diff --git a/Build/lldb-mi/lldb-mi-sign.template.yml b/Build/lldb-mi/lldb-mi-sign.template.yml
index f6e2f256e..7d6cd0348 100644
--- a/Build/lldb-mi/lldb-mi-sign.template.yml
+++ b/Build/lldb-mi/lldb-mi-sign.template.yml
@@ -3,7 +3,8 @@ parameters:
   archs: ["x86_64", "arm64"]
 
 jobs:
-- job:
+- job: Sign
+  displayName: Sign LLDB-MI
   pool:
     name: VSEngSS-MicroBuild2022-1ES
   steps:
@@ -27,4 +28,102 @@ jobs:
       inputs:
         targetPath: '$(Pipeline.Workspace)\Artifacts\lldb-mi_${{ arch }}.zip'
         artifactName: 'lldb-mi_${{ arch }}_zip'
+
+- job: VerifySignatures
+  displayName: Verify LLDB-MI signatures
+  dependsOn: Sign
+  pool:
+    vmImage: macOS-latest
+  steps:
+  - ${{ each arch in parameters.archs }}:
+    - task: DownloadPipelineArtifact@1
+      displayName: 'Downloading lldb-mi_${{ arch }}_zip'
+      inputs:
+        targetPath: '$(Pipeline.Workspace)/signed_lldb-mi_${{ arch }}'
+        artifactName: 'lldb-mi_${{ arch }}_zip'
+
+    - task: Bash@3
+      displayName: 'Verify lldb-mi_${{ arch }} signature'
+      inputs:
+        targetType: inline
+        script: |
+          set -euo pipefail
+
+          arch='${{ arch }}'
+          artifact_dir='$(Pipeline.Workspace)/signed_lldb-mi_${{ arch }}'
+          zip_path="${artifact_dir}/lldb-mi_${arch}.zip"
+          extract_dir="${artifact_dir}/extracted"
+          expected_binary="${extract_dir}/debugAdapters/lldb-mi_${arch}/bin/lldb-mi"
+          expected_entitlements='$(Build.SourcesDirectory)/Build/lldb-mi/debugger-entitlements.plist'
+
+          rm -rf "$extract_dir"
+          mkdir -p "$extract_dir"
+          unzip -q "$zip_path" -d "$extract_dir"
+
+          binary_count="$(find "$extract_dir" -type f -name lldb-mi | wc -l | tr -d '[:space:]')"
+          if [[ "$binary_count" != 1 || ! -f "$expected_binary" ]]; then
+            echo "##[error]Expected exactly one lldb-mi binary at $expected_binary."
+            find "$extract_dir" -name lldb-mi -print
+            exit 1
+          fi
+
+          actual_archs="$(lipo -archs "$expected_binary")"
+          if [[ "$actual_archs" != "$arch" ]]; then
+            echo "##[error]Expected architecture $arch, found $actual_archs."
+            exit 1
+          fi
+
+          codesign --verify --strict --verbose=4 "$expected_binary"
+          signature_details="$(codesign --display --verbose=4 "$expected_binary" 2>&1)"
+          printf '%s\n' "$signature_details"
+
+          if printf '%s\n' "$signature_details" | grep -q '^Signature=adhoc$'; then
+            echo '##[error]The final lldb-mi binary still has an ad-hoc signature.'
+            exit 1
+          fi
+
+          authority_count="$(printf '%s\n' "$signature_details" | grep -c '^Authority=' || true)"
+          if (( authority_count < 2 )); then
+            echo "##[error]Expected a signing authority chain, found $authority_count authority entries."
+            exit 1
+          fi
+
+          actual_entitlements="${artifact_dir}/actual-entitlements-${arch}.plist"
+          codesign --display --entitlements "$actual_entitlements" --xml "$expected_binary"
+          python3 - "$expected_entitlements" "$actual_entitlements" <<'PY'
+          import plistlib
+          import sys
+
+          with open(sys.argv[1], "rb") as expected_file:
+              expected = plistlib.load(expected_file)
+          with open(sys.argv[2], "rb") as actual_file:
+              actual = plistlib.load(actual_file)
+
+          if actual != expected:
+              print(f"##[error]Expected entitlements: {expected}")
+              print(f"##[error]Actual entitlements: {actual}")
+              sys.exit(1)
+          PY
+
+          tampered_binary="${artifact_dir}/tampered-lldb-mi-${arch}"
+          cp "$expected_binary" "$tampered_binary"
+          python3 - "$tampered_binary" <<'PY'
+          import os
+          import sys
+
+          tamper_offset = 16384
+          with open(sys.argv[1], "r+b") as binary_file:
+              if os.fstat(binary_file.fileno()).st_size <= tamper_offset:
+                  print("##[error]The lldb-mi binary is too small for the tamper check.")
+                  sys.exit(1)
+              binary_file.seek(tamper_offset)
+              original = binary_file.read(1)
+              binary_file.seek(tamper_offset)
+              binary_file.write(bytes([original[0] ^ 1]))
+          PY
+
+          if codesign --verify --strict --verbose=4 "$tampered_binary"; then
+            echo '##[error]codesign accepted a modified lldb-mi binary.'
+            exit 1
+          fi
 ...
\ No newline at end of file
diff --git a/Build/lldb-mi/lldb-mi.template.yml b/Build/lldb-mi/lldb-mi.template.yml
index 539ed5836..066939ad5 100644
--- a/Build/lldb-mi/lldb-mi.template.yml
+++ b/Build/lldb-mi/lldb-mi.template.yml
@@ -27,11 +27,34 @@ jobs:
 - job: LLDB_MI_${{ parameters.llvm_arch }}
   timeoutInMinutes: 360
   pool:
-    ${{if eq(parameters['llvm_arch'], 'arm64')}}:
-      name: cpptoolsMacM1pool
+    name: Azure Pipelines
+    ${{ if eq(parameters['llvm_arch'], 'arm64') }}:
+      vmImage: macOS-15-arm64
     ${{ else }}:
-      vmImage: macOS-latest
+      vmImage: macOS-15
   steps:
+  - task: UsePythonVersion@0
+    displayName: 'Use Python 3.11'
+    inputs:
+      versionSpec: '3.11'
+      ${{ if eq(parameters['llvm_arch'], 'arm64') }}:
+        architecture: arm64
+      ${{ else }}:
+        architecture: x64
+
+  - task: CmdLine@2
+    displayName: 'Verify Python 3.11'
+    inputs:
+      script: |
+        set -euo pipefail
+        python_executable="$(command -v python3)"
+        python_architecture="$("$python_executable" -c 'import platform; print(platform.machine())')"
+        if [[ "$python_architecture" != '${{ parameters.llvm_arch }}' ]]; then
+          echo "##[error]Expected Python architecture ${{ parameters.llvm_arch }}, found $python_architecture."
+          exit 1
+        fi
+        "$python_executable" -c "import distutils.sysconfig; print(distutils.sysconfig.get_python_lib(True, False, ''))"
+
   - task: CmdLine@2
     displayName: 'Install Dependencies'
     inputs:
@@ -53,6 +76,9 @@ jobs:
           $1
         }
 
