diff --git a/src/shared/dynamic-truncator.test.ts b/src/shared/dynamic-truncator.test.ts
index d090dd260..aae20aed9 100644
--- a/src/shared/dynamic-truncator.test.ts
+++ b/src/shared/dynamic-truncator.test.ts
@@ -2,7 +2,11 @@
 
 import { describe, expect, it, afterEach } from "bun:test"
 
-import { getContextWindowUsage, invalidateContextWindowUsageCache } from "./dynamic-truncator"
+import {
+  _setContextWindowUsageFetchTimeoutMsForTesting,
+  getContextWindowUsage,
+  invalidateContextWindowUsageCache,
+} from "./dynamic-truncator"
 
 const ANTHROPIC_CONTEXT_ENV_KEY = "ANTHROPIC_1M_CONTEXT"
 const VERTEX_CONTEXT_ENV_KEY = "VERTEX_ANTHROPIC_1M_CONTEXT"
@@ -89,6 +93,114 @@ function createCountingContextUsageMockContext(inputTokens: number) {
 describe("getContextWindowUsage", () => {
   afterEach(() => {
     resetContextLimitEnv()
+    _setContextWindowUsageFetchTimeoutMsForTesting(undefined)
+  })
+
+  describe("#given client.session.messages never settles", () => {
+    describe("#when getContextWindowUsage is called with a fast fetch timeout", () => {
+      it("#then returns null instead of hanging forever", async () => {
+        // given
+        _setContextWindowUsageFetchTimeoutMsForTesting(50)
+        const ctx = {
+          client: {
+            session: {
+              messages: () => new Promise<never>(() => {}),
+            },
+          },
+        }
+
+        // when
+        const start = Date.now()
+        const usage = await getContextWindowUsage(ctx as never, "ses_hang_messages", {
+          anthropicContext1MEnabled: false,
+        })
+        const elapsed = Date.now() - start
+
+        // then
+        expect(usage).toBeNull()
+        expect(elapsed).toBeLessThan(2000)
+      })
+
+      it("#then a parallel concurrent caller also resolves to null instead of hanging on the cached promise", async () => {
+        // given
+        _setContextWindowUsageFetchTimeoutMsForTesting(50)
+        const ctx = {
+          client: {
+            session: {
+              messages: () => new Promise<never>(() => {}),
+            },
+          },
+        }
+
+        // when
+        const start = Date.now()
+        const [first, second] = await Promise.all([
+          getContextWindowUsage(ctx as never, "ses_hang_messages_parallel", {
+            anthropicContext1MEnabled: false,
+          }),
+          getContextWindowUsage(ctx as never, "ses_hang_messages_parallel", {
+            anthropicContext1MEnabled: false,
+          }),
+        ])
+        const elapsed = Date.now() - start
+
+        // then
+        expect(first).toBeNull()
+        expect(second).toBeNull()
+        expect(elapsed).toBeLessThan(2000)
+      })
+
+      it("#then a follow-up call after invalidation retries fresh instead of being poisoned by the timeout", async () => {
+        // given
+        _setContextWindowUsageFetchTimeoutMsForTesting(50)
+        let messagesCalls = 0
+        let shouldHang = true
+        const ctx = {
+          client: {
+            session: {
+              messages: () => {
+                messagesCalls += 1
+                if (shouldHang) {
+                  return new Promise<never>(() => {})
+                }
+                return Promise.resolve({
+                  data: [
+                    {
+                      info: {
+                        role: "assistant",
+                        providerID: "anthropic",
+                        modelID: "claude-sonnet-4-5",
+                        tokens: {
+                          input: 100000,
+                          output: 0,
+                          reasoning: 0,
+                          cache: { read: 0, write: 0 },
+                        },
+                      },
+                    },
+                  ],
+                })
+              },
+            },
+          },
+        }
+
+        // when
+        const firstUsage = await getContextWindowUsage(ctx as never, "ses_hang_then_recover", {
+          anthropicContext1MEnabled: false,
+        })
+        invalidateContextWindowUsageCache(ctx as never, "ses_hang_then_recover")
+        shouldHang = false
+        const secondUsage = await getContextWindowUsage(ctx as never, "ses_hang_then_recover", {
+          anthropicContext1MEnabled: false,
+        })
+
+        // then
+        expect(firstUsage).toBeNull()
+        expect(secondUsage?.remainingTokens).toBe(100000)
+        expect(messagesCalls).toBe(2)
+      })
+    })
   })
 
