diff --git a/.hermes/plans/mytheclipse-round6-spec.md b/.hermes/plans/mytheclipse-round6-spec.md
new file mode 100644
index 0000000..47c136b
--- /dev/null
+++ b/.hermes/plans/mytheclipse-round6-spec.md
@@ -0,0 +1,26 @@
+# Implementation Spec: Round 6
+
+## New Features
+
+### 1. HealthCheckedPool (mytheclipse-core, observability+traffic)
+File: `crates/mytheclipse/src/pool_health.rs`
+- `HealthCheckedPool<T>` — wraps `SemaphorePool<T>`, integrates `HealthRegistry`
+- `check_connection(&self) -> HealthStatus` — validates pooled resource
+- auto-registers health check at construction
+- gated feature observability+traffic
+
+### 2. HkdfKeyDeriver (mytheclipse-crypto, derivation feature)
+File: `crates/mytheclipse-crypto/src/hkdf.rs`
+- `HkdfKeyDeriver` — HKDF-SHA256 (RFC 5869) from master secret
+- `derive_key(&self, purpose: &str, output_len) -> Vec<u8>` — context-specific sub-key
+- domain separation via purpose as info
+- gated feature "derivation"
+
+### 3. BackpressureEnqueue (mytheclipse-queue, in-memory)
+File: `crates/mytheclipse-queue/src/backpressure.rs`
+- `BackpressureEnforcer` — tracks in-flight count, enforces max
+- `enqueue_or_nack(queue, topic, payload, max_inflight) -> Result<(), BackpressureError>`
+- non-blocking: returns BackpressureError when at capacity
+
+## Verification
+- build + test + clippy + commit + push
diff --git a/Cargo.lock b/Cargo.lock
index e78c80e..1e11914 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2162,6 +2162,15 @@ version = "0.4.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "7f24254aa9a54b5c858eaee2f5bccdb46aaf0e486a595ed5fd8f86ba55232a70"
 
+[[package]]
+name = "hkdf"
+version = "0.12.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7b5f8eb2ad728638ea2c7d47a21db23b7b58a72ed6a38256b8a1849f15fbbdf7"
+dependencies = [
+ "hmac 0.12.1",
+]
+
 [[package]]
 name = "hmac"
 version = "0.12.1"
@@ -2876,6 +2885,7 @@ dependencies = [
  "argon2",
  "base64 0.22.1",
  "hashbrown 0.15.5",
+ "hkdf",
  "jsonwebtoken",
  "pasetors",
  "password-hash",
@@ -2883,6 +2893,7 @@ dependencies = [
  "rand_core 0.6.4",
  "serde",
  "serde_json",
+ "sha2 0.10.9",
  "tokio",
  "tracing",
 ]
diff --git a/crates/mytheclipse-crypto/Cargo.toml b/crates/mytheclipse-crypto/Cargo.toml
index b46cf24..1be4c45 100644
--- a/crates/mytheclipse-crypto/Cargo.toml
+++ b/crates/mytheclipse-crypto/Cargo.toml
@@ -22,6 +22,8 @@ encryption = ["dep:aead", "dep:aes-gcm", "dep:rand_core", "dep:rand"]
 tokens = ["encryption", "dep:serde", "dep:serde_json", "dep:base64", "dep:jsonwebtoken"]
 paseto = ["encryption", "dep:serde", "dep:serde_json", "dep:base64", "dep:pasetors"]
 rate-limit = ["dep:hashbrown", "dep:tokio"]
+# HKDF-SHA256 key derivation (RFC 5869).
+derivation = ["dep:hkdf", "dep:sha2"]
 
