diff --git a/.github/workflows/__with-checkout-path.yml b/.github/workflows/__with-checkout-path.yml
index 0636bb88a1..95ac46a1a4 100644
--- a/.github/workflows/__with-checkout-path.yml
+++ b/.github/workflows/__with-checkout-path.yml
@@ -24,47 +24,10 @@ jobs:
     strategy:
       matrix:
         include:
-        - os: ubuntu-latest
-          version: stable-20210308
         - os: macos-latest
-          version: stable-20210308
-        - os: windows-2019
-          version: stable-20210308
-        - os: ubuntu-latest
-          version: stable-20210319
-        - os: macos-latest
-          version: stable-20210319
-        - os: windows-2019
-          version: stable-20210319
-        - os: ubuntu-latest
-          version: stable-20210809
-        - os: macos-latest
-          version: stable-20210809
-        - os: windows-2019
-          version: stable-20210809
-        - os: ubuntu-latest
-          version: cached
-        - os: macos-latest
-          version: cached
-        - os: windows-2019
-          version: cached
-        - os: ubuntu-latest
-          version: latest
-        - os: macos-latest
-          version: latest
-        - os: windows-2019
-          version: latest
-        - os: windows-2022
-          version: latest
-        - os: ubuntu-latest
-          version: nightly-latest
-        - os: macos-latest
-          version: nightly-latest
-        - os: windows-2019
-          version: nightly-latest
-        - os: windows-2022
           version: nightly-latest
     name: Use a custom `checkout_path`
+    timeout-minutes: 30
     runs-on: ${{ matrix.os }}
     steps:
     - name: Check out repository
@@ -94,7 +57,7 @@ jobs:
 
         $CODEQL_RUNNER x/y/z/some-path/tests/multi-language-repo/build.sh &
         PID=$!
-        sleep 60
+        sleep 300
 
         ps -ef
 
diff --git a/pr-checks/checks/with-checkout-path.yml b/pr-checks/checks/with-checkout-path.yml
index ba57f82d8e..932f8968c5 100644
--- a/pr-checks/checks/with-checkout-path.yml
+++ b/pr-checks/checks/with-checkout-path.yml
@@ -3,7 +3,7 @@ description: "Checks that a custom `checkout_path` will find the proper commit_o
 # Build tracing currently does not support Windows 2022, so use `windows-2019` instead of
 # `windows-latest`.
 # Must test on all three platforms since this test does path manipulation
-os: [ubuntu-latest, macos-latest, windows-2019]
+os: [macos-latest]
 env:
   DOTNET_CLI_TELEMETRY_OPTOUT: true
 steps:
@@ -29,7 +29,7 @@ steps:
 
       $CODEQL_RUNNER x/y/z/some-path/tests/multi-language-repo/build.sh &
       PID=$!
-      sleep 60
+      sleep 300
 
       ps -ef
 
diff --git a/pr-checks/sync.py b/pr-checks/sync.py
index beb1d4dfd4..acbad76854 100644
--- a/pr-checks/sync.py
+++ b/pr-checks/sync.py
@@ -2,20 +2,9 @@
 import os
 
 defaultTestVersions = [
-    # The oldest supported CodeQL version: 2.4.5. If bumping, update `CODEQL_MINIMUM_VERSION` in `codeql.ts`
-    "stable-20210308",
-    # The last CodeQL release in the 2.4 series: 2.4.6.
-    "stable-20210319",
-    # The last CodeQL release in the 2.5 series: 2.5.9.
-    "stable-20210809",
-    # The version of CodeQL currently in the toolcache. Typically either the latest release or the one before.
-    "cached",
-    # The latest release of CodeQL.
-    "latest",
-    # A nightly build directly from the our private repo, built in the last 24 hours.
     "nightly-latest"
 ]
-defaultOperatingSystems = ["ubuntu-latest", "macos-latest", "windows-2019"]
+defaultOperatingSystems = ["macos-latest"]
 header = """# Warning: This file is generated automatically, and should not be modified.
 # Instead, please modify the template in the pr-checks directory and run:
 #     pip install ruamel.yaml && python3 sync.py
@@ -69,14 +58,6 @@ def writeHeader(checkStream):
                 'os': os,
                 'version': version
             })
-            if (version == 'latest' or version == 'nightly-latest') and os == 'windows-2019':
-                # New versions of the CLI should also work with Windows Server 2022.
-                # Once all versions of the CLI that we test against work with Windows Server 2022,
-                # we should remove this logic and instead just add windows-2022 to the test matrix.
-                matrix.append({
-                    'os': 'windows-2022',
-                    'version': version
-                })
 
     checkJob = {
         'strategy': {