiac:
     _bin: aiac
@@ -7321,7 +7321,7 @@ softwarePackages:
     _github: https://github.com/responsively-org/responsively-app
     _home: null
     _name: Responsively
-    _when:cask: '! test -d /Applications/ResponsivelyApp.app'
+    _when:cask: '! test -d /Applications/ResponsivelyApp.app && ! test -d ~/Applications/ResponsivelyApp.app'
     cask: responsively
     choco: responsively
     github: github.com/responsively-org/responsively-app
@@ -7453,7 +7453,7 @@ softwarePackages:
     _github: https://github.com/lukehaas/RunJS
     _home: null
     _name: RunJS
-    _when:cask: '! test -d /Applications/RunJS.app'
+    _when:cask: '! test -d /Applications/RunJS.app && ! test -d ~/Applications/RunJS.app'
     cask: runjs
     choco: runjs
     github: github.com/lukehaas/RunJS
@@ -7563,7 +7563,7 @@ softwarePackages:
     _home: null
     _name: Sanoid
     # Only install Sanoid when there are ZFS shares listed in the command `zfs list`
-    _when: echo '! zfs list' | bash
+    _when:linux: echo 'command -v zfs > /dev/null && ! zfs list' | bash
     ansible:linux: professormanhattan.sanoid
     apt:
       - libcapture-tiny-perl
@@ -7594,7 +7594,7 @@ softwarePackages:
     _home: https://www.blender.org/
     _name: Blender
     _snapClassic: true
-    _when:cask: '! test -d /Applications/Blender.app'
+    _when:cask: '! test -d /Applications/Blender.app && ! test -d ~/Applications/Blender.app'
     apt: blender
     cask: blender
     choco: blender
@@ -7628,7 +7628,7 @@ softwarePackages:
     _github: https://github.com/audacity/audacity
     _home: https://www.audacityteam.org/
     _name: Audacity
-    _when:cask: '! test -d /Applications/Audacity.app'
+    _when:cask: '! test -d /Applications/Audacity.app && ! test -d ~/Applications/Audacity.app'
     appimage: Audacity
     apt: audacity
     cask: audacity
@@ -7715,7 +7715,7 @@ softwarePackages:
     _github: https://github.com/maxgoedjen/secretive
     _home: null
     _name: null
-    _when:cask: '! test -d /Applications/Secretive.app'
+    _when:cask: '! test -d /Applications/Secretive.app && ! test -d ~/Applications/Secretive.app'
     cask: secretive
   security:
     _bin: null
@@ -7878,7 +7878,7 @@ softwarePackages:
     _home: https://shotcut.org/
     _name: Shotcut
     _snapClassic: true
-    _when:cask: '! test -d /Applications/Shotcut.app'
+    _when:cask: '! test -d /Applications/Shotcut.app && ! test -d ~/Applications/Shotcut.app'
     ansible: professormanhattan.shotcut
     apt: shotcut
     cask: shotcut
@@ -7928,7 +7928,7 @@ softwarePackages:
     _github: Not open-source
     _home: https://www.skype.com/en/
     _name: Skype
-    _when:cask: '! test -d /Applications/Skype.app'
+    _when:cask: '! test -d /Applications/Skype.app && ! test -d ~/Applications/Skype.app'
     ansible: professormanhattan.skype
     cask: skype
     choco: skype
@@ -7942,7 +7942,7 @@ softwarePackages:
     _github: https://github.com/slackhq/SlackTextViewController
     _home: https://slack.com/
     _name: Slack
-    _when:cask: '! test -d /Applications/Slack.app'
+    _when:cask: '! test -d /Applications/Slack.app && ! test -d ~/Applications/Slack.app'
     ansible: professormanhattan.slack
     cask: slack
     choco: slack
@@ -7964,7 +7964,7 @@ softwarePackages:
     _github: https://github.com/sveinbjornt/Sloth
     _home: https://sveinbjorn.org/sloth
     _name: Sloth
-    _when:cask: '! test -d /Applications/Sloth.app'
