diff --git a/src/main/aiService.ts b/src/main/aiService.ts
index 34c742e..8c84b7c 100644
--- a/src/main/aiService.ts
+++ b/src/main/aiService.ts
@@ -58,16 +58,29 @@ SUGGESTION: [how to fix it]`,
     style: `Analyze the writing style and provide specific improvement suggestions:
 - Pacing: identify slow passages or rushed moments
 - Sentence variety: flag runs of similar length or structure
-- Show don't tell: identify passages that tell emotion/state rather than showing it
 - Gothic atmosphere: passages where the atmospheric tone is inconsistent
 - Dialogue: any dialogue that feels stilted or unnatural
 
 For each suggestion:
-ISSUE: [type: Pacing / Sentence Variety / Show-Don't-Tell / Atmosphere / Dialogue]
+ISSUE: [type: Pacing / Sentence Variety / Atmosphere / Dialogue]
 PASSAGE: "[exact quoted text]"
 PROBLEM: [specific explanation]
 SUGGESTION: [concrete rewrite or approach]`,
 
+    show_tell: `Identify every passage in this chapter where the author tells the reader something that should instead be shown through action, dialogue, sensation, or concrete detail.
+
+Focus on:
+- Emotions or inner states stated directly ("she felt afraid", "he was relieved") instead of expressed through physical reaction or behaviour
+- Character motivations or intentions explained by the narrator rather than revealed through what characters do or say
+- Abstract or evaluative description ("the room was oppressive", "it was a beautiful day") instead of specific sensory detail that lets the reader feel it
+- Dialogue tags or beats that tell the reader how something was said rather than letting word choice and action carry it
+
+For each instance:
+ISSUE: Show Don't Tell
+PASSAGE: "[exact quoted text from the chapter]"
+PROBLEM: [one sentence explaining what is being told that should be shown]
+SUGGESTION: "[a concrete rewrite that shows the same moment through action, sensation, or dialogue]"`,
+
     critique: `Give an honest, detailed critique of this chapter as a whole. Structure your response as follows:
 
 **Overall impression** (2–3 sentences on what the chapter achieves and its most significant weakness)
diff --git a/src/renderer/components/Editor/MarkdownEditor.tsx b/src/renderer/components/Editor/MarkdownEditor.tsx
index 8a7c974..5a0d2bf 100644
--- a/src/renderer/components/Editor/MarkdownEditor.tsx
+++ b/src/renderer/components/Editor/MarkdownEditor.tsx
@@ -98,8 +98,10 @@ export function analyseAnnotation(
   ann: TextAnnotation,
   onUpdate: (text: string, streaming: boolean, suggestion: string | null) => void
 ): () => void {
-  const cached = tooltipAnalysisCache.get(ann.id)
+  const cached = tooltipAnalysisCache.get(ann.id) ?? ann.analysisCache ?? null
   if (cached) {
+    // Warm the in-memory cache so subsequent calls this session are instant
+    if (!tooltipAnalysisCache.has(ann.id)) tooltipAnalysisCache.set(ann.id, cached)
     onUpdate(cached.text, false, cached.suggestion)
     return () => {}
   }
@@ -131,6 +133,7 @@ export function analyseAnnotation(
       const text = accumulated || ann.message
       const suggestion = extractBlockquote(text) ?? ann.suggestion ?? null
       tooltipAnalysisCache.set(ann.id, { text, suggestion })
+      useEditorStore.getState().setAnnotationAnalysis(ann.id, { text, suggestion })
       onUpdate(text, false, suggestion)
     }).catch(() => {
       if (!cancelled) onUpdate(ann.message, false, ann.suggestion ?? null)
@@ -363,6 +366,11 @@ function buildTheme(fontSize: number, dark: boolean): ReturnType<typeof EditorVi
       borderBottom: '2px solid rgba(80, 160, 255, 0.7)',
       borderRadius: '2px'
     },
+    '.annotation-show_tell': {
+      backgroundColor: 'rgba(255, 140, 30, 0.18)',
+      borderBottom: '2px solid rgba(255, 140, 30, 0.7)',
+      borderRadius: '2px'
+    },
     '.annotation-critique': {
       backgroundColor: 'rgba(160, 80, 220, 0.18)',
       borderBottom: '2px solid rgba(160, 80, 220, 0.7)',
diff --git a/src/renderer/components/Feedback/FeedbackPanel.tsx b/src/renderer/components/Feedback/FeedbackPanel.tsx
index 0ee0ee8..c69a787 100644
--- a/src/renderer/components/Feedback/FeedbackPanel.tsx
+++ b/src/renderer/components/Feedback/FeedbackPanel.tsx
@@ -22,6 +22,7 @@ function badgeColor(type: TextAnnotation['type']): string {
     case 'passive_voice': return 'rgba(255, 200, 0, 0.75)'
     case 'consistency':   return 'rgba(220, 80, 80, 0.75)'
     case 'style':         return 'rgba(80, 160, 255, 0.75)'
+    case 'show_tell':     return 'rgba(255, 140, 30, 0.75)'
     case 'critique':      return 'rgba(160, 80, 220, 0.75)'
     case 'custom':        return 'rgba(30, 200, 150, 0.8)'
   }
@@ -40,7 +41,7 @@ interface FeedbackCardProps {
 
