diff --git a/.github/workflows/build-cli.yml b/.github/workflows/build-cli.yml
index 3e6c1937583..45d57bbe202 100644
--- a/.github/workflows/build-cli.yml
+++ b/.github/workflows/build-cli.yml
@@ -52,7 +52,7 @@ permissions:
 jobs:
   setup:
     name: Setup
-    runs-on: ubuntu-22.04
+    runs-on: ubuntu-24.04
     outputs:
       package_version: ${{ steps.retrieve-package-version.outputs.package_version }}
       node_version: ${{ steps.retrieve-node-version.outputs.node_version }}
@@ -61,7 +61,7 @@ jobs:
       - name: Check out repo
         uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
         with:
-          ref: ${{  github.event.pull_request.head.sha }}
+          ref: ${{ github.event.pull_request.head.sha }}
 
       - name: Get Package Version
         id: retrieve-package-version
@@ -85,25 +85,25 @@ jobs:
           has_secrets=${{ secrets.AZURE_KV_CI_SERVICE_PRINCIPAL != '' }}
           echo "has_secrets=$has_secrets" >> $GITHUB_OUTPUT
 
+
   cli:
     name: CLI ${{ matrix.os.base }}${{ matrix.os.target_suffix }} - ${{ matrix.license_type.readable }}
     strategy:
       matrix:
         os:
-         [
-          { base: "linux", distro: "ubuntu-22.04", target_suffix: "" },
-          { base: "linux", distro: "ubuntu-22.04-arm", target_suffix: "-arm64" },
-          { base: "mac", distro: "macos-13", target_suffix: "" },
-          { base: "mac", distro: "macos-14", target_suffix: "-arm64" }
-         ]
+          [
+            { base: "linux", distro: "ubuntu-22.04", target_suffix: "" },
+            { base: "linux", distro: "ubuntu-22.04-arm", target_suffix: "-arm64" },
+            { base: "mac", distro: "macos-13", target_suffix: "" },
+            { base: "mac", distro: "macos-14", target_suffix: "-arm64" }
+          ]
         license_type:
           [
             { build_prefix: "oss", artifact_prefix: "-oss", readable: "open source license" },
             { build_prefix: "bit", artifact_prefix: "", readable: "commercial license" }
           ]
     runs-on: ${{ matrix.os.distro }}
-    needs:
-      - setup
+    needs: setup
     env:
       _PACKAGE_VERSION: ${{ needs.setup.outputs.package_version }}
       _NODE_VERSION: ${{ needs.setup.outputs.node_version }}
@@ -113,7 +113,7 @@ jobs:
       - name: Check out repo
         uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
         with:
-          ref: ${{  github.event.pull_request.head.sha }}
+          ref: ${{ github.event.pull_request.head.sha }}
 
       - name: Setup Unix Vars
         run: |
@@ -155,11 +155,69 @@ jobs:
       - name: Build & Package Unix
         run: npm run dist:${{ matrix.license_type.build_prefix }}:${{ env.SHORT_RUNNER_OS }}${{ matrix.os.target_suffix }} --quiet
 
+      - name: Login to Azure
+        if: ${{ matrix.os.base == 'mac' && needs.setup.outputs.has_secrets == 'true' }}
+        uses: Azure/login@e15b166166a8746d1a47596803bd8c1b595455cf # v1.6.0
+        with:
+          creds: ${{ secrets.AZURE_KV_CI_SERVICE_PRINCIPAL }}
+
+      - name: Get certificates
+        if: ${{ matrix.os.base == 'mac' && needs.setup.outputs.has_secrets == 'true' }}
+        run: |
+          mkdir -p $HOME/certificates
+
+          az keyvault secret show --id https://bitwarden-ci.vault.azure.net/certificates/devid-app-cert |
+            jq -r .value | base64 -d > $HOME/certificates/devid-app-cert.p12
+
+      - name: Set up keychain
+        if: ${{ matrix.os.base == 'mac' && needs.setup.outputs.has_secrets == 'true' }}
+        env:
+          KEYCHAIN_PASSWORD: ${{ secrets.KEYCHAIN_PASSWORD }}
+        run: |
+          security create-keychain -p $KEYCHAIN_PASSWORD build.keychain
+          security default-keychain -s build.keychain
+          security unlock-keychain -p $KEYCHAIN_PASSWORD build.keychain
+          security set-keychain-settings -lut 1200 build.keychain
+
+          security import "$HOME/certificates/devid-app-cert.p12" -k build.keychain -P "" \
+            -T /usr/bin/codesign -T /usr/bin/security -T /usr/bin/productbuild
+
+          security set-key-partition-list -S apple-tool:,apple:,codesign: -s -k $KEYCHAIN_PASSWORD build.keychain
+
+      - name: Sign binary
+        if: ${{ matrix.os.base == 'mac' && needs.setup.outputs.has_secrets == 'true' }}
+        env:
+          MACOS_CERTIFICATE_NAME: "Developer ID Application: 8bit Solutions LLC"
+        run: codesign --sign "$MACOS_CERTIFICATE_NAME" --verbose=3 --force --options=runtime --entitlements ./entitlements.plist --timestamp ./dist/${{ matrix.license_type.build_prefix }}/${{ env.LOWER_RUNNER_OS }}${{ matrix.os.target_suffix }}/bw
+
       - name: Zip Unix
         run: |
           cd ./dist/${{ matrix.license_type.build_prefix }}/${{ env.LOWER_RUNNER_OS }}${{ matrix.os.target_suffix }}
           zip ../../bw${{ matrix.license_type.artifact_prefix }}-${{ env.LOWER_RUNNER_OS }}${{ matrix.os.target_suffix }}-${{ env._PACKAGE_VERSION }}.zip ./bw
 
