diff --git a/.changeset/empty-rings-bow.md b/.changeset/empty-rings-bow.md
new file mode 100644
index 000000000000..fd928d548c04
--- /dev/null
+++ b/.changeset/empty-rings-bow.md
@@ -0,0 +1,5 @@
+---
+'astro': patch
+---
+
+Fixes remote assets caching logic to not use expired assets
diff --git a/packages/astro/src/assets/build/generate.ts b/packages/astro/src/assets/build/generate.ts
index b2004fad01c8..71903e9945fe 100644
--- a/packages/astro/src/assets/build/generate.ts
+++ b/packages/astro/src/assets/build/generate.ts
@@ -75,7 +75,7 @@ export async function generateImage(
 			const JSONData = JSON.parse(readFileSync(cachedFileURL, 'utf-8')) as RemoteCacheEntry;
 
 			// If the cache entry is not expired, use it
-			if (JSONData.expires < Date.now()) {
+			if (JSONData.expires > Date.now()) {
 				await fs.promises.writeFile(finalFileURL, Buffer.from(JSONData.data, 'base64'));
 
 				return {