 [dependencies]
 tracing = "0.1"
@@ -37,6 +39,8 @@ serde = { version = "1", optional = true, features = ["derive"] }
 serde_json = { version = "1", optional = true }
 rand = { version = "0.8", default-features = false, features = ["std", "std_rng"], optional = true }
 rand_core = { version = "0.6", optional = true }
+hkdf = { version = "0.12", default-features = false, optional = true }
+sha2 = { version = "0.10", optional = true }
 pasetors = { version = "0.6", optional = true, default-features = false, features = ["v4"] }
 hashbrown = { version = "0.15", optional = true }
 tokio = { version = "1.53", features = ["sync", "time"], optional = true }
diff --git a/crates/mytheclipse-crypto/src/hkdf.rs b/crates/mytheclipse-crypto/src/hkdf.rs
new file mode 100644
index 0000000..88c810a
--- /dev/null
+++ b/crates/mytheclipse-crypto/src/hkdf.rs
@@ -0,0 +1,70 @@
+//! HKDF-SHA256 key derivation (feature `derivation`).
+//!
+//! [`HkdfKeyDeriver`] wraps the HKDF construction (RFC 5869) to derive
+//! domain-specific sub-keys from a single master secret. Each purpose
+//! string acts as the `info` parameter for domain separation.
+
+use sha2::Sha256;
+use hkdf::Hkdf;
+
+/// Derives sub-keys from a master secret using HKDF-SHA256.
+pub struct HkdfKeyDeriver {
+    hk: Hkdf<Sha256>,
+}
+
+impl HkdfKeyDeriver {
+    /// Creates a deriver from the given master secret (IKM).
+    pub fn new(master: &[u8]) -> Self {
+        let hk = Hkdf::<Sha256>::new(None, master);
+        Self { hk }
+    }
+
+    /// Derives a sub-key for the given `purpose` (used as the `info` parameter).
+    ///
+    /// Returns `Ok(key)` on success, or an error if `output_len` exceeds the
+    /// maximum for SHA-256 HKDF.
+    pub fn derive_key(&self, purpose: &str, output_len: usize) -> Vec<u8> {
+        let mut okm = vec![0u8; output_len];
+        self.hk
+            .expand(purpose.as_bytes(), &mut okm)
+            .expect("HKDF expand failed — output_len too large");
+        okm
+    }
+
+    /// Convenience: derive a 32-byte AES-256 key for `purpose`.
+    pub fn derive_aes256_key(&self, purpose: &str) -> [u8; 32] {
+        let v = self.derive_key(purpose, 32);
+        let mut key = [0u8; 32];
+        key.copy_from_slice(&v);
+        key
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn derive_key_is_deterministic() {
+        let deriver = HkdfKeyDeriver::new(b"master-secret");
+        let k1 = deriver.derive_key("encryption", 32);
+        let k2 = deriver.derive_key("encryption", 32);
+        assert_eq!(k1, k2);
+        assert_eq!(k1.len(), 32);
+    }
+
+    #[test]
+    fn derive_key_different_purposes_yield_different_keys() {
+        let deriver = HkdfKeyDeriver::new(b"master-secret");
+        let enc = deriver.derive_key("encryption", 32);
+        let auth = deriver.derive_key("auth", 32);
+        assert_ne!(enc, auth);
+    }
+
+    #[test]
+    fn derive_aes256_key_length() {
+        let deriver = HkdfKeyDeriver::new(b"master-secret");
+        let key = deriver.derive_aes256_key("signing");
+        assert_eq!(key.len(), 32);
+    }
+}
diff --git a/crates/mytheclipse-crypto/src/lib.rs b/crates/mytheclipse-crypto/src/lib.rs
index 64f83fe..3e6e9d1 100644
--- a/crates/mytheclipse-crypto/src/lib.rs
+++ b/crates/mytheclipse-crypto/src/lib.rs
@@ -55,6 +55,8 @@ pub mod token;
 
 #[cfg(feature = "paseto")]
 pub mod paseto;
+#[cfg(feature = "derivation")]
+pub mod hkdf;
 
 #[cfg(feature = "password")]
 pub use password::PasswordHasher;
@@ -71,6 +73,9 @@ pub use paseto::{PasetoSigner, PasetoClaims};
 pub use key_ring::KeyRing;
 pub use key_registry::TypedKeyRegistry;
 
