Resolve latest patches per major Gradle version in CI workflow

.github/scripts/dependency_age.py

@@ -20,6 +20,9 @@
 MAVEN_SEARCH_URL = "https://search.maven.org/solrsearch/select"
 MAVEN_REPO_URL = "https://repo1.maven.org/maven2"
 DEFAULT_MIN_AGE_HOURS = 48
+# Oldest Gradle major release we track a latest-patch for. The legacy Gradle instrumentation
+# targets Gradle 3.0+ (the `gradle-3.0` module), so older majors are never exercised.
+OLDEST_TRACKED_GRADLE_MAJOR = 3
 
 
 @dataclass(frozen=True)
@@ -171,7 +174,7 @@ def select_gradle_release(args: argparse.Namespace) -> int:
         if published_at <= cutoff:
             candidates.append(Candidate(version=version, published_at=published_at))
 
-    return emit_selection_result(
+    status = emit_selection_result(
         label="Gradle",
         github_output=args.github_output,
         candidates=candidates,
@@ -181,6 +184,26 @@ def select_gradle_release(args: argparse.Namespace) -> int:
         current_version=args.current_version,
     )
 
+    # Also emit the newest eligible stable patch for every major release, as ready-to-write
+    # `gradle.latest.<major>=<version>` property lines. The Gradle smoke tests use these to
+    # resolve the "oldest" Gradle version dynamically (the latest patch of the major that the
+    # current Gradle TestKit still supports), so the tested floor follows Gradle automatically
+    # instead of being hardcoded.
+    latest_by_major = {
+        major: candidate
+        for major, candidate in newest_stable_per_major(candidates).items()
+        if major >= OLDEST_TRACKED_GRADLE_MAJOR
+    }
+    block = "\n".join(
+        f"gradle.latest.{major}={candidate.version}"
+        for major, candidate in sorted(latest_by_major.items())
+    )
+    emit_outputs({"latest_by_major": block}, args.github_output)
+    for major, candidate in sorted(latest_by_major.items()):
+        print(f"Latest eligible stable Gradle {major}.x: {candidate.version}")
+
+    return status
+
 
 # select latest Maven artifact release that is at least MIN_DEPENDENCY_AGE_HOURS hours old
 def select_maven_release(args: argparse.Namespace) -> int:
@@ -283,6 +306,27 @@ def _version_sort_key(version: str) -> tuple:
     return (tuple(release), not bool(prerelease), tuple(prerelease))
 
 
+# parse the leading integer of a version string as its major release number
+def _major_version(version: str) -> int:
+    match = re.match(r"\s*(\d+)", version)
+    if not match:
+        raise ValueError(f"Cannot determine major version from '{version}'")
+    return int(match.group(1))
+
+
+# group candidates by major release and keep the newest one in each group
+def newest_stable_per_major(candidates: list[Candidate]) -> dict[int, Candidate]:
+    newest: dict[int, Candidate] = {}
+    for candidate in candidates:
+        major = _major_version(candidate.version)
+        current = newest.get(major)
+        if current is None or _version_sort_key(candidate.version) > _version_sort_key(
+            current.version
+        ):
+            newest[major] = candidate
+    return newest
+
+
 # emit selection result to stdout and GitHub Actions output file for select-gradle and select-maven
 def emit_selection_result(
     *,

.github/workflows/update-smoke-test-latest-versions.yaml

@@ -35,9 +35,9 @@ jobs:
           gradle_props="dd-smoke-tests/gradle/src/test/resources/latest-tool-versions.properties"
           maven_props="dd-smoke-tests/maven/src/test/resources/latest-tool-versions.properties"
           get_prop() { grep "^$1=" "$2" 2>/dev/null | cut -d= -f2 || true; }
-          echo "gradle_version=$(get_prop gradle.version "$gradle_props")" >> "$GITHUB_OUTPUT"
-          echo "maven_version=$(get_prop maven.version "$maven_props")" >> "$GITHUB_OUTPUT"
-          echo "surefire_version=$(get_prop maven-surefire.version "$maven_props")" >> "$GITHUB_OUTPUT"
+          echo "gradle_version=$(get_prop gradle.latest "$gradle_props")" >> "$GITHUB_OUTPUT"
+          echo "maven_version=$(get_prop maven.latest "$maven_props")" >> "$GITHUB_OUTPUT"
+          echo "surefire_version=$(get_prop maven-surefire.latest "$maven_props")" >> "$GITHUB_OUTPUT"
 
