diff --git a/apps/server/src/routes/features/routes/update.ts b/apps/server/src/routes/features/routes/update.ts
index 9cb8f25e..1a89cda3 100644
--- a/apps/server/src/routes/features/routes/update.ts
+++ b/apps/server/src/routes/features/routes/update.ts
@@ -10,14 +10,21 @@ import { getErrorMessage, logError } from '../common.js';
 export function createUpdateHandler(featureLoader: FeatureLoader) {
   return async (req: Request, res: Response): Promise<void> => {
     try {
-      const { projectPath, featureId, updates, descriptionHistorySource, enhancementMode } =
-        req.body as {
-          projectPath: string;
-          featureId: string;
-          updates: Partial<Feature>;
-          descriptionHistorySource?: 'enhance' | 'edit';
-          enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer';
-        };
+      const {
+        projectPath,
+        featureId,
+        updates,
+        descriptionHistorySource,
+        enhancementMode,
+        preEnhancementDescription,
+      } = req.body as {
+        projectPath: string;
+        featureId: string;
+        updates: Partial<Feature>;
+        descriptionHistorySource?: 'enhance' | 'edit';
+        enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer';
+        preEnhancementDescription?: string;
+      };
 
       if (!projectPath || !featureId || !updates) {
         res.status(400).json({
@@ -32,7 +39,8 @@ export function createUpdateHandler(featureLoader: FeatureLoader) {
         featureId,
         updates,
         descriptionHistorySource,
-        enhancementMode
+        enhancementMode,
+        preEnhancementDescription
       );
       res.json({ success: true, feature: updated });
     } catch (error) {
diff --git a/apps/server/src/services/feature-loader.ts b/apps/server/src/services/feature-loader.ts
index 62570b6b..409abd2a 100644
--- a/apps/server/src/services/feature-loader.ts
+++ b/apps/server/src/services/feature-loader.ts
@@ -308,13 +308,15 @@ export class FeatureLoader {
    * @param updates - Partial feature updates
    * @param descriptionHistorySource - Source of description change ('enhance' or 'edit')
    * @param enhancementMode - Enhancement mode if source is 'enhance'
+   * @param preEnhancementDescription - Description before enhancement (for restoring original)
    */
   async update(
     projectPath: string,
     featureId: string,
     updates: Partial<Feature>,
     descriptionHistorySource?: 'enhance' | 'edit',
-    enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer'
+    enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer',
+    preEnhancementDescription?: string
   ): Promise<Feature> {
     const feature = await this.get(projectPath, featureId);
     if (!feature) {
@@ -338,9 +340,31 @@ export class FeatureLoader {
       updates.description !== feature.description &&
       updates.description.trim()
     ) {
+      const timestamp = new Date().toISOString();
+
+      // If this is an enhancement and we have the pre-enhancement description,
+      // add the original text to history first (so user can restore to it)
+      if (
+        descriptionHistorySource === 'enhance' &&
+        preEnhancementDescription &&
+        preEnhancementDescription.trim()
+      ) {
+        // Check if this pre-enhancement text is different from the last history entry
+        const lastEntry = updatedHistory[updatedHistory.length - 1];
+        if (!lastEntry || lastEntry.description !== preEnhancementDescription) {
+          const preEnhanceEntry: DescriptionHistoryEntry = {
+            description: preEnhancementDescription,
+            timestamp,
+            source: updatedHistory.length === 0 ? 'initial' : 'edit',
+          };
+          updatedHistory = [...updatedHistory, preEnhanceEntry];
+        }
+      }
+
+      // Add the new/enhanced description to history
       const historyEntry: DescriptionHistoryEntry = {
         description: updates.description,
-        timestamp: new Date().toISOString(),
+        timestamp,
         source: descriptionHistorySource || 'edit',
