diff --git a/apps/desktop/src/components/config/DriverStoreDialog.vue b/apps/desktop/src/components/config/DriverStoreDialog.vue
index 4b069732fd..35ed02f7a0 100644
--- a/apps/desktop/src/components/config/DriverStoreDialog.vue
+++ b/apps/desktop/src/components/config/DriverStoreDialog.vue
@@ -659,7 +659,7 @@ onUnmounted(() => {
                   <span
                     v-if="driver.jre"
                     class="rounded-full px-2 py-0.5 text-[11px]"
-                    :class="driver.jre !== '17' ? 'bg-blue-500/10 text-blue-600' : 'bg-muted text-muted-foreground'"
+                    :class="driver.jre !== '21' ? 'bg-blue-500/10 text-blue-600' : 'bg-muted text-muted-foreground'"
                     >JRE {{ driver.jre }}</span
                   >
                   <template v-if="driver.installed">
diff --git a/crates/dbx-core/src/agent_manager.rs b/crates/dbx-core/src/agent_manager.rs
index 898966e879..f6af233f23 100644
--- a/crates/dbx-core/src/agent_manager.rs
+++ b/crates/dbx-core/src/agent_manager.rs
@@ -8,7 +8,7 @@ use crate::database_capabilities;
 use crate::db::agent_driver::{AgentDriverClient, AgentMethod};
 use crate::models::connection::DatabaseType;
 
-pub const DEFAULT_JRE_KEY: &str = "17";
+pub const DEFAULT_JRE_KEY: &str = "21";
 
 fn default_jre_key() -> String {
     DEFAULT_JRE_KEY.to_string()
@@ -64,12 +64,12 @@ mod tests {
     #[test]
     fn resolves_managed_java_runtime_by_default() {
         let manager = test_manager("managed");
-        let java = manager.jre_java_path("17");
+        let java = manager.jre_java_path(DEFAULT_JRE_KEY);
         touch(&java);
 
         let state = AgentState::default();
 
-        assert_eq!(manager.resolve_java_runtime(&state, "17").unwrap(), java);
+        assert_eq!(manager.resolve_java_runtime(&state, DEFAULT_JRE_KEY).unwrap(), java);
     }
 
     #[test]
@@ -85,7 +85,7 @@ mod tests {
             ..AgentState::default()
         };
 
-        assert_eq!(manager.resolve_java_runtime(&state, "17").unwrap(), custom_java);
+        assert_eq!(manager.resolve_java_runtime(&state, DEFAULT_JRE_KEY).unwrap(), custom_java);
     }
 
     #[test]
@@ -99,7 +99,7 @@ mod tests {
             ..AgentState::default()
         };
 
-        let err = manager.resolve_java_runtime(&state, "17").unwrap_err();
+        let err = manager.resolve_java_runtime(&state, DEFAULT_JRE_KEY).unwrap_err();
 
         assert!(err.contains("Custom Java runtime does not exist"));
     }
diff --git a/crates/dbx-core/src/agent_service.rs b/crates/dbx-core/src/agent_service.rs
index fe7db30d82..9c8b28b9ea 100644
--- a/crates/dbx-core/src/agent_service.rs
+++ b/crates/dbx-core/src/agent_service.rs
@@ -1,7 +1,9 @@
 use std::io::Read;
 use std::path::{Path, PathBuf};
 
-use crate::agent_manager::{AgentDriverInfo, AgentManager, AgentRegistry, InstalledDriver, DEFAULT_JRE_KEY};
+use crate::agent_manager::{
+    AgentDriverInfo, AgentManager, AgentRegistry, InstalledDriver, JavaRuntimeMode, DEFAULT_JRE_KEY,
+};
 
 const REGISTRY_PATH: &str = "https://github.com/t8y2/dbx-agents/releases/latest/download/agent-registry.json";
 const REGISTRY_R2_PATH: &str = "agents/agent-registry.json";
@@ -56,6 +58,11 @@ pub fn build_agent_list(am: &AgentManager, registry: Option<&AgentRegistry>) ->
                 .map(|r| r.jre.clone())
                 .or_else(|| local.map(|l| l.jre.clone()))
                 .unwrap_or_else(|| DEFAULT_JRE_KEY.to_string());
+            let remote_jre_version = registry.and_then(|r| r.resolve_jre(&jre_key)).map(|j| &j.version);
+            let local_jre_version = local_state.jre_versions.get(&jre_key);
+            let jre_update_available = installed
+                && (!am.is_jre_installed(&jre_key)
+                    || remote_jre_version.is_some_and(|version| local_jre_version != Some(version)));
             AgentDriverInfo {
                 db_type: key.to_string(),
                 label: label.to_string(),
@@ -64,7 +71,7 @@ pub fn build_agent_list(am: &AgentManager, registry: Option<&AgentRegistry>) ->
                 installed,
                 installed_version: local.map(|l| l.version.clone()),
                 update_available: match (local, remote) {
-                    (Some(l), Some(r)) => l.version != r.version,
+                    (Some(l), Some(r)) => l.version != r.version || jre_update_available,
                     _ => false,
                 },
                 jre: jre_key.clone(),
@@ -74,6 +81,17 @@ pub fn build_agent_list(am: &AgentManager, registry: Option<&AgentRegistry>) ->
         .collect()
 }
 
