diff --git a/.circleci/config.yml b/.circleci/config.yml
index 5ee28a62d9fe..133de26cabc0 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -12,7 +12,7 @@ parameters:
   previous_crystal_base_url:
     description: "Prefix for URLs to Crystal bootstrap compiler"
     type: string
-    default: "https://github.com/crystal-lang/crystal/releases/download/1.16.1/crystal-1.16.1-1"
+    default: "https://github.com/crystal-lang/crystal/releases/download/1.16.2/crystal-1.16.2-1"
 
 defaults:
   environment: &env
diff --git a/.github/workflows/aarch64-github.yml b/.github/workflows/aarch64-github.yml
index 6457fc71f4d5..f88cb18ed0b5 100644
--- a/.github/workflows/aarch64-github.yml
+++ b/.github/workflows/aarch64-github.yml
@@ -28,7 +28,7 @@ jobs:
       - name: Install Crystal
         uses: crystal-lang/install-crystal@v1
         with:
-          crystal: "1.16.1"
+          crystal: "1.16.2"
 
       - name: Cross-compile Crystal
         run: make target=aarch64-linux-gnu release=1
diff --git a/.github/workflows/forward-compatibility.yml b/.github/workflows/forward-compatibility.yml
index 212d1c6b0a16..7b919760acae 100644
--- a/.github/workflows/forward-compatibility.yml
+++ b/.github/workflows/forward-compatibility.yml
@@ -34,7 +34,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        crystal_bootstrap_version: [1.7.3, 1.8.2, 1.9.2, 1.10.1, 1.11.2, 1.12.2, 1.13.3, 1.14.1, 1.15.1, 1.16.1]
+        crystal_bootstrap_version: [1.7.3, 1.8.2, 1.9.2, 1.10.1, 1.11.2, 1.12.2, 1.13.3, 1.14.1, 1.15.1, 1.16.2]
         flags: [""]
         include:
           # libffi is only available starting from the 1.2.2 build images
diff --git a/.github/workflows/interpreter.yml b/.github/workflows/interpreter.yml
index 11adc6d8b727..36293c1b5058 100644
--- a/.github/workflows/interpreter.yml
+++ b/.github/workflows/interpreter.yml
@@ -15,7 +15,7 @@ jobs:
   test-interpreter_spec:
     runs-on: ubuntu-24.04
     container:
-      image: crystallang/crystal:1.16.1-build
+      image: crystallang/crystal:1.16.2-build
     name: "Test Interpreter"
     steps:
       - uses: actions/checkout@v4
@@ -26,7 +26,7 @@ jobs:
   build-interpreter:
     runs-on: ubuntu-24.04
     container:
-      image: crystallang/crystal:1.16.1-build
+      image: crystallang/crystal:1.16.2-build
     name: Build interpreter
     steps:
       - uses: actions/checkout@v4
@@ -45,7 +45,7 @@ jobs:
     needs: build-interpreter
     runs-on: ubuntu-24.04
     container:
-      image: crystallang/crystal:1.16.1-build
+      image: crystallang/crystal:1.16.2-build
     strategy:
       matrix:
         part: [0, 1, 2, 3]
@@ -69,7 +69,7 @@ jobs:
     needs: build-interpreter
     runs-on: ubuntu-24.04
     container:
-      image: crystallang/crystal:1.16.1-build
+      image: crystallang/crystal:1.16.2-build
     name: "Test primitives_spec with interpreter"
     steps:
       - uses: actions/checkout@v4
diff --git a/.github/workflows/linux.yml b/.github/workflows/linux.yml
index b4129ba507b7..d188af0f5487 100644
--- a/.github/workflows/linux.yml
+++ b/.github/workflows/linux.yml
@@ -31,7 +31,7 @@ jobs:
           # libffi is only available starting from the 1.2.2 build images
           - crystal_bootstrap_version: 1.0.0
             flags: "FLAGS=-Dwithout_ffi USE_PCRE1=true"
-          - crystal_bootstrap_version: 1.16.1 # LATEST RELEASE
+          - crystal_bootstrap_version: 1.16.2 # LATEST RELEASE
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v4
diff --git a/.github/workflows/llvm.yml b/.github/workflows/llvm.yml
index 1e05761aa31e..4d8929492a82 100644
--- a/.github/workflows/llvm.yml
+++ b/.github/workflows/llvm.yml
@@ -56,7 +56,7 @@ jobs:
       - name: Install Crystal
         uses: crystal-lang/install-crystal@v1
         with:
-          crystal: "1.16.1"
+          crystal: "1.16.2"
 
