diff --git a/src/core/tools/SearchAndReplaceTool.ts b/src/core/tools/SearchAndReplaceTool.ts
index 49d159f455..7d03a6a22c 100644
--- a/src/core/tools/SearchAndReplaceTool.ts
+++ b/src/core/tools/SearchAndReplaceTool.ts
@@ -111,6 +111,8 @@ export class SearchAndReplaceTool extends BaseTool<"search_and_replace"> {
 			let fileContent: string
 			try {
 				fileContent = await fs.readFile(absolutePath, "utf8")
+				// Normalize line endings to LF for consistent matching
+				fileContent = fileContent.replace(/\r\n/g, "\n")
 			} catch (error) {
 				task.consecutiveMistakeCount++
 				task.recordToolError("search_and_replace")
@@ -125,7 +127,9 @@ export class SearchAndReplaceTool extends BaseTool<"search_and_replace"> {
 			const errors: string[] = []
 
 			for (let i = 0; i < operations.length; i++) {
-				const { search, replace } = operations[i]
+				// Normalize line endings in search/replace strings to match file content
+				const search = operations[i].search.replace(/\r\n/g, "\n")
+				const replace = operations[i].replace.replace(/\r\n/g, "\n")
 				const searchPattern = new RegExp(escapeRegExp(search), "g")
 
 				const matchCount = newContent.match(searchPattern)?.length ?? 0
diff --git a/src/core/tools/SearchReplaceTool.ts b/src/core/tools/SearchReplaceTool.ts
index b0150d04a1..dadb97fde5 100644
--- a/src/core/tools/SearchReplaceTool.ts
+++ b/src/core/tools/SearchReplaceTool.ts
@@ -105,6 +105,8 @@ export class SearchReplaceTool extends BaseTool<"search_replace"> {
 			let fileContent: string
 			try {
 				fileContent = await fs.readFile(absolutePath, "utf8")
+				// Normalize line endings to LF for consistent matching
+				fileContent = fileContent.replace(/\r\n/g, "\n")
 			} catch (error) {
 				task.consecutiveMistakeCount++
 				task.recordToolError("search_replace")
@@ -114,8 +116,12 @@ export class SearchReplaceTool extends BaseTool<"search_replace"> {
 				return
 			}
 
+			// Normalize line endings in search/replace strings to match file content
+			const normalizedOldString = old_string.replace(/\r\n/g, "\n")
+			const normalizedNewString = new_string.replace(/\r\n/g, "\n")
+
 			// Check for exact match (literal string, not regex)
-			const matchCount = fileContent.split(old_string).length - 1
+			const matchCount = fileContent.split(normalizedOldString).length - 1
 
 			if (matchCount === 0) {
 				task.consecutiveMistakeCount++
@@ -142,7 +148,7 @@ export class SearchReplaceTool extends BaseTool<"search_replace"> {
 			}
 
 			// Apply the single replacement
-			const newContent = fileContent.replace(old_string, new_string)
+			const newContent = fileContent.replace(normalizedOldString, normalizedNewString)
 
