diff --git a/.github/workflows/build-cli.yml b/.github/workflows/build-cli.yml
index 2c3ea3982a..5436f97684 100644
--- a/.github/workflows/build-cli.yml
+++ b/.github/workflows/build-cli.yml
@@ -59,11 +59,20 @@ jobs:
 
 
   cli:
-    name: Build CLI ${{ matrix.os }}
+    name: "${{ matrix.os.base }} - ${{ matrix.license_type.readable }}"
     strategy:
       matrix:
-        os: [ubuntu-22.04, macos-11]
-    runs-on: ${{ matrix.os }}
+        os:
+         [
+          { base: "linux", distro: "ubuntu-22.04" },
+          { base: "mac", distro: "macos-11" }
+         ]
+        license_type:
+         [
+          { prefix: "oss", readable: "open source license" },
+          { prefix: "bit", readable: "commercial license"}
+         ]
+    runs-on: ${{ matrix.os.distro }}
     needs:
       - setup
     env:
@@ -93,16 +102,16 @@ jobs:
         working-directory: ./
 
       - name: Build & Package Unix
-        run: npm run dist:${{ env.SHORT_RUNNER_OS }} --quiet
+        run: npm run dist:${{ matrix.license_type.prefix }}:${{ env.SHORT_RUNNER_OS }} --quiet
 
       - name: Zip Unix
         run: |
-          cd ./dist/${{ env.LOWER_RUNNER_OS }}
-          zip ../bw-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip ./bw
+          cd ./dist/${{ matrix.license_type.prefix }}/${{ env.LOWER_RUNNER_OS }}
+          zip ../../bw-${{ matrix.license_type.prefix }}-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip ./bw
 
       - name: Version Test
         run: |
-          unzip "./dist/bw-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip" -d "./test"
+          unzip "./dist/bw-${{ matrix.license_type.prefix }}-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip" -d "./test"
           testVersion=$(./test/bw -v)
           echo "version: $_PACKAGE_VERSION"
           echo "testVersion: $testVersion"
@@ -114,25 +123,32 @@ jobs:
       - name: Create checksums Unix
         run: |
           cd ./dist
-          shasum -a 256 bw-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip \
-            | awk '{split($0, a); print a[1]}' > bw-${{ env.LOWER_RUNNER_OS }}-sha256-${{ env._PACKAGE_VERSION }}.txt
+          shasum -a 256 bw-${{ matrix.license_type.prefix }}-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip \
+            | awk '{split($0, a); print a[1]}' > bw-${{ matrix.license_type.prefix }}-${{ env.LOWER_RUNNER_OS }}-sha256-${{ env._PACKAGE_VERSION }}.txt
 
       - name: Upload unix zip asset
         uses: actions/upload-artifact@5d5d22a31266ced268874388b861e4b58bb5c2f3 # v4.3.1
         with:
-          name: bw-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip
-          path: apps/cli/dist/bw-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip
+          name: bw-${{ matrix.license_type.prefix }}-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip
+          path: apps/cli/dist/bw-${{ matrix.license_type.prefix }}-${{ env.LOWER_RUNNER_OS }}-${{ env._PACKAGE_VERSION }}.zip
           if-no-files-found: error
 
       - name: Upload unix checksum asset
         uses: actions/upload-artifact@5d5d22a31266ced268874388b861e4b58bb5c2f3 # v4.3.1
         with:
-          name: bw-${{ env.LOWER_RUNNER_OS }}-sha256-${{ env._PACKAGE_VERSION }}.txt
-          path: apps/cli/dist/bw-${{ env.LOWER_RUNNER_OS }}-sha256-${{ env._PACKAGE_VERSION }}.txt
+          name: bw-${{ matrix.license_type.prefix }}-${{ env.LOWER_RUNNER_OS }}-sha256-${{ env._PACKAGE_VERSION }}.txt
+          path: apps/cli/dist/bw-${{ matrix.license_type.prefix }}-${{ env.LOWER_RUNNER_OS }}-sha256-${{ env._PACKAGE_VERSION }}.txt
           if-no-files-found: error
 
   cli-windows:
-    name: Build CLI Windows
+    name: "windows - ${{ matrix.license_type.readable }}"
+    strategy:
+      matrix:
+        license_type:
+         [
+          { prefix: "oss", readable: "open source license" },
+          { prefix: "bit", readable: "commercial license"}
+         ]
     runs-on: windows-2022
     needs:
       - setup
@@ -218,25 +234,26 @@ jobs:
         working-directory: ./
 