 function FeedbackCard({ ann, autoAnalyse, onDismiss }: FeedbackCardProps): JSX.Element {
   const [state, setState] = useState<AnalysisState>(() => {
-    const cached = tooltipAnalysisCache.get(ann.id)
+    const cached = tooltipAnalysisCache.get(ann.id) ?? ann.analysisCache ?? null
     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.
diff --git a/src/renderer/components/Toolbar/AnalysisToolbar.tsx b/src/renderer/components/Toolbar/AnalysisToolbar.tsx
index e3abb2c..1e8a798 100644
--- a/src/renderer/components/Toolbar/AnalysisToolbar.tsx
+++ b/src/renderer/components/Toolbar/AnalysisToolbar.tsx
@@ -59,7 +59,7 @@ export function AnalysisToolbar(): JSX.Element {
     setAnalysisMode('passive_voice')
   }
 
-  const runAIAnalysis = async (mode: 'consistency' | 'style' | 'critique'): Promise<void> => {
+  const runAIAnalysis = async (mode: 'consistency' | 'style' | 'show_tell' | 'critique'): Promise<void> => {
     if (!activeFilePath || isAILoading) return
 
     setAnalysisMode(mode)
@@ -70,7 +70,9 @@ export function AnalysisToolbar(): JSX.Element {
         ? 'Please check this chapter for consistency issues (character names, timeline, repeated phrases).'
         : mode === 'style'
           ? 'Please analyze the style and pacing of this chapter and suggest improvements.'
-          : 'Please give me an honest critique of this chapter.'
+          : mode === 'show_tell'
+            ? 'Please identify every passage in this chapter where I am telling rather than showing.'
+            : 'Please give me an honest critique of this chapter.'
 
     addUserMessage(prompt)
     startAssistantMessage()
@@ -96,7 +98,10 @@ export function AnalysisToolbar(): JSX.Element {
       const currentHistory = useEditorStore.getState().chatHistory
       const lastMsg = currentHistory[currentHistory.length - 1]
       if (lastMsg?.role === 'assistant' && lastMsg.content.length > 0) {
-        const newAnnotations = parseAnnotationsFromAIResponse(lastMsg.content, activeFileContent)
+        // For show_tell mode, force all annotations to the show_tell type so the
+        // classifier doesn't accidentally mis-label them as 'style' or 'consistency'.
+        const overrideType = mode === 'show_tell' ? 'show_tell' : undefined
+        const newAnnotations = parseAnnotationsFromAIResponse(lastMsg.content, activeFileContent, overrideType)
         if (newAnnotations.length > 0) {
           const existing = useEditorStore.getState().annotations.filter((a) => a.type !== mode)
           setAnnotations([...existing, ...newAnnotations])
@@ -113,6 +118,7 @@ export function AnalysisToolbar(): JSX.Element {
   const passiveCount = annotations.filter((a) => a.type === 'passive_voice').length
   const consistencyCount = annotations.filter((a) => a.type === 'consistency').length
   const styleCount = annotations.filter((a) => a.type === 'style').length
+  const showTellCount = annotations.filter((a) => a.type === 'show_tell').length
   const critiqueCount = annotations.filter((a) => a.type === 'critique').length
   const docWordCount = countWords(activeFileContent)
 
@@ -155,6 +161,18 @@ export function AnalysisToolbar(): JSX.Element {
           )}
         </button>
 