 			// Check if any changes were made
 			if (newContent === fileContent) {
diff --git a/src/core/tools/__tests__/searchAndReplaceTool.spec.ts b/src/core/tools/__tests__/searchAndReplaceTool.spec.ts
new file mode 100644
index 0000000000..c73744ec57
--- /dev/null
+++ b/src/core/tools/__tests__/searchAndReplaceTool.spec.ts
@@ -0,0 +1,405 @@
+import * as path from "path"
+import fs from "fs/promises"
+
+import type { MockedFunction } from "vitest"
+
+import { fileExistsAtPath } from "../../../utils/fs"
+import { isPathOutsideWorkspace } from "../../../utils/pathUtils"
+import { getReadablePath } from "../../../utils/path"
+import { ToolUse, ToolResponse } from "../../../shared/tools"
+import { searchAndReplaceTool } from "../SearchAndReplaceTool"
+
+vi.mock("fs/promises", () => ({
+	default: {
+		readFile: vi.fn().mockResolvedValue(""),
+	},
+}))
+
+vi.mock("path", async () => {
+	const originalPath = await vi.importActual("path")
+	return {
+		...originalPath,
+		resolve: vi.fn().mockImplementation((...args) => {
+			const separator = process.platform === "win32" ? "\\" : "/"
+			return args.join(separator)
+		}),
+		isAbsolute: vi.fn().mockReturnValue(false),
+		relative: vi.fn().mockImplementation((from, to) => to),
+	}
+})
+
+vi.mock("delay", () => ({
+	default: vi.fn(),
+}))
+
+vi.mock("../../../utils/fs", () => ({
+	fileExistsAtPath: vi.fn().mockResolvedValue(true),
+}))
+
+vi.mock("../../prompts/responses", () => ({
+	formatResponse: {
+		toolError: vi.fn((msg) => `Error: ${msg}`),
+		rooIgnoreError: vi.fn((path) => `Access denied: ${path}`),
+		createPrettyPatch: vi.fn(() => "mock-diff"),
+	},
+}))
+
+vi.mock("../../../utils/pathUtils", () => ({
+	isPathOutsideWorkspace: vi.fn().mockReturnValue(false),
+}))
+
+vi.mock("../../../utils/path", () => ({
+	getReadablePath: vi.fn().mockReturnValue("test/path.txt"),
+}))
+
+vi.mock("../../diff/stats", () => ({
+	sanitizeUnifiedDiff: vi.fn((diff) => diff),
+	computeDiffStats: vi.fn(() => ({ additions: 1, deletions: 1 })),
+}))
+
+vi.mock("vscode", () => ({
+	window: {
+		showWarningMessage: vi.fn().mockResolvedValue(undefined),
+	},
+	env: {
+		openExternal: vi.fn(),
+	},
+	Uri: {
+		parse: vi.fn(),
+	},
+}))
+
+describe("searchAndReplaceTool", () => {
+	// Test data
+	const testFilePath = "test/file.txt"
+	const absoluteFilePath = process.platform === "win32" ? "C:\\test\\file.txt" : "/test/file.txt"
+	const testFileContent = "Line 1\nLine 2\nLine 3\nLine 4"
+
+	// Mocked functions
+	const mockedFileExistsAtPath = fileExistsAtPath as MockedFunction<typeof fileExistsAtPath>
+	const mockedFsReadFile = fs.readFile as unknown as MockedFunction<
+		(path: string, encoding: string) => Promise<string>
+	>
+	const mockedIsPathOutsideWorkspace = isPathOutsideWorkspace as MockedFunction<typeof isPathOutsideWorkspace>
+	const mockedGetReadablePath = getReadablePath as MockedFunction<typeof getReadablePath>
+	const mockedPathResolve = path.resolve as MockedFunction<typeof path.resolve>
+	const mockedPathIsAbsolute = path.isAbsolute as MockedFunction<typeof path.isAbsolute>
+
+	const mockTask: any = {}
+	let mockAskApproval: ReturnType<typeof vi.fn>
+	let mockHandleError: ReturnType<typeof vi.fn>
+	let mockPushToolResult: ReturnType<typeof vi.fn>
+	let mockRemoveClosingTag: ReturnType<typeof vi.fn>
+	let toolResult: ToolResponse | undefined
+
+	beforeEach(() => {
+		vi.clearAllMocks()
+
+		mockedPathResolve.mockReturnValue(absoluteFilePath)
+		mockedPathIsAbsolute.mockReturnValue(false)
+		mockedFileExistsAtPath.mockResolvedValue(true)
+		mockedFsReadFile.mockResolvedValue(testFileContent)
+		mockedIsPathOutsideWorkspace.mockReturnValue(false)
