diff --git a/lib/responses.js b/lib/responses.js
index f44e605..2712011 100644
--- a/lib/responses.js
+++ b/lib/responses.js
@@ -112,8 +112,11 @@ export const RICKROLL_BLOCKS = {
 
 export function isImageRequest(text) {
   if (!text) return false;
-  return /(?:can you |could you |please |)(?:create|generate|make|draw).+(?:image|picture|drawing|illustration)/i.test(
-    text
+  return (
+    text.length <= 240 &&
+    /(?:can you |could you |please )?(?:create|generate|make|draw)\b.+\b(?:image|picture|drawing|illustration)\b/i.test(
+      text
+    )
   );
 }
 
diff --git a/test/responses.test.js b/test/responses.test.js
index e70ffb4..cced89b 100644
--- a/test/responses.test.js
+++ b/test/responses.test.js
@@ -72,6 +72,7 @@ test('isImageRequest catches several phrasings', () => {
   assert.ok(isImageRequest('can you create an image of a cat'));
   assert.ok(isImageRequest('please draw me a picture'));
   assert.ok(isImageRequest('generate an illustration of a sunset'));
+  assert.ok(!isImageRequest(`please make ${'draw '.repeat(250)}this eventually become an image`));
   assert.ok(!isImageRequest('what is an image'));
   assert.ok(!isImageRequest(''));
 });