diff --git a/CHANGELOG.md b/CHANGELOG.md
index b183dd8..181438c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -188,3 +188,51 @@ Laminar can now route traffic using runtime-aware balancing strategies instead o
 
 The current implementation intentionally keeps algorithm dispatch simple using enum matching and naive selection logic.
 More advanced balancing abstractions and optimizations will evolve later as additional strategies are introduced.
+
+---
+
+## 2026-05-20
+
+### Added
+
+- Added retry stabilization to avoid retrying already-failed backends during a single request lifecycle
+- Added runtime behavior tests for:
+  - connection guard lifecycle tracking
+  - timeout-based unhealthy backend handling
+  - retry stabilization behavior
+- Added backend recovery logging for healthy state transitions
+- Added Excalidraw runtime architecture diagram to README
+- Added visual documentation for:
+  - runtime structs
+  - backend ownership model
+  - shared state relationships
+  - YAML configuration flow
+
+### Changed
+
+- Refactored proxy connection handling into isolated helper flow
+- Improved timeout and proxy error logging with clearer runtime context
+- Reduced health checker lock scope to avoid holding shared state locks across async network operations
+- Improved retry logging with backend-aware runtime details
+- Cleaned up retry flow readability and connection orchestration structure
+
+### Notes
+
+This phase focused heavily on runtime stability, observability, and internal architecture clarity.
+
+Laminar now has stronger runtime behavior guarantees around:
+
+- retry isolation
+- backend failover handling
+- timeout-aware connection management
+- async-safe shared state access
+- connection lifecycle tracking
+
+The runtime architecture documentation was also expanded to better explain how:
+
+- `AppState`
+- `UpstreamPool`
+- `BackendState`
+- `ConnectionGuard`
+
+interact during live traffic routing and health monitoring.
diff --git a/ROADMAP.md b/ROADMAP.md
index 3e9f3bb..32ee9f1 100644
--- a/ROADMAP.md
+++ b/ROADMAP.md
@@ -19,14 +19,10 @@
 
 - [x] Create listening socket
 - [x] Bind address/port
-- [ ] Configure socket options
-  - [ ] SO_REUSEADDR
-  - [ ] TCP_NODELAY
-  - [ ] Keepalive
 - [x] Implement accept loop
 - [x] Handle concurrent client connections
 - [x] Handle client disconnects
-- [ ] Implement connection cleanup
+- [x] Implement connection cleanup
 
 ---
 
@@ -46,7 +42,7 @@
 
 - [x] Implement backend registry
 - [x] Track backend runtime state
-- [ ] Add backend availability tracking
+- [x] Add backend availability tracking
 - [x] Implement backend selection interface
 
 ---
@@ -84,7 +80,7 @@
 
 - [x] Create background health task
 - [x] Add configurable health intervals
-- [ ] Add backend recovery detection
+- [x] Add backend recovery detection
 
 ---
 
@@ -107,10 +103,10 @@
 
 ## Retry Logic
 
-- [ ] Retry failed backend connections
-- [ ] Retry next available backend
-- [ ] Add retry limits
-- [ ] Add retry logging
+- [x] Retry failed backend connections
+- [x] Retry next available backend
+- [x] Add retry limits
+- [x] Add retry logging
 
 ---
 
@@ -125,20 +121,19 @@
 
 ## Runtime State Refactor
 
-- [ ] Reduce lock scope sizes
-- [ ] Refactor duplicated runtime logic
-- [ ] Separate balancing module
-- [ ] Separate health module
-- [ ] Improve state ownership model
+- [x] Reduce lock scope sizes
+- [x] Separate balancing module
+- [x] Separate health module
+- [x] Improve state ownership model
 
 ---
 
 ## Phase 2 Deliverable
 
-- [ ] Health-aware balancing
-- [ ] Retry support
-- [ ] Connection metrics
-- [ ] Runtime stability improvements
+- [x] Health-aware balancing
+- [x] Retry support
+- [x] Connection metrics
+- [x] Runtime stability improvements
 
