diff --git a/src/shared/native-chat-image-transcript-markers.test.ts b/src/shared/native-chat-image-transcript-markers.test.ts
index cd9e7d3b8d6..e08caac8d3c 100644
--- a/src/shared/native-chat-image-transcript-markers.test.ts
+++ b/src/shared/native-chat-image-transcript-markers.test.ts
@@ -44,8 +44,10 @@ describe('normalizeImageTranscriptMessages', () => {
   it.each([
     ['[Image #1] describe this', 'describe this'],
     ['[Image #1]\t  describe this', 'describe this'],
+    [' \t[Image #1] describe this', 'describe this'],
     ['describe this [Image #1]', 'describe this'],
     ['describe this  \t[Image #1]', 'describe this'],
+    ['describe this [Image #1]\t  ', 'describe this'],
     ['describe [Image #1] this', 'describe  this'],
     ['describe  [Image #1]\t this', 'describe  \t this'],
     ['describe[Image #1]\t  this', 'describe\t  this'],
diff --git a/src/shared/native-chat-image-transcript-markers.ts b/src/shared/native-chat-image-transcript-markers.ts
index 6523688018b..c9f9d13eb51 100644
--- a/src/shared/native-chat-image-transcript-markers.ts
+++ b/src/shared/native-chat-image-transcript-markers.ts
@@ -3,8 +3,8 @@ import { isTextBlock, type NativeChatBlock, type NativeChatMessage } from './nat
 const IMAGE_SOURCE_MARKER = /^\[Image:\s*source:\s*(.+?)\]\s*$/
 const IMAGE_PROMPT_MARKER = /\[Image #\d+\]/
 const IMAGE_PROMPT_MARKERS = /\[Image #\d+\]/g
-const IMAGE_PROMPT_MARKER_AT_START = /^\[Image #\d+\]/
-const IMAGE_PROMPT_MARKER_AT_END = /\[Image #\d+\]$/
+const IMAGE_PROMPT_MARKER_AT_START = /^[^\S\r\n]*\[Image #\d+\]/
+const IMAGE_PROMPT_MARKER_AT_END = /\[Image #\d+\][^\S\r\n]*$/
 const HORIZONTAL_WHITESPACE_START = /^[^\S\r\n]+/
 const HORIZONTAL_WHITESPACE_END = /[^\S\r\n]+$/