+    _when:cask: '! test -d /Applications/Sloth.app && ! test -d ~/Applications/Sloth.app'
     cask: sloth
   snapcraft:
     _deps:
@@ -7995,7 +7995,7 @@ softwarePackages:
     _github: https://github.com/evilsocket/opensnitch
     _home: https://www.obdev.at/products/littlesnitch/index.html
     _name: OpenSnitch/Little Snitch
-    _when:cask: '! test -d "/Applications/Little Snitch.app"'
+    _when:cask: '! test -d "/Applications/Little Snitch.app" && ! test -d "~/Applications/Little Snitch.app"'
     # Not loading on Ubuntu 22.04
     # ansible: professormanhattan.snitch
     cask: little-snitch
@@ -8046,13 +8046,13 @@ softwarePackages:
     _github: https://github.com/sqlectron/sqlectron-gui
     _home: null
     _name: SQLectron
-    _when:cask: '! test -d /Applications/sqlectron.app'
+    _when:cask: '! test -d /Applications/sqlectron.app && ! test -d ~/Applications/sqlectron.app'
     cask: sqlectron
     github: github.com/sqlectron/sqlectron-gui
     yay: sqlectron-gui
   handbrake:
     _bin: handbrake
-    _when:cask: '! test -d "/Applications/HandBrake.app"'
+    _when:cask: '! test -d "/Applications/HandBrake.app" && ! test -d "~/Applications/HandBrake.app"'
     cask: handbrake
     choco: handbrake
     flatpak: fr.handbrake.ghb
@@ -8104,7 +8104,7 @@ softwarePackages:
     _github: https://github.com/Tunnelblick/Tunnelblick
     _home: https://tunnelblick.net/
     _name: Tunnelblick
-    _when: '! test -d "/Applications/Tunnelblick.app"'
+    _when: '! test -d "/Applications/Tunnelblick.app" && ! test -d "~/Applications/Tunnelblick.app"'
     cask: tunnelblick
   endlessh:
     _bin: endlessh
@@ -8123,7 +8123,7 @@ softwarePackages:
     _bin: kap
     _github: https://github.com/wulkano/Kap
     _name: Kap
-    _when:cask: '! test -d /Applications/Kap.app'
+    _when:cask: '! test -d /Applications/Kap.app && ! test -d ~/Applications/Kap.app'
     cask: kap
   autodoc:
     _bin: doc
@@ -8209,7 +8209,7 @@ softwarePackages:
     _github: https://github.com/exelban/stats
     _home: null
     _name: stats
-    _when:cask: '! test -d /Applications/Stats.app'
+    _when:cask: '! test -d /Applications/Stats.app && ! test -d ~/Applications/Stats.app'
     cask: stats
     _service: null
   stegcloak:
@@ -8261,7 +8261,7 @@ softwarePackages:
     _github: https://github.com/oldj/SwitchHosts
     _home: https://swh.app/
     _name: SwitchHosts
-    _when:cask: '! test -d "/Applications/SwitchHosts.app"'
+    _when:cask: '! test -d "/Applications/SwitchHosts.app" && ! test -d "~/Applications/SwitchHosts.app"'
     ansible: professormanhattan.switchhosts
     appimage: oldj/SwitchHosts
     cask: switchhosts
@@ -8295,7 +8295,7 @@ softwarePackages:
     _github: https://github.com/lapce/lapce
     _home: https://lapce.dev/
     _name: Lapce
-    _when:cask: '! test -d /Applications/Lapce.app'
+    _when:cask: '! test -d /Applications/Lapce.app && ! test -d ~/Applications/Lapce.app'
     brew: lapce
     emerge: app-editors/lapce
     flatpak: dev.lapce.lapce
@@ -8455,7 +8455,7 @@ softwarePackages:
     _name: Tabby
     _snapClassic: true
     _notes: TODO Update the direct links periodically and keep eye out for Snap / Flatpak
-    _when:cask: '! test -d /Applications/Tabby.app'
+    _when:cask: '! test -d /Applications/Tabby.app && ! test -d ~/Applications/Tabby.app'
     ansible:linux: professormanhattan.tabby
