diff --git a/Build/setup_glass.py b/Build/setup_glass.py
index a272e43748..d545b9be83 100644
--- a/Build/setup_glass.py
+++ b/Build/setup_glass.py
@@ -146,6 +146,16 @@ def get_test_console_app():
         print(f"Error: Test console app not found at {test_console_app}")
         exit(1)
 
+def restore_glass_newtonsoft_json():
+    source = os.path.join(glass_debugger_dir, "Newtonsoft.Json.dll")
+    target = os.path.join(glass_dir, "Newtonsoft.Json.dll")
+
+    if not os.path.exists(source):
+        print(f"Error: Glass-compatible Newtonsoft.Json.dll not found at {source}")
+        exit(1)
+
+    shutil.copy(source, target)
+
 def copy_ptvs_output(build_output_dir: str | None = None):
     # Copy the PythonTests folder into the glass directory
     print(f"Copying PythonTests from {python_tests_source_dir} to {python_tests_target_dir}")
@@ -174,6 +184,10 @@ def copy_ptvs_output(build_output_dir: str | None = None):
             print(f)
         exit(1)
 
+    # VSIX extraction can overwrite the runner root with an older Newtonsoft.Json.
+    # Glass.TestAdapter.dll is compiled against the copy from the Glass drop.
+    restore_glass_newtonsoft_json()
+
     # Whenever we copy new bits, we have to regenerate the Python.GlassTestGroup file
     generate_python_version_props(build_output_dir)
 
@@ -306,7 +320,9 @@ def generate_python_version_props(build_output_dir: str | None):
 def main(build_output_dir: str | None = None):
     get_drop_exe()
     get_glass()
+
     get_test_console_app()
+
     copy_ptvs_output(build_output_dir)
     generate_python_version_props(build_output_dir)
     verify_listing()
diff --git a/Build/templates/run_tests.yml b/Build/templates/run_tests.yml
index 860881b0ea..17ca41f443 100644
--- a/Build/templates/run_tests.yml
+++ b/Build/templates/run_tests.yml
@@ -63,11 +63,11 @@ steps:
       Copy-Item -Path "$source\*" -Destination $dest -Recurse -Force
     displayName: 'Copy binaries to expected location'
 
-  - task: CacheBeta@2
+  - task: Cache@2
     displayName: 'Restore glass binaries from cache'
     condition: eq('${{ parameters.skipGlassCache }}', 'false')
     inputs:
-      key: 'glass'
+      key: 'glass | Build/setup_glass.py'
       path: '$(Build.SourcesDirectory)\GlassTests'
       cacheHitVar: 'CACHE_RESTORED'
 
@@ -121,9 +121,9 @@ steps:
       testResultsFormat: 'VSTest'
       failTaskOnFailedTests: true
 
-  - task: CacheBeta@2
+  - task: Cache@2
     displayName: 'Cache glass binaries'
     condition: and(succeeded(), or(eq(variables['CACHE_RESTORED'], 'false'), eq('${{ parameters.skipGlassCache }}', 'true')))
     inputs:
-      key: 'glass'
+      key: 'glass | Build/setup_glass.py'
       path: '$(Build.SourcesDirectory)\GlassTests'
diff --git a/Python/Tests/GlassTests/PythonTests/PythonEngine.regdef b/Python/Tests/GlassTests/PythonTests/PythonEngine.regdef
index 944d2b7679..63c38caef7 100644
--- a/Python/Tests/GlassTests/PythonTests/PythonEngine.regdef
+++ b/Python/Tests/GlassTests/PythonTests/PythonEngine.regdef
@@ -16,20 +16,20 @@ Windows Registry Editor Version 5.00
 "HitCountBP"=dword:00000000
 "JustMyCodeStepping"=dword:00000001
 "EngineClass"="Microsoft.PythonTools.Debugger.DebugEngine.AD7Engine"
-"EngineAssembly"="Microsoft.PythonTools.Debugger, Version=17.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a"
+"EngineAssembly"="Microsoft.PythonTools.Debugger, Version=18.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a"
 "LoadProgramProviderUnderWOW64"=dword:00000001
 "AlwaysLoadProgramProviderLocal"=dword:00000001
 "LoadUnderWOW64"=dword:00000001
 
 [$RootKey$\CLSID\{0DA53AFE-069E-47A3-AE34-32610A8253A3}]
-"Assembly"="Microsoft.PythonTools.Debugger, Version=17.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a"
+"Assembly"="Microsoft.PythonTools.Debugger, Version=18.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a"
 "Class"="Microsoft.PythonTools.Debugger.DebugEngine.AD7Engine"
 "InprocServer32"="C:\\windows\\SYSTEM32\\MSCOREE.DLL"
 "CodeBase"="$GlassInstallDir$\\Microsoft.PythonTools.Debugger.dll"
 "ThreadingModel"="Free"
 
 [$RootKey$\CLSID\{FA452F5D-539E-4B55-BCC6-5DE7E342BC44}]
-"Assembly"="Microsoft.PythonTools.Debugger, Version=17.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a"
+"Assembly"="Microsoft.PythonTools.Debugger, Version=18.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a"
 "Class"="Microsoft.PythonTools.Debugger.DebugEngine.AD7ProgramProvider"
 "InprocServer32"="C:\\windows\\SYSTEM32\\MSCOREE.DLL"
 "CodeBase"="$GlassInstallDir$\\Microsoft.PythonTools.Debugger.dll"