diff --git a/Cargo.toml b/Cargo.toml
index 74c1c7c..d86f30b 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -30,6 +30,7 @@ strum = "0.26.2"
 strum_macros = "0.26.2"
 clap = { version = "4.5.7", features = ["derive", "env"] }
 num-traits = "0.2.19"
+itertools = "0.13.0"
 
 [dev-dependencies]
 rand = "0.8.5"
diff --git a/src/commands/keys.rs b/src/commands/keys.rs
index 203c8fe..d79c975 100644
--- a/src/commands/keys.rs
+++ b/src/commands/keys.rs
@@ -1,5 +1,6 @@
 use bytes::Bytes;
 use glob_match::glob_match;
+use itertools::Itertools;
 
 use crate::commands::executable::Executable;
 use crate::commands::CommandParser;
@@ -20,11 +21,12 @@ pub struct Keys {
 impl Executable for Keys {
     fn exec(self, store: Store) -> Result<Frame, Error> {
         let store = store.lock();
-        let matching_keys: Vec<Frame> = store
-            .keys()
-            .filter(|key| glob_match(self.pattern.as_str(), key))
-            .map(|key| Frame::Bulk(Bytes::from(key.to_string())))
-            .collect();
+        let matching_keys = store
+            .iter()
+            .filter(|(key, _)| glob_match(self.pattern.as_str(), key))
+            .sorted_by(|(_, a), (_, b)| b.inserted_at.cmp(&a.inserted_at))
+            .map(|(key, _)| Frame::Bulk(Bytes::from(key.to_string())))
+            .collect::<Vec<_>>();
 
         Ok(Frame::Array(matching_keys))
     }
diff --git a/src/store.rs b/src/store.rs
index b83a575..980fd1d 100644
--- a/src/store.rs
+++ b/src/store.rs
@@ -59,23 +59,29 @@ pub struct InnerStoreLocked<'a> {
 impl<'a> InnerStoreLocked<'a> {
     pub fn set(&mut self, key: String, data: Bytes) {
         // Ensure any previous TTL is removed.
-        self.remove(&key);
+        let removed = self.remove(&key);
+
+        let inserted_at = removed.map(|v| v.inserted_at).unwrap_or(Instant::now());
 
         let value = Value {
             data,
             expires_at: None,
+            inserted_at,
         };
         self.state.keys.insert(key, value);
     }
 
     pub fn set_with_ttl(&mut self, key: Key, data: Bytes, ttl: Duration) {
         // Ensure any previous TTL is removed.
-        self.remove(&key);
+        let removed = self.remove(&key);
+
+        let inserted_at = removed.map(|v| v.inserted_at).unwrap_or(Instant::now());
 
         let expires_at = Instant::now() + ttl;
         let value = Value {
             data,
             expires_at: Some(expires_at),
+            inserted_at,
         };
 
         self.state.keys.insert(key.clone(), value);
@@ -142,11 +148,11 @@ impl<'a> InnerStoreLocked<'a> {
         self.state.keys.keys()
     }
 
-    pub fn iter(&self) -> impl Iterator<Item = (&String, &Bytes)> {
+    pub fn iter(&self) -> impl Iterator<Item = (&String, &Value)> {
         self.state
             .keys
             .iter()
-            .map(|(key, value)| (key, &value.data))
+            .map(|(key, value)| (key, value))
     }
 
     pub fn incr_by<T, R>(&mut self, key: &str, increment: T) -> Result<R, String>
@@ -232,6 +238,7 @@ type Key = String;
 pub struct Value {
     pub data: Bytes,
     pub expires_at: Option<Instant>,
+    pub inserted_at: Instant,
 }
 
 pub struct State {
diff --git a/tests/integration.rs b/tests/integration.rs
index 0e12570..99434ae 100644
--- a/tests/integration.rs
+++ b/tests/integration.rs
@@ -349,9 +349,11 @@ async fn test_getrange() {
 #[tokio::test]
 #[serial]
 async fn test_keys() {
-    // TODO: The response order from the server is not guaranteed, to ensure accurate comparison
-    // with the expected result, we need to sort the response before performing the comparison.
     test_compare::<Vec<Value>>(|p| {
+        // Redis keys order is deterministice but not guaranteed.
+        // We sort the keys by insertion order to make the test deterministic.
+        // Testing with a different set of keys produces different results,
+        // but matching the implementation is out of the scope of the project.
         p.cmd("SET").arg("keys_key_1").arg("Argentina");
         p.cmd("SET").arg("keys_key_2").arg("Spain");
         p.cmd("SET").arg("keys_key_3").arg("Netherlands");