       - name: Build & Package Windows
-        run: npm run dist:win --quiet
+        run: npm run dist:${{ matrix.license_type.prefix }}:win --quiet
 
       - name: Package Chocolatey
         shell: pwsh
+        if: ${{ matrix.license_type.prefix }} == 'oss'
         run: |
           Copy-Item -Path stores/chocolatey -Destination dist/chocolatey -Recurse
-          Copy-Item dist/windows/bw.exe -Destination dist/chocolatey/tools
+          Copy-Item dist/${{ matrix.license_type.prefix }}/windows/bw.exe -Destination dist/chocolatey/tools
           Copy-Item ${{ github.workspace }}/LICENSE.txt -Destination dist/chocolatey/tools
           choco pack dist/chocolatey/bitwarden-cli.nuspec --version ${{ env._PACKAGE_VERSION }} --out dist/chocolatey
 
       - name: Zip Windows
         shell: cmd
-        run: 7z a ./dist/bw-windows-%_PACKAGE_VERSION%.zip ./dist/windows/bw.exe
+        run: 7z a ./dist/bw-${{ matrix.license_type.prefix }}-windows-%_PACKAGE_VERSION%.zip ./dist/${{ matrix.license_type.prefix }}/windows/bw.exe
 
       - name: Version Test
         run: |
           dir ./dist/
-          Expand-Archive -Path "./dist/bw-windows-${env:_PACKAGE_VERSION}.zip" -DestinationPath "./test/windows"
-          $testVersion = Invoke-Expression '& ./test/windows/bw.exe -v'
+          Expand-Archive -Path "./dist/bw-${{ matrix.license_type.prefix }}-windows-${env:_PACKAGE_VERSION}.zip" -DestinationPath "./test/${{ matrix.license_type.prefix }}/windows"
+          $testVersion = Invoke-Expression '& ./test/${{ matrix.license_type.prefix }}/windows/bw.exe -v'
           echo "version: $env:_PACKAGE_VERSION"
           echo "testVersion: $testVersion"
           if($testVersion -ne $env:_PACKAGE_VERSION) {
@@ -245,24 +262,25 @@ jobs:
 
       - name: Create checksums Windows
         run: |
-          checksum -f="./dist/bw-windows-${env:_PACKAGE_VERSION}.zip" `
-            -t sha256 | Out-File -Encoding ASCII ./dist/bw-windows-sha256-${env:_PACKAGE_VERSION}.txt
+          checksum -f="./dist/bw-${{ matrix.license_type.prefix }}-windows-${env:_PACKAGE_VERSION}.zip" `
+            -t sha256 | Out-File -Encoding ASCII ./dist/bw-${{ matrix.license_type.prefix }}-windows-sha256-${env:_PACKAGE_VERSION}.txt
 
       - name: Upload windows zip asset
         uses: actions/upload-artifact@5d5d22a31266ced268874388b861e4b58bb5c2f3 # v4.3.1
         with:
-          name: bw-windows-${{ env._PACKAGE_VERSION }}.zip
-          path: apps/cli/dist/bw-windows-${{ env._PACKAGE_VERSION }}.zip
+          name: bw-${{ matrix.license_type.prefix }}-windows-${{ env._PACKAGE_VERSION }}.zip
+          path: apps/cli/dist/bw-${{ matrix.license_type.prefix }}-windows-${{ env._PACKAGE_VERSION }}.zip
           if-no-files-found: error
 
