diff --git a/.github/workflows/update-gradle-versions.yml b/.github/workflows/update-gradle-versions.yml
new file mode 100644
index 00000000..3583fba4
--- /dev/null
+++ b/.github/workflows/update-gradle-versions.yml
@@ -0,0 +1,41 @@
+name: Update Gradle Versions
+
+on:
+  schedule:
+    - cron: '0 9 * * 1'
+  workflow_dispatch:
+
+permissions:
+  contents: write
+  pull-requests: write
+
+jobs:
+  update-gradle-versions:
+    runs-on: ubuntu-latest
+    timeout-minutes: 60
+
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v6
+
+      - name: Set up JDK 21
+        uses: actions/setup-java@v5
+        with:
+          distribution: temurin
+          java-version: '21'
+
+      - name: Update bundled Gradle wrappers
+        run: ./scripts/update_gradle_versions.sh
+
+      - name: Run tests
+        run: ./gradlew :project-generator:test :cli:test
+
+      - name: Create pull request
+        uses: peter-evans/create-pull-request@v7
+        with:
+          commit-message: Update bundled Gradle versions
+          title: Update bundled Gradle versions
+          body: |
+            Updates the bundled Gradle wrapper resources and README to the latest three minor lines for Gradle 9 and Gradle 8 from the official Gradle versions feed.
+          branch: codex/update-gradle-versions
+          delete-branch: true
diff --git a/README.md b/README.md
index 8dc53748..a81ba327 100644
--- a/README.md
+++ b/README.md
@@ -45,7 +45,7 @@ Then, you can use the versions.yaml in the `generate-project` command:
 - `--classes-module-type`: fixed (default), random
 - `--type-of-string-resources`: normal (default), large
 - `--generate-unit-test`: Generate unit tests (default: false)
-- `--gradle`: gradle_8_14_3, gradle_9_1_0, gradle_9_2_0, gradle_9_3_0, gradle_9_3_1, gradle_9_4_0 (default: gradle_9_4_0)
+- `--gradle`: gradle_9_4_1, gradle_9_3_1, gradle_9_2_1, gradle_8_14_4, gradle_8_13, gradle_8_12_1 (default: gradle_9_4_1)
 - `--develocity`: Enables the Develocity build scan plugin (default: false). If --develocity-url is not specified, the build scan will be published to Gradle Scans.
 - `--develocity-url`: Specify Develocity URL
 - `--versions-file`: Path to a custom YAML file with dependency versions
@@ -77,7 +77,7 @@ ProjectGenerator(
     typeOfStringResources = TypeOfStringResources.LARGE,
     layers = 5,
     generateUnitTest = true,
-    gradle = GradleWrapper(Gradle.GRADLE_9_3_1),
+    gradle = GradleWrapper(Gradle.fromValue("9.3.1")),
     projectRootPath = file.path
 ).write()
 
@@ -200,12 +200,15 @@ If enabled, each module will generate n unit tests, where n is the argument `cla
 ```
 ## Gradle
 Gradle used, versions supported:
-* Gradle 8.14.3
-* Gradle 9.1.0
-* Gradle 9.2.0
-* Gradle 9.3.0
-* Gradle 9.3.1
-* Gradle 9.4.0 **default**
+* Gradle 9.x
+  * 9.4.1
+  * 9.3.1
+  * 9.2.1
+* Gradle 8.x
+  * 8.14.4
+  * 8.13
+  * 8.12.1
+* The newest bundled version is the default.
 
 ##### Example
 ```kotlin
diff --git a/backend/server.cjs b/backend/server.cjs
index 73556c9a..db1dec7b 100644
--- a/backend/server.cjs
+++ b/backend/server.cjs
@@ -76,10 +76,10 @@ app.post('/api/generate', upload.single('versions-file'), async (req, res) => {
             `--type`, type,
             `--classes-module`, classesModule,
             `--classes-module-type`, body['classes-module-type'] || 'fixed',
-            `--type-of-string-resources`, body['type-of-string-resources'] || 'normal',
-            `--gradle`, body.gradle || 'GRADLE_9_4_0'
+            `--type-of-string-resources`, body['type-of-string-resources'] || 'normal'
         ];
 