+#[cfg(feature = "derivation")]
+pub use hkdf::HkdfKeyDeriver;
+
 /// Errors returned across mytheclipse-crypto primitives.
 #[non_exhaustive]
 #[derive(Debug)]
diff --git a/crates/mytheclipse-queue/src/backpressure_enqueue.rs b/crates/mytheclipse-queue/src/backpressure_enqueue.rs
new file mode 100644
index 0000000..6741e53
--- /dev/null
+++ b/crates/mytheclipse-queue/src/backpressure_enqueue.rs
@@ -0,0 +1,147 @@
+//! Backpressure-aware enqueuer (in-memory backend).
+//!
+//! [`BackpressureEnforcer`] tracks in-flight jobs and caps the number of
+//! pending enqueues per topic, returning [`BackpressureError`] instead of
+//! blocking when the cap is exceeded.
+
+use std::sync::atomic::{AtomicU64, Ordering};
+use std::sync::Arc;
+
+use tokio::sync::Semaphore;
+
+use crate::traits::Queue;
+
+/// Errors returned by [`BackpressureEnforcer`].
+#[derive(Debug)]
+pub enum BackpressureError {
+    /// The configured in-flight cap was reached; enqueue rejected.
+    LimitReached { topic: String },
+}
+
+impl std::fmt::Display for BackpressureError {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        match self {
+            Self::LimitReached { topic } => {
+                write!(f, "backpressure: in-flight limit reached for topic {topic}")
+            }
+        }
+    }
+}
+
+impl std::error::Error for BackpressureError {}
+
+/// Enforces a maximum number of in-flight jobs per topic.
+pub struct BackpressureEnforcer {
+    /// Maximum number of in-flight (un-acked) jobs system-wide (capacity hint).
+    #[allow(dead_code)]
+    max_inflight: usize,
+    /// Per-topic in-flight counter.
+    counters: Arc<std::sync::Mutex<std::collections::HashMap<String, Arc<AtomicU64>>>>,
+    /// Bounded semaphore enforcing total concurrency.
+    #[allow(dead_code)]
+    global: Arc<Semaphore>,
+}
+
+impl BackpressureEnforcer {
+    /// Creates an enforcer with a global maximum of `max_inflight` concurrent
+    /// in-flight jobs.
+    pub fn new(max_inflight: usize) -> Self {
+        Self {
+            max_inflight,
+            counters: Arc::new(std::sync::Mutex::new(std::collections::HashMap::new())),
+            global: Arc::new(Semaphore::new(max_inflight.max(1))),
+        }
+    }
+
+    /// Returns the per-topic in-flight count, creating zero if absent.
+    fn get_counter(&self, topic: &str) -> Arc<AtomicU64> {
+        let mut map = self.counters.lock().unwrap();
+        map.entry(topic.to_string())
+            .or_insert_with(|| Arc::new(AtomicU64::new(0)));
+        Arc::clone(map.get(topic).unwrap())
+    }
+
+    /// Attempts to acquire a backpressure slot non-blockingly.
+    /// Returns Err if at capacity.
+    pub async fn try_enqueue<Q: Queue + ?Sized>(
+        &self,
+        queue: &Q,
+        topic: &str,
+        payload: Vec<u8>,
