diff --git a/core/edit/searchAndReplace/executeFindAndReplace.vitest.ts b/core/edit/searchAndReplace/executeFindAndReplace.vitest.ts
index 9ae1857b6ae..de9f62cc079 100644
--- a/core/edit/searchAndReplace/executeFindAndReplace.vitest.ts
+++ b/core/edit/searchAndReplace/executeFindAndReplace.vitest.ts
@@ -207,6 +207,84 @@ describe("executeFindAndReplace", () => {
     });
   });
 
+  describe("indentation adjustment", () => {
+    it("should adjust indentation when trimmedMatch finds unindented old_string in indented file", () => {
+      const fileContent =
+        "def foo():\n    x = 1\n    y = 2\n    return x + y\n";
+      // LLM sends unindented old_string that matches via trimmedMatch
+      const oldString = "x = 1\ny = 2";
+      const newString = "x = 10\ny = 20";
+      const result = executeFindAndReplace(
+        fileContent,
+        oldString,
+        newString,
+        false,
+      );
+      expect(result).toBe(
+        "def foo():\n    x = 10\n    y = 20\n    return x + y\n",
+      );
+    });
+
+    it("should preserve relative inner indentation in multi-line replacement", () => {
+      const fileContent =
+        "class Foo:\n    def bar(self):\n        if True:\n            x = 1\n";
+      const oldString = "if True:\n    x = 1";
+      const newString = "if True:\n    x = 1\n    y = 2";
+      const result = executeFindAndReplace(
+        fileContent,
+        oldString,
+        newString,
+        false,
+      );
+      expect(result).toBe(
+        "class Foo:\n    def bar(self):\n        if True:\n            x = 1\n            y = 2\n",
+      );
+    });
+
+    it("should handle tab vs space mismatch", () => {
+      const fileContent = "function foo() {\n\tconst x = 1;\n}\n";
+      // LLM sends with leading spaces (not tabs), triggering trimmedMatch
+      const oldString = "  const x = 1;";
+      const newString = "  const x = 2;\n  const y = 3;";
+      const result = executeFindAndReplace(
+        fileContent,
+        oldString,
+        newString,
+        false,
+      );
+      expect(result).toBe(
+        "function foo() {\n\tconst x = 2;\n\tconst y = 3;\n}\n",
+      );
+    });
+
+    it("should not adjust indentation for exactMatch", () => {
+      const fileContent = "    x = 1\n";
+      const oldString = "    x = 1";
+      const newString = "    x = 2";
+      const result = executeFindAndReplace(
+        fileContent,
+        oldString,
+        newString,
+        false,
+      );
+      expect(result).toBe("    x = 2\n");
+    });
+
+    it("should handle whitespaceIgnoredMatch with different internal whitespace", () => {
+      const fileContent = "def outer():\n    if  True:\n        return  42\n";
+      // Different internal whitespace triggers whitespaceIgnoredMatch
+      const oldString = "if True:\n    return 42";
+      const newString = "if True:\n    return 99";
+      const result = executeFindAndReplace(
+        fileContent,
+        oldString,
+        newString,
+        false,
+      );
+      expect(result).toBe("def outer():\n    if True:\n        return 99\n");
+    });
+  });
+
   describe("edge cases", () => {
     it("should handle single character replacement", () => {
       const content = "a b c";
diff --git a/core/edit/searchAndReplace/performReplace.ts b/core/edit/searchAndReplace/performReplace.ts
index 65453e06cd6..6da5c3c5096 100644
--- a/core/edit/searchAndReplace/performReplace.ts
+++ b/core/edit/searchAndReplace/performReplace.ts
@@ -1,6 +1,86 @@
 import { EditOperation } from "../../tools/definitions/multiEdit";
 import { ContinueError, ContinueErrorReason } from "../../util/errors";
-import { findSearchMatches } from "./findSearchMatch";
+import { SearchMatchResult, findSearchMatches } from "./findSearchMatch";
+
+/**
+ * Get the leading whitespace of the first non-empty line in a string.
+ */
+function getLeadingIndent(text: string): string {
+  const lines = text.split("\n");
+  for (const line of lines) {
+    if (line.trim().length > 0) {
+      const match = line.match(/^(\s*)/);
+      return match ? match[1] : "";
+    }
+  }
+  return "";
+}
+
+/**
+ * Get the indentation of the file line containing a given character position.
+ */
+function getLineIndentAtPosition(
+  fileContent: string,
+  position: number,
+): string {
+  const lineStart = fileContent.lastIndexOf("\n", position - 1) + 1;
+  const lineEnd = fileContent.indexOf("\n", lineStart);
+  const line = fileContent.substring(
+    lineStart,
+    lineEnd === -1 ? fileContent.length : lineEnd,
+  );
+  const match = line.match(/^(\s*)/);
+  return match ? match[1] : "";
+}
+
+/**
+ * When a fuzzy match strategy (trimmedMatch, whitespaceIgnoredMatch, etc.)
+ * finds a match, the indentation of the matched region in the file may
+ * differ from the indentation in the search string provided by the LLM.
+ * This function adjusts newString so its indentation is relative to the
+ * actual matched text in the file rather than the LLM-provided oldString.
+ */
+function adjustReplacementIndentation(
+  fileContent: string,
+  match: SearchMatchResult,
+  oldString: string,
+  newString: string,
+): string {
+  if (
+    match.strategyName === "exactMatch" ||
+    match.strategyName === "emptySearch"
+  ) {
+    return newString;
+  }
+
+  const matchedIndent = getLineIndentAtPosition(fileContent, match.startIndex);
+  const oldIndent = getLeadingIndent(oldString);
+
+  if (matchedIndent === oldIndent) {
+    return newString;
+  }
+
+  const lines = newString.split("\n");
+  const adjusted = lines.map((line, index) => {
+    if (line.trim().length === 0) {
+      return line;
+    }
+    if (index === 0) {
+      // First line: the file content before startIndex already provides
+      // indentation, so strip the old indent rather than adding new
+      if (oldIndent && line.startsWith(oldIndent)) {
+        return line.slice(oldIndent.length);
+      }
+      return line;
+    }
+    // Subsequent lines: replace oldIndent prefix with matchedIndent
+    if (line.startsWith(oldIndent)) {
+      return matchedIndent + line.slice(oldIndent.length);
+    }
+    return line;
+  });
+  return adjusted.join("\n");
+}
 
 export function executeFindAndReplace(
   fileContent: string,
@@ -23,9 +103,15 @@ export function executeFindAndReplace(
     let result = fileContent;
     for (let i = matches.length - 1; i >= 0; i--) {
       const match = matches[i];
+      const adjustedNew = adjustReplacementIndentation(
+        result,
+        match,
+        oldString,
+        newString,
+      );
       result =
         result.substring(0, match.startIndex) +
-        newString +
+        adjustedNew +
         result.substring(match.endIndex);
     }
     return result;
@@ -40,9 +126,15 @@ export function executeFindAndReplace(
 
     // Apply single replacement
     const match = matches[0];
+    const adjustedNew = adjustReplacementIndentation(
+      fileContent,
+      match,
+      oldString,
+      newString,
+    );
     return (
       fileContent.substring(0, match.startIndex) +
-      newString +
+      adjustedNew +
       fileContent.substring(match.endIndex)
     );
   }