         ...(descriptionHistorySource === 'enhance' && enhancementMode ? { enhancementMode } : {}),
       };
diff --git a/apps/ui/src/components/views/board-view/dialogs/add-feature-dialog.tsx b/apps/ui/src/components/views/board-view/dialogs/add-feature-dialog.tsx
index 126fe688..797b64b9 100644
--- a/apps/ui/src/components/views/board-view/dialogs/add-feature-dialog.tsx
+++ b/apps/ui/src/components/views/board-view/dialogs/add-feature-dialog.tsx
@@ -396,16 +396,29 @@ export function AddFeatureDialog({
             <EnhanceWithAI
               value={description}
               onChange={setDescription}
-              onHistoryAdd={({ mode, enhancedText }) => {
-                setDescriptionHistory((prev) => [
-                  ...prev,
-                  {
+              onHistoryAdd={({ mode, originalText, enhancedText }) => {
+                const timestamp = new Date().toISOString();
+                setDescriptionHistory((prev) => {
+                  const newHistory = [...prev];
+                  // Add original text first (so user can restore to pre-enhancement state)
+                  // Only add if it's different from the last entry to avoid duplicates
+                  const lastEntry = prev[prev.length - 1];
+                  if (!lastEntry || lastEntry.description !== originalText) {
+                    newHistory.push({
+                      description: originalText,
+                      timestamp,
+                      source: prev.length === 0 ? 'initial' : 'edit',
+                    });
+                  }
+                  // Add enhanced text
+                  newHistory.push({
                     description: enhancedText,
-                    timestamp: new Date().toISOString(),
+                    timestamp,
                     source: 'enhance',
                     enhancementMode: mode,
-                  },
-                ]);
+                  });
+                  return newHistory;
+                });
               }}
             />
           </div>
diff --git a/apps/ui/src/components/views/board-view/dialogs/edit-feature-dialog.tsx b/apps/ui/src/components/views/board-view/dialogs/edit-feature-dialog.tsx
index 92d633dc..9912201d 100644
--- a/apps/ui/src/components/views/board-view/dialogs/edit-feature-dialog.tsx
+++ b/apps/ui/src/components/views/board-view/dialogs/edit-feature-dialog.tsx
@@ -64,7 +64,8 @@ interface EditFeatureDialogProps {
       requirePlanApproval: boolean;
     },
     descriptionHistorySource?: 'enhance' | 'edit',
-    enhancementMode?: EnhancementMode
+    enhancementMode?: EnhancementMode,
+    preEnhancementDescription?: string
   ) => void;
   categorySuggestions: string[];
   branchSuggestions: string[];
@@ -117,6 +118,12 @@ export function EditFeatureDialog({
   >(null);
   // Track the original description when the dialog opened for comparison
   const [originalDescription, setOriginalDescription] = useState(feature?.description ?? '');
+  // Track the description before enhancement (so it can be restored)
+  const [preEnhancementDescription, setPreEnhancementDescription] = useState<string | null>(null);
+  // Local history state for real-time display (combines persisted + session history)
+  const [localHistory, setLocalHistory] = useState<DescriptionHistoryEntry[]>(
+    feature?.descriptionHistory ?? []
+  );
 
   useEffect(() => {
     setEditingFeature(feature);
@@ -128,6 +135,8 @@ export function EditFeatureDialog({
       // Reset history tracking state
       setOriginalDescription(feature.description ?? '');
       setDescriptionChangeSource(null);
+      setPreEnhancementDescription(null);
+      setLocalHistory(feature.descriptionHistory ?? []);
       // Reset model entry
       setModelEntry({
         model: (feature.model as ModelAlias) || 'opus',
@@ -137,6 +146,8 @@ export function EditFeatureDialog({
     } else {
       setEditFeaturePreviewMap(new Map());
       setDescriptionChangeSource(null);
+      setPreEnhancementDescription(null);
+      setLocalHistory([]);
     }
   }, [feature]);
 
