diff --git a/rewrite-core/src/main/java/org/openrewrite/semver/LatestRelease.java b/rewrite-core/src/main/java/org/openrewrite/semver/LatestRelease.java
index 947cf16e795..18fc5d4b12e 100644
--- a/rewrite-core/src/main/java/org/openrewrite/semver/LatestRelease.java
+++ b/rewrite-core/src/main/java/org/openrewrite/semver/LatestRelease.java
@@ -100,12 +100,14 @@ static int countVersionParts(String version) {
     public int compare(@Nullable String currentVersion, String v1, String v2) {
         if (v1.equalsIgnoreCase(v2)) {
             return 0;
-        }
-        if (v1.equalsIgnoreCase("RELEASE")) {
-            return v2.equalsIgnoreCase("LATEST") ? -1 : 1;
-        }
-        if (v1.equalsIgnoreCase("LATEST")) {
+        } else if (v1.equalsIgnoreCase("LATEST")) {
+            return 1;
+        } else if (v2.equalsIgnoreCase("LATEST")) {
+            return -1;
+        } else if (v1.equalsIgnoreCase("RELEASE")) {
             return 1;
+        } else if (v2.equalsIgnoreCase("RELEASE")) {
+            return -1;
         }
 
         String nv1 = normalizeVersion(v1);
diff --git a/rewrite-core/src/test/java/org/openrewrite/semver/LatestReleaseTest.java b/rewrite-core/src/test/java/org/openrewrite/semver/LatestReleaseTest.java
index b9acf749a8f..fc92187fda7 100644
--- a/rewrite-core/src/test/java/org/openrewrite/semver/LatestReleaseTest.java
+++ b/rewrite-core/src/test/java/org/openrewrite/semver/LatestReleaseTest.java
@@ -107,10 +107,12 @@ void preReleases() {
     @Test
     void releaseOrLatestKeyword_beatsEverything() {
         assertThat(latestRelease.compare(null, "RELEASE", "1.2.3")).isPositive();
+        assertThat(latestRelease.compare(null, "1.2.3", "RELEASE")).isNegative();
         assertThat(latestRelease.compare(null, "RELEASE", "999.999.999")).isPositive();
         assertThat(latestRelease.compare(null, "RELEASE", "RELEASE")).isZero();
 
         assertThat(latestRelease.compare(null, "LATEST", "1.2.3")).isPositive();
+        assertThat(latestRelease.compare(null, "1.2.3", "LATEST")).isNegative();
         assertThat(latestRelease.compare(null, "LATEST", "999.999.999")).isPositive();
         assertThat(latestRelease.compare(null, "LATEST", "LATEST")).isZero();