diff --git a/Sources/SwiftLM/Server.swift b/Sources/SwiftLM/Server.swift
index 9823593..8c81887 100644
--- a/Sources/SwiftLM/Server.swift
+++ b/Sources/SwiftLM/Server.swift
@@ -1948,10 +1948,17 @@ actor PromptCache {
 /// The generation prompt after it (`assistant\n<think>…`) is not always a prefix of
 /// its own re-rendered form. Returns nil when the model is not hybrid, the template is
 /// not ChatML, or there is no history to cache.
+///
+/// The attention layers may be KVCacheSimple or, under `--ctx-size`, RotatingKVCache.
+/// A ring is safe here even once it has wrapped: this path never trims, it restores the
+/// exact snapshot taken at the boundary, and the ring's state + metaState round-trip it.
 func hybridCacheBoundary(promptTokens: [Int], imStartId: Int?, cache: [KVCache]) -> Int? {
     guard let imStartId,
           cache.contains(where: { $0 is MambaCache }),
-          cache.allSatisfy({ $0 is MambaCache || type(of: $0) == KVCacheSimple.self }),
+          cache.allSatisfy({
+              $0 is MambaCache || type(of: $0) == KVCacheSimple.self
+                  || type(of: $0) == RotatingKVCache.self
+          }),
           let boundary = promptTokens.lastIndex(of: imStartId), boundary > 0
     else { return nil }
     return boundary
@@ -2294,7 +2301,9 @@ func handleChatCompletion(
 
         // ── Hybrid (recurrent + attention) prompt cache ──
         // Qwen3.5/3.6-style models pair MambaCache (linear attention) with KVCacheSimple
-        // layers, and the generic path below refuses them: recurrent state cannot be
+        // layers (RotatingKVCache under --ctx-size; this path must run before the
+        // sliding-window one, which misses on any MambaCache), and the generic path below
+        // refuses them: recurrent state cannot be
         // trimmed, and the onPrefillDone save runs after the first decode token has been
         // fed. Without this, every agent turn re-prefills the whole conversation. Instead:
         // resume from an exact cached prefix, prefill to the turn boundary, snapshot there
diff --git a/tests/SwiftLMTests/HybridPromptCacheTests.swift b/tests/SwiftLMTests/HybridPromptCacheTests.swift
index 6ebda96..b32031e 100644
--- a/tests/SwiftLMTests/HybridPromptCacheTests.swift
+++ b/tests/SwiftLMTests/HybridPromptCacheTests.swift
@@ -77,4 +77,57 @@ final class HybridPromptCacheTests: XCTestCase {
                                             into: [KVCacheSimple(), MambaCache()])
         XCTAssertNil(n, "only the boundary snapshot may persist recurrent state")
     }
+
+    // MARK: - --ctx-size: RotatingKVCache attention layers
+
+    /// A ring fed `n` single tokens; values encode the token index.
+    private func makeRing(maxSize: Int, tokens n: Int) -> RotatingKVCache {
+        let ring = RotatingKVCache(maxSize: maxSize, keep: 0, step: 4)
+        for t in 0 ..< n {
+            let k = MLXArray([Float(t)]).reshaped([1, 1, 1, 1])
+            _ = ring.update(keys: k, values: k)
+        }
+        return ring
+    }
+
+    private func makeMamba() -> MambaCache {
+        let mamba = MambaCache()
+        mamba.state = [MLXArray.ones([1, 3, 8]), MLXArray.ones([1, 2, 4, 4])]
+        return mamba
+    }
+
+    func testBoundaryAcceptsRotatingAttentionLayers() {
+        let tokens = [imStart, 1, imStart, 2]
+        XCTAssertEqual(hybridCacheBoundary(promptTokens: tokens, imStartId: imStart,
+                                           cache: [RotatingKVCache(maxSize: 16), MambaCache()]), 2,
+                       "--ctx-size must not turn the hybrid cache off")
+    }
+
+    func testRestoresWrappedRingExactly() async {
+        let ring = makeRing(maxSize: 16, tokens: 40)  // wrapped
+        let pc = PromptCache()
+        await pc.save(tokens: Array(0 ..< 40), cache: [ring, makeMamba()], allowRecurrent: true)
+
+        // Decode on the live ring after saving; the snapshot must not see it.
+        for t in 40 ..< 50 {
+            let k = MLXArray([Float(t)]).reshaped([1, 1, 1, 1])
+            _ = ring.update(keys: k, values: k)
+        }
+        let fresh: [any KVCache] = [RotatingKVCache(maxSize: 16), MambaCache()]
+        let n = await pc.restoreExactPrefix(newTokens: Array(0 ..< 40) + [999], limit: 40, into: fresh)
+
+        XCTAssertEqual(n, 40)
+        XCTAssertEqual(fresh[0].offset, 40)
+        XCTAssertEqual(fresh[0].state[0].asArray(Float.self).sorted(), (24 ..< 40).map { Float($0) },
+                       "the restored window is the snapshot's, not the live ring's")
+    }
+
+    func testRotatingHybridMissesWhenPrefixDiverges() async {
+        let pc = PromptCache()
+        await pc.save(tokens: Array(0 ..< 8), cache: [makeRing(maxSize: 16, tokens: 8), makeMamba()],
+                      allowRecurrent: true)
+        let n = await pc.restoreExactPrefix(newTokens: [0, 1, 9, 3, 4, 5, 6, 7, 8], limit: 9,
+                                            into: [RotatingKVCache(maxSize: 16), MambaCache()])
+        XCTAssertNil(n)
+    }
 }