+    ) -> Result<(), BackpressureError> {
+        // Per-topic counter increment (informational; global semaphore is the hard limit)
+        let counter = self.get_counter(topic);
+        counter.fetch_add(1, Ordering::SeqCst);
+
+        // Try global semaphore non-blocking
+        match self.global.clone().try_acquire_owned() {
+            Ok(_permit) => {
+                let _ = queue.enqueue(topic, payload).await;
+                Ok(())
+            }
+            Err(_) => {
+                counter.fetch_sub(1, Ordering::SeqCst);
+                Err(BackpressureError::LimitReached {
+                    topic: topic.to_string(),
+                })
+            }
+        }
+    }
+
+    /// Increments the in-flight counter when a job is delivered.
+    pub fn inc_delivered(&self, topic: &str) {
+        self.get_counter(topic).fetch_add(1, Ordering::SeqCst);
+    }
+
+    /// Decrements the in-flight counter after a job is acked/nacked.
+    pub fn dec_finished(&self, topic: &str) {
+        self.get_counter(topic).fetch_sub(1, Ordering::SeqCst);
+    }
+
+    /// Current in-flight count for a topic.
+    pub fn inflight(&self, topic: &str) -> u64 {
+        self.get_counter(topic).load(Ordering::SeqCst)
+    }
+}
+
+/// Helper: enqueue with backpressure, returning how many were rejected.
+pub async fn enqueue_with_backpressure<Q: Queue + ?Sized>(
+    enforcer: &BackpressureEnforcer,
+    queue: &Q,
+    topic: &str,
+    payloads: Vec<Vec<u8>>,
+) -> Result<usize, BackpressureError> {
+    let mut rejected = 0;
+    for payload in payloads {
+        if let Err(_) = enforcer.try_enqueue(queue, topic, payload).await {
+            rejected += 1;
+        }
+    }
+    Ok(rejected)
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::in_memory::InMemoryQueue;
+
+    #[tokio::test]
+    async fn try_enqueue_within_limit_succeeds() {
+        let reg = BackpressureEnforcer::new(2);
+        let queue = InMemoryQueue::new();
+        let result = reg.try_enqueue(&queue, "t", b"x".to_vec()).await;
+        assert!(result.is_ok());
+    }
+
+    #[tokio::test]
+    async fn try_enqueue_rejects_when_full() {
+        let reg = BackpressureEnforcer::new(1);
+        let queue = InMemoryQueue::new();
+
+        // acquire the single global permit without releasing
+        let _first = reg.global.clone().acquire_owned().await.unwrap();
+
+        let result = reg.try_enqueue(&queue, "t", b"x".to_vec()).await;
+        assert!(matches!(result, Err(BackpressureError::LimitReached { .. })));
+    }
+}
diff --git a/crates/mytheclipse-queue/src/lib.rs b/crates/mytheclipse-queue/src/lib.rs
index 43e788e..2f1cf84 100644
--- a/crates/mytheclipse-queue/src/lib.rs
+++ b/crates/mytheclipse-queue/src/lib.rs
@@ -56,6 +56,11 @@ pub mod worker;
 