+pub fn jre_needs_install(am: &AgentManager, registry: &AgentRegistry, jre_key: &str) -> bool {
+    let state = am.load_state();
+    if state.java_runtime.mode != JavaRuntimeMode::Managed {
+        return false;
+    }
+    if !am.is_jre_installed(jre_key) {
+        return true;
+    }
+    registry.resolve_jre(jre_key).is_some_and(|jre| state.jre_versions.get(jre_key) != Some(&jre.version))
+}
+
 pub fn local_agent_jar_candidates(db_type: &str) -> Vec<PathBuf> {
     let jar_name = format!("dbx-agent-{db_type}.jar");
     let relative = PathBuf::from("..").join("dbx-agents").join(db_type).join("build").join("libs").join(&jar_name);
diff --git a/crates/dbx-core/tests/agent_service.rs b/crates/dbx-core/tests/agent_service.rs
index b2c43ae3cf..e1af38c9dd 100644
--- a/crates/dbx-core/tests/agent_service.rs
+++ b/crates/dbx-core/tests/agent_service.rs
@@ -1,7 +1,7 @@
 use dbx_core::agent_manager::{
-    AgentManager, AgentRegistry, ArtifactInfo, DriverInfo, InstalledDriver, DEFAULT_JRE_KEY,
+    AgentManager, AgentRegistry, ArtifactInfo, DriverInfo, InstalledDriver, JreInfo, DEFAULT_JRE_KEY,
 };
-use dbx_core::agent_service::{build_agent_list, github_url_to_r2_path, local_agent_jar_candidates};
+use dbx_core::agent_service::{build_agent_list, github_url_to_r2_path, jre_needs_install, local_agent_jar_candidates};
 use dbx_core::agent_service::{is_app_version_compatible, replace_download};
 
 fn test_manager(name: &str) -> AgentManager {
@@ -24,6 +24,15 @@ fn registry_with_driver(db_type: &str, version: &str, jre: &str) -> AgentRegistr
     AgentRegistry { jre: None, jres: std::collections::HashMap::new(), drivers }
 }
 
+fn registry_with_jre_driver(db_type: &str, driver_version: &str, jre: &str, jre_version: &str) -> AgentRegistry {
+    let mut registry = registry_with_driver(db_type, driver_version, jre);
+    registry.jres.insert(
+        jre.to_string(),
+        JreInfo { version: jre_version.to_string(), platforms: std::collections::HashMap::new() },
+    );
+    registry
+}
+
 #[test]
 fn built_in_agent_list_includes_expected_driver_labels() {
     let manager = test_manager("labels");
@@ -69,6 +78,56 @@ fn agent_list_marks_installed_driver_update_when_registry_version_differs() {
     assert!(h2.update_available);
 }
 
