diff --git a/src/bootstrap/test.rs b/src/bootstrap/test.rs
index 43561fa4f2fc1..3d6d4065fe80c 100644
--- a/src/bootstrap/test.rs
+++ b/src/bootstrap/test.rs
@@ -1051,10 +1051,10 @@ impl Step for Compiletest {
         cmd.arg("--docck-python").arg(builder.python());
 
         if builder.config.build.ends_with("apple-darwin") {
-            // Force /usr/bin/python on macOS for LLDB tests because we're loading the
+            // Force /usr/bin/python3 on macOS for LLDB tests because we're loading the
             // LLDB plugin's compiled module which only works with the system python
             // (namely not Homebrew-installed python)
-            cmd.arg("--lldb-python").arg("/usr/bin/python");
+            cmd.arg("--lldb-python").arg("/usr/bin/python3");
         } else {
             cmd.arg("--lldb-python").arg(builder.python());
         }
diff --git a/src/ci/azure-pipelines/auto.yml b/src/ci/azure-pipelines/auto.yml
index 79a49fc48be72..74b7469ea27b7 100644
--- a/src/ci/azure-pipelines/auto.yml
+++ b/src/ci/azure-pipelines/auto.yml
@@ -63,7 +63,7 @@ jobs:
 - job: macOS
   timeoutInMinutes: 600
   pool:
-    vmImage: macos-10.13
+    vmImage: macos-10.15
   steps:
   - template: steps/run.yml
   strategy:
diff --git a/src/ci/azure-pipelines/steps/run.yml b/src/ci/azure-pipelines/steps/run.yml
index f536388b25b96..1532608f0c020 100644
--- a/src/ci/azure-pipelines/steps/run.yml
+++ b/src/ci/azure-pipelines/steps/run.yml
@@ -48,10 +48,6 @@ steps:
   displayName: Install clang
   condition: and(succeeded(), not(variables.SKIP_JOB))
 
-- bash: src/ci/scripts/switch-xcode.sh
-  displayName: Switch to Xcode 9.3
-  condition: and(succeeded(), not(variables.SKIP_JOB))
-
 - bash: src/ci/scripts/install-wix.sh
   displayName: Install wix
   condition: and(succeeded(), not(variables.SKIP_JOB))
diff --git a/src/ci/azure-pipelines/try.yml b/src/ci/azure-pipelines/try.yml
index b6177b2cc9b25..f8ddf0eb46cfd 100644
--- a/src/ci/azure-pipelines/try.yml
+++ b/src/ci/azure-pipelines/try.yml
@@ -25,7 +25,7 @@ jobs:
 # - job: macOS
 #   timeoutInMinutes: 600
 #   pool:
-#     vmImage: macos-10.13
+#     vmImage: macos-10.15
 #   steps:
 #   - template: steps/run.yml
 #   strategy:
diff --git a/src/ci/scripts/install-clang.sh b/src/ci/scripts/install-clang.sh
index e16a4814197b3..c242f5d456269 100755
--- a/src/ci/scripts/install-clang.sh
+++ b/src/ci/scripts/install-clang.sh
@@ -19,9 +19,7 @@ if isMacOS; then
     # native clang is configured to use the correct path, but our custom one
     # doesn't. This sets the SDKROOT environment variable to the SDK so that
     # our own clang can figure out the correct include path on its own.
-    if ! [[ -d "/usr/include" ]]; then
-        ciCommandSetEnv SDKROOT "$(xcrun --sdk macosx --show-sdk-path)"
-    fi
+    ciCommandSetEnv SDKROOT "$(xcrun --sdk macosx --show-sdk-path)"
 
     # Configure `AR` specifically so rustbuild doesn't try to infer it as
     # `clang-ar` by accident.
diff --git a/src/ci/scripts/switch-xcode.sh b/src/ci/scripts/switch-xcode.sh
deleted file mode 100755
index 2cbb2ddbc7046..0000000000000
--- a/src/ci/scripts/switch-xcode.sh
+++ /dev/null
@@ -1,13 +0,0 @@
-#!/bin/bash
-# Switch to XCode 9.3 on OSX since it seems to be the last version that supports
-# i686-apple-darwin. We'll eventually want to upgrade this and it will probably
-# force us to drop i686-apple-darwin, but let's keep the wheels turning for now.
-
-set -euo pipefail
-IFS=$'\n\t'
-
-source "$(cd "$(dirname "$0")" && pwd)/../shared.sh"
-
-if isMacOS; then
-    sudo xcode-select --switch /Applications/Xcode_9.3.app
-fi