diff --git a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/RedisClientAdapter.java b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/RedisClientAdapter.java
index 1f91a9d5ea..98878f9379 100644
--- a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/RedisClientAdapter.java
+++ b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/RedisClientAdapter.java
@@ -92,6 +92,16 @@ public interface RedisClientAdapter {
      */
     void addToSet(String key, String member);
 
+    /**
+     * Remove a member from a set.
+     *
+     * @param key the Redis set key
+     * @param member the member to remove
+     */
+    default void removeFromSet(String key, String member) {
+        // Default no-op for custom adapters that do not track session keys in a Redis set.
+    }
+
     /**
      * Get all members of a set.
      *
diff --git a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/RedisSession.java b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/RedisSession.java
index 7bb86e3414..14a3c26d19 100644
--- a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/RedisSession.java
+++ b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/RedisSession.java
@@ -348,6 +348,19 @@ public void delete(SessionKey sessionKey) {
         }
     }
 
+    @Override
+    public void delete(SessionKey sessionKey, String key) {
+        String sessionId = sessionKey.toIdentifier();
+        String keysKey = getKeysKey(sessionId);
+
+        try {
+            client.deleteKeys(getStateKey(sessionId, key));
+            client.removeFromSet(keysKey, key);
+        } catch (Exception e) {
+            throw new RuntimeException("Failed to delete state: " + key, e);
+        }
+    }
+
     @Override
     public Set<SessionKey> listSessionKeys() {
         try {
diff --git a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/jedis/JedisClientAdapter.java b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/jedis/JedisClientAdapter.java
index 83e0bcfa51..ebd496f087 100644
--- a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/jedis/JedisClientAdapter.java
+++ b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/jedis/JedisClientAdapter.java
@@ -136,6 +136,11 @@ public void addToSet(String key, String member) {
         unifiedJedis.sadd(key, member);
     }
 
+    @Override
+    public void removeFromSet(String key, String member) {
+        unifiedJedis.srem(key, member);
+    }
+
     @Override
     public Set<String> getSetMembers(String key) {
         return unifiedJedis.smembers(key);
diff --git a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/lettuce/LettuceClientAdapter.java b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/lettuce/LettuceClientAdapter.java
index 8ca1304e23..89c9671934 100644
--- a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/lettuce/LettuceClientAdapter.java
+++ b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/lettuce/LettuceClientAdapter.java
@@ -217,6 +217,15 @@ public void addToSet(String key, String member) {
         }
     }
 
+    @Override
+    public void removeFromSet(String key, String member) {
+        if (commands != null) {
+            commands.srem(key, member);
+        } else {
+            clusterCommands.srem(key, member);
+        }
+    }
+
     @Override
     public Set<String> getSetMembers(String key) {
         if (commands != null) {
diff --git a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/redisson/RedissonClientAdapter.java b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/redisson/RedissonClientAdapter.java
index 542793afca..7b631279db 100644
--- a/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/redisson/RedissonClientAdapter.java
+++ b/agentscope-extensions/agentscope-extensions-session-redis/src/main/java/io/agentscope/core/session/redis/redisson/RedissonClientAdapter.java
@@ -184,6 +184,12 @@ public void addToSet(String key, String member) {
         rSet.add(member);
     }
 
+    @Override
+    public void removeFromSet(String key, String member) {
+        RSet<String> rSet = redissonClient.getSet(key, StringCodec.INSTANCE);
+        rSet.remove(member);
+    }
+
     @Override
     public Set<String> getSetMembers(String key) {
         RSet<String> rSet = redissonClient.getSet(key, StringCodec.INSTANCE);
diff --git a/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/JedisSessionTest.java b/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/JedisSessionTest.java
index 5eb156ea4c..26e9676031 100644
--- a/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/JedisSessionTest.java
+++ b/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/JedisSessionTest.java
@@ -27,12 +27,17 @@
 import static org.mockito.Mockito.verify;
 import static org.mockito.Mockito.when;
 
