diff --git a/.cirrus.yml b/.cirrus.yml
index 04420c306d..3b0b6bc8d9 100644
--- a/.cirrus.yml
+++ b/.cirrus.yml
@@ -219,16 +219,16 @@ alpine_task:
 
 # Apple doesn't publish official long-term support timelines.
 # We aim to support both the current and previous macOS release.
-macos_big_sur_task:
+macos_monterey_task:
   macos_instance:
-    image: big-sur-xcode-12.5
+    image: monterey-xcode-13.1
   prepare_script: ./ci/macos/prepare.sh
   << : *CI_TEMPLATE
   << : *MACOS_RESOURCES_TEMPLATE
 
-macos_catalina_task:
+macos_big_sur_task:
   macos_instance:
-    image: catalina-xcode
+    image: big-sur-xcode-12.5
   prepare_script: ./ci/macos/prepare.sh
   << : *CI_TEMPLATE
   << : *MACOS_RESOURCES_TEMPLATE
diff --git a/ci/build.sh b/ci/build.sh
index 20ca3237cc..051d119f62 100755
--- a/ci/build.sh
+++ b/ci/build.sh
@@ -10,6 +10,11 @@ set -x
 # some problems with Catalina specifically, but it doesn't break anything on Big Sur either.
 if [[ "${CIRRUS_OS}" == "darwin" ]]; then
     export ZEEK_CI_CONFIGURE_FLAGS="${ZEEK_CI_CONFIGURE_FLAGS} --osx-sysroot=$(xcrun --show-sdk-path)"
+
+    # Starting with Monterey & Xcode 13.1 we need to help it find OpenSSL
+    if [ -d /usr/local/opt/openssl@1.1/lib/pkgconfig ]; then
+        export PKG_CONFIG_PATH=$PKG_CONFIG_PATH:/usr/local/opt/openssl@1.1/lib/pkgconfig
+    fi
 fi
 
 if [[ "${ZEEK_CI_CREATE_ARTIFACT}" != "1" ]]; then