diff --git a/backend/utils.py b/backend/utils.py
index 4d97d8b..ba3a118 100644
--- a/backend/utils.py
+++ b/backend/utils.py
@@ -273,9 +273,9 @@ def search_notes(notes_dir: str, query: str) -> List[Dict]:
     """
     Full-text search through note contents only.
     Does NOT search in file names, folder names, or paths - only note content.
+    Uses character-based context extraction for better snippet quality.
     """
     results = []
-    query_lower = query.lower()
     notes_path = Path(notes_dir)
     
     for md_file in notes_path.rglob("*.md"):
@@ -283,29 +283,48 @@ def search_notes(notes_dir: str, query: str) -> List[Dict]:
             with open(md_file, 'r', encoding='utf-8') as f:
                 content = f.read()
             
-            # Only search in note content (not file name, folder name, or path)
-            if query_lower in content.lower():
-                # Find context around match
-                lines = content.split('\n')
+            # Find all matches using regex (case-insensitive)
+            matches = list(re.finditer(re.escape(query), content, re.IGNORECASE))
+            
+            if matches:
                 matched_lines = []
                 
-                for i, line in enumerate(lines):
-                    if query_lower in line.lower():
-                        # Get surrounding context
-                        start = max(0, i - 1)
-                        end = min(len(lines), i + 2)
-                        context = '\n'.join(lines[start:end])
-                        matched_lines.append({
-                            "line_number": i + 1,
-                            "context": context[:200]  # Limit context length
-                        })
+                for match in matches[:3]:  # Limit to 3 matches per file
+                    start_index = match.start()
+                    end_index = match.end()
+                    
+                    # Create slice window: ±30 characters around match
+                    context_start = max(0, start_index - 30)
+                    context_end = min(len(content), end_index + 30)
+                    
+                    # Extract snippet
+                    snippet = content[context_start:context_end]
+                    
+                    # Replace all newlines with spaces to ensure UI doesn't break
+                    snippet = snippet.replace('\n', ' ')
+                    
+                    # Add ellipsis if truncated at start
+                    if context_start > 0:
+                        snippet = '...' + snippet
+                    
+                    # Add ellipsis if truncated at end
+                    if context_end < len(content):
+                        snippet = snippet + '...'
+                    
+                    # Calculate line number by counting newlines up to match start
+                    line_number = content.count('\n', 0, start_index) + 1
+                    
+                    matched_lines.append({
+                        "line_number": line_number,
+                        "context": snippet
+                    })
                 
                 relative_path = md_file.relative_to(notes_path)
                 results.append({
                     "name": md_file.stem,
                     "path": str(relative_path.as_posix()),
                     "folder": str(relative_path.parent.as_posix()) if str(relative_path.parent) != "." else "",
-                    "matches": matched_lines[:3]  # Limit to 3 matches per file
+                    "matches": matched_lines
                 })
         except Exception:
             continue
diff --git a/frontend/index.html b/frontend/index.html
index 503a999..08af448 100644
--- a/frontend/index.html
+++ b/frontend/index.html
@@ -953,9 +953,10 @@
                                 :style="currentNote === note.path ? 'background-color: var(--accent-light); color: var(--accent-primary);' : 'color: var(--text-primary);'"
                                 onmouseover="if(this.style.backgroundColor !== 'var(--accent-light)') this.style.backgroundColor='var(--bg-hover)'"
                                 onmouseout="if(this.style.backgroundColor !== 'var(--accent-light)') this.style.backgroundColor='transparent'"
+                                :title="note.path"
                             >
                                 <div class="font-medium truncate" x-text="note.name"></div>
-                                <div class="text-xs truncate" style="color: var(--text-tertiary);" x-text="note.folder || 'Root'"></div>
+                                <div class="text-xs truncate" style="color: var(--text-tertiary);" x-text="(note.matches && note.matches.length > 0) ? note.matches[0].context : (note.folder || 'Root')"></div>
                             </div>
                         </template>
                     </div>