     apt: https://github.com/Eugeny/tabby/releases/download/v1.0.188/tabby-1.0.188-linux-x64.deb
     cask: tabby
@@ -8483,7 +8483,7 @@ softwarePackages:
     _github: https://github.com/tailscale/tailscale
     _home: https://tailscale.com/
     _name: Tailscale Client
-    _when:cask: '! test -d "/Applications/Tailscale.app"'
+    _when:cask: '! test -d "/Applications/Tailscale.app" && ! test -d "~/Applications/Tailscale.app"'
     cask: tailscale
     choco: tailscale
   task:
@@ -8512,7 +8512,7 @@ softwarePackages:
   soduto:
     _github:
     _name: Soduto
-    _when:cask: '! test -d /Applications/Soduto.app'
+    _when:cask: '! test -d /Applications/Soduto.app && ! test -d ~/Applications/Soduto.app'
     cask: soduto
   envio:
     _bin: envio
@@ -8565,7 +8565,7 @@ softwarePackages:
     _bin: sparkleshare
     _github: https://github.com/hbons/SparkleShare
     _name: Sparkle Share
-    _when:cask: '! test -d /Applications/SparkleShare.app'
+    _when:cask: '! test -d /Applications/SparkleShare.app && ! test -d ~/Applications/SparkleShare.app'
     cask: sparkleshare
     choco: sparkleshare
     flatpak: org.sparkleshare.SparkleShare
@@ -8576,7 +8576,7 @@ softwarePackages:
     _github: null
     _home: null
     _name: Microsoft Teams
-    _when:cask: '! test -d "/Applications/Microsoft Teams.app"'
+    _when:cask: '! test -d "/Applications/Microsoft Teams.app" && ! test -d "~/Applications/Microsoft Teams.app"'
     ansible: professormanhattan.teams
     cask: microsoft-teams
     choco: microsoft-teams
@@ -8590,7 +8590,7 @@ softwarePackages:
     _github: Not open-source
     _home: https://www.teamviewer.com/en-us/
     _name: TeamViewer
-    _when:cask: '! test -d /Applications/TeamViewer.app'
+    _when:cask: '! test -d /Applications/TeamViewer.app && ! test -d ~/Applications/TeamViewer.app'
     ansible:linux: professormanhattan.teamviewer
     apt: https://download.teamviewer.com/download/linux/teamviewer_amd64.deb
     cask: teamviewer
@@ -9002,14 +9002,14 @@ softwarePackages:
     scoop: upx
   cutter:
     _bin: cutter
-    _when:cask: '! test -d "/Applications/Cutter.app"'
+    _when:cask: '! test -d "/Applications/Cutter.app" && ! test -d "~/Applications/Cutter.app"'
     cask: cutter
     choco: cutter
     flatpak: re.rizin.cutter
   librewolf:
     _bin: librewolf
     _scoopExtras: true
-    _when:cask: '! test -d "/Applications/LibreWolf.app"'
+    _when:cask: '! test -d "/Applications/LibreWolf.app" && ! test -d "~/Applications/LibreWolf.app"'
     cask: librewolf
     choco: librewolf
     flatpak: io.gitlab.librewolf-community
@@ -9063,7 +9063,7 @@ softwarePackages:
     _github: https://github.com/vincelwt/chatgpt-mac
     _home: https://github.com/vincelwt/chatgpt-mac
     _name: ChatGPT Menubar for macOS
-    _when:cask: '! test -d /Applications/Chatgpt.app'
+    _when:cask: '! test -d /Applications/Chatgpt.app && ! test -d ~/Applications/Chatgpt.app'
     cask: vincelwt-chatgpt
   vector:
     _bin: vector
@@ -9092,7 +9092,7 @@ softwarePackages:
     yay: velero-bin
   macvim:
     _todo: Integrate this into macOS setup
-    _when:cask: '! test -d /Applications/MacVim.app'
+    _when:cask: '! test -d /Applications/MacVim.app && ! test -d ~/Applications/MacVim.app'
     cask: macvim
   vim:
     _bin: vim
@@ -9165,7 +9165,7 @@ softwarePackages:
       EOF
       sudo dnf -y install @development-tools
