diff --git a/src/main/aiService.ts b/src/main/aiService.ts
index 2ca22f0..34c742e 100644
--- a/src/main/aiService.ts
+++ b/src/main/aiService.ts
@@ -93,12 +93,23 @@ Name the single most important thing to fix in a revision of this chapter.`
 
   if (payload.attachments && payload.attachments.length > 0) {
     const names = payload.attachments.map((a) => a.name).join(', ')
-    prompt += `\n\nThe user has attached the following reference file(s): ${names}.
-When suggesting edits based on the attached material, identify exact passages in the chapter and use this format for each suggestion:
-ISSUE: [category of improvement]
-PASSAGE: "[exact quoted text from the chapter]"
-PROBLEM: [brief explanation of why this needs changing]
-SUGGESTION: "[revised text]"`
+    prompt += `\n\n---
+ATTACHED REFERENCE MATERIAL: ${names}
+
+The user has provided reference file(s) above. Based on these references and the user's instruction, identify specific passages in the chapter that should be changed.
+
+You MUST output every suggested edit in this exact structured format — no other format will create highlights in the editor:
+
+ISSUE: [short category label, e.g. "Tone", "Vocabulary", "Style Match", "Pacing"]
+PASSAGE: "[copy the exact verbatim text from the chapter — at least 10 characters, unique enough to be found]"
+PROBLEM: [one sentence explaining why this passage needs changing in light of the reference material]
+SUGGESTION: "[the revised replacement text]"
+
+Rules:
+- PASSAGE must be a verbatim copy of text that exists in the chapter above. Do not paraphrase.
+- Include as many ISSUE/PASSAGE/PROBLEM/SUGGESTION blocks as are genuinely warranted.
+- After all structured blocks, you may add a brief overall summary.
+---`
   }
 
   return prompt
diff --git a/src/renderer/components/AIChat/ChatPanel.tsx b/src/renderer/components/AIChat/ChatPanel.tsx
index f5ed241..d93cbfc 100644
--- a/src/renderer/components/AIChat/ChatPanel.tsx
+++ b/src/renderer/components/AIChat/ChatPanel.tsx
@@ -68,11 +68,14 @@ export function ChatPanel(): JSX.Element {
         }
       )
 
-      // After streaming, parse AI response for annotations
+      // After streaming, parse AI response for annotations.
+      // Attachment-driven messages are tagged 'custom' so they appear with a
+      // distinct visual treatment in the Feedback panel.
       const currentHistory = useEditorStore.getState().chatHistory
       const lastMsg = currentHistory[currentHistory.length - 1]
       if (lastMsg?.role === 'assistant' && lastMsg.content.length > 0) {
-        const parsed = parseAnnotationsFromAIResponse(lastMsg.content, activeFileContent)
+        const overrideType = attachments.length > 0 ? 'custom' as const : undefined
+        const parsed = parseAnnotationsFromAIResponse(lastMsg.content, activeFileContent, overrideType)
         if (parsed.length > 0) {
           setAnnotations(parsed)
         }
diff --git a/src/renderer/components/Feedback/FeedbackPanel.css b/src/renderer/components/Feedback/FeedbackPanel.css
index 9fce220..81e3750 100644
--- a/src/renderer/components/Feedback/FeedbackPanel.css
+++ b/src/renderer/components/Feedback/FeedbackPanel.css
@@ -123,6 +123,14 @@
   color: var(--text-primary);
 }
 
+/* Wrapper that holds the type badge + optional source tag side by side */
+.fb-card-header-badges {
+  display: flex;
+  align-items: center;
+  gap: 6px;
+  flex-wrap: wrap;
+}
+
 /* Coloured type badge */
 .fb-card-badge {
   font-size: 10px;
@@ -137,6 +145,20 @@
   align-self: flex-start;
 }
 
+/* Small label shown on attachment-driven (custom) annotations */
+.fb-card-source-tag {
+  font-size: 9px;
+  font-weight: 600;
+  letter-spacing: 0.06em;
+  text-transform: uppercase;
+  color: rgba(30, 200, 150, 0.75);
+  border: 1px solid rgba(30, 200, 150, 0.3);
+  border-radius: 3px;
+  padding: 1px 5px;
+  align-self: flex-start;
+  white-space: nowrap;
+}
+
 /* Passage excerpt — wraps so the full text is always visible */
 .fb-card-excerpt {
   font-size: 12px;
diff --git a/src/renderer/components/Feedback/FeedbackPanel.tsx b/src/renderer/components/Feedback/FeedbackPanel.tsx
index 4d96114..723328c 100644
--- a/src/renderer/components/Feedback/FeedbackPanel.tsx
+++ b/src/renderer/components/Feedback/FeedbackPanel.tsx
@@ -23,6 +23,7 @@ function badgeColor(type: TextAnnotation['type']): string {
     case 'consistency':   return 'rgba(220, 80, 80, 0.75)'
     case 'style':         return 'rgba(80, 160, 255, 0.75)'
     case 'critique':      return 'rgba(160, 80, 220, 0.75)'
+    case 'custom':        return 'rgba(30, 200, 150, 0.8)'
   }
 }
 
