diff --git a/libcxx/utils/ci/Dockerfile b/libcxx/utils/ci/Dockerfile
--- a/libcxx/utils/ci/Dockerfile
+++ b/libcxx/utils/ci/Dockerfile
@@ -54,9 +54,11 @@
 RUN locale-gen
 
 # Install Clang <latest>, <latest-1> and ToT, which are the ones we support.
-ENV LLVM_LATEST_VERSION=13
+# We also install <latest-2> to allow smooth CI transitions around release points.
+ENV LLVM_LATEST_VERSION=14
 RUN apt-get update && apt-get install -y lsb-release wget software-properties-common
 RUN wget https://apt.llvm.org/llvm.sh -O /tmp/llvm.sh
+RUN bash /tmp/llvm.sh $(($LLVM_LATEST_VERSION - 2)) # for CI transitions
 RUN bash /tmp/llvm.sh $(($LLVM_LATEST_VERSION - 1)) # previous release
 RUN bash /tmp/llvm.sh $LLVM_LATEST_VERSION          # latest release
 RUN bash /tmp/llvm.sh $(($LLVM_LATEST_VERSION + 1)) # current ToT