@@ -198,7 +209,13 @@ export function EditFeatureDialog({
       }
     }
 
-    onUpdate(editingFeature.id, updates, historySource, historyEnhancementMode);
+    onUpdate(
+      editingFeature.id,
+      updates,
+      historySource,
+      historyEnhancementMode,
+      preEnhancementDescription ?? undefined
+    );
     setEditFeaturePreviewMap(new Map());
     onClose();
   };
@@ -246,20 +263,18 @@ export function EditFeatureDialog({
             <div className="space-y-2">
               <div className="flex items-center justify-between">
                 <Label htmlFor="edit-description">Description</Label>
-                {/* Version History Button */}
-                {feature?.descriptionHistory && feature.descriptionHistory.length > 0 && (
-                  <EnhancementHistoryButton
-                    history={feature.descriptionHistory}
-                    currentValue={editingFeature.description}
-                    onRestore={(description) => {
-                      setEditingFeature((prev) => (prev ? { ...prev, description } : prev));
-                      setDescriptionChangeSource('edit');
-                    }}
-                    valueAccessor={(entry) => entry.description}
-                    title="Version History"
-                    restoreMessage="Description restored from history"
-                  />
-                )}
+                {/* Version History Button - uses local history for real-time updates */}
+                <EnhancementHistoryButton
+                  history={localHistory}
+                  currentValue={editingFeature.description}
+                  onRestore={(description) => {
+                    setEditingFeature((prev) => (prev ? { ...prev, description } : prev));
+                    setDescriptionChangeSource('edit');
+                  }}
+                  valueAccessor={(entry) => entry.description}
+                  title="Version History"
+                  restoreMessage="Description restored from history"
+                />
               </div>
               <DescriptionImageDropZone
                 value={editingFeature.description}
@@ -316,7 +331,33 @@ export function EditFeatureDialog({
               onChange={(enhanced) =>
                 setEditingFeature((prev) => (prev ? { ...prev, description: enhanced } : prev))
               }
-              onHistoryAdd={({ mode }) => setDescriptionChangeSource({ source: 'enhance', mode })}
+              onHistoryAdd={({ mode, originalText, enhancedText }) => {
+                setDescriptionChangeSource({ source: 'enhance', mode });
+                setPreEnhancementDescription(originalText);
+
+                // Update local history for real-time display
+                const timestamp = new Date().toISOString();
+                setLocalHistory((prev) => {
+                  const newHistory = [...prev];
+                  // Add original text first (so user can restore to pre-enhancement state)
+                  const lastEntry = prev[prev.length - 1];
+                  if (!lastEntry || lastEntry.description !== originalText) {
+                    newHistory.push({
+                      description: originalText,
+                      timestamp,
+                      source: prev.length === 0 ? 'initial' : 'edit',
+                    });
+                  }
+                  // Add enhanced text
+                  newHistory.push({
+                    description: enhancedText,
+                    timestamp,
+                    source: 'enhance',
+                    enhancementMode: mode,
+                  });
+                  return newHistory;
+                });
+              }}
             />
           </div>
 