+        if (body.gradle) args.push('--gradle', body.gradle);
         // Add project name if provided
         if (body['project-name']) { args.push('--project-name', body['project-name']);}
         if (toBool(body['generate-unit-test']) || toBool(body.generateUnitTest)) args.push('--generate-unit-test');
diff --git a/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/GenerateVersionsYaml.kt b/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/GenerateVersionsYaml.kt
index 9758f6fc..5210f5f3 100644
--- a/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/GenerateVersionsYaml.kt
+++ b/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/GenerateVersionsYaml.kt
@@ -10,7 +10,7 @@ class GenerateVersionsYaml {
         val file = File("versions.yaml")
         val versions = Versions()
         val content = """
-            |gradle: ${Gradle.GRADLE_9_4_0.version}
+            |gradle: ${Gradle.latest().version}
             |project:
             |  develocity: ${versions.project.develocity}
             |  develocityUrl: ${versions.project.develocityUrl}
diff --git a/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/Main.kt b/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/Main.kt
index a70c4cac..523dcc89 100644
--- a/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/Main.kt
+++ b/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/Main.kt
@@ -42,14 +42,13 @@ class GenerateProjects : CliktCommand(name = "generate-project") {
     private val typeOfStringResources: String by option().choice("large", "normal").default("normal")
     private val layers by option().int().default(5)
     private val generateUnitTest by option().flag(default = false)
-    private val gradle: String? by option().choice(
-        "gradle_8_14_3",
-        "gradle_9_1_0",
-        "gradle_9_2_0",
-        "gradle_9_3_0",
-        "gradle_9_3_1",
-        "gradle_9_4_0"
-    )
+    private val gradle: String? by option()
+        .convert {
+            if (!Gradle.isSupportedValue(it)) {
+                fail("Unknown Gradle version: $it. Supported versions: ${Gradle.supportedDisplayValues()}")
+            }
+            it
+        }
     private val develocity by option().flag(default = false)
     private val versionsFile by option().file()
     private val outputDir by option("--output-dir")
@@ -151,7 +150,7 @@ internal fun resolveProjectRootPath(outputDir: String?, language: Language, proj
 internal fun resolveGradle(cliGradle: String?, versionsFile: VersionsFile?): Gradle {
     return cliGradle?.let(Gradle::fromValue)
         ?: versionsFile?.gradle
-        ?: Gradle.GRADLE_9_4_0
+        ?: Gradle.latest()
 }
 
 class GenerateYaml : CliktCommand(name = "generate-yaml-versions") {
diff --git a/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/VersionsParser.kt b/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/VersionsParser.kt
index 3f05c109..7de22c7c 100644
--- a/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/VersionsParser.kt
+++ b/cli/src/main/kotlin/io/github/cdsap/projectgenerator/cli/VersionsParser.kt
@@ -7,7 +7,13 @@ import com.fasterxml.jackson.databind.node.ObjectNode
 import com.fasterxml.jackson.databind.ObjectMapper
 import com.fasterxml.jackson.dataformat.yaml.YAMLFactory
 import com.fasterxml.jackson.module.kotlin.KotlinModule
+import io.github.cdsap.projectgenerator.model.AdditionalPlugin
+import io.github.cdsap.projectgenerator.model.Android
+import io.github.cdsap.projectgenerator.model.DependencyInjection
 import io.github.cdsap.projectgenerator.model.Gradle
+import io.github.cdsap.projectgenerator.model.Kotlin
+import io.github.cdsap.projectgenerator.model.Project
+import io.github.cdsap.projectgenerator.model.Testing
 import io.github.cdsap.projectgenerator.model.VersionsFile
 import java.io.File
 
@@ -28,7 +34,17 @@ object VersionsParser {
         val tree = mapper.readTree(file)
         normalizeGradleVersion(tree)
         normalizeProjectDefaults(tree)
-        return mapper.treeToValue(tree, VersionsFile::class.java)
+        val payload = mapper.treeToValue(tree, VersionsFilePayload::class.java)
+        return VersionsFile(
+            gradle = payload.gradle?.let(Gradle::fromValue),
+            kotlin = payload.kotlin,
+            android = payload.android,
+            testing = payload.testing,
+            project = payload.project,
+            di = payload.di,
+            additionalBuildGradleRootPlugins = payload.additionalBuildGradleRootPlugins,
+            additionalSettingsPlugins = payload.additionalSettingsPlugins
+        )
     }
 
     private fun normalizeGradleVersion(tree: com.fasterxml.jackson.databind.JsonNode) {
@@ -36,7 +52,7 @@ object VersionsParser {
         val gradleNode = tree.get("gradle") ?: return
         if (!gradleNode.isTextual) return
 