       sudo dnf -y install kernel-headers kernel-devel dkms elfutils-libelf-devel qt5-qtx11extras
-    _when:cask: '! test -d /Applications/VirtualBox.app'
+    _when:cask: '! test -d /Applications/VirtualBox.app && ! test -d ~/Applications/VirtualBox.app'
     ansible: professormanhattan.virtualbox
     apt: virtualbox
     cask: virtualbox
@@ -9189,14 +9189,14 @@ softwarePackages:
     _home: https://visualstudio.microsoft.com/
     _name: Visual Studio
     _post:cask: 'APP_LINK="$(find /usr/local/Caskroom/visual-studio -mindepth 2 -maxdepth 2 -name "*.app*" | head -n1)" && open "$APP_LINK"'
-    _when:cask: '! test -d "/Applications/Visual Studio.app"'
+    _when:cask: '! test -d "/Applications/Visual Studio.app" && ! test -d "~/Applications/Visual Studio.app"'
     ansible:windows: professormanhattan.visualstudio
     cask: visual-studio
     choco: visualstudio2022community
   vscodium:
     _bin: codium
     _snapClassic: true
-    _when:cask: '! test -d "/Applications/VSCodium.app"'
+    _when:cask: '! test -d "/Applications/VSCodium.app" && ! test -d "~/Applications/VSCodium.app"'
     appimage: vscodium/vscodium
     cask: vscodium
     choco: vscodium
@@ -9213,7 +9213,7 @@ softwarePackages:
     _github: https://github.com/videolan/vlc
     _home: https://www.videolan.org/vlc/
     _name: VLC Media Player
-    _when:cask: '! test -d /Applications/VLC.app'
+    _when:cask: '! test -d /Applications/VLC.app && ! test -d ~/Applications/VLC.app'
     ansible: professormanhattan.vlc
     apt: vlc
     cask: vlc
@@ -9263,7 +9263,7 @@ softwarePackages:
     _home: https://code.visualstudio.com/
     _name: Visual Studio Code
     _snapClassic: true
-    _when:cask: '! test -d "/Applications/Visual Studio Code.app"'
+    _when:cask: '! test -d "/Applications/Visual Studio Code.app" && ! test -d "~/Applications/Visual Studio Code.app"'
     ansible: professormanhattan.vscode
     cask: visual-studio-code
     choco: vscode
@@ -9397,7 +9397,7 @@ softwarePackages:
     _github: https://github.com/webtorrent/webtorrent-desktop
     _home: webtorrent.io/desktop
     _name: WebTorrent Desktop
-    _when:cask: '! test -d /Applications/WebTorrent.app'
+    _when:cask: '! test -d /Applications/WebTorrent.app && ! test -d ~/Applications/WebTorrent.app'
     cask: webtorrent
     choco: webtorrent-desktop
     flatpak: io.webtorrent.WebTorrent
@@ -9482,7 +9482,7 @@ softwarePackages:
     _github: https://github.com/will-stone/browserosaurus
     _home: https://browserosaurus.com/
     _name: Browserosaurus
-    _when:cask: '! test -d /Applications/Browserosaurus.app'
+    _when:cask: '! test -d /Applications/Browserosaurus.app && ! test -d ~/Applications/Browserosaurus.app'
     cask: browserosaurus
   docker:
     _bin: docker
@@ -9514,7 +9514,7 @@ softwarePackages:
       - docker-compose-plugin
   openssh-server:
     _service: sshd
-    _when: echo '! grep Microsoft /proc/version > /dev/null && ! test -d /Applications' | bash
+    _when: echo 'test -f /proc/version && ! grep Microsoft /proc/version > /dev/null && ! test -d /Applications' | bash
     apt: openssh-server
     dnf: openssh-server
     pacman: openssh
@@ -9527,9 +9527,10 @@ softwarePackages:
     _name: KubeKey
     brew: kubekey
   fail2ban:
+    _bin: fail2ban-client
     _service: fail2ban
     # fail2ban cannot be installed on Qubes Fedora 36 without messing with the qubes-firewall since firewalld is required