@@ -41,6 +42,11 @@ function FeedbackCard({ ann, autoAnalyse, onDismiss }: FeedbackCardProps): JSX.E
   const [state, setState] = useState<AnalysisState>(() => {
     const cached = tooltipAnalysisCache.get(ann.id)
     if (cached) return { status: 'done', text: cached.text, suggestion: cached.suggestion }
+    // Custom (attachment-driven) annotations already carry their analysis — show
+    // the problem description and suggestion immediately without an extra AI call.
+    if (ann.type === 'custom') {
+      return { status: 'done', text: ann.message, suggestion: ann.suggestion ?? null }
+    }
     return { status: 'idle' }
   })
 
@@ -85,7 +91,12 @@ function FeedbackCard({ ann, autoAnalyse, onDismiss }: FeedbackCardProps): JSX.E
       {/* Header — click to jump to passage in editor */}
       <div className="fb-card-header" onClick={() => scrollToAnnotation(ann)} title="Jump to passage">
         <div className="fb-card-header-top">
-          <span className="fb-card-badge">{typeName}</span>
+          <div className="fb-card-header-badges">
+            <span className="fb-card-badge">{typeName}</span>
+            {ann.type === 'custom' && (
+              <span className="fb-card-source-tag">from attachment</span>
+            )}
+          </div>
           <button
             className="fb-card-dismiss"
             onClick={(e) => { e.stopPropagation(); onDismiss() }}
@@ -135,7 +146,7 @@ function FeedbackCard({ ann, autoAnalyse, onDismiss }: FeedbackCardProps): JSX.E
 }
 
 export function FeedbackPanel(): JSX.Element {
-  const { annotations, setAnnotations, removeAnnotation } = useEditorStore()
+  const { annotations, clearAnnotations, removeAnnotation } = useEditorStore()
   const [analyseAll, setAnalyseAll] = useState(false)
 
   // Reset "Analyse all" whenever the annotation set changes (new critique run),
@@ -149,7 +160,7 @@ export function FeedbackPanel(): JSX.Element {
   }, [annotations])
 
   function handleClearAll(): void {
-    setAnnotations([])
+    clearAnnotations()
     tooltipAnalysisCache.clear()
   }
 
diff --git a/src/renderer/components/Toolbar/AnalysisToolbar.tsx b/src/renderer/components/Toolbar/AnalysisToolbar.tsx
index 692f468..a3ac132 100644
--- a/src/renderer/components/Toolbar/AnalysisToolbar.tsx
+++ b/src/renderer/components/Toolbar/AnalysisToolbar.tsx
@@ -2,6 +2,7 @@ import { useEffect } from 'react'
 import { useEditorStore } from '../../store/editorStore'
 import { detectPassiveVoice } from '../../utils/passiveVoice'
 import { parseAnnotationsFromAIResponse } from '../../utils/annotationParser'
+import { tooltipAnalysisCache } from '../Editor/MarkdownEditor'
 import './Toolbar.css'
 
 function countWords(text: string): number {
@@ -167,7 +168,7 @@ export function AnalysisToolbar(): JSX.Element {
         {annotations.length > 0 && (
           <button
             className="toolbar-btn toolbar-btn-clear"
-            onClick={clearAnnotations}
+            onClick={() => { clearAnnotations(); tooltipAnalysisCache.clear() }}
             title="Remove all highlights"
           >
             Clear
diff --git a/src/renderer/types/editor.ts b/src/renderer/types/editor.ts
index 9396819..849f55a 100644
--- a/src/renderer/types/editor.ts
+++ b/src/renderer/types/editor.ts
@@ -21,7 +21,7 @@ export interface ChatMessage {
   attachments?: AttachmentMeta[] // metadata only — stored in history for display
 }
 
-export type AnnotationType = 'passive_voice' | 'consistency' | 'style' | 'critique'
+export type AnnotationType = 'passive_voice' | 'consistency' | 'style' | 'critique' | 'custom'
 
 export interface TextAnnotation {
   id: string
diff --git a/src/renderer/utils/annotationParser.ts b/src/renderer/utils/annotationParser.ts
index b5741a5..8e1dd38 100644
--- a/src/renderer/utils/annotationParser.ts
+++ b/src/renderer/utils/annotationParser.ts
@@ -1,9 +1,12 @@
 import type { TextAnnotation, AnnotationType } from '../types/editor'
 
-// Attempt to locate AI-quoted text in the document and create highlight annotations
+// Attempt to locate AI-quoted text in the document and create highlight annotations.
+// Pass `overrideType` to force every resulting annotation to use that type (e.g. 'custom'
+// for attachment-driven feedback) instead of inferring it from surrounding context.
 export function parseAnnotationsFromAIResponse(
   aiResponse: string,
-  documentContent: string
+  documentContent: string,
+  overrideType?: AnnotationType
 ): TextAnnotation[] {
   const annotations: TextAnnotation[] = []
   let id = 0
@@ -33,10 +36,11 @@ export function parseAnnotationsFromAIResponse(
     )
     if (alreadyAnnotated) continue
 
-    // Determine annotation type from context around the quote in the AI response
+    // Determine annotation type — use override when provided (e.g. 'custom' for
+    // attachment-driven feedback), otherwise infer from context around the quote.
     const contextStart = Math.max(0, match.index - 200)
     const contextBefore = aiResponse.slice(contextStart, match.index).toLowerCase()
-    const type = classifyType(contextBefore)
+    const type = overrideType ?? classifyType(contextBefore)
 
     // Try to extract a suggestion from text after the quote
     const afterQuote = aiResponse.slice(match.index + match[0].length, match.index + match[0].length + 400)