-        val normalized = Gradle.fromValue(gradleNode.asText()).name
+        val normalized = Gradle.fromValue(gradleNode.asText()).version
         tree.put("gradle", normalized)
     }
 
@@ -49,4 +65,15 @@ object VersionsParser {
             projectNode.put("develocityUrl", "")
         }
     }
+
+    private data class VersionsFilePayload(
+        val gradle: String? = null,
+        val kotlin: Kotlin = Kotlin(),
+        val android: Android = Android(),
+        val testing: Testing = Testing(),
+        val project: Project = Project(),
+        val di: DependencyInjection = DependencyInjection.HILT,
+        val additionalBuildGradleRootPlugins: List<AdditionalPlugin>? = null,
+        val additionalSettingsPlugins: List<AdditionalPlugin>? = null
+    )
 }
diff --git a/cli/src/test/kotlin/io/github/cdsap/projectgenerator/cli/GenerateProjectsCliTest.kt b/cli/src/test/kotlin/io/github/cdsap/projectgenerator/cli/GenerateProjectsCliTest.kt
index 384bb85c..7ee56652 100644
--- a/cli/src/test/kotlin/io/github/cdsap/projectgenerator/cli/GenerateProjectsCliTest.kt
+++ b/cli/src/test/kotlin/io/github/cdsap/projectgenerator/cli/GenerateProjectsCliTest.kt
@@ -41,25 +41,41 @@ class GenerateProjectsCliTest {
         assertTrue(error.message?.contains("classes per module must be >= 10") == true)
     }
 
+    @Test
+    fun `unsupported gradle version lists supported values`() {
+        val error = assertThrows<UsageError> {
+            GenerateProjects().parse(
+                listOf(
+                    "--modules", "6",
+                    "--gradle", "9.9.9"
+                )
+            )
+        }
+
+        assertTrue(error.message?.contains("Unknown Gradle version: 9.9.9") == true)
+        assertTrue(error.message?.contains(Gradle.supportedDisplayValues()) == true)
+    }
+
     @Test
     fun `gradle from versions file is used when flag is absent`() {
-        val resolved = resolveGradle(null, VersionsFile(gradle = Gradle.GRADLE_9_3_1))
+        val configured = Gradle.supported()[1]
+        val resolved = resolveGradle(null, VersionsFile(gradle = configured))
 
-        assertEquals(Gradle.GRADLE_9_3_1, resolved)
+        assertEquals(configured, resolved)
     }
 
     @Test
     fun `gradle flag overrides versions file`() {
-        val resolved = resolveGradle("gradle_9_4_0", VersionsFile(gradle = Gradle.GRADLE_9_3_1))
+        val resolved = resolveGradle(Gradle.latest().cliValue, VersionsFile(gradle = Gradle.oldest()))
 
-        assertEquals(Gradle.GRADLE_9_4_0, resolved)
+        assertEquals(Gradle.latest(), resolved)
     }
 
     @Test
     fun `latest gradle is used when neither flag nor versions file provide one`() {
         val resolved = resolveGradle(null, null)
 
-        assertEquals(Gradle.GRADLE_9_4_0, resolved)
+        assertEquals(Gradle.latest(), resolved)
     }
 
     @Test
diff --git a/cli/src/test/kotlin/io/github/cdsap/projectgenerator/cli/VersionsParserTest.kt b/cli/src/test/kotlin/io/github/cdsap/projectgenerator/cli/VersionsParserTest.kt
index 354dec66..61e214a5 100644
--- a/cli/src/test/kotlin/io/github/cdsap/projectgenerator/cli/VersionsParserTest.kt
+++ b/cli/src/test/kotlin/io/github/cdsap/projectgenerator/cli/VersionsParserTest.kt
@@ -148,24 +148,24 @@ class VersionsParserTest {
     @Test
     fun `parses gradle from YAML case insensitively`() {
         val yaml = """
-            gradle: 9.3.1
+            gradle: ${Gradle.supported()[1].version}
         """.trimIndent()
 
         val file = File(tempDir.toFile(), "versions.yaml").apply { writeText(yaml) }
         val versionsFile = VersionsParser.fromFile(file)
 
-        assertEquals(Gradle.GRADLE_9_3_1, versionsFile.gradle)
+        assertEquals(Gradle.supported()[1], versionsFile.gradle)
     }
 
