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