   it("uses 1M limit when model cache flag is enabled", async () => {
diff --git a/src/shared/dynamic-truncator.ts b/src/shared/dynamic-truncator.ts
index 504f1a73b..59cbc81ca 100644
--- a/src/shared/dynamic-truncator.ts
+++ b/src/shared/dynamic-truncator.ts
@@ -3,10 +3,20 @@ import {
 	resolveActualContextLimit,
 	type ContextLimitModelCacheState,
 } from "./context-limit-resolver"
+import { log } from "./logger"
 import { normalizeSDKResponse } from "./normalize-sdk-response"
 
 const CHARS_PER_TOKEN_ESTIMATE = 4;
 const DEFAULT_TARGET_MAX_TOKENS = 50_000;
+// Hard ceiling on how long `session.messages()` is allowed to block inside
+// `fetchContextWindowUsage`. Without it, a stuck OpenCode RPC (observed when
+// `session.processor` enters an "Aborted process" loop) would leave the cached
+// promise pending forever and every hook that calls `truncator.truncate(...)`
+// would hang on it (issue #4086).
+export const DEFAULT_CONTEXT_WINDOW_USAGE_FETCH_TIMEOUT_MS = 5_000;
+
+declare function setTimeout(callback: () => void, delay?: number): ReturnType<typeof globalThis.setTimeout>
+declare function clearTimeout(timeout: ReturnType<typeof globalThis.setTimeout>): void
 
 interface AssistantMessageInfo {
 	role: "assistant";
@@ -34,6 +44,16 @@ type ContextWindowUsageClient = Pick<PluginInput["client"], "session">
 
 const usageCacheByClient = new WeakMap<object, Map<string, Map<string, Promise<ContextWindowUsage | null>>>>()
 
+// Test-only override for the fetch timeout used by `fetchContextWindowUsage`.
+// `undefined` means "use the production default".
+let contextWindowUsageFetchTimeoutMsForTesting: number | undefined = undefined
+
+export function _setContextWindowUsageFetchTimeoutMsForTesting(
+	ms: number | undefined,
+): void {
+	contextWindowUsageFetchTimeoutMsForTesting = ms
+}
+
 function createModelCacheKey(modelCacheState?: ContextLimitModelCacheState): string {
 	if (!modelCacheState) {
 		return "default"
@@ -184,15 +204,41 @@ export async function getContextWindowUsage(
 	return usagePromise
 }
 
+function withFetchTimeout<T>(operation: Promise<T>, timeoutMs: number): Promise<T> {
+	if (timeoutMs <= 0) {
+		return operation
+	}
+	let timeoutID: ReturnType<typeof globalThis.setTimeout> | undefined
+	const timeoutPromise = new Promise<never>((_, reject) => {
+		timeoutID = setTimeout(
+			() =>
+				reject(
+					new Error(
+						`[dynamic-truncator] session.messages timed out after ${timeoutMs}ms`,
+					),
+				),
+			timeoutMs,
+		)
+	})
+	return Promise.race([operation, timeoutPromise]).finally(() => {
+		if (timeoutID !== undefined) clearTimeout(timeoutID)
+	})
+}
+
 async function fetchContextWindowUsage(
 	ctx: PluginInput,
 	sessionID: string,
 	modelCacheState?: ContextLimitModelCacheState,
 ): Promise<ContextWindowUsage | null> {
+	const fetchTimeoutMs =
+		contextWindowUsageFetchTimeoutMsForTesting ?? DEFAULT_CONTEXT_WINDOW_USAGE_FETCH_TIMEOUT_MS
 	try {
-		const response = await ctx.client.session.messages({
-			path: { id: sessionID },
-		});
+		const response = await withFetchTimeout(
+			ctx.client.session.messages({
+				path: { id: sessionID },
+			}),
+			fetchTimeoutMs,
+		);
 
 		const messages = normalizeSDKResponse(response, [] as MessageWrapper[], { preferResponseOnMissingData: true })
 
@@ -228,7 +274,11 @@ async function fetchContextWindowUsage(
 			remainingTokens,
 			usagePercentage: usedTokens / actualLimit,
 		};
-	} catch {
+	} catch (error) {
+		log("[dynamic-truncator] fetchContextWindowUsage failed; falling back to null", {
+			sessionID,
+			error: error instanceof Error ? error.message : String(error),
+		})
 		return null;
 	}
 }