       - name: Upload windows checksum asset
         uses: actions/upload-artifact@5d5d22a31266ced268874388b861e4b58bb5c2f3 # v4.3.1
         with:
-          name: bw-windows-sha256-${{ env._PACKAGE_VERSION }}.txt
-          path: apps/cli/dist/bw-windows-sha256-${{ env._PACKAGE_VERSION }}.txt
+          name: bw-${{ matrix.license_type.prefix }}-windows-sha256-${{ env._PACKAGE_VERSION }}.txt
+          path: apps/cli/dist/bw-${{ matrix.license_type.prefix }}-windows-sha256-${{ env._PACKAGE_VERSION }}.txt
           if-no-files-found: error
 
       - name: Upload Chocolatey asset
+        if: matrix.license_type.prefix == 'oss'
         uses: actions/upload-artifact@5d5d22a31266ced268874388b861e4b58bb5c2f3 # v4.3.1
         with:
           name: bitwarden-cli.${{ env._PACKAGE_VERSION }}.nupkg
@@ -270,6 +288,7 @@ jobs:
           if-no-files-found: error
 
       - name: Upload NPM Build Directory asset
+        if: matrix.license_type.prefix == 'oss'
         uses: actions/upload-artifact@5d5d22a31266ced268874388b861e4b58bb5c2f3 # v4.3.1
         with:
           name: bitwarden-cli-${{ env._PACKAGE_VERSION }}-npm-build.zip
@@ -299,9 +318,14 @@ jobs:
       - name: Get bw linux cli
         uses: actions/download-artifact@c850b930e6ba138125429b7e5c93fc707a7f8427 # v4.1.4
         with:
-          name: bw-linux-${{ env._PACKAGE_VERSION }}.zip
+          name: bw-oss-linux-${{ env._PACKAGE_VERSION }}.zip
           path: apps/cli/dist/snap
 