diff --git a/apps/ui/src/components/views/board-view/dialogs/follow-up-dialog.tsx b/apps/ui/src/components/views/board-view/dialogs/follow-up-dialog.tsx
index 4457b5d0..6df1eea0 100644
--- a/apps/ui/src/components/views/board-view/dialogs/follow-up-dialog.tsx
+++ b/apps/ui/src/components/views/board-view/dialogs/follow-up-dialog.tsx
@@ -126,10 +126,22 @@ export function FollowUpDialog({
           <EnhanceWithAI
             value={prompt}
             onChange={onPromptChange}
-            onHistoryAdd={({ mode, enhancedText }) => {
+            onHistoryAdd={({ mode, originalText, enhancedText }) => {
+              const timestamp = new Date().toISOString();
+              // Add original text first (so user can restore to pre-enhancement state)
+              // Only add if it's different from the last history entry
+              const lastEntry = promptHistory[promptHistory.length - 1];
+              if (!lastEntry || lastEntry.prompt !== originalText) {
+                onHistoryAdd?.({
+                  prompt: originalText,
+                  timestamp,
+                  source: promptHistory.length === 0 ? 'initial' : 'edit',
+                });
+              }
+              // Add enhanced text
               onHistoryAdd?.({
                 prompt: enhancedText,
-                timestamp: new Date().toISOString(),
+                timestamp,
                 source: 'enhance',
                 enhancementMode: mode,
               });
diff --git a/apps/ui/src/components/views/board-view/hooks/use-board-actions.ts b/apps/ui/src/components/views/board-view/hooks/use-board-actions.ts
index 8efacd8b..e25d963e 100644
--- a/apps/ui/src/components/views/board-view/hooks/use-board-actions.ts
+++ b/apps/ui/src/components/views/board-view/hooks/use-board-actions.ts
@@ -30,7 +30,8 @@ interface UseBoardActionsProps {
     featureId: string,
     updates: Partial<Feature>,
     descriptionHistorySource?: 'enhance' | 'edit',
-    enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer'
+    enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer',
+    preEnhancementDescription?: string
   ) => Promise<void>;
   persistFeatureDelete: (featureId: string) => Promise<void>;
   saveCategory: (category: string) => Promise<void>;
@@ -251,7 +252,8 @@ export function useBoardActions({
         workMode?: 'current' | 'auto' | 'custom';
       },
       descriptionHistorySource?: 'enhance' | 'edit',
-      enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer'
+      enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer',
+      preEnhancementDescription?: string
     ) => {
       const workMode = updates.workMode || 'current';
 
@@ -308,7 +310,13 @@ export function useBoardActions({
       };
 
       updateFeature(featureId, finalUpdates);
-      persistFeatureUpdate(featureId, finalUpdates, descriptionHistorySource, enhancementMode);
+      persistFeatureUpdate(
+        featureId,
+        finalUpdates,
+        descriptionHistorySource,
+        enhancementMode,
+        preEnhancementDescription
+      );
       if (updates.category) {
         saveCategory(updates.category);
       }
diff --git a/apps/ui/src/components/views/board-view/hooks/use-board-persistence.ts b/apps/ui/src/components/views/board-view/hooks/use-board-persistence.ts
index df281a56..3c860251 100644
--- a/apps/ui/src/components/views/board-view/hooks/use-board-persistence.ts
+++ b/apps/ui/src/components/views/board-view/hooks/use-board-persistence.ts
@@ -19,7 +19,8 @@ export function useBoardPersistence({ currentProject }: UseBoardPersistenceProps
       featureId: string,
       updates: Partial<Feature>,
       descriptionHistorySource?: 'enhance' | 'edit',
-      enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer'
+      enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer',
+      preEnhancementDescription?: string
     ) => {
       if (!currentProject) return;
 
@@ -35,7 +36,8 @@ export function useBoardPersistence({ currentProject }: UseBoardPersistenceProps
           featureId,
           updates,
           descriptionHistorySource,
-          enhancementMode
+          enhancementMode,
+          preEnhancementDescription
         );
         if (result.success && result.feature) {
           updateFeature(result.feature.id, result.feature);
diff --git a/apps/ui/src/components/views/board-view/shared/enhancement/enhance-with-ai.tsx b/apps/ui/src/components/views/board-view/shared/enhancement/enhance-with-ai.tsx
index 530b43cd..63b9dedc 100644
--- a/apps/ui/src/components/views/board-view/shared/enhancement/enhance-with-ai.tsx
+++ b/apps/ui/src/components/views/board-view/shared/enhancement/enhance-with-ai.tsx
@@ -22,7 +22,11 @@ interface EnhanceWithAIProps {
   /** Callback when text is enhanced */
   onChange: (enhancedText: string) => void;
   /** Optional callback to track enhancement in history */
-  onHistoryAdd?: (entry: { mode: EnhancementMode; enhancedText: string }) => void;
+  onHistoryAdd?: (entry: {
+    mode: EnhancementMode;
+    originalText: string;
+    enhancedText: string;
+  }) => void;
   /** Disable the enhancement feature */
   disabled?: boolean;
   /** Additional CSS classes */
@@ -69,11 +73,12 @@ export function EnhanceWithAI({
       );
 
       if (result?.success && result.enhancedText) {
+        const originalText = value;
         const enhancedText = result.enhancedText;
         onChange(enhancedText);
 
