diff --git a/src/core/__tests__/contextProxy.test.ts b/src/core/__tests__/contextProxy.test.ts
index ea9e79736d..e2d6c4ad12 100644
--- a/src/core/__tests__/contextProxy.test.ts
+++ b/src/core/__tests__/contextProxy.test.ts
@@ -102,6 +102,29 @@ describe("ContextProxy", () => {
 			const result = proxy.getGlobalState("apiProvider", "default-value")
 			expect(result).toBe("default-value")
 		})
+
+		it("should bypass cache for pass-through state keys", async () => {
+			// Setup mock return value
+			mockGlobalState.get.mockReturnValue("pass-through-value")
+
+			// Use a pass-through key (taskHistory)
+			const result = proxy.getGlobalState("taskHistory" as GlobalStateKey)
+
+			// Should get value directly from original context
+			expect(result).toBe("pass-through-value")
+			expect(mockGlobalState.get).toHaveBeenCalledWith("taskHistory")
+		})
+
+		it("should respect default values for pass-through state keys", async () => {
+			// Setup mock to return undefined
+			mockGlobalState.get.mockReturnValue(undefined)
+
+			// Use a pass-through key with default value
+			const result = proxy.getGlobalState("taskHistory" as GlobalStateKey, "default-value")
+
+			// Should return default value when original context returns undefined
+			expect(result).toBe("default-value")
+		})
 	})
 
 	describe("updateGlobalState", () => {
@@ -115,6 +138,21 @@ describe("ContextProxy", () => {
 			const storedValue = await proxy.getGlobalState("apiProvider")
 			expect(storedValue).toBe("new-value")
 		})
+
+		it("should bypass cache for pass-through state keys", async () => {
+			await proxy.updateGlobalState("taskHistory" as GlobalStateKey, "new-value")
+
+			// Should update original context
+			expect(mockGlobalState.update).toHaveBeenCalledWith("taskHistory", "new-value")
+
+			// Setup mock for subsequent get
+			mockGlobalState.get.mockReturnValue("new-value")
+
+			// Should get fresh value from original context
+			const storedValue = proxy.getGlobalState("taskHistory" as GlobalStateKey)
+			expect(storedValue).toBe("new-value")
+			expect(mockGlobalState.get).toHaveBeenCalledWith("taskHistory")
+		})
 	})
 
 	describe("getSecret", () => {
diff --git a/src/core/contextProxy.ts b/src/core/contextProxy.ts
index 40d8b475bc..698713179d 100644
--- a/src/core/contextProxy.ts
+++ b/src/core/contextProxy.ts
@@ -10,6 +10,7 @@ import {
 	ConfigurationValues,
 	isSecretKey,
 	isGlobalStateKey,
+	isPassThroughStateKey,
 } from "../shared/globalState"
 import { API_CONFIG_KEYS, ApiConfiguration } from "../shared/api"
 
@@ -80,11 +81,18 @@ export class ContextProxy {
 	getGlobalState<T>(key: GlobalStateKey): T | undefined
 	getGlobalState<T>(key: GlobalStateKey, defaultValue: T): T
 	getGlobalState<T>(key: GlobalStateKey, defaultValue?: T): T | undefined {
+		if (isPassThroughStateKey(key)) {
+			const value = this.originalContext.globalState.get(key)
+			return value === undefined || value === null ? defaultValue : (value as T)
+		}
 		const value = this.stateCache.get(key) as T | undefined
 		return value !== undefined ? value : (defaultValue as T | undefined)
 	}
 
 	updateGlobalState<T>(key: GlobalStateKey, value: T) {
+		if (isPassThroughStateKey(key)) {
+			return this.originalContext.globalState.update(key, value)
+		}
 		this.stateCache.set(key, value)
 		return this.originalContext.globalState.update(key, value)
 	}
@@ -114,12 +122,14 @@ export class ContextProxy {
 	setValue(key: ConfigurationKey, value: any) {
 		if (isSecretKey(key)) {
 			return this.storeSecret(key, value)
-		} else if (isGlobalStateKey(key)) {
-			return this.updateGlobalState(key, value)
-		} else {
-			logger.warn(`Unknown key: ${key}. Storing as global state.`)
+		}
+
+		if (isGlobalStateKey(key)) {
 			return this.updateGlobalState(key, value)
 		}
+
+		logger.warn(`Unknown key: ${key}. Storing as global state.`)
+		return this.updateGlobalState(key, value)
 	}
 
 	/**
diff --git a/src/shared/globalState.ts b/src/shared/globalState.ts
index 4c0adb0fcf..4331effce9 100644
--- a/src/shared/globalState.ts
+++ b/src/shared/globalState.ts
@@ -124,6 +124,8 @@ export const GLOBAL_STATE_KEYS = [
 	"maxWorkspaceFiles",
 ] as const
 
+export const PASS_THROUGH_STATE_KEYS = ["taskHistory"] as const
+
 type CheckGlobalStateKeysExhaustiveness =
 	Exclude<GlobalStateKey, (typeof GLOBAL_STATE_KEYS)[number]> extends never ? true : false
 
@@ -133,3 +135,6 @@ export const isSecretKey = (key: string): key is SecretKey => SECRET_KEYS.includ
 
 export const isGlobalStateKey = (key: string): key is GlobalStateKey =>
 	GLOBAL_STATE_KEYS.includes(key as GlobalStateKey)
+
+export const isPassThroughStateKey = (key: string): key is (typeof PASS_THROUGH_STATE_KEYS)[number] =>
+	PASS_THROUGH_STATE_KEYS.includes(key as (typeof PASS_THROUGH_STATE_KEYS)[number])