diff --git a/.appveyor.yml b/.appveyor.yml
index 8be46ea0344b..dbea6e3a5494 100644
--- a/.appveyor.yml
+++ b/.appveyor.yml
@@ -9,6 +9,12 @@ environment:
       nodejs_version: "8.9.1"
       APPVEYOR: "true"
       DEBUGGER_TEST: "true"
+    - PYTHON: "C:\\Python36"
+      PYTHON_VERSION: "3.6.3"
+      PYTHON_ARCH: "32"
+      nodejs_version: "8.9.1"
+      APPVEYOR: "true"
+      DEBUGGER_TEST_RELEASE: "true"
     - PYTHON: "C:\\Python36"
       PYTHON_VERSION: "3.6.3"
       PYTHON_ARCH: "32"
@@ -28,6 +34,15 @@ environment:
       APPVEYOR: "true"
       ANALYSIS_TEST: "true"
 
+matrix:
+  allow_failures:
+    - PYTHON: "C:\\Python36"
+      PYTHON_VERSION: "3.6.3"
+      PYTHON_ARCH: "32"
+      nodejs_version: "8.9.1"
+      APPVEYOR: "true"
+      DEBUGGER_TEST_RELEASE: "true"
+
 init:
   - "ECHO %PYTHON% %PYTHON_VERSION% %PYTHON_ARCH%"
 
@@ -58,6 +73,10 @@ test_script:
   - yarn run vscode:prepublish
   - if [%DEBUGGER_TEST%]==[true] (
       yarn run testDebugger --silent)
+  - yarn run clean:ptvsd
+  - pip install -t ./pythonFiles/experimental/ptvsd ptvsd --pre --no-cache-dir
+  - if [%DEBUGGER_TEST_RELEASE%]==[true] (
+      yarn run testDebugger --silent)
   - if [%SINGLE_WORKSPACE_TEST%]==[true] (
       yarn run testSingleWorkspace --silent)
   - if [%MULTIROOT_WORKSPACE_TEST%]==[true] (
diff --git a/.travis.yml b/.travis.yml
index 99ec74c36292..52ae4e0b99f9 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -6,6 +6,9 @@ matrix:
         - os: linux
           python: "2.7"
           env: DEBUGGER_TEST=true
+        - os: linux
+          python: "2.7"
+          env: DEBUGGER_TEST_RELEASE=true
         - os: linux
           python: "2.7"
           env: SINGLE_WORKSPACE_TEST=true
@@ -15,12 +18,22 @@ matrix:
         - os: linux
           python: "3.6-dev"
           env: DEBUGGER_TEST=true
+        - os: linux
+          python: "3.6-dev"
+          env: DEBUGGER_TEST_RELEASE=true
         - os: linux
           python: "3.6-dev"
           env: SINGLE_WORKSPACE_TEST=true
         - os: linux
           python: "3.6-dev"
           env: MULTIROOT_WORKSPACE_TEST=true
+    allow_failures:
+        - os: linux
+          python: "2.7"
+          env: DEBUGGER_TEST=true
+        - os: linux
+          python: "3.6-dev"
+          env: DEBUGGER_TEST=true
 before_install: |
   if [ $TRAVIS_OS_NAME == "linux" ]; then
     export CXX="g++-4.9" CC="gcc-4.9" DISPLAY=:99.0;
@@ -51,12 +64,18 @@ script:
   - if [ $TRAVIS_UPLOAD_COVERAGE == "true" ]; then
         bash <(curl -s https://codecov.io/bash);
     fi
-  # - rm -rf ./pythonFiles/experimental/ptvsd
-  # - pip install -t ./pythonFiles/experimental/ptvsd ptvsd
-  # - yarn run testDebugger --silent
-  # - if [ $TRAVIS_UPLOAD_COVERAGE == "true" ]; then
-  #       bash <(curl -s https://codecov.io/bash);
-  #   fi
+  - yarn run clean:ptvsd
+  - pip install -t ./pythonFiles/experimental/ptvsd ptvsd --pre --no-cache-dir;
+  - if [ $DEBUGGER_TEST_RELEASE == "true" ]; then
+        yarn run clean;
+        yarn run vscode:prepublish;
+        yarn run cover:enable;
+        yarn run testDebugger --silent;
+    fi
+  - yarn run debugger-coverage
+  - if [ $TRAVIS_UPLOAD_COVERAGE == "true" ]; then
+        bash <(curl -s https://codecov.io/bash);
+    fi
   - if [ $SINGLE_WORKSPACE_TEST == "true" ]; then
         yarn run clean;
         yarn run vscode:prepublish;
diff --git a/gulpfile.js b/gulpfile.js
index ba89b0a92e2f..753af8c46292 100644
--- a/gulpfile.js
+++ b/gulpfile.js
@@ -95,6 +95,8 @@ gulp.task('output:clean', () => del(['coverage', 'debug_coverage*']));
 
 gulp.task('cover:clean', () => del(['coverage', 'debug_coverage*']));
 
+gulp.task('clean:ptvsd', () => del(['coverage', 'pythonFiles/experimental/ptvsd*']));
+
 gulp.task('cover:enable', () => {
     return gulp.src("./coverconfig.json")
         .pipe(jeditor((json) => {
diff --git a/news/3 Code Health/1253.md b/news/3 Code Health/1253.md
new file mode 100644
index 000000000000..5dcc6d79bfec
--- /dev/null
+++ b/news/3 Code Health/1253.md	
@@ -0,0 +1 @@
+Run CI tests against the release version and master branch of PTVSD (experimental debugger), allowing tests to fail against the mastre branch of PTVSD.
diff --git a/package.json b/package.json
index 906ad9e94b14..546445b45674 100644
--- a/package.json
+++ b/package.json
@@ -1849,6 +1849,7 @@
         "lint-staged": "node gulpfile.js",
         "lint": "tslint src/**/*.ts -t verbose",
         "clean": "gulp clean",
+        "clean:ptvsd": "gulp clean:ptvsd",
         "cover:enable": "gulp cover:enable",
         "debugger-coverage": "gulp debugger-coverage"
     },