diff --git a/src/core/diff/strategies/__tests__/search-replace.test.ts b/src/core/diff/strategies/__tests__/search-replace.test.ts
index cdfa137..9afb9e4 100644
--- a/src/core/diff/strategies/__tests__/search-replace.test.ts
+++ b/src/core/diff/strategies/__tests__/search-replace.test.ts
@@ -416,6 +416,93 @@ class Example {
             console.error(e);
         }
     }
+}`);
+        });
+
+        it('should handle negative indentation relative to search content', () => {
+            const originalContent = `class Example {
+    constructor() {
+        if (true) {
+            this.init();
+            this.setup();
+        }
+    }
+}`.trim();
+            const diffContent = `test.ts
+<<<<<<< SEARCH
+            this.init();
+            this.setup();
+=======
+        this.init();
+        this.setup();
+>>>>>>> REPLACE`;
+        
+            const result = strategy.applyDiff(originalContent, diffContent);
+            expect(result).toBe(`class Example {
+    constructor() {
+        if (true) {
+        this.init();
+        this.setup();
+        }
+    }
+}`);
+        });
+        
+        it('should handle extreme negative indentation (no indent)', () => {
+    const originalContent = `class Example {
+    constructor() {
+        if (true) {
+            this.init();
+        }
+    }
+}`.trim();
+            const diffContent = `test.ts
+<<<<<<< SEARCH
+            this.init();
+=======
+this.init();
+>>>>>>> REPLACE`;
+        
+            const result = strategy.applyDiff(originalContent, diffContent);
+            expect(result).toBe(`class Example {
+    constructor() {
+        if (true) {
+this.init();
+        }
+    }
+}`);
+        });
+        
+        it('should handle mixed indentation changes in replace block', () => {
+    const originalContent = `class Example {
+    constructor() {
+        if (true) {
+            this.init();
+            this.setup();
+            this.validate();
+        }
+    }
+}`.trim();
+            const diffContent = `test.ts
+<<<<<<< SEARCH
+            this.init();
+            this.setup();
+            this.validate();
+=======
+        this.init();
+            this.setup();
+    this.validate();
+>>>>>>> REPLACE`;
+        
+            const result = strategy.applyDiff(originalContent, diffContent);
+            expect(result).toBe(`class Example {
+    constructor() {
+        if (true) {
+        this.init();
+            this.setup();
+    this.validate();
+        }
+    }
 }`);
         });
     })
diff --git a/src/core/diff/strategies/search-replace.ts b/src/core/diff/strategies/search-replace.ts
index 3d524b1..021aa12 100644
--- a/src/core/diff/strategies/search-replace.ts
+++ b/src/core/diff/strategies/search-replace.ts
@@ -211,11 +211,18 @@ Your search/replace content here
             const currentIndent = currentIndentMatch ? currentIndentMatch[0] : '';
             const searchBaseIndent = searchIndents[0] || '';
             
-            // Calculate the relative indentation from the search content
-            const relativeIndent = currentIndent.slice(searchBaseIndent.length);
+            // Calculate the relative indentation level
+            const searchBaseLevel = searchBaseIndent.length;
+            const currentLevel = currentIndent.length;
+            const relativeLevel = currentLevel - searchBaseLevel;
             
-            // Apply the matched indentation plus any relative indentation
-            return matchedIndent + relativeIndent + line.trim();
+            // If relative level is negative, remove indentation from matched indent
+            // If positive, add to matched indent
+            const finalIndent = relativeLevel < 0
+                ? matchedIndent.slice(0, Math.max(0, matchedIndent.length + relativeLevel))
+                : matchedIndent + currentIndent.slice(searchBaseLevel);
+            
+            return finalIndent + line.trim();
         });
 
         // Construct the final content