+        python_executable="$(command -v python3)"
+        python_home="$("$python_executable" -c 'import sys; print(sys.prefix)')"
+
         log_and_exec_cmd "sudo rm -rf /Library/Developer/CommandLineTools"
         log_and_exec_cmd "sudo xcode-select --switch /Applications/XCode.app"
 
@@ -62,6 +88,11 @@ jobs:
         log_and_exec_cmd "git clone ${{ parameters.llvm_repo }} llvm-project"
         log_and_exec_cmd "cd llvm-project"
         log_and_exec_cmd "git checkout ${{ parameters.llvm_commit }}"
+        if ! log_and_exec_cmd "git cherry-pick --no-commit 81fc5f7909a4ef5a8d4b5da2a10f77f7cb01ba63 73e15b5edb4fa4a77e68c299a6e3b21e610d351f f0a25fe0b746f56295d5c02116ba28d2f965c175"
+        then
+          echo "##[error] applying LLVM compatibility fixes failed"
+          exit 1
+        fi
 
         log_and_exec_cmd "./lldb/scripts/macos-setup-codesign.sh"
 
@@ -70,7 +101,7 @@ jobs:
         log_and_exec_cmd "mkdir $(Build.StagingDirectory)/buildspace/llvm-build"
         log_and_exec_cmd "cd $(Build.StagingDirectory)/buildspace/llvm-build"
 
-        log_and_exec_cmd "cmake -DLLVM_ENABLE_PROJECTS=clang;lldb -DCMAKE_BUILD_TYPE=${{ parameters.llvm_build_type }} -DCMAKE_INSTALL_PREFIX=$(Build.StagingDirectory)/buildspace/llvm-inst/ -DCMAKE_OSX_ARCHITECTURES=${{ parameters.llvm_arch }} ${{ parameters.llvm_additional_parameters }} -GNinja $(Build.StagingDirectory)/llvm-project/llvm"
+        log_and_exec_cmd "cmake -DLLVM_ENABLE_PROJECTS=clang;lldb -DCMAKE_BUILD_TYPE=${{ parameters.llvm_build_type }} -DCMAKE_INSTALL_PREFIX=$(Build.StagingDirectory)/buildspace/llvm-inst/ -DCMAKE_OSX_ARCHITECTURES=${{ parameters.llvm_arch }} -DPYTHON_HOME=$python_home -DPython3_EXECUTABLE=$python_executable ${{ parameters.llvm_additional_parameters }} -GNinja $(Build.StagingDirectory)/llvm-project/llvm"
         if [[ $? -ne 0 ]]
         then
           echo "##[error] cmake llvm failed"
@@ -112,7 +143,11 @@ jobs:
         # Create a separate build directory for building lldb-mi.
         log_and_exec_cmd "mkdir build"
         log_and_exec_cmd "cd build"
-        log_and_exec_cmd "cmake -DCMAKE_PREFIX_PATH=$(Build.StagingDirectory)/buildspace/llvm-inst/ -DCMAKE_OSX_ARCHITECTURES=${{ parameters.llvm_arch }} ${{ parameters.lldb_mi_additional_parameters }} -GNinja .."
+        if ! log_and_exec_cmd "cmake -DCMAKE_POLICY_VERSION_MINIMUM=3.5 -DCMAKE_PREFIX_PATH=$(Build.StagingDirectory)/buildspace/llvm-inst/ -DCMAKE_OSX_ARCHITECTURES=${{ parameters.llvm_arch }} ${{ parameters.lldb_mi_additional_parameters }} -GNinja .."
+        then
+          echo "##[error] cmake lldb-mi failed"
+          exit 1
+        fi
         log_and_exec_cmd "ninja"
         if [[ $? -ne 0 ]]
         then