diff --git a/src/shared/connected-providers-cache.ts b/src/shared/connected-providers-cache.ts
index 582c26f01..f27e9f76d 100644
--- a/src/shared/connected-providers-cache.ts
+++ b/src/shared/connected-providers-cache.ts
@@ -2,6 +2,10 @@ import { log } from "./logger"
 import * as dataPath from "./data-path"
 import { createJsonFileCacheStore } from "./json-file-cache-store"
 
+// Track if provider models cache has been successfully written in the current process
+// This helps in sandbox environments where filesystem state may not persist across contexts
+let providerModelsCacheWrittenInCurrentProcess = false
+
 const CONNECTED_PROVIDERS_CACHE_FILE = "connected-providers.json"
 const PROVIDER_MODELS_CACHE_FILE = "provider-models.json"
 
@@ -84,6 +88,12 @@ export function createConnectedProvidersCacheStore(
 	}
 
 	function hasProviderModelsCache(): boolean {
+		// First check if we've written the cache in the current process
+		// This handles sandbox environments where filesystem state may not persist across contexts
+		if (providerModelsCacheWrittenInCurrentProcess) {
+			return true
+		}
+		// Fall back to the store's has() method (which also checks in-memory state)
 		return providerModelsCacheStore.has()
 	}
 
@@ -92,6 +102,7 @@ export function createConnectedProvidersCacheStore(
 			...data,
 			updatedAt: new Date().toISOString(),
 		})
+		providerModelsCacheWrittenInCurrentProcess = true
 	}
 
 	async function updateConnectedProvidersCache(client: {
@@ -161,6 +172,7 @@ export function createConnectedProvidersCacheStore(
 	function _resetMemCacheForTesting(): void {
 		connectedProvidersCacheStore.resetMemory()
 		providerModelsCacheStore.resetMemory()
+		providerModelsCacheWrittenInCurrentProcess = false
 	}
 
 	return {
diff --git a/src/shared/json-file-cache-store.ts b/src/shared/json-file-cache-store.ts
index 5561a66b9..18ee6c0d1 100644
--- a/src/shared/json-file-cache-store.ts
+++ b/src/shared/json-file-cache-store.ts
@@ -27,6 +27,7 @@ export function createJsonFileCacheStore<TValue>(
 	options: JsonFileCacheStoreOptions<TValue>,
 ): JsonFileCacheStore<TValue> {
 	let memoryValue: TValue | null | undefined
+	let writtenInCurrentProcess = false
 
 	function getCacheFilePath(): string {
 		return join(options.getCacheDir(), options.filename)
@@ -67,6 +68,17 @@ export function createJsonFileCacheStore<TValue>(
 	}
 
 	function has(): boolean {
+		// First check if we have a valid in-memory cache value
+		// This handles sandbox environments where existsSync may fail across contexts
+		if (memoryValue !== undefined && memoryValue !== null) {
+			return true
+		}
+		// Check if we've written to this cache in the current process
+		// This helps in sandbox environments where filesystem state may not persist across contexts
+		if (writtenInCurrentProcess) {
+			return true
+		}
+		// Fall back to filesystem check
 		return existsSync(getCacheFilePath())
 	}
 
@@ -77,6 +89,7 @@ export function createJsonFileCacheStore<TValue>(
 		try {
 			writeFileSync(cacheFile, options.serialize?.(value) ?? JSON.stringify(value, null, 2))
 			memoryValue = value
+			writtenInCurrentProcess = true
 			log(`[${options.logPrefix}] ${options.cacheLabel} written`, options.describe(value))
 		} catch (error) {
 			log(`[${options.logPrefix}] Error writing ${toLogLabel(options.cacheLabel)}`, {
@@ -87,6 +100,7 @@ export function createJsonFileCacheStore<TValue>(
 
 	function resetMemory(): void {
 		memoryValue = undefined
+		writtenInCurrentProcess = false
 	}
 
 	return {