     @Test
     fun `parses legacy gradle enum name from YAML for backwards compatibility`() {
         val yaml = """
-            gradle: GRADLE_9_3_1
+            gradle: ${Gradle.supported()[1].legacyEnumName}
         """.trimIndent()
 
         val file = File(tempDir.toFile(), "versions.yaml").apply { writeText(yaml) }
         val versionsFile = VersionsParser.fromFile(file)
 
-        assertEquals(Gradle.GRADLE_9_3_1, versionsFile.gradle)
+        assertEquals(Gradle.supported()[1], versionsFile.gradle)
     }
 }
diff --git a/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/ProjectGenerator.kt b/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/ProjectGenerator.kt
index 96dccd07..664c5966 100644
--- a/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/ProjectGenerator.kt
+++ b/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/ProjectGenerator.kt
@@ -15,7 +15,7 @@ class ProjectGenerator(
     private val typeOfStringResources: TypeOfStringResources = TypeOfStringResources.NORMAL,
     private val layers: Int,
     private val generateUnitTest: Boolean = false,
-    private val gradle: GradleWrapper = GradleWrapper(Gradle.GRADLE_9_4_0),
+    private val gradle: GradleWrapper = GradleWrapper(Gradle.latest()),
     private val projectRootPath: String = "projects_generated/generated_project/project_kts",
     private val develocity: Boolean = false,
     private val layerNames: List<String> = DefaultNames.layerNames,
diff --git a/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/model/Gradle.kt b/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/model/Gradle.kt
index a0668370..807a3b47 100644
--- a/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/model/Gradle.kt
+++ b/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/model/Gradle.kt
@@ -1,18 +1,59 @@
 package io.github.cdsap.projectgenerator.model
 
-enum class Gradle(val version: String) {
-    GRADLE_8_14_3("8.14.3"),
-    GRADLE_9_1_0("9.1.0"),
-    GRADLE_9_2_0("9.2.0"),
-    GRADLE_9_3_0("9.3.0"),
-    GRADLE_9_3_1("9.3.1"),
-    GRADLE_9_4_0("9.4.0");
+data class Gradle(val version: String) {
+
+    val cliValue: String
+        get() = "gradle_${version.replace('.', '_')}"
+
+    val legacyEnumName: String
+        get() = cliValue.uppercase()
+
+    val resourceZipName: String
+        get() = "${cliValue.lowercase()}.zip"
 
     companion object {
+        private const val SUPPORTED_VERSIONS_RESOURCE = "supported-gradle-versions.txt"
+
+        private val supportedVersions: List<Gradle> by lazy {
+            val stream = requireNotNull(Gradle::class.java.classLoader.getResourceAsStream(SUPPORTED_VERSIONS_RESOURCE)) {
+                "Missing resource: $SUPPORTED_VERSIONS_RESOURCE"
+            }
+            stream.bufferedReader().useLines { lines ->
+                lines
+                    .map(String::trim)
+                    .filter { it.isNotEmpty() && !it.startsWith("#") }
+                    .map(::Gradle)
+                    .toList()
+            }
+        }
+
+        private val supportedLookup: Map<String, Gradle> by lazy {
+            supportedVersions.flatMap { gradle ->
+                listOf(
+                    gradle.version.lowercase() to gradle,
+                    gradle.cliValue.lowercase() to gradle,
+                    gradle.legacyEnumName.lowercase() to gradle
+                )
+            }.toMap()
+        }
+
+        fun supported(): List<Gradle> = supportedVersions
+
+        fun latest(): Gradle = supported().first()
+
+        fun oldest(): Gradle = supported().last()
+
+        fun supportedCliChoices(): List<String> = supported().flatMap { listOf(it.cliValue, it.version) }
+
+        fun supportedDisplayValues(): String = supported().joinToString(", ") { "${it.cliValue} (${it.version})" }
+
+        fun isSupportedValue(value: String): Boolean = supportedLookup.containsKey(value.lowercase())
+
         fun fromValue(value: String): Gradle {
-            return entries.firstOrNull { it.version == value }
-                ?: entries.firstOrNull { it.name.equals(value, ignoreCase = true) }
-                ?: throw IllegalArgumentException("Unknown Gradle version: $value")
+            return supportedLookup[value.lowercase()]
+                ?: throw IllegalArgumentException(
+                    "Unknown Gradle version: $value. Supported versions: ${supportedDisplayValues()}"
+                )
         }
     }
 }
diff --git a/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/writer/GradleWrapper.kt b/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/writer/GradleWrapper.kt
index 56f0e6e6..926834fe 100644
--- a/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/writer/GradleWrapper.kt
+++ b/project-generator/src/main/kotlin/io/github/cdsap/projectgenerator/writer/GradleWrapper.kt
@@ -8,7 +8,7 @@ import java.util.zip.ZipInputStream
 class GradleWrapper(val gradle: Gradle) {
 