       - name: Build libllvm_ext
         run: make -B deps
diff --git a/.github/workflows/openssl.yml b/.github/workflows/openssl.yml
index 76e3bd681e93..c35fe3605bf9 100644
--- a/.github/workflows/openssl.yml
+++ b/.github/workflows/openssl.yml
@@ -27,7 +27,7 @@ jobs:
   libssl_test:
     runs-on: ubuntu-latest
     name: "${{ matrix.pkg }}"
-    container: crystallang/crystal:1.16.1-alpine
+    container: crystallang/crystal:1.16.2-alpine
     strategy:
       fail-fast: false
       matrix:
diff --git a/.github/workflows/regex-engine.yml b/.github/workflows/regex-engine.yml
index fa2a26310bdd..799ad461d5be 100644
--- a/.github/workflows/regex-engine.yml
+++ b/.github/workflows/regex-engine.yml
@@ -29,7 +29,7 @@ jobs:
   pcre:
     runs-on: ubuntu-latest
     name: "PCRE"
-    container: crystallang/crystal:1.16.1-alpine
+    container: crystallang/crystal:1.16.2-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v4
@@ -44,7 +44,7 @@ jobs:
   pcre2:
     runs-on: ubuntu-latest
     name: "PCRE2"
-    container: crystallang/crystal:1.16.1-alpine
+    container: crystallang/crystal:1.16.2-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v4
diff --git a/.github/workflows/wasm32.yml b/.github/workflows/wasm32.yml
index 354d1c76c78a..322e05e3fe8c 100644
--- a/.github/workflows/wasm32.yml
+++ b/.github/workflows/wasm32.yml
@@ -14,7 +14,7 @@ env:
 jobs:
   wasm32-test:
     runs-on: ubuntu-24.04
-    container: crystallang/crystal:1.16.1-build
+    container: crystallang/crystal:1.16.2-build
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v4
diff --git a/.github/workflows/win_build_portable.yml b/.github/workflows/win_build_portable.yml
index 78f3d6ca316c..b88bfed625dd 100644
--- a/.github/workflows/win_build_portable.yml
+++ b/.github/workflows/win_build_portable.yml
@@ -27,7 +27,7 @@ jobs:
         uses: crystal-lang/install-crystal@v1
         id: install-crystal
         with:
-          crystal: "1.16.1"
+          crystal: "1.16.2"
 
       - name: Download Crystal source
         uses: actions/checkout@v4
diff --git a/bin/ci b/bin/ci
index 58d0f5bc00fe..5fb7ffb2ee63 100755
--- a/bin/ci
+++ b/bin/ci
@@ -135,8 +135,8 @@ format() {
 prepare_build() {
   on_linux verify_linux_environment
 
-  on_osx curl -L https://github.com/crystal-lang/crystal/releases/download/1.16.1/crystal-1.16.1-1-darwin-universal.tar.gz -o ~/crystal.tar.gz
-  on_osx 'pushd ~;gunzip -c ~/crystal.tar.gz | tar xopf -;mv crystal-1.16.1-1 crystal;popd'
+  on_osx curl -L https://github.com/crystal-lang/crystal/releases/download/1.16.2/crystal-1.16.2-1-darwin-universal.tar.gz -o ~/crystal.tar.gz
+  on_osx 'pushd ~;gunzip -c ~/crystal.tar.gz | tar xopf -;mv crystal-1.16.2-1 crystal;popd'
 