-        // Track in history if callback provided
-        onHistoryAdd?.({ mode: enhancementMode, enhancedText });
+        // Track in history if callback provided (includes original for restoration)
+        onHistoryAdd?.({ mode: enhancementMode, originalText, enhancedText });
 
         toast.success('Enhanced successfully!');
       } else {
diff --git a/apps/ui/src/components/views/board-view/shared/enhancement/enhancement-history-button.tsx b/apps/ui/src/components/views/board-view/shared/enhancement/enhancement-history-button.tsx
index 77dac898..bf31fde7 100644
--- a/apps/ui/src/components/views/board-view/shared/enhancement/enhancement-history-button.tsx
+++ b/apps/ui/src/components/views/board-view/shared/enhancement/enhancement-history-button.tsx
@@ -45,6 +45,11 @@ export function EnhancementHistoryButton<T extends BaseHistoryEntry>({
 }: EnhancementHistoryButtonProps<T>) {
   const [showHistory, setShowHistory] = useState(false);
 
+  // Memoize reversed history to avoid creating new array on every render
+  // NOTE: This hook MUST be called before any early returns to follow Rules of Hooks
+  const reversedHistory = useMemo(() => [...history].reverse(), [history]);
+
+  // Early return AFTER all hooks are called
   if (history.length === 0) {
     return null;
   }
@@ -71,9 +76,6 @@ export function EnhancementHistoryButton<T extends BaseHistoryEntry>({
     });
   };
 
-  // Memoize reversed history to avoid creating new array on every render
-  const reversedHistory = useMemo(() => [...history].reverse(), [history]);
-
   return (
     <Popover open={showHistory} onOpenChange={setShowHistory}>
       <PopoverTrigger asChild>
diff --git a/apps/ui/src/lib/electron.ts b/apps/ui/src/lib/electron.ts
index e06ed639..3abe43fa 100644
--- a/apps/ui/src/lib/electron.ts
+++ b/apps/ui/src/lib/electron.ts
@@ -462,7 +462,8 @@ export interface FeaturesAPI {
     featureId: string,
     updates: Partial<Feature>,
     descriptionHistorySource?: 'enhance' | 'edit',
-    enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer'
+    enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer',
+    preEnhancementDescription?: string
   ) => Promise<{ success: boolean; feature?: Feature; error?: string }>;
   delete: (projectPath: string, featureId: string) => Promise<{ success: boolean; error?: string }>;
   getAgentOutput: (
diff --git a/apps/ui/src/lib/http-api-client.ts b/apps/ui/src/lib/http-api-client.ts
index 7d442836..c64c427e 100644
--- a/apps/ui/src/lib/http-api-client.ts
+++ b/apps/ui/src/lib/http-api-client.ts
@@ -1459,7 +1459,8 @@ export class HttpApiClient implements ElectronAPI {
       featureId: string,
       updates: Partial<Feature>,
       descriptionHistorySource?: 'enhance' | 'edit',
-      enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer'
+      enhancementMode?: 'improve' | 'technical' | 'simplify' | 'acceptance' | 'ux-reviewer',
+      preEnhancementDescription?: string
     ) =>
       this.post('/api/features/update', {
         projectPath,
@@ -1467,6 +1468,7 @@ export class HttpApiClient implements ElectronAPI {
         updates,
         descriptionHistorySource,
         enhancementMode,
+        preEnhancementDescription,
       }),
     delete: (projectPath: string, featureId: string) =>
       this.post('/api/features/delete', { projectPath, featureId }),