     fun installGradleVersion(path: String) {
-        val zipFileName = "${gradle.name.lowercase()}.zip"
+        val zipFileName = gradle.resourceZipName
         val outputDir = path
         unzipResourceFile(zipFileName, outputDir)
 
diff --git a/project-generator/src/main/resources/gradle_8_12_1.zip b/project-generator/src/main/resources/gradle_8_12_1.zip
new file mode 100644
index 00000000..d9e94709
Binary files /dev/null and b/project-generator/src/main/resources/gradle_8_12_1.zip differ
diff --git a/project-generator/src/main/resources/gradle_8_13.zip b/project-generator/src/main/resources/gradle_8_13.zip
new file mode 100644
index 00000000..a2a9b4f5
Binary files /dev/null and b/project-generator/src/main/resources/gradle_8_13.zip differ
diff --git a/project-generator/src/main/resources/gradle_8_14_4.zip b/project-generator/src/main/resources/gradle_8_14_4.zip
new file mode 100644
index 00000000..b06b0ce7
Binary files /dev/null and b/project-generator/src/main/resources/gradle_8_14_4.zip differ
diff --git a/project-generator/src/main/resources/gradle_9_2_1.zip b/project-generator/src/main/resources/gradle_9_2_1.zip
new file mode 100644
index 00000000..179cc298
Binary files /dev/null and b/project-generator/src/main/resources/gradle_9_2_1.zip differ
diff --git a/project-generator/src/main/resources/gradle_9_4_0.zip b/project-generator/src/main/resources/gradle_9_4_1.zip
similarity index 98%
rename from project-generator/src/main/resources/gradle_9_4_0.zip
rename to project-generator/src/main/resources/gradle_9_4_1.zip
index 93be226f..4f714998 100644
Binary files a/project-generator/src/main/resources/gradle_9_4_0.zip and b/project-generator/src/main/resources/gradle_9_4_1.zip differ
diff --git a/project-generator/src/main/resources/supported-gradle-versions.txt b/project-generator/src/main/resources/supported-gradle-versions.txt
new file mode 100644
index 00000000..d9e4aa6c
--- /dev/null
+++ b/project-generator/src/main/resources/supported-gradle-versions.txt
@@ -0,0 +1,6 @@
+9.4.1
+9.3.1
+9.2.1
+8.14.4
+8.13
+8.12.1
diff --git a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/DefaultTestVersions.kt b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/DefaultTestVersions.kt
index 9a509167..c3e94d3e 100644
--- a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/DefaultTestVersions.kt
+++ b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/DefaultTestVersions.kt
@@ -5,6 +5,7 @@ import io.github.cdsap.projectgenerator.model.Versions
 
 class DefaultTestVersions {
     companion object {
-        val LATEST_GRADLE = Gradle.GRADLE_9_4_0
+        val LATEST_GRADLE = Gradle.latest()
+        val OLDEST_SUPPORTED_GRADLE = Gradle.oldest()
     }
 }
diff --git a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/ProjectGeneratorE2ETest.kt b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/ProjectGeneratorE2ETest.kt
index 69b86dbe..49d03dca 100644
--- a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/ProjectGeneratorE2ETest.kt
+++ b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/ProjectGeneratorE2ETest.kt
@@ -1,10 +1,10 @@
 package io.github.cdsap.projectgenerator
 