+      - name: Set up private auth key
+        if: ${{ matrix.os.base == 'mac' && needs.setup.outputs.has_secrets == 'true' }}
+        run: |
+          mkdir ~/private_keys
+          cat << EOF > ~/private_keys/AuthKey_6TV9MKN3GP.p8
+          ${{ secrets.APP_STORE_CONNECT_AUTH_KEY }}
+          EOF
+
+      - name: Notarize app
+        if: ${{ matrix.os.base == 'mac' && needs.setup.outputs.has_secrets == 'true' }}
+        env:
+          APP_STORE_CONNECT_TEAM_ISSUER: ${{ secrets.APP_STORE_CONNECT_TEAM_ISSUER }}
+          APP_STORE_CONNECT_AUTH_KEY: 6TV9MKN3GP
+          APP_STORE_CONNECT_AUTH_KEY_PATH: ~/private_keys/AuthKey_6TV9MKN3GP.p8
+        run: |
+          echo "Create keychain profile"
+          xcrun notarytool store-credentials "notarytool-profile" --key-id "$APP_STORE_CONNECT_AUTH_KEY" --key "$APP_STORE_CONNECT_AUTH_KEY_PATH" --issuer "$APP_STORE_CONNECT_TEAM_ISSUER"
+
+          codesign --sign "Developer ID Application: 8bit Solutions LLC" --verbose=3 --force --options=runtime --timestamp ./dist/bw${{ matrix.license_type.artifact_prefix }}-${{ env.LOWER_RUNNER_OS }}${{ matrix.os.target_suffix }}-${{ env._PACKAGE_VERSION }}.zip
+
+          echo "Notarize app"
+          xcrun notarytool submit ./dist/bw${{ matrix.license_type.artifact_prefix }}-${{ env.LOWER_RUNNER_OS }}${{ matrix.os.target_suffix }}-${{ env._PACKAGE_VERSION }}.zip --keychain-profile "notarytool-profile" --wait
+
       - name: Version Test
         run: |
           unzip "./dist/bw${{ matrix.license_type.artifact_prefix }}-${{ env.LOWER_RUNNER_OS }}${{ matrix.os.target_suffix }}-${{ env._PACKAGE_VERSION }}.zip" -d "./test"
@@ -193,6 +251,7 @@ jobs:
       - name: Output help
         run: node ./build/bw.js --help
 
+
   cli-windows:
     name: Windows - ${{ matrix.license_type.readable }}
     strategy:
@@ -203,8 +262,7 @@ jobs:
             { build_prefix: "bit", artifact_prefix: "", readable: "commercial license" }
           ]
     runs-on: windows-2022
-    needs:
-      - setup
+    needs: setup
     env:
       _PACKAGE_VERSION: ${{ needs.setup.outputs.package_version }}
       _NODE_VERSION: ${{ needs.setup.outputs.node_version }}
@@ -462,7 +520,7 @@ jobs:
   check-failures:
     name: Check for failures
     if: always()
-    runs-on: ubuntu-22.04
+    runs-on: ubuntu-24.04
     needs:
       - setup
       - cli
diff --git a/apps/cli/entitlements.plist b/apps/cli/entitlements.plist
new file mode 100644
index 00000000000..f00fbb59495
--- /dev/null
+++ b/apps/cli/entitlements.plist
@@ -0,0 +1,10 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
+<plist version="1.0">
+<dict>
+    <key>com.apple.security.cs.allow-jit</key>
+    <true/>
+    <key>com.apple.security.cs.allow-unsigned-executable-memory</key>
+    <true/>
+</dict>
+</plist>