diff --git a/.github/workflows/forward-compatibility.yml b/.github/workflows/forward-compatibility.yml
new file mode 100644
index 000000000000..e5d8bb16eff1
--- /dev/null
+++ b/.github/workflows/forward-compatibility.yml
@@ -0,0 +1,64 @@
+name: Forward Compatibility
+
+on:
+  push:
+    paths:
+      - .github/workflows/forward-compatibility.yml
+  schedule:
+  - cron: '0 3 * * *'
+  workflow_dispatch:
+
+permissions: {}
+
+concurrency:
+  group: ${{ github.workflow }}-${{ github.ref }}-${{ github.event_name }}
+  cancel-in-progress: ${{ github.ref != 'refs/heads/master' }}
+
+env:
+  TRAVIS_OS_NAME: linux
+  SPEC_SPLIT_DOTS: 160
+
+jobs:
+  # Test against *each* supported Crystal version for forward compatibility.
+  #
+  # This workflow runs on a nightly schedule on `master`.
+  # It can also be dispatched manually when necessary.
+  #
+  # We run a basic version of this test on every commit which covers only the earliest and latest supported versions in `linux.yml#x86_64-gnu-test`.
+  x86_64-gnu-test-forward_compatibility:
+    env:
+      ARCH: x86_64
+      ARCH_CMD: linux64
+      DOCKER_TEST_PREFIX: crystallang/crystal:${{ matrix.crystal_bootstrap_version }}
+    runs-on: ubuntu-latest
+    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]
+        flags: [""]
+        include:
+          # libffi is only available starting from the 1.2.2 build images
+          - crystal_bootstrap_version: 1.1.1
+            flags: "FLAGS=-Dwithout_ffi USE_PCRE1=true"
+          - crystal_bootstrap_version: 1.2.2
+            flags: "USE_PCRE1=true"
+          - crystal_bootstrap_version: 1.3.2
+            flags: "USE_PCRE1=true"
+          - crystal_bootstrap_version: 1.4.1
+            flags: "USE_PCRE1=true"
+          - crystal_bootstrap_version: 1.5.1
+            flags: "USE_PCRE1=true"
+          - crystal_bootstrap_version: 1.6.2
+            flags: "USE_PCRE1=true"
+    steps:
+      - name: Download Crystal source
+        uses: actions/checkout@v4
+
+      - name: Prepare System
+        run: bin/ci prepare_system
+
+      - name: Prepare Build
+        run: bin/ci prepare_build
+
+      - name: Test
+        run: ${{ matrix.flags }} bin/ci build
diff --git a/.github/workflows/linux.yml b/.github/workflows/linux.yml
index aff46c8d76be..2d7852f06965 100644
--- a/.github/workflows/linux.yml
+++ b/.github/workflows/linux.yml
@@ -13,6 +13,10 @@ env:
   SPEC_SPLIT_DOTS: 160
 
 jobs:
+  # Test against latest release and the earliest supported Crystal version for forward compatibility.
+  #
+  # A more advanced test which runs against *each* supported version is available in `forward-compatibility.yml` and
+  # runs regularly on a nightly schedule.
   x86_64-gnu-test:
     env:
       ARCH: x86_64
@@ -22,24 +26,12 @@ 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]
         flags: [""]
         include:
           # 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: 1.1.1
-            flags: "FLAGS=-Dwithout_ffi USE_PCRE1=true"
-          - crystal_bootstrap_version: 1.2.2
-            flags: "USE_PCRE1=true"
-          - crystal_bootstrap_version: 1.3.2
-            flags: "USE_PCRE1=true"
-          - crystal_bootstrap_version: 1.4.1
-            flags: "USE_PCRE1=true"
-          - crystal_bootstrap_version: 1.5.1
-            flags: "USE_PCRE1=true"
-          - crystal_bootstrap_version: 1.6.2
-            flags: "USE_PCRE1=true"
+          - crystal_bootstrap_version: 1.15.1 # LATEST RELEASE
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v4
diff --git a/scripts/release-update.sh b/scripts/release-update.sh
index b6216ce3d6df..ed2f8c111685 100755
--- a/scripts/release-update.sh
+++ b/scripts/release-update.sh
@@ -34,7 +34,9 @@ sed -i -E "s|crystal-[0-9.]+-[0-9]|crystal-$CRYSTAL_VERSION-1|g" bin/ci
 
 # Edit .github/workflows/*.yml to point to docker image
 # Update the patch version of the latest entry if same minor version to have only one item per minor version
-sed -i -E "/crystal_bootstrap_version:/ s/(, ${CRYSTAL_VERSION%.*}\.[0-9]*)?\]\$/, $CRYSTAL_VERSION]/" .github/workflows/linux.yml
+previous_release=$(grep -o -P '(?<=crystal_bootstrap_version: ).*(?= # LATEST RELEASE)' .github/workflows/linux.yml)
+sed -i -E "s/crystal_bootstrap_version: .+ # LATEST RELEASE/crystal_bootstrap_version: $CRYSTAL_VERSION # LATEST RELEASE/" .github/workflows/linux.yml
+sed -i -E "/crystal_bootstrap_version:/ s/(, ${previous_release%.*}\.[0-9]*)?\]\$/, $previous_release]/" .github/workflows/forward-compatibility.yml
 sed -i -E "s|crystallang/crystal:[0-9.]+|crystallang/crystal:$CRYSTAL_VERSION|g" .github/workflows/*.yml
 
 # Edit .github/workflows/*.yml to update version for install-crystal action