+import io.agentscope.core.agent.Agent;
+import io.agentscope.core.shutdown.GracefulShutdownManager;
+import io.agentscope.core.shutdown.ShutdownInterruptedState;
 import io.agentscope.core.state.SessionKey;
 import io.agentscope.core.state.SimpleSessionKey;
 import io.agentscope.core.state.State;
 import java.util.ArrayList;
+import java.util.HashMap;
 import java.util.HashSet;
 import java.util.List;
+import java.util.Map;
 import java.util.Optional;
 import java.util.Set;
 import org.junit.jupiter.api.BeforeEach;
@@ -221,6 +226,66 @@ void testDeleteSession() {
         verify(unifiedJedis).smembers("agentscope:session:session1:_keys");
     }
 
+    @Test
+    @DisplayName("Should delete single state key and remove tracking metadata")
+    void testDeleteSingleStateKey() {
+        RedisSession session =
+                RedisSession.builder()
+                        .jedisClient(unifiedJedis)
+                        .keyPrefix("agentscope:session:")
+                        .build();
+
+        SessionKey sessionKey = SimpleSessionKey.of("session1");
+        session.delete(sessionKey, "shutdown_interrupted");
+
+        verify(unifiedJedis).del(new String[] {"agentscope:session:session1:shutdown_interrupted"});
+        verify(unifiedJedis).srem("agentscope:session:session1:_keys", "shutdown_interrupted");
+    }
+
+    @Test
+    @DisplayName("Should not return single state after deleting it")
+    void testDeleteSingleStateKeyRemovesPersistedValue() {
+        RedisSession session =
+                RedisSession.builder()
+                        .clientAdapter(new StatefulRedisClientAdapter())
+                        .keyPrefix("agentscope:session:")
+                        .build();
+
+        SessionKey sessionKey = SimpleSessionKey.of("session1");
+        session.save(sessionKey, "shutdown_interrupted", new TestState("interrupted", 1));
+
+        assertTrue(session.get(sessionKey, "shutdown_interrupted", TestState.class).isPresent());
+
+        session.delete(sessionKey, "shutdown_interrupted");
+
+        assertFalse(session.get(sessionKey, "shutdown_interrupted", TestState.class).isPresent());
+    }
+
+    @Test
+    @DisplayName("Should clear shutdown interrupted flag after first manager check")
+    void testManagerCheckAndClearShutdownInterruptedWithRedisSession() {
+        GracefulShutdownManager manager = GracefulShutdownManager.getInstance();
+        manager.resetForTesting();
+        try {
+            RedisSession session =
+                    RedisSession.builder()
+                            .clientAdapter(new StatefulRedisClientAdapter())
+                            .keyPrefix("agentscope:session:")
+                            .build();
+            SessionKey sessionKey = SimpleSessionKey.of("session1");
+            Agent agent = mock(Agent.class);
+            when(agent.getAgentId()).thenReturn("agent-1");
+
+            session.save(sessionKey, "shutdown_interrupted", new ShutdownInterruptedState(true));
+            manager.bindSession(agent, session, sessionKey);
+
+            assertTrue(manager.checkAndClearShutdownInterrupted(agent));
+            assertFalse(manager.checkAndClearShutdownInterrupted(agent));
+        } finally {
+            manager.resetForTesting();
+        }
+    }
+
     @Test
     @DisplayName("Should list all session keys")
     void testListSessionKeys() {
@@ -280,4 +345,76 @@ void testCloseShutsDownClient() {
 