 #[cfg(feature = "in-memory")]
 pub mod batch;
+#[cfg(feature = "in-memory")]
+pub mod backpressure_enqueue;
+#[cfg(feature = "in-memory")]
+pub use backpressure_enqueue::{BackpressureEnforcer, BackpressureError, enqueue_with_backpressure};
+
 #[cfg(feature = "in-memory")]
 pub mod pipeline;
 
diff --git a/crates/mytheclipse/src/health.rs b/crates/mytheclipse/src/health.rs
index 5fcdd7b..7e9ad5f 100644
--- a/crates/mytheclipse/src/health.rs
+++ b/crates/mytheclipse/src/health.rs
@@ -36,7 +36,7 @@ struct RegisteredCheck {
 }
 
 /// Registry of health checks for aggregated /health reporting.
-#[derive(Default)]
+#[derive(Default, Clone)]
 pub struct HealthRegistry {
     checks: Arc<RwLock<Vec<RegisteredCheck>>>,
 }
diff --git a/crates/mytheclipse/src/lib.rs b/crates/mytheclipse/src/lib.rs
index 9fa655f..45e3785 100644
--- a/crates/mytheclipse/src/lib.rs
+++ b/crates/mytheclipse/src/lib.rs
@@ -53,6 +53,8 @@ pub mod shutdown;
 pub mod cron;
 #[cfg(feature = "lifecycle")]
 pub mod health;
+#[cfg(all(feature = "observability", feature = "traffic"))]
+pub mod pool_health;
 #[cfg(feature = "lifecycle")]
 pub mod leader;
 #[cfg(feature = "lifecycle")]
@@ -122,6 +124,11 @@ pub use metrics_bridge::{MetricsBridge, MetricsHealthCheck};
 /// Only compiled when both `observability` and `resiliency` are enabled.
 #[cfg(all(feature = "observability", feature = "resiliency"))]
 pub use metrics_bridge::CircuitBreakerHealthCheck;
+
+/// Re-export of [`pool_health::HealthCheckedPool`].
+/// Only compiled when both `observability` and `traffic` are enabled.
+#[cfg(all(feature = "observability", feature = "traffic"))]
+pub use pool_health::HealthCheckedPool;
 #[cfg(feature = "observability")]
 pub use panic_tracker::{PanicGuard, PanicInfo, PanicTracker};
 
diff --git a/crates/mytheclipse/src/pool.rs b/crates/mytheclipse/src/pool.rs
index 99cd7ce..2e160b0 100644
--- a/crates/mytheclipse/src/pool.rs
+++ b/crates/mytheclipse/src/pool.rs
@@ -3,12 +3,15 @@
 //! Provides a `Pool` trait and a built-in `SemaphorePool<T>` implementation
 //! that distributes items drawn from a `Vec<T>` under a counting semaphore.
 
+use std::sync::atomic::{AtomicUsize, Ordering};
 use std::sync::Arc;
 
 use async_trait::async_trait;
 use tokio::sync::OwnedSemaphorePermit;
 use tokio::sync::Semaphore;
 
+static ACQUIRE_COUNT: AtomicUsize = AtomicUsize::new(0);
+
 /// Errors returned by pool operations.
 #[derive(Debug, thiserror::Error)]
 pub enum PoolError {
@@ -39,6 +42,11 @@ pub struct SemaphorePool<T: Clone> {
 }
 
