diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index 29a1df8e121..63d877e0b11 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -101,7 +101,7 @@ jobs:
   displayName: 'Verify src/azure-cli/requirements.*.Darwin.txt'
   condition: succeeded()
   pool:
-    vmImage: 'macOS-10.14'
+    vmImage: 'macOS-10.15'
 
   steps:
   - task: UsePythonVersion@0
@@ -576,7 +576,7 @@ jobs:
                   -e CLI_VERSION=$CLI_VERSION \
                   -e HOMEBREW_UPSTREAM_URL=$HOMEBREW_UPSTREAM_URL \
                   --name azurecli \
-                  python:3.6 \
+                  python:3.9 \
                   /mnt/scripts/run.sh
 
        # clean up
@@ -598,7 +598,7 @@ jobs:
   dependsOn: BuildHomebrewFormula
   condition: succeeded()
   pool:
-    vmImage: 'macOS-10.14'
+    vmImage: 'macOS-10.15'
   steps:
   - task: DownloadPipelineArtifact@1
     displayName: 'Download Metadata'
@@ -638,7 +638,7 @@ jobs:
   # condition: and(succeeded(), in(variables['Build.Reason'], 'IndividualCI', 'BatchedCI', 'Manual', 'Schedule'))
   condition: false
   pool:
-    vmImage: 'macOS-10.14'
+    vmImage: 'macOS-10.15'
   steps:
   - task: DownloadPipelineArtifact@1
     displayName: 'Download Metadata'