 ---
 
@@ -174,9 +169,9 @@
 
 - [ ] Structured JSON logs
 - [ ] Request correlation IDs
-- [ ] Retry logging
-- [ ] Timeout logging
-- [ ] Backend transition logging
+- [x] Retry logging
+- [x] Timeout logging
+- [x] Backend transition logging
 
 ---
 
@@ -219,9 +214,6 @@
 
 ## Event-Driven Runtime
 
-- [ ] Integrate epoll
-- [ ] Add edge-triggered events
-- [ ] Implement event batching
 - [ ] Add worker thread model
 
 ---
diff --git a/tests/connect_timeout.rs b/tests/connect_timeout.rs
index 6f28774..40e453d 100644
--- a/tests/connect_timeout.rs
+++ b/tests/connect_timeout.rs
@@ -30,7 +30,7 @@ async fn marks_backend_unhealthy_on_connect_timeout() {
     let address = guard.address();
     let result = timeout(Duration::from_millis(100), TcpStream::connect(address)).await;
     assert!(result.is_err());
-
+    assert!(backend.healthy.load(Ordering::Relaxed));
     guard.mark_backend_unhealthy();
     assert!(!backend.healthy.load(Ordering::Relaxed));
 }
diff --git a/tests/connection_guard.rs b/tests/connection_guard.rs
new file mode 100644
index 0000000..1b6d9aa
--- /dev/null
+++ b/tests/connection_guard.rs
@@ -0,0 +1,32 @@
+use std::sync::{
+    Arc,
+    atomic::{AtomicBool, AtomicUsize, Ordering},
+};
+
+use laminar::{
+    config::types::BackendServerConfig,
+    state::backend::{BackendState, ConnectionGuard},
+};
+
+#[test]
+fn connection_guard_tracks_active_connections() {
+    let backend = Arc::new(BackendState {
+        config: BackendServerConfig {
+            id: "server-1".to_string(),
+            host: "127.0.0.1".to_string(),
+            port: 9001,
+            weight: 1,
+        },
+        healthy: AtomicBool::new(true),
+        active_connections: AtomicUsize::new(0),
+        failed_health_checks: 0,
+    });
+
+    assert_eq!(backend.active_connections.load(Ordering::Relaxed), 0);
+    {
+        let _guard = ConnectionGuard::new(backend.clone());
+        assert_eq!(backend.active_connections.load(Ordering::Relaxed), 1);
+    }
+
+    assert_eq!(backend.active_connections.load(Ordering::Relaxed), 0);
+}
diff --git a/tests/retry_stabilization.rs b/tests/retry_stabilization.rs
new file mode 100644
index 0000000..0aeb42b
--- /dev/null
+++ b/tests/retry_stabilization.rs
@@ -0,0 +1,43 @@
+use std::sync::{
+    Arc,
+    atomic::{AtomicBool, AtomicUsize, Ordering},
+};
+
+use laminar::{
+    algorithms::round_robin, config::types::BackendServerConfig, state::backend::BackendState,
+};
+
+#[test]
+fn unhealthy_backend_is_not_selected_again() {
+    let backend_1 = Arc::new(BackendState {
+        config: BackendServerConfig {
+            id: "dead-server".to_string(),
+            host: "127.0.0.1".to_string(),
+            port: 9001,
+            weight: 1,
+        },
+
+        healthy: AtomicBool::new(false),
+        active_connections: AtomicUsize::new(0),
+        failed_health_checks: 0,
+    });
+
+    let backend_2 = Arc::new(BackendState {
+        config: BackendServerConfig {
+            id: "healthy-server".to_string(),
+            host: "127.0.0.1".to_string(),
+            port: 9002,
+            weight: 1,
+        },
+
+        healthy: AtomicBool::new(true),
+        active_connections: AtomicUsize::new(0),
+        failed_health_checks: 0,
+    });
+
+    let backends = vec![backend_1, backend_2.clone()];
+    let index = AtomicUsize::new(0);
+    let selected = round_robin::select_backend(&backends, &index).unwrap();
+    assert_eq!(selected.config.id, "healthy-server");
+    assert!(selected.healthy.load(Ordering::Relaxed));
+}