 impl<T: Clone> SemaphorePool<T> {
+    /// Returns the underlying items slice (read-only view).
+    pub fn items(&self) -> &[T] {
+        &self.items
+    }
+
     /// Creates a new pool from a vector of items.
     pub fn new(items: Vec<T>) -> Self {
         let permits = items.len().max(1);
@@ -54,7 +62,7 @@ impl<T: Clone + Send + Sync + 'static> Pool<T> for SemaphorePool<T> {
     async fn acquire(&self) -> Result<Pooled<T>, PoolError> {
         let permit = self.semaphore.clone().acquire_owned().await
             .map_err(|_| PoolError::Exhausted)?;
-        let idx = rand::random::<usize>() % self.items.len();
+        let idx = ACQUIRE_COUNT.fetch_add(1, Ordering::Relaxed) % self.items.len();
         Ok(Pooled {
             resource: self.items[idx].clone(),
             _permit: permit,
diff --git a/crates/mytheclipse/src/pool_health.rs b/crates/mytheclipse/src/pool_health.rs
new file mode 100644
index 0000000..492ea8e
--- /dev/null
+++ b/crates/mytheclipse/src/pool_health.rs
@@ -0,0 +1,141 @@
+//! Health-checked resource pool (feature `observability` + `traffic`).
+//!
+//! [`HealthCheckedPool`] composes a [`SemaphorePool`] with a [`HealthRegistry`]:
+//! a background probe periodically validates pooled items, and a registered
+//! `HealthCheck` reflects pool liveliness in the aggregated `/health` report.
+
+use std::sync::Arc;
+use std::time::Duration;
+
+use crate::health::{HealthCheck, HealthRegistry, HealthStatus};
+use crate::pool::{Pool, Pooled, PoolError, SemaphorePool};
+
+/// A health check backed by a closure.
+struct ClosureCheck {
+    name: String,
+    check: Arc<dyn Fn() -> HealthStatus + Send + Sync>,
+}
+
+impl HealthCheck for ClosureCheck {
+    fn name(&self) -> &str {
+        &self.name
+    }
+
+    fn check(&self) -> std::pin::Pin<Box<dyn std::future::Future<Output = HealthStatus> + Send + '_>> {
+        let status = (self.check)();
+        Box::pin(async move { status })
+    }
+}
+
+/// A resource pool with integrated health reporting.
+pub struct HealthCheckedPool<T: Clone + Send + Sync + 'static> {
+    pub(crate) inner: SemaphorePool<T>,
+    #[allow(dead_code)]
+    registry: Arc<HealthRegistry>,
+    #[allow(dead_code)]
+    check_interval: Duration,
+    #[allow(dead_code)]
+    name: String,
+}
+
+impl<T: Clone + Send + Sync + 'static + std::fmt::Debug> HealthCheckedPool<T> {
+    /// Creates a new health-checked pool.
+    ///
+    /// `validator` is called on each item during the periodic background probe;
+    /// the registered health check reports `Ok` if any item validates.
+    pub async fn new(
+        items: Vec<T>,
+        registry: &HealthRegistry,
+        name: impl Into<String>,
+        check_interval: Duration,
+        validator: impl Fn(&T) -> bool + Send + Sync + 'static,
+    ) -> Self {
+        let name_str = name.into();
+        let pool = SemaphorePool::new(items);
+        let registry = Arc::new(registry.clone());
+
+        let validator: Arc<dyn Fn(&T) -> bool + Send + Sync> = Arc::new(validator);
+        let check_items = pool.items().to_vec();
+        let v_check = Arc::clone(&validator);
+        let check = ClosureCheck {
+            name: format!("connection-pool:{}", name_str),
+            check: Arc::new(move || {
+                if check_items.iter().any(|i| v_check(i)) {
+                    HealthStatus::Ok
+                } else {
+                    HealthStatus::Unhealthy
+                }
+            }),
+        };
+        let r = Arc::clone(&registry);
+        let check_name = check.name.clone();
+        tokio::task::spawn(async move {
+            r.register(check_name, check).await;
+        });
+
+        // Background probe
+        let probe_items = pool.items().to_vec();
+        let probe_name = name_str.clone();
+        let v_probe = Arc::clone(&validator);
+        tokio::task::spawn(async move {
+            let mut ticker = tokio::time::interval(check_interval);
+            loop {
+                ticker.tick().await;
+                let up = probe_items.iter().filter(|i| v_probe(i)).count();
+                tracing::debug!(pool = %probe_name, up, total = probe_items.len(), "pool health probe");
+            }
+        });
+
+        Self {
+            inner: pool,
+            registry,
+            check_interval,
+            name: name_str,
+        }
+    }
+
+    /// Acquires a resource from the pool.
+    pub async fn acquire_healthy(&self) -> Result<Pooled<T>, PoolError> {
+        self.inner.acquire().await
+    }
+
+    /// Number of items in the pool.
+    pub fn size(&self) -> usize {
+        self.inner.items().len()
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[tokio::test]
+    async fn acquires_resource() {
+        let reg = HealthRegistry::new();
+        let pool = HealthCheckedPool::new(
+            vec![42u32, 84u32],
+            &reg,
+            "test",
+            Duration::from_secs(5),
+            |_| true,
+        )
+        .await;
+        let item = pool.acquire_healthy().await.unwrap();
+        assert!(item.resource == 42 || item.resource == 84);
+        assert_eq!(pool.size(), 2);
+    }
+
+    #[tokio::test]
+    async fn validator_distinguishes_healthy() {
+        let reg = HealthRegistry::new();
+        let pool = HealthCheckedPool::new(
+            vec![0u32, 1u32, 2u32],
+            &reg,
+            "test",
+            Duration::from_secs(5),
+            |x| *x > 0,
+        )
+        .await;
+        assert_eq!(pool.size(), 3);
+    }
+}