+#[test]
+fn agent_list_marks_update_when_installed_managed_jre_version_differs() {
+    let manager = test_manager("jre-update");
+    let jar_path = manager.driver_jar_path("h2");
+    let java_path = manager.jre_java_path(DEFAULT_JRE_KEY);
+    std::fs::create_dir_all(jar_path.parent().unwrap()).unwrap();
+    std::fs::create_dir_all(java_path.parent().unwrap()).unwrap();
+    std::fs::write(&jar_path, b"jar").unwrap();
+    std::fs::write(&java_path, b"java").unwrap();
+    manager
+        .save_state(&dbx_core::agent_manager::AgentState {
+            jre_versions: [(DEFAULT_JRE_KEY.to_string(), "21.0.10".to_string())].into_iter().collect(),
+            installed_drivers: [(
+                "h2".to_string(),
+                InstalledDriver {
+                    version: "0.2.0".to_string(),
+                    installed_at: "2026-05-18T00:00:00Z".to_string(),
+                    jre: DEFAULT_JRE_KEY.to_string(),
+                },
+            )]
+            .into_iter()
+            .collect(),
+            ..Default::default()
+        })
+        .unwrap();
+    let registry = registry_with_jre_driver("h2", "0.2.0", DEFAULT_JRE_KEY, "21.0.11");
+
+    let agents = build_agent_list(&manager, Some(&registry));
+    let h2 = agents.iter().find(|agent| agent.db_type == "h2").unwrap();
+
+    assert!(h2.update_available);
+}
+
+#[test]
+fn jre_needs_install_when_managed_runtime_version_differs() {
+    let manager = test_manager("jre-needs-install");
+    let java_path = manager.jre_java_path(DEFAULT_JRE_KEY);
+    std::fs::create_dir_all(java_path.parent().unwrap()).unwrap();
+    std::fs::write(&java_path, b"java").unwrap();
+    manager
+        .save_state(&dbx_core::agent_manager::AgentState {
+            jre_versions: [(DEFAULT_JRE_KEY.to_string(), "21.0.10".to_string())].into_iter().collect(),
+            ..Default::default()
+        })
+        .unwrap();
+    let registry = registry_with_jre_driver("h2", "0.2.0", DEFAULT_JRE_KEY, "21.0.11");
+
+    assert!(jre_needs_install(&manager, &registry, DEFAULT_JRE_KEY));
+}
+
 #[test]
 fn local_agent_jar_candidates_include_sibling_build_output() {
     let candidates = local_agent_jar_candidates("tdengine");
@@ -79,8 +138,8 @@ fn local_agent_jar_candidates_include_sibling_build_output() {
 #[test]
 fn github_agent_asset_urls_map_to_r2_paths_by_category() {
     assert_eq!(
-        github_url_to_r2_path("https://github.com/t8y2/dbx-agents/releases/download/v1/jre-17.tar.gz", "jre"),
-        "agents/jre/jre-17.tar.gz"
+        github_url_to_r2_path("https://github.com/t8y2/dbx-agents/releases/download/v1/dbx-jre-21.tar.gz", "jre"),
+        "agents/jre/dbx-jre-21.tar.gz"
     );
     assert_eq!(
         github_url_to_r2_path("https://github.com/t8y2/dbx-agents/releases/download/v1/dbx-agent-h2.jar", "driver"),
diff --git a/crates/dbx-web/src/routes/agents.rs b/crates/dbx-web/src/routes/agents.rs
index 1898f5fe0f..e8aca12944 100644
--- a/crates/dbx-web/src/routes/agents.rs
+++ b/crates/dbx-web/src/routes/agents.rs
@@ -9,7 +9,8 @@ use dbx_core::agent_manager::{
 };
 use dbx_core::agent_service::{
     build_agent_list, download_temp_path, fetch_registry, find_local_agent_jar, github_url_to_r2_path,
-    import_offline_zip, install_local_agent, invalidate_registry_cache, replace_download, OfflineImportProgress,
+    import_offline_zip, install_local_agent, invalidate_registry_cache, jre_needs_install, replace_download,
+    OfflineImportProgress,
 };
 use futures::Stream;
 use serde::Deserialize;
@@ -258,7 +259,7 @@ async fn install_agent_from_registry(
         return Err(format!("Unknown driver type: {db_type}"));
     };
     let jre_key = &driver.jre;
-    let needs_jre = am.load_state().java_runtime.mode == JavaRuntimeMode::Managed && !am.is_jre_installed(jre_key);
+    let needs_jre = jre_needs_install(am, registry, jre_key);
     if needs_jre {
         let jre_info =
             registry.resolve_jre(jre_key).ok_or_else(|| format!("No JRE definition for version: {jre_key}"))?;
@@ -282,7 +283,11 @@ async fn install_agent_from_registry(
         )
         .await?;
         send_install_progress(tx, "jre-extract", 0, 0, Some(db_type), current, total_drivers);
-        extract_archive(&jre_archive, &am.jre_dir(jre_key))?;
+        let jre_dir = am.jre_dir(jre_key);
+        if jre_dir.exists() {
+            std::fs::remove_dir_all(&jre_dir).map_err(|err| format!("Failed to remove old JRE: {err}"))?;
+        }
+        extract_archive(&jre_archive, &jre_dir)?;
         std::fs::remove_file(&jre_archive).ok();
     }
 