       - name: Resolve latest eligible Gradle version
         id: gradle
@@ -77,6 +77,7 @@ jobs:
         env:
           GRADLE_VERSION: ${{ steps.gradle.outputs.version }}
           GRADLE_PUBLISHED: ${{ steps.gradle.outputs.published_at }}
+          GRADLE_LATEST_BY_MAJOR: ${{ steps.gradle.outputs.latest_by_major }}
           MAVEN_VERSION: ${{ steps.maven.outputs.version }}
           MAVEN_PUBLISHED: ${{ steps.maven.outputs.published_at }}
           SUREFIRE_VERSION: ${{ steps.surefire.outputs.version }}
@@ -96,14 +97,17 @@ jobs:
           printf '%s\n' \
             "# Pinned latest eligible stable versions (>=${MIN_DEPENDENCY_AGE_HOURS}h old) for CI Visibility Gradle smoke tests." \
             "# Updated automatically by the update-smoke-test-latest-versions workflow." \
-            "gradle.version=${GRADLE_VERSION}" \
+            "gradle.latest=${GRADLE_VERSION}" \
+            "# Latest eligible stable patch per Gradle major release. Used to resolve the \"oldest\" smoke-test" \
+            "# Gradle version (the latest patch of the oldest major the current TestKit supports)." \
+            "${GRADLE_LATEST_BY_MAJOR}" \
             > dd-smoke-tests/gradle/src/test/resources/latest-tool-versions.properties
 
           printf '%s\n' \
             "# Pinned latest eligible stable versions (>=${MIN_DEPENDENCY_AGE_HOURS}h old) for CI Visibility Maven smoke tests." \
             "# Updated automatically by the update-smoke-test-latest-versions workflow." \
-            "maven.version=${MAVEN_VERSION}" \
-            "maven-surefire.version=${SUREFIRE_VERSION}" \
+            "maven.latest=${MAVEN_VERSION}" \
+            "maven-surefire.latest=${SUREFIRE_VERSION}" \
             > dd-smoke-tests/maven/src/test/resources/latest-tool-versions.properties
 
       - name: Check for changes

dd-smoke-tests/gradle/src/test/java/datadog/smoketest/AbstractGradleTest.java

@@ -30,7 +30,8 @@
 @TestInstance(TestInstance.Lifecycle.PER_CLASS)
 public abstract class AbstractGradleTest extends CiVisibilitySmokeTest {
 
-  protected static final String LATEST_GRADLE_VERSION = getLatestGradleVersion();
+  private static final Properties TOOL_VERSIONS = loadToolVersions();
+  protected static final String LATEST_GRADLE_VERSION = toolVersion("gradle.latest");
 
   // test resources use this instead of ".gradle" to avoid unwanted evaluation
   private static final String GRADLE_TEST_RESOURCE_EXTENSION = ".gradleTest";
@@ -247,7 +248,7 @@ protected void givenConfigurationCacheIsCompatibleWithCurrentPlatform(
     }
   }
 
-  private static String getLatestGradleVersion() {
+  private static Properties loadToolVersions() {
     Properties properties = new Properties();
     try (InputStream stream =
         AbstractGradleTest.class
@@ -261,6 +262,18 @@ private static String getLatestGradleVersion() {
     } catch (IOException e) {
       throw new RuntimeException(e);
     }
-    return properties.getProperty("gradle.version");
+    return properties;
+  }
+
+  protected static String toolVersion(String key) {
+    String value = TOOL_VERSIONS.getProperty(key);
+    if (value == null) {
+      throw new IllegalStateException(
+          "Missing '"
+              + key
+              + "' in latest-tool-versions.properties; re-run the "
+              + "update-smoke-test-latest-versions workflow.");
+    }
+    return value;
   }
 }

dd-smoke-tests/gradle/src/test/java/datadog/smoketest/GradleDaemonSmokeTest.java

@@ -63,7 +63,7 @@ void stopGradleTestKitDaemons() {
 
   @TableTest({
     "scenario                    | gradleVersion | projectName                                      | successExpected | expectedTraces | expectedCoverages",
-    "succeed-old-gradle-4.10     | 4.10          | test-succeed-old-gradle                          | true            | 5              | 1                ",
+    "succeed-old-gradle-oldest   | oldest        | test-succeed-old-gradle                          | true            | 5              | 1                ",
     "succeed-legacy              | 7.6.4         | test-succeed-legacy-instrumentation              | true            | 5              | 1                ",
     "succeed-multi-module-legacy | 7.6.4         | test-succeed-multi-module-legacy-instrumentation | true            | 7              | 2                ",
     "succeed-multi-forks-legacy  | 7.6.4         | test-succeed-multi-forks-legacy-instrumentation  | true            | 6              | 2                ",
@@ -117,9 +117,8 @@ void testNew(
       int expectedTraces,
       int expectedCoverages)
       throws IOException {
-    String resolvedGradleVersion = resolveLatest(gradleVersion);
     runGradleTest(
-        resolvedGradleVersion,
+        gradleVersion,
         projectName,
         configurationCache,
         successExpected,
@@ -159,8 +158,27 @@ void testJunit4ClassOrdering(
     verifyTestOrder(mockBackend.waitForEvents(eventsNumber), expectedOrder);
   }
 