 import io.github.cdsap.projectgenerator.DefaultTestVersions.Companion.LATEST_GRADLE
+import io.github.cdsap.projectgenerator.DefaultTestVersions.Companion.OLDEST_SUPPORTED_GRADLE
 import io.github.cdsap.projectgenerator.model.Android
 import io.github.cdsap.projectgenerator.model.ClassesPerModule
 import io.github.cdsap.projectgenerator.model.ClassesPerModuleType
-import io.github.cdsap.projectgenerator.model.Gradle
 import io.github.cdsap.projectgenerator.model.Language
 import io.github.cdsap.projectgenerator.model.Project
 import io.github.cdsap.projectgenerator.model.Shape
@@ -88,7 +88,7 @@ class ProjectGeneratorE2ETest {
             TypeOfStringResources.LARGE,
             5,
             true,
-            GradleWrapper(Gradle.GRADLE_8_14_3),
+            GradleWrapper(OLDEST_SUPPORTED_GRADLE),
             projectRootPath = "${tempDir.toFile().path}/${shape.name.lowercase().capitalize()}$modules/project_kts",
             develocity = false,
             projectName = "${shape.name.lowercase().capitalize()}$modules"
diff --git a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/SupportedGradleVersionsE2ETest.kt b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/SupportedGradleVersionsE2ETest.kt
new file mode 100644
index 00000000..b667d658
--- /dev/null
+++ b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/SupportedGradleVersionsE2ETest.kt
@@ -0,0 +1,69 @@
+package io.github.cdsap.projectgenerator
+
+import io.github.cdsap.projectgenerator.model.ClassesPerModule
+import io.github.cdsap.projectgenerator.model.ClassesPerModuleType
+import io.github.cdsap.projectgenerator.model.Gradle
+import io.github.cdsap.projectgenerator.model.Language
+import io.github.cdsap.projectgenerator.model.Project
+import io.github.cdsap.projectgenerator.model.Shape
+import io.github.cdsap.projectgenerator.model.TypeOfStringResources
+import io.github.cdsap.projectgenerator.model.TypeProjectRequested
+import io.github.cdsap.projectgenerator.model.Versions
+import io.github.cdsap.projectgenerator.writer.GradleWrapper
+import org.gradle.testkit.runner.GradleRunner
+import org.junit.jupiter.api.io.TempDir
+import org.junit.jupiter.params.ParameterizedTest
+import org.junit.jupiter.params.provider.MethodSource
+import java.io.File
+import java.nio.file.Path
+
+class SupportedGradleVersionsE2ETest {
+
+    @TempDir
+    lateinit var tempDir: Path
+
+    @ParameterizedTest(name = "builds generated JVM project with Gradle {0}")
+    @MethodSource("supportedGradleVersions")
+    fun `all supported gradle versions can build generated JVM project`(gradle: Gradle) {
+        val projectName = "gradle_${gradle.version.replace('.', '_')}"
+        val projectPath = tempDir.resolve(projectName).resolve("project_kts").toFile()
+
+        ProjectGenerator(
+            modules = 6,
+            shape = Shape.FLAT,
+            language = Language.KTS,
+            typeOfProjectRequested = TypeProjectRequested.JVM,
+            classesPerModule = ClassesPerModule(ClassesPerModuleType.FIXED, 10),
+            versions = Versions(project = Project(jdk = "17")),
+            typeOfStringResources = TypeOfStringResources.NORMAL,
+            layers = 2,
+            generateUnitTest = false,
+            gradle = GradleWrapper(gradle),
+            projectRootPath = projectPath.absolutePath,
+            develocity = false,
+            projectName = projectName
+        ).write()
+
+        val result = GradleRunner.create()
+            .withProjectDir(projectPath)
+            .withArguments("build")
+            .build()
+
+        val sampleModuleBuildDir = File(
+            projectPath,
+            "${NameMappings.layerName(0)}/${NameMappings.moduleName("module_0_1")}/build"
+        )
+
+        assert(result.output.contains("BUILD SUCCESSFUL")) {
+            "Expected build to succeed for Gradle ${gradle.version}"
+        }
+        assert(sampleModuleBuildDir.exists() && sampleModuleBuildDir.isDirectory) {
+            "Expected sample module build directory to exist for Gradle ${gradle.version}"
+        }
+    }
+
+    companion object {
+        @JvmStatic
+        fun supportedGradleVersions(): List<Gradle> = Gradle.supported()
+    }
+}
diff --git a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/model/GradleTest.kt b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/model/GradleTest.kt
new file mode 100644
index 00000000..8e57eb45
--- /dev/null
+++ b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/model/GradleTest.kt
@@ -0,0 +1,35 @@
+package io.github.cdsap.projectgenerator.model
+
+import org.junit.jupiter.api.Assertions.assertEquals
+import org.junit.jupiter.api.Test
+
+class GradleTest {
+
+    @Test
+    fun `supported gradle list is capped to six entries`() {
+        assertEquals(6, Gradle.supported().size)
+    }
+
+    @Test
+    fun `latest gradle is the first supported entry`() {
+        assertEquals(Gradle.supported().first(), Gradle.latest())
+    }
+
+    @Test
+    fun `fromValue accepts version cli value and legacy enum name`() {
+        val gradle = Gradle.supported()[1]
+
+        assertEquals(gradle, Gradle.fromValue(gradle.version))
+        assertEquals(gradle, Gradle.fromValue(gradle.cliValue))
+        assertEquals(gradle, Gradle.fromValue(gradle.legacyEnumName))
+    }
+
+    @Test
+    fun `supported gradle list keeps three minor lines for each targeted major`() {
+        val grouped = Gradle.supported().groupBy { it.version.substringBefore('.') }
+
+        assertEquals(setOf("8", "9"), grouped.keys)
+        assertEquals(3, grouped.getValue("8").size)
+        assertEquals(3, grouped.getValue("9").size)
+    }
+}
diff --git a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/model/VersionsFileTest.kt b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/model/VersionsFileTest.kt
index 3b5b2afa..2bc2bbac 100644
--- a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/model/VersionsFileTest.kt
+++ b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/model/VersionsFileTest.kt
@@ -38,8 +38,8 @@ class VersionsFileTest {
 