-    _when: echo '! command -v qubes-firewall > /dev/null && ! grep Microsoft /proc/version > /dev/null' | bash
+    _when:linux: echo '! command -v qubes-firewall > /dev/null && test -f /proc/version && ! grep Microsoft /proc/version > /dev/null' | bash
     apt: fail2ban
     brew: fail2ban
     dnf: fail2ban
@@ -9594,7 +9595,7 @@ softwarePackages:
     _github: https://github.com/wireshark/wireshark
     _home: https://www.wireshark.org/
     _name: Wireshark
-    _when:cask: '! test -d /Applications/Wireshark.app'
+    _when:cask: '! test -d /Applications/Wireshark.app && ! test -d ~/Applications/Wireshark.app'
     apt: wireshark
     cask: wireshark
     choco: wireshark
@@ -9608,7 +9609,7 @@ softwarePackages:
     _github: https://github.com/wkhtmltopdf/wkhtmltopdf
     _home: null
     _name: wkhtmltopdf
-    _when:cask: '! test -d /usr/local/Caskroom/wkhtmltopdf'
+    _when:cask: '! test -d /usr/local/Caskroom/wkhtmltopdf && ! test -d ~/usr/local/Caskroom/wkhtmltopdf'
     # CentOS Stream 9 does not have a supported GitHub release available
     # ansible: professormanhattan.wkhtmltopdf
     apt: wkhtmltopdf
@@ -9637,7 +9638,7 @@ softwarePackages:
   adobe-creative-cloud:
     _bin: adobe-creative-cloud
     _name: Adobe Creative Cloud
-    _when:cask: '! test -d /Applications/'
+    _when:cask: '! test -d /Applications/Adobe Creative Cloud'
     cask: adobe-creative-cloud
   wrangler:
     _bin: wrangler
@@ -9838,7 +9839,7 @@ softwarePackages:
     _github: null
     _home: https://www.yubico.com/products/yubico-authenticator/
     _name: Yubico Authenticator
-    _when:script:darwin: '! test -d "/Applications/Yubico Authenticator.app"'
+    _when:script:darwin: '! test -d "/Applications/Yubico Authenticator.app" && ! test -d "~/Applications/Yubico Authenticator.app"'
     choco: yubico-authenticator
     flatpak: com.yubico.yubioath
     script:darwin: curl -sSL https://developers.yubico.com/yubioath-flutter/Releases/yubico-authenticator-latest-mac.dmg > "/tmp/Yubico Authenticator.dmg" && hdiutil attach "/tmp/Yubico Authenticator.dmg" &&  sudo cp -R "/Volumes/Yubico Authenticator/Yubico Authenticator.app" /Applications && sudo hdiutil detach "/Volumes/Yubico Authenticator" && rm -f "/tmp/Yubico Authenticator.dmg"
@@ -9866,7 +9867,7 @@ softwarePackages:
     _github: https://github.com/Yubico/yubikey-manager-qt
     _home: https://developers.yubico.com/yubikey-manager-qt/
     _name: YubiKey Manager
-    _when:cask: echo '! test -d "/Applications/YubiKey Manager.app"' | bash
+    _when:cask: echo '! test -d "/Applications/YubiKey Manager.app" && ! test -d "~/Applications/YubiKey Manager.app"' | bash
     appimage: Yubico/yubikey-manager-qt
     cask: yubico-yubikey-manager
     choco: yubikey-manager
@@ -9887,7 +9888,7 @@ softwarePackages:
     _bin: obs-studio
     _github: https://github.com/obsproject/obs-studio
     _name: OBS Studio
-    _when:cask: '! test -d /Applications/OBS.app'
+    _when:cask: '! test -d /Applications/OBS.app && ! test -d ~/Applications/OBS.app'
     cask: obs
     choco: obs-studio
     flatpak: com.obsproject.Studio
@@ -9924,7 +9925,7 @@ softwarePackages:
     _github: Not open-source
     _home: https://zoom.us/
     _name: Zoom
-    _when:cask: '! test -d /Applications/zoom.us.app'
+    _when:cask: '! test -d /Applications/zoom.us.app && ! test -d ~/Applications/zoom.us.app'
     ansible: professormanhattan.zoom
     cask: zoom
     choco: zoom