   # These commands may take a few minutes to run due to the large size of the repositories.
   # This restriction has been made on GitHub's request because updating shallow
@@ -189,7 +189,7 @@ with_build_env() {
 
   on_linux verify_linux_environment
 
-  export DOCKER_TEST_PREFIX="${DOCKER_TEST_PREFIX:=crystallang/crystal:1.16.1}"
+  export DOCKER_TEST_PREFIX="${DOCKER_TEST_PREFIX:=crystallang/crystal:1.16.2}"
 
   case $ARCH in
     x86_64)
diff --git a/scripts/release-update.sh b/scripts/release-update.sh
index 68a4c2ef622e..53572ccc556b 100755
--- a/scripts/release-update.sh
+++ b/scripts/release-update.sh
@@ -24,9 +24,12 @@ rm -f src/SOURCE_DATE_EPOCH
 
 # Truncate CHANGELOG.md
 sed -i -E '/^## \[/,/^## Previous Releases/{/^## Previous Releases/!d}' CHANGELOG.md
-sed -i -E "/For information on prior releases/{ N;a\
-* [${CRYSTAL_VERSION%.*}](https://github.com/crystal-lang/crystal/blob/release/${CRYSTAL_VERSION%.*}/CHANGELOG.md)
-}" CHANGELOG.md
+
+if ! grep -q https://github.com/crystal-lang/crystal/blob/release/${CRYSTAL_VERSION%.*}/CHANGELOG.md CHANGELOG.md; then
+  sed -i -E "/For information on prior releases/{ N;a\
+  * [${CRYSTAL_VERSION%.*}](https://github.com/crystal-lang/crystal/blob/release/${CRYSTAL_VERSION%.*}/CHANGELOG.md)
+  }" CHANGELOG.md
+fi
 
 # Edit PREVIOUS_CRYSTAL_BASE_URL in .circleci/config.yml
 sed -i -E "s|[0-9.]+/crystal-[0-9.]+-[0-9]|$CRYSTAL_VERSION/crystal-$CRYSTAL_VERSION-1|g" .circleci/config.yml
diff --git a/shell.nix b/shell.nix
index e1aef7793b4b..a3e9690ee069 100644
--- a/shell.nix
+++ b/shell.nix
@@ -53,18 +53,18 @@ let
   # Hashes obtained using `nix-prefetch-url --unpack <url>`
   latestCrystalBinary = genericBinary ({
     x86_64-darwin = {
-      url = "https://github.com/crystal-lang/crystal/releases/download/1.16.1/crystal-1.16.1-1-darwin-universal.tar.gz";
-      sha256 = "sha256:1xpqc6063c50p1780ksr6m4gnk1kwf3nl6hf8aj0gjliy2qfn95i";
+      url = "https://github.com/crystal-lang/crystal/releases/download/1.16.2/crystal-1.16.2-1-darwin-universal.tar.gz";
+      sha256 = "sha256:1jgy7035bid7gg413yawl4v8wdacjs8hd9y6l04gvvajd3zc7asq";
     };
 
     aarch64-darwin = {
-      url = "https://github.com/crystal-lang/crystal/releases/download/1.16.1/crystal-1.16.1-1-darwin-universal.tar.gz";
-      sha256 = "sha256:1xpqc6063c50p1780ksr6m4gnk1kwf3nl6hf8aj0gjliy2qfn95i";
+      url = "https://github.com/crystal-lang/crystal/releases/download/1.16.2/crystal-1.16.2-1-darwin-universal.tar.gz";
+      sha256 = "sha256:1jgy7035bid7gg413yawl4v8wdacjs8hd9y6l04gvvajd3zc7asq";
     };
 
     x86_64-linux = {
-      url = "https://github.com/crystal-lang/crystal/releases/download/1.16.1/crystal-1.16.1-1-linux-x86_64.tar.gz";
-      sha256 = "sha256:0dbdi011nlzqfslzjs5z25pa62k532886mx1lrwaggr06a7z2mhd";
+      url = "https://github.com/crystal-lang/crystal/releases/download/1.16.2/crystal-1.16.2-1-linux-x86_64.tar.gz";
+      sha256 = "sha256:14d7p6lfyiccqj6ymlrz3zpjh8idrg179pw62nlcak4sail80ijk";
     };
   }.${pkgs.stdenv.system});