     @Test
     fun `gradle override is preserved in versions file`() {
-        val versionsFile = VersionsFile(gradle = Gradle.GRADLE_9_3_1)
+        val versionsFile = VersionsFile(gradle = Gradle.supported()[1])
 
-        assertEquals(Gradle.GRADLE_9_3_1, versionsFile.gradle)
+        assertEquals(Gradle.supported()[1], versionsFile.gradle)
     }
 }
diff --git a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/writer/ProjectWriterTest.kt b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/writer/ProjectWriterTest.kt
index 3ddb10ff..996caf3a 100644
--- a/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/writer/ProjectWriterTest.kt
+++ b/project-generator/src/test/kotlin/io/github/cdsap/projectgenerator/writer/ProjectWriterTest.kt
@@ -1,6 +1,7 @@
 package io.github.cdsap.projectgenerator
 
 import io.github.cdsap.projectgenerator.DefaultTestVersions.Companion.LATEST_GRADLE
+import io.github.cdsap.projectgenerator.DefaultTestVersions.Companion.OLDEST_SUPPORTED_GRADLE
 import io.github.cdsap.projectgenerator.model.*
 import io.github.cdsap.projectgenerator.writer.GradleWrapper
 import io.github.cdsap.projectgenerator.writer.ProjectWriter
@@ -39,7 +40,7 @@ class ProjectWriterTest {
             typeOfProjectRequested,
             TypeOfStringResources.NORMAL,
             false,
-            GradleWrapper(Gradle.GRADLE_8_14_3),
+            GradleWrapper(OLDEST_SUPPORTED_GRADLE),
             true,
             "awesomeapp"
         )
diff --git a/scripts/update_gradle_versions.sh b/scripts/update_gradle_versions.sh
new file mode 100755
index 00000000..5c06a41f
--- /dev/null
+++ b/scripts/update_gradle_versions.sh
@@ -0,0 +1,141 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+ROOT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")/.." && pwd)"
+RESOURCES_DIR="$ROOT_DIR/project-generator/src/main/resources"
+VERSIONS_FILE="$RESOURCES_DIR/supported-gradle-versions.txt"
+README_FILE="$ROOT_DIR/README.md"
+TARGET_MAJORS="${TARGET_MAJORS:-9 8}"
+MINORS_PER_MAJOR="${MINORS_PER_MAJOR:-3}"
+VERSIONS_ENDPOINT="https://services.gradle.org/versions/all"
+TEMP_DIR="$(mktemp -d)"
+GRADLE_USER_HOME="$TEMP_DIR/gradle-user-home"
+
+cleanup() {
+  rm -rf "$TEMP_DIR"
+}
+trap cleanup EXIT
+
+fetch_versions() {
+  curl -fsSL "$VERSIONS_ENDPOINT" | python3 -c '
+import json
+import os
+import sys
+
+items = json.load(sys.stdin)
+target_majors = os.environ["TARGET_MAJORS"].split()
+minors_per_major = int(os.environ["MINORS_PER_MAJOR"])
+selected_by_minor = {major: [] for major in target_majors}
+seen_minor = {major: set() for major in target_majors}
+
+for item in items:
+    version = item.get("version", "").strip()
+    if not version:
+        continue
+    if item.get("snapshot") or item.get("nightly") or item.get("releaseNightly") or item.get("broken"):
+        continue
+    if any(ch.isalpha() for ch in version):
+        continue
+    parts = version.split(".")
+    if len(parts) < 2:
+        continue
+    major = parts[0]
+    if major not in selected_by_minor:
+        continue
+    minor_key = ".".join(parts[:2])
+    if minor_key in seen_minor[major]:
+        continue
+    selected_by_minor[major].append(version)
+    seen_minor[major].add(minor_key)
+
+    if all(len(selected_by_minor[major]) >= minors_per_major for major in target_majors):
+        break
+
+for major in target_majors:
+    print("\n".join(selected_by_minor[major][:minors_per_major]))
+' 
+}
+
+generate_wrapper_bundle() {
+  local version="$1"
+  local bundle_name="gradle_${version//./_}.zip"
+  local work_dir="$TEMP_DIR/$version"
+
+  mkdir -p "$work_dir/gradle/wrapper"
+  cp "$ROOT_DIR/gradlew" "$ROOT_DIR/gradlew.bat" "$work_dir/"
+  cp "$ROOT_DIR/gradle/wrapper/gradle-wrapper.jar" "$ROOT_DIR/gradle/wrapper/gradle-wrapper.properties" "$work_dir/gradle/wrapper/"
+  printf 'rootProject.name = "wrapper-bundle"\n' > "$work_dir/settings.gradle.kts"
+  printf '\n' > "$work_dir/build.gradle.kts"
+
+  GRADLE_USER_HOME="$GRADLE_USER_HOME" "$work_dir/gradlew" -p "$work_dir" wrapper --gradle-version "$version" --distribution-type bin
+  (
+    cd "$work_dir"
+    zip -qr "$RESOURCES_DIR/$bundle_name" gradle gradlew gradlew.bat
+  )
+}
+
+prune_removed_bundles() {
+  local versions=("$@")
+  local keep_list=()
+
+  for version in "${versions[@]}"; do
+    keep_list+=("gradle_${version//./_}.zip")
+  done
+
+  while IFS= read -r existing; do
+    local base
+    base="$(basename "$existing")"
+    if [[ ! " ${keep_list[*]} " == *" ${base} "* ]]; then
+      rm -f "$existing"
+    fi
+  done < <(find "$RESOURCES_DIR" -maxdepth 1 -name 'gradle_*.zip' -type f | sort)
+}
+
+update_readme() {
+  python3 - "$README_FILE" <<'PY'
+from pathlib import Path
+import re
+
+readme = Path(__import__("sys").argv[1])
+versions = Path(__import__("os").environ["VERSIONS_FILE"]).read_text().strip().splitlines()
+majors = {}
+for version in versions:
+    major = version.split(".", 1)[0]
+    majors.setdefault(major, []).append(version)
+
+lines = []
+for major, items in majors.items():
+    lines.append(f"* Gradle {major}.x")
+    lines.extend(f"  * {version}" for version in items)
+
+replacement = "Gradle used, versions supported:\n" + "\n".join(lines) + "\n* The newest bundled version is the default."
+content = readme.read_text()
+pattern = re.compile(
+    r"Gradle used, versions supported:\n(?:.*\n)*?\* The newest bundled version is the default\.",
+    re.MULTILINE
+)
+updated = pattern.sub(replacement, content)
+readme.write_text(updated)
+PY
+}
+
+export TARGET_MAJORS MINORS_PER_MAJOR VERSIONS_FILE
+mapfile -t versions < <(fetch_versions)
+
+if [[ "${#versions[@]}" -eq 0 ]]; then
+  echo "No stable Gradle versions found from $VERSIONS_ENDPOINT" >&2
+  exit 1
+fi
+
+printf '%s\n' "${versions[@]}" > "$VERSIONS_FILE"
+
+for version in "${versions[@]}"; do
+  echo "Generating wrapper bundle for Gradle $version"
+  generate_wrapper_bundle "$version"
+done
+
+prune_removed_bundles "${versions[@]}"
+update_readme
+
+echo "Updated supported Gradle versions:"
+cat "$VERSIONS_FILE"