diff --git a/.azure-pipelines/steps/create-virtualenv.yml b/.azure-pipelines/steps/create-virtualenv.yml
index 3151d15e..4dbdb685 100644
--- a/.azure-pipelines/steps/create-virtualenv.yml
+++ b/.azure-pipelines/steps/create-virtualenv.yml
@@ -5,26 +5,27 @@ steps:
     if (!$env:PY_EXE) {
         $env:PY_EXE="python"
     }
-    Write-Host "##vso[task.setvariable variable=PY_EXE]"$env:PY_EXE
+    Write-Host "##vso[task.setvariable variable=PY_EXE]$env:PY_EXE"
     Write-Host "Found Python: $env:PY_EXE"
-    Invoke-Expression "$env:PY_EXE -m virtualenv D:\.venv"
+    Invoke-Expression "& '$env:PY_EXE' -m virtualenv D:\.venv"
     Write-Host "##vso[task.setvariable variable=VIRTUAL_ENV]D:\.venv"
-    Invoke-Expression "D:\.venv\Scripts\activate.ps1"
+    Invoke-Expression "& 'D:\.venv\Scripts\activate.ps1'"
     $env:VIRTUAL_ENV="D:\.venv"
     Write-Host "Installing local package..."
-    Invoke-Expression "$env:PY_EXE -m pip install -e .[test] --upgrade"
+    Invoke-Expression "& '$env:PY_EXE' -m pip install -e .[test] --upgrade"
     Write-Host "upgrading local package in virtual env"
     $venv_scripts = Join-Path -path D:\.venv -childpath Scripts
     $venv_py = Join-Path -path $venv_scripts -childpath python.exe
-    Invoke-Expression "$venv_py -m pip install -e .[test] --upgrade"
+    Write-Host "##vso[task.setvariable variable=VIRTUAL_ENV_PY]$venv_py"
+    Invoke-Expression "& '$venv_py' -m pip install -e .[test] --upgrade"
     Write-Host "Installing pipenv development packages"
-    Invoke-Expression "$venv_py -m pipenv install --dev"
+    Invoke-Expression "& '$venv_py' -m pipenv install --dev"
     Write-Host "Installing local package in pipenv environment"
-    Invoke-Expression "$venv_py -m pipenv run pip install -e .[test]"
+    Invoke-Expression "& '$venv_py' -m pipenv run pip install -e .[test]"
     Write-Host "Printing metadata"
-    Write-Host $(Invoke-Expression "$venv_py -m pipenv --venv")
-    Write-Host $(Invoke-Expression "$venv_py -m pipenv --py")
-    Write-Host $(Invoke-Expression "$venv_py -m pipenv run python --version")
+    Write-Host $(Invoke-Expression "& '$venv_py' -m pipenv --venv")
+    Write-Host $(Invoke-Expression "& '$venv_py' -m pipenv --py")
+    Write-Host $(Invoke-Expression "& '$venv_py' -m pipenv run python --version")
   displayName: Make Virtualenv
   env:
     PIPENV_DEFAULT_PYTHON_VERSION: $(PIPENV_DEFAULT_PYTHON_VERSION)
diff --git a/.azure-pipelines/steps/run-tests.yml b/.azure-pipelines/steps/run-tests.yml
index f33523f1..c3c7c1c6 100644
--- a/.azure-pipelines/steps/run-tests.yml
+++ b/.azure-pipelines/steps/run-tests.yml
@@ -1,8 +1,8 @@
 steps:
 - powershell: |
     # Fix Git SSL errors
-    pip install certifi
-    python -m certifi > cacert.txt
+    Invoke-Expression "& '$VIRTUAL_ENV_PY' -m pip install certifi"
+    Invoke-Expression "& '$VIRTUAL_ENV_PY' -m certifi > cacert.txt"
     Write-Host "##vso[task.setvariable variable=GIT_SSL_CAINFO]$(Get-Content cacert.txt)"
     $env:GIT_SSL_CAINFO="$(Get-Content cacert.txt)"
     # Shorten paths to get under MAX_PATH or else integration tests will fail
@@ -14,8 +14,11 @@ steps:
     $env:TMP='T:\'
     git submodule sync
     git submodule update --init --recursive
-    D:\.venv\Scripts\pipenv run pytest -ra --ignore=pipenv\patched --ignore=pipenv\vendor --junitxml=test-results.xml tests
+    Invoke-Expression "& '$VIRTUAL_ENV_PY' -m pipenv run pytest -ra --ignore=pipenv\patched --ignore=pipenv\vendor --junitxml=test-results.xml tests"
   displayName: Run integration tests
+  env:
+    VIRTUAL_ENV: $(VIRTUAL_ENV)
+    VIRTUAL_ENV_PY: $(VIRTUAL_ENV_PY)
 
 - task: PublishTestResults@2
   displayName: Publish Test Results
diff --git a/pipenv/resolver.py b/pipenv/resolver.py
index 4f91350b..126dc809 100644
--- a/pipenv/resolver.py
+++ b/pipenv/resolver.py
@@ -185,10 +185,17 @@ def main():
     sys.stderr = get_wrapped_stream(stderr)
     sys.stdout = get_wrapped_stream(stdout)
     from pipenv.vendor import colorama
-    colorama.init()
-    if os.name == "nt":
-        sys.stderr = colorama.AnsiToWin32(sys.stderr)
-        sys.stdout = colorama.AnsiToWin32(sys.stdout)
+    if os.name == "nt" and (
+        all(getattr(stream, method, None) for stream in [sys.stdout, sys.stderr] for method in ["write", "isatty"]) and
+        all(stream.isatty() for stream in [sys.stdout, sys.stderr])
+    ):
+        stderr_wrapper = colorama.AnsiToWin32(sys.stderr, autoreset=False, convert=None, strip=None)
+        stdout_wrapper = colorama.AnsiToWin32(sys.stdout, autoreset=False, convert=None, strip=None)
+        sys.stderr = stderr_wrapper.stream
+        sys.stdout = stdout_wrapper.stream
+        colorama.init(wrap=False)
+    elif os.name != "nt":
+        colorama.init()
     os.environ["PIP_DISABLE_PIP_VERSION_CHECK"] = str("1")
     os.environ["PYTHONIOENCODING"] = str("utf-8")
     parsed = handle_parsed_args(parsed)