-  private static String resolveLatest(String gradleVersion) {
-    return "latest".equals(gradleVersion) ? LATEST_GRADLE_VERSION : gradleVersion;
+  // Resolves the symbolic versions used in the scenario tables:
+  //  - "latest": the newest eligible Gradle release
+  //  - "oldest": the latest patch of the oldest major the current Gradle TestKit still supports
+  // Any other value is treated as a concrete version and returned as-is.
+  private static String resolveVersion(String gradleVersion) {
+    if ("latest".equals(gradleVersion)) {
+      return LATEST_GRADLE_VERSION;
+    }
+    if ("oldest".equals(gradleVersion)) {
+      return oldestSupportedGradleVersion();
+    }
+    return gradleVersion;
+  }
+
+  private static String oldestSupportedGradleVersion() {
+    // The oldest major the current Gradle TestKit can run is dictated by Gradle itself; tracking it
+    // dynamically (rather than hardcoding a version) means the floor follows TestKit automatically.
+    // We test the latest patch of that major rather than its initial release for stability.
+    int oldestSupportedMajor =
+        DefaultGradleConnector.MINIMUM_SUPPORTED_GRADLE_VERSION.getMajorVersion();
+    return toolVersion("gradle.latest." + oldestSupportedMajor);
   }
 
   private static void givenGradleVersionIsSupportedByCurrentGradleTestKit(String gradleVersion) {
@@ -183,6 +201,7 @@ private void runGradleTest(
       int expectedTraces,
       int expectedCoverages)
       throws IOException {
+    gradleVersion = resolveVersion(gradleVersion);
     givenGradleVersionIsCompatibleWithCurrentJvm(gradleVersion);
     givenGradleVersionIsSupportedByCurrentGradleTestKit(gradleVersion);
     givenConfigurationCacheIsCompatibleWithCurrentPlatform(configurationCache);

dd-smoke-tests/gradle/src/test/resources/latest-tool-versions.properties

@@ -1,3 +1,12 @@
 # Pinned latest eligible stable versions (>=48h old) for CI Visibility Gradle smoke tests.
 # Updated automatically by the update-smoke-test-latest-versions workflow.
-gradle.version=9.5.1
+gradle.latest=9.5.1
+# Latest eligible stable patch per Gradle major release. Used to resolve the "oldest" smoke-test
+# Gradle version (the latest patch of the oldest major the current TestKit supports).
+gradle.latest.3=3.5.1
+gradle.latest.4=4.10.3
+gradle.latest.5=5.6.4
+gradle.latest.6=6.9.4
+gradle.latest.7=7.6.6
+gradle.latest.8=8.14.5
+gradle.latest.9=9.5.1

dd-smoke-tests/maven/src/test/java/datadog/smoketest/MavenSmokeTest.java

@@ -587,13 +587,13 @@ private static Properties loadLatestToolVersions() {
   }
 
   private static String getLatestMavenVersion() {
-    String version = loadLatestToolVersions().getProperty("maven.version");
+    String version = loadLatestToolVersions().getProperty("maven.latest");
     LOGGER.info("Will run the 'latest' tests with Maven version {}", version);
     return version;
   }
 
   private static String getLatestMavenSurefireVersion() {
-    String version = loadLatestToolVersions().getProperty("maven-surefire.version");
+    String version = loadLatestToolVersions().getProperty("maven-surefire.latest");
     LOGGER.info("Will run the 'latest' tests with Maven Surefire version {}", version);
     return version;
   }

dd-smoke-tests/maven/src/test/resources/latest-tool-versions.properties

@@ -1,4 +1,4 @@
 # Pinned latest eligible stable versions (>=48h old) for CI Visibility Maven smoke tests.
 # Updated automatically by the update-smoke-test-latest-versions workflow.
-maven.version=4.0.0-beta-3
-maven-surefire.version=3.5.5
+maven.latest=4.0.0-beta-3
+maven-surefire.latest=3.5.5