diff --git a/plugins/jdbc/src/main/java/app/dbx/jdbc/DbxJdbcPlugin.java b/plugins/jdbc/src/main/java/app/dbx/jdbc/DbxJdbcPlugin.java
index 0411412682..05bcf67c8f 100644
--- a/plugins/jdbc/src/main/java/app/dbx/jdbc/DbxJdbcPlugin.java
+++ b/plugins/jdbc/src/main/java/app/dbx/jdbc/DbxJdbcPlugin.java
@@ -40,7 +40,7 @@ public final class DbxJdbcPlugin {
     private static final ObjectMapper MAPPER = new ObjectMapper();
     private static final int MAX_ROWS = 10_000;
     private static final JdbcDriverQuirks DEFAULT_QUIRKS = new JdbcDriverQuirks(false, false);
-    private static final JdbcDriverQuirks YASHAN_QUIRKS = new JdbcDriverQuirks(true, false);
+    private static final JdbcDriverQuirks YASHAN_QUIRKS = new JdbcDriverQuirks(true, true);
     private static final JdbcDriverQuirks ORACLE_QUIRKS = new JdbcDriverQuirks(false, true);
     private static final List<JdbcDriverQuirkRule> DRIVER_QUIRK_RULES = List.of(
         new JdbcDriverQuirkRule("jdbc:yasdb:", YASHAN_QUIRKS),
diff --git a/plugins/jdbc/src/test/java/app/dbx/jdbc/DbxJdbcPluginTest.java b/plugins/jdbc/src/test/java/app/dbx/jdbc/DbxJdbcPluginTest.java
index dfa74f54a2..46fbf0c463 100644
--- a/plugins/jdbc/src/test/java/app/dbx/jdbc/DbxJdbcPluginTest.java
+++ b/plugins/jdbc/src/test/java/app/dbx/jdbc/DbxJdbcPluginTest.java
@@ -74,7 +74,9 @@ final class DbxJdbcPluginTest {
             """);
 
         assertEquals(true, DbxJdbcPlugin.driverQuirks(yashan).skipExecutionContext());
+        assertEquals(true, DbxJdbcPlugin.driverQuirks(yashan).useOracleMetadata());
         assertEquals(false, DbxJdbcPlugin.driverQuirks(h2).skipExecutionContext());
+        assertEquals(false, DbxJdbcPlugin.driverQuirks(h2).useOracleMetadata());
     }
 
     @Test
diff --git a/src-tauri/src/commands/agents.rs b/src-tauri/src/commands/agents.rs
index 58e910890b..899cb35baf 100644
--- a/src-tauri/src/commands/agents.rs
+++ b/src-tauri/src/commands/agents.rs
@@ -7,8 +7,8 @@ use dbx_core::agent_manager::{
 };
 use dbx_core::agent_service::{
     build_agent_list, download_temp_path, fetch_registry, find_local_agent_jar, github_url_to_r2_path,
-    import_agent_jar, import_offline_zip, install_local_agent, invalidate_registry_cache, replace_download,
-    OfflineImportProgress,
+    import_agent_jar, import_offline_zip, install_local_agent, invalidate_registry_cache, jre_needs_install,
+    replace_download, OfflineImportProgress,
 };
 use dbx_core::connection::AppState;
 
@@ -51,7 +51,7 @@ pub async fn install_agent(
         return Err(format!("Unknown driver type: {db_type}"));
     };
     let jre_key = &driver.jre;
-    let needs_jre = am.load_state().java_runtime.mode == JavaRuntimeMode::Managed && !am.is_jre_installed(jre_key);
+    let needs_jre = jre_needs_install(am, &registry, jre_key);
 
     if needs_jre {
         let jre_info =
@@ -83,7 +83,11 @@ pub async fn install_agent(
                 "step": "jre-extract", "downloaded": 0u64, "total": 0u64,
             }),
         );
-        extract_archive(&jre_archive, &am.jre_dir(jre_key))?;
+        let jre_dir = am.jre_dir(jre_key);
+        if jre_dir.exists() {
+            std::fs::remove_dir_all(&jre_dir).map_err(|e| format!("Failed to remove old JRE: {e}"))?;
+        }
+        extract_archive(&jre_archive, &jre_dir)?;
         std::fs::remove_file(&jre_archive).ok();
     }
 
@@ -137,7 +141,7 @@ pub async fn upgrade_all_agents(app: tauri::AppHandle, state: State<'_, Arc<AppS
         let db_type = &agent.db_type;
         let driver = registry.drivers.get(db_type).ok_or_else(|| format!("Unknown driver type: {db_type}"))?;
         let jre_key = &driver.jre;
-        let needs_jre = am.load_state().java_runtime.mode == JavaRuntimeMode::Managed && !am.is_jre_installed(jre_key);
+        let needs_jre = jre_needs_install(am, &registry, jre_key);
 
         if needs_jre {
             let jre_info =
@@ -171,7 +175,11 @@ pub async fn upgrade_all_agents(app: tauri::AppHandle, state: State<'_, Arc<AppS
                     "db_type": db_type, "current": current, "total_drivers": total_drivers,
                 }),
             );
-            extract_archive(&jre_archive, &am.jre_dir(jre_key))?;
+            let jre_dir = am.jre_dir(jre_key);
+            if jre_dir.exists() {
+                std::fs::remove_dir_all(&jre_dir).map_err(|e| format!("Failed to remove old JRE: {e}"))?;
+            }
+            extract_archive(&jre_archive, &jre_dir)?;
             std::fs::remove_file(&jre_archive).ok();
         }