diff --git a/it-and-security/fleets/workstations.yml b/it-and-security/fleets/workstations.yml
index 8c932ae568..1f7e8ce490 100644
--- a/it-and-security/fleets/workstations.yml
+++ b/it-and-security/fleets/workstations.yml
@@ -267,23 +267,25 @@ software:
     - slug: brave-browser/darwin # Brave for macOS (ARM)
       self_service: true
       labels_include_any:
-        - Apple Silicon macOS hosts
+        - Macs with Brave Browser installed
       categories:
         - Browsers
     - slug: docker-desktop/darwin # Docker for macOS (ARM)
       self_service: true
       labels_include_any:
-        - Apple Silicon macOS hosts
+        - Macs with Docker Desktop installed
       categories:
         - Developer tools
     - slug: visual-studio-code/darwin # Microsoft Visual Studio for macOS (ARM)
       self_service: true
       labels_include_any:
-        - Apple Silicon macOS hosts
+        - Macs with Visual Studio Code installed
       categories:
         - Developer tools
     - slug: microsoft-teams/darwin # Microsoft Teams for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Microsoft Teams installed
       categories:
         - Communication
     - slug: slack/darwin # Slack for macOS
@@ -309,74 +311,110 @@ software:
         - Productivity
     - slug: github/darwin # GitHub Desktop for macOS
       self_service: true
+      labels_include_any:
+        - Macs with GitHub Desktop installed
       categories:
         - Developer tools
     - slug: utm/darwin # UTM for macOS
       self_service: true
+      labels_include_any:
+        - Macs with UTM installed
       categories:
         - Productivity
     - slug: postman/darwin # Postman for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Postman installed
       categories:
         - Developer tools
     - slug: grammarly-desktop/darwin # Grammarly Desktop for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Grammarly Desktop installed
       categories:
         - Productivity
     - slug: iterm2/darwin # iTerm2 for macOS
       self_service: true
+      labels_include_any:
+        - Macs with iTerm2 installed
       categories:
         - Developer tools
     - slug: sublime-text/darwin # Sublime Text for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Sublime Text installed
       categories:
         - Developer tools
     - slug: parallels/darwin # Parallels Desktop for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Parallels Desktop installed
       categories:
         - Productivity
     - slug: loom/darwin # Loom for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Loom installed
       categories:
         - Productivity
     - slug: spotify/darwin # Spotify for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Spotify installed
       categories:
         - Productivity
     - slug: rectangle/darwin # Rectangle for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Rectangle installed
       categories:
         - Productivity
     - slug: logi-options+/darwin # Logi Options+ for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Logi Options+ installed
       categories:
         - Productivity
     - slug: figma/darwin # Figma for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Figma installed
       categories:
         - Productivity
     - slug: whatsapp/darwin # WhatsApp for macOS
       self_service: true
+      labels_include_any:
+        - Macs with WhatsApp installed
       categories:
         - Communication
     - slug: android-studio/darwin # Android Studio for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Android Studio installed
       categories:
         - Developer tools
     - slug: zed/darwin # Zed for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Zed installed
       categories:
         - Developer tools
     - slug: obsidian/darwin # Obsidian for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Obsidian installed
       categories:
         - Productivity
     - slug: google-drive/darwin # Google Drive for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Google Drive installed
       categories:
         - Productivity
     - slug: cursor/darwin # Cursor for macOS
       self_service: true
+      labels_include_any:
+        - Macs with Cursor installed
       categories:
         - Developer tools
     # Windows apps
@@ -416,5 +454,7 @@ software:
         - "x86-based Windows hosts"
     - slug: visual-studio-code/windows # Microsoft Visual Studio for Windows
       self_service: true
+      labels_include_any:
+        - "x86 Windows hosts with Visual Studio Code installed"
       categories:
         - Developer tools