+		mockedGetReadablePath.mockReturnValue("test/path.txt")
+
+		mockTask.cwd = "/"
+		mockTask.consecutiveMistakeCount = 0
+		mockTask.didEditFile = false
+		mockTask.providerRef = {
+			deref: vi.fn().mockReturnValue({
+				getState: vi.fn().mockResolvedValue({
+					diagnosticsEnabled: true,
+					writeDelayMs: 1000,
+					experiments: {},
+				}),
+			}),
+		}
+		mockTask.rooIgnoreController = {
+			validateAccess: vi.fn().mockReturnValue(true),
+		}
+		mockTask.rooProtectedController = {
+			isWriteProtected: vi.fn().mockReturnValue(false),
+		}
+		mockTask.diffViewProvider = {
+			editType: undefined,
+			isEditing: false,
+			originalContent: "",
+			open: vi.fn().mockResolvedValue(undefined),
+			update: vi.fn().mockResolvedValue(undefined),
+			reset: vi.fn().mockResolvedValue(undefined),
+			revertChanges: vi.fn().mockResolvedValue(undefined),
+			saveChanges: vi.fn().mockResolvedValue({
+				newProblemsMessage: "",
+				userEdits: null,
+				finalContent: "final content",
+			}),
+			saveDirectly: vi.fn().mockResolvedValue(undefined),
+			scrollToFirstDiff: vi.fn(),
+			pushToolWriteResult: vi.fn().mockResolvedValue("Tool result message"),
+		}
+		mockTask.fileContextTracker = {
+			trackFileContext: vi.fn().mockResolvedValue(undefined),
+		}
+		mockTask.say = vi.fn().mockResolvedValue(undefined)
+		mockTask.ask = vi.fn().mockResolvedValue(undefined)
+		mockTask.recordToolError = vi.fn()
+		mockTask.recordToolUsage = vi.fn()
+		mockTask.processQueuedMessages = vi.fn()
+		mockTask.sayAndCreateMissingParamError = vi.fn().mockResolvedValue("Missing param error")
+
+		mockAskApproval = vi.fn().mockResolvedValue(true)
+		mockHandleError = vi.fn().mockResolvedValue(undefined)
+		mockRemoveClosingTag = vi.fn((tag, content) => content)
+
+		toolResult = undefined
+	})
+
+	/**
+	 * Helper function to execute the search and replace tool with different parameters
+	 */
+	async function executeSearchAndReplaceTool(
+		params: Partial<ToolUse["params"]> = {},
+		options: {
+			fileExists?: boolean
+			fileContent?: string
+			isPartial?: boolean
+			accessAllowed?: boolean
+		} = {},
+	): Promise<ToolResponse | undefined> {
+		const fileExists = options.fileExists ?? true
+		const fileContent = options.fileContent ?? testFileContent
+		const isPartial = options.isPartial ?? false
+		const accessAllowed = options.accessAllowed ?? true
+
+		mockedFileExistsAtPath.mockResolvedValue(fileExists)
+		mockedFsReadFile.mockResolvedValue(fileContent)
+		mockTask.rooIgnoreController.validateAccess.mockReturnValue(accessAllowed)
+
+		const toolUse: ToolUse = {
+			type: "tool_use",
+			name: "search_and_replace",
+			params: {
+				path: testFilePath,
+				operations: JSON.stringify([{ search: "Line 2", replace: "Modified Line 2" }]),
+				...params,
+			},
+			partial: isPartial,
+		}
+
+		mockPushToolResult = vi.fn((result: ToolResponse) => {
+			toolResult = result
+		})
+
+		await searchAndReplaceTool.handle(mockTask, toolUse as ToolUse<"search_and_replace">, {
+			askApproval: mockAskApproval,
+			handleError: mockHandleError,
+			pushToolResult: mockPushToolResult,
+			removeClosingTag: mockRemoveClosingTag,
+			toolProtocol: "native",
+		})
+
+		return toolResult
+	}
+
+	describe("parameter validation", () => {
+		it("returns error when path is missing", async () => {
+			const result = await executeSearchAndReplaceTool({ path: undefined })
+
+			expect(result).toBe("Missing param error")
+			expect(mockTask.consecutiveMistakeCount).toBe(1)
+			expect(mockTask.recordToolError).toHaveBeenCalledWith("search_and_replace")
+		})
+
+		it("returns error when operations is missing", async () => {
+			const result = await executeSearchAndReplaceTool({