     /** Simple test state record for testing. */
     public record TestState(String value, int count) implements State {}
+
+    private static class StatefulRedisClientAdapter implements RedisClientAdapter {
+
+        private final Map<String, String> values = new HashMap<>();
+        private final Map<String, Set<String>> sets = new HashMap<>();
+
+        @Override
+        public void set(String key, String value) {
+            values.put(key, value);
+        }
+
+        @Override
+        public String get(String key) {
+            return values.get(key);
+        }
+
+        @Override
+        public void rightPushList(String key, String value) {}
+
+        @Override
+        public List<String> rangeList(String key, long start, long end) {
+            return List.of();
+        }
+
+        @Override
+        public long getListLength(String key) {
+            return 0;
+        }
+
+        @Override
+        public void deleteKeys(String... keys) {
+            for (String key : keys) {
+                values.remove(key);
+            }
+        }
+
+        @Override
+        public void addToSet(String key, String member) {
+            sets.computeIfAbsent(key, unused -> new HashSet<>()).add(member);
+        }
+
+        @Override
+        public void removeFromSet(String key, String member) {
+            Set<String> members = sets.get(key);
+            if (members != null) {
+                members.remove(member);
+            }
+        }
+
+        @Override
+        public Set<String> getSetMembers(String key) {
+            return sets.getOrDefault(key, Set.of());
+        }
+
+        @Override
+        public long getSetSize(String key) {
+            return getSetMembers(key).size();
+        }
+
+        @Override
+        public boolean keyExists(String key) {
+            return values.containsKey(key) || sets.containsKey(key);
+        }
+
+        @Override
+        public Set<String> findKeysByPattern(String pattern) {
+            return Set.of();
+        }
+
+        @Override
+        public void close() {}
+    }
 }
diff --git a/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/LettuceSessionTest.java b/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/LettuceSessionTest.java
index 8a8b8e51dd..14f178c7ce 100644
--- a/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/LettuceSessionTest.java
+++ b/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/LettuceSessionTest.java
@@ -206,6 +206,22 @@ void testDeleteSession() {
             verify(commands).smembers("agentscope:session:session1:_keys");
         }
 
+        @Test
+        @DisplayName("Should delete single state key and remove tracking metadata")
+        void testDeleteSingleStateKey() {
+            RedisSession session =
+                    RedisSession.builder()
+                            .lettuceClient(redisClient)
+                            .keyPrefix("agentscope:session:")
+                            .build();
+
+            SessionKey sessionKey = SimpleSessionKey.of("session1");
+            session.delete(sessionKey, "shutdown_interrupted");
+
+            verify(commands).del("agentscope:session:session1:shutdown_interrupted");
+            verify(commands).srem("agentscope:session:session1:_keys", "shutdown_interrupted");
+        }
+
         @Test
         @DisplayName("Should list session keys correctly")
         void testListSessionKeys() {
@@ -424,6 +440,23 @@ void testDeleteSessionCluster() {
             verify(clusterCommands).smembers("agentscope:session:clusterSession:_keys");
         }
 
+        @Test
+        @DisplayName("Should delete single state key and remove tracking metadata in cluster mode")
+        void testDeleteSingleStateKeyCluster() {
+            RedisSession session =
+                    RedisSession.builder()
+                            .lettuceClusterClient(redisClusterClient)
+                            .keyPrefix("agentscope:session:")
+                            .build();
+
+            SessionKey sessionKey = SimpleSessionKey.of("clusterSession");
+            session.delete(sessionKey, "shutdown_interrupted");
+
+            verify(clusterCommands).del("agentscope:session:clusterSession:shutdown_interrupted");
+            verify(clusterCommands)
+                    .srem("agentscope:session:clusterSession:_keys", "shutdown_interrupted");
+        }
+
         @Test
         @DisplayName("Should list session keys correctly in cluster mode")
         void testListSessionKeysCluster() {
diff --git a/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/RedissonSessionTest.java b/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/RedissonSessionTest.java
index 00dc98b5a9..adc3672f0e 100644
--- a/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/RedissonSessionTest.java
+++ b/agentscope-extensions/agentscope-extensions-session-redis/src/test/java/io/agentscope/core/session/redis/RedissonSessionTest.java
@@ -251,6 +251,22 @@ void testDeleteSession() {
         verify(rSet).iterator();
     }
 
+    @Test
+    @DisplayName("Should delete single state key and remove tracking metadata")
+    void testDeleteSingleStateKey() {
+        RedisSession session =
+                RedisSession.builder()
+                        .redissonClient(redissonClient)
+                        .keyPrefix("agentscope:session:")
+                        .build();
+
+        SessionKey sessionKey = SimpleSessionKey.of("session1");
+        session.delete(sessionKey, "shutdown_interrupted");
+
+        verify(keys).delete("agentscope:session:session1:shutdown_interrupted");
+        verify(rSet).remove("shutdown_interrupted");
+    }
+
     @Test
     @DisplayName("Should list all session keys")
     void testListSessionKeys() {