+      - name: Rename snap artifact
+        run: |
+          cd dist/snap
+          mv bw-oss-linux-${{ env._PACKAGE_VERSION }}.zip bw-linux-${{ env._PACKAGE_VERSION }}.zip
+
       - name: Setup Snap Package
         run: |
           cp -r stores/snap/* -t dist/snap
diff --git a/.github/workflows/release-cli.yml b/.github/workflows/release-cli.yml
index add0c539e9..5b511cd1d9 100644
--- a/.github/workflows/release-cli.yml
+++ b/.github/workflows/release-cli.yml
@@ -100,12 +100,18 @@ jobs:
         env:
           PKG_VERSION: ${{ steps.version.outputs.version }}
         with:
-          artifacts: "apps/cli/bw-windows-${{ env.PKG_VERSION }}.zip,
-                      apps/cli/bw-windows-sha256-${{ env.PKG_VERSION }}.txt,
-                      apps/cli/bw-macos-${{ env.PKG_VERSION }}.zip,
-                      apps/cli/bw-macos-sha256-${{ env.PKG_VERSION }}.txt,
-                      apps/cli/bw-linux-${{ env.PKG_VERSION }}.zip,
-                      apps/cli/bw-linux-sha256-${{ env.PKG_VERSION }}.txt,
+          artifacts: "apps/cli/bw-oss-windows-${{ env.PKG_VERSION }}.zip,
+                      apps/cli/bw-oss-windows-sha256-${{ env.PKG_VERSION }}.txt,
+                      apps/cli/bw-bit-windows-${{ env.PKG_VERSION }}.zip,
+                      apps/cli/bw-bit-windows-sha256-${{ env.PKG_VERSION }}.txt,
+                      apps/cli/bw-oss-macos-${{ env.PKG_VERSION }}.zip,
+                      apps/cli/bw-oss-macos-sha256-${{ env.PKG_VERSION }}.txt,
+                      apps/cli/bw-bit-macos-${{ env.PKG_VERSION }}.zip,
+                      apps/cli/bw-bit-macos-sha256-${{ env.PKG_VERSION }}.txt,
+                      apps/cli/bw-oss-linux-${{ env.PKG_VERSION }}.zip,
+                      apps/cli/bw-oss-linux-sha256-${{ env.PKG_VERSION }}.txt,
+                      apps/cli/bw-bit-linux-${{ env.PKG_VERSION }}.zip,
+                      apps/cli/bw-bit-linux-sha256-${{ env.PKG_VERSION }}.txt,
                       apps/cli/bitwarden-cli.${{ env.PKG_VERSION }}.nupkg,
                       apps/cli/bw_${{ env.PKG_VERSION }}_amd64.snap,
                       apps/cli/bw-snap-sha256-${{ env.PKG_VERSION }}.txt"
diff --git a/apps/cli/package.json b/apps/cli/package.json
index 4d1636c51a..3da80a0dda 100644
--- a/apps/cli/package.json
+++ b/apps/cli/package.json
@@ -18,30 +18,27 @@
   "license": "GPL-3.0-only",
   "scripts": {
     "clean": "rimraf dist",
-    "build": "webpack",
-    "build:debug": "npm run build && node --inspect ./build/bw.js",
-    "build:watch": "webpack --watch",
-    "build:prod": "cross-env NODE_ENV=production webpack",
-    "build:prod:watch": "cross-env NODE_ENV=production webpack --watch",
-    "package": "npm run package:win && npm run package:mac && npm run package:lin",
-    "package:win": "pkg . --targets win-x64 --output ./dist/windows/bw.exe",
-    "package:mac": "pkg . --targets macos-x64 --output ./dist/macos/bw",
-    "package:lin": "pkg . --targets linux-x64 --output ./dist/linux/bw",
+    "build:oss": "webpack",
+    "build:oss:debug": "npm run build:oss && node --inspect ./build/bw.js",
+    "build:oss:watch": "webpack --watch",
+    "build:oss:prod": "cross-env NODE_ENV=production webpack",
+    "build:oss:prod:watch": "cross-env NODE_ENV=production webpack --watch",
     "debug": "node --inspect ./build/bw.js",
-    "dist": "npm run build:prod && npm run clean && npm run package",
-    "dist:win": "npm run build:prod && npm run clean && npm run package:win",
-    "dist:mac": "npm run build:prod && npm run clean && npm run package:mac",
-    "dist:lin": "npm run build:prod && npm run clean && npm run package:lin",
-    "publish:npm": "npm run build:prod && npm publish --access public",
+    "publish:npm": "npm run build:oss:prod && npm publish --access public",
     "build:bit": "webpack -c ../../bitwarden_license/bit-cli/webpack.config.js",
     "build:bit:debug": "npm run build:bit && node --inspect ./build/bw.js",
     "build:bit:watch": "webpack --watch -c ../../bitwarden_license/bit-cli/webpack.config.js",
     "build:bit:prod": "cross-env NODE_ENV=production npm run build:bit",
     "build:bit:prod:watch": "cross-env NODE_ENV=production npm run build:bit:watch",
-    "dist:bit": "npm run build:bit:prod && npm run clean && npm run package",
+    "dist:oss:win": "npm run build:oss:prod && npm run clean && npm run package:oss:win",
+    "dist:oss:mac": "npm run build:oss:prod && npm run clean && npm run package:oss:mac",
+    "dist:oss:lin": "npm run build:oss:prod && npm run clean && npm run package:oss:lin",
     "dist:bit:win": "npm run build:bit:prod && npm run clean && npm run package:bit:win",
     "dist:bit:mac": "npm run build:bit:prod && npm run clean && npm run package:bit:mac",
     "dist:bit:lin": "npm run build:bit:prod && npm run clean && npm run package:bit:lin",
+    "package:oss:win": "pkg . --targets win-x64 --output ./dist/oss/windows/bw.exe",
+    "package:oss:mac": "pkg . --targets macos-x64 --output ./dist/oss/macos/bw",
+    "package:oss:lin": "pkg . --targets linux-x64 --output ./dist/oss/linux/bw",
     "package:bit:win": "pkg . --targets win-x64 --output ./dist/bit/windows/bw.exe",
     "package:bit:mac": "pkg . --targets macos-x64 --output ./dist/bit/macos/bw",
     "package:bit:lin": "pkg . --targets linux-x64 --output ./dist/bit/linux/bw",