+        <button
+          className={`toolbar-btn${analysisMode === 'show_tell' ? ' active' : ''}`}
+          onClick={() => runAIAnalysis('show_tell')}
+          disabled={!hasFile || isAILoading}
+          title="Find passages that tell rather than show via AI"
+        >
+          {isAILoading && analysisMode === 'show_tell' ? 'Reading…' : 'Show vs Tell'}
+          {showTellCount > 0 && (
+            <span className="toolbar-badge">{showTellCount}</span>
+          )}
+        </button>
+
         <button
           className={`toolbar-btn${analysisMode === 'critique' ? ' active' : ''}`}
           onClick={() => runAIAnalysis('critique')}
diff --git a/src/renderer/store/editorStore.ts b/src/renderer/store/editorStore.ts
index 3f1e63e..9de8392 100644
--- a/src/renderer/store/editorStore.ts
+++ b/src/renderer/store/editorStore.ts
@@ -43,6 +43,7 @@ interface EditorState {
   linkAnnotationsToMessage: (messageId: string, annotationIds: string[]) => void
   clearArchivedAnnotations: () => void
   removeArchivedAnnotation: (id: string) => void
+  setAnnotationAnalysis: (id: string, result: { text: string; suggestion: string | null }) => void
 
   // Analysis mode
   analysisMode: AnalysisMode
@@ -457,6 +458,37 @@ export const useEditorStore = create<EditorState>((set, get) => ({
     })
   },
 
+  setAnnotationAnalysis: (id, result) => {
+    set((s) => {
+      if (!s.activeFilePath) return {}
+      const fileState = s.annotationsByFile[s.activeFilePath]
+      if (!fileState) return {}
+      const updatedAll = fileState.annotations.map(a =>
+        a.id === id ? { ...a, analysisCache: result } : a
+      )
+      const annotations = s.annotations.map(a =>
+        a.id === id ? { ...a, analysisCache: result } : a
+      )
+      return {
+        annotations,
+        annotationsByFile: {
+          ...s.annotationsByFile,
+          [s.activeFilePath]: { ...fileState, annotations: updatedAll }
+        }
+      }
+    })
+    scheduleSave(() => {
+      const st = get()
+      return {
+        activeFilePath: st.activeFilePath,
+        scrollPositions: st.scrollPositions,
+        chatSessionsByFile: st.chatSessionsByFile,
+        activeSessionIdByFile: st.activeSessionIdByFile,
+        annotationsByFile: st.annotationsByFile
+      }
+    })
+  },
+
   analysisMode: 'none',
   setAnalysisMode: (analysisMode) => {
     set((s) => {
diff --git a/src/renderer/types/editor.ts b/src/renderer/types/editor.ts
index a4eefaa..382e6a3 100644
--- a/src/renderer/types/editor.ts
+++ b/src/renderer/types/editor.ts
@@ -28,7 +28,7 @@ export interface ChatSession {
   messages: ChatMessage[]
 }
 
-export type AnnotationType = 'passive_voice' | 'consistency' | 'style' | 'critique' | 'custom'
+export type AnnotationType = 'passive_voice' | 'consistency' | 'style' | 'show_tell' | 'critique' | 'custom'
 
 export interface TextAnnotation {
   id: string
@@ -41,11 +41,12 @@ export interface TextAnnotation {
   applied?: boolean // true when the suggestion has been applied to the document
   dismissed?: boolean // true when the user dismissed this annotation (archived)
   autoAnalyse?: boolean // true when created via context menu — FeedbackCard starts AI analysis immediately
+  analysisCache?: { text: string; suggestion: string | null } // persisted AI analysis result
 }
 
-export type AnalysisMode = 'none' | 'passive_voice' | 'consistency' | 'style' | 'critique'
+export type AnalysisMode = 'none' | 'passive_voice' | 'consistency' | 'style' | 'show_tell' | 'critique'
 
-export type AIMode = 'chat' | 'passive_voice' | 'consistency' | 'style' | 'critique'
+export type AIMode = 'chat' | 'passive_voice' | 'consistency' | 'style' | 'show_tell' | 'critique'
 
 export interface AIPayload {
   mode: AIMode
diff --git a/src/renderer/utils/annotationParser.ts b/src/renderer/utils/annotationParser.ts
index db2af4a..36c1bc7 100644
--- a/src/renderer/utils/annotationParser.ts
+++ b/src/renderer/utils/annotationParser.ts
@@ -68,13 +68,22 @@ function classifyType(contextBefore: string): AnnotationType {
   if (contextBefore.includes('passive')) return 'passive_voice'
   if (
     contextBefore.includes('consistency') ||
-    contextBefore.includes('character') ||
     contextBefore.includes('timeline') ||
     contextBefore.includes('repeated') ||
     contextBefore.includes('contradiction')
   ) {
     return 'consistency'
   }
+  if (
+    contextBefore.includes('show don') ||
+    contextBefore.includes('show-don') ||
+    contextBefore.includes('show vs tell') ||
+    contextBefore.includes('show/tell') ||
+    contextBefore.includes('telling') ||
+    contextBefore.includes('told') && contextBefore.includes('show')
+  ) {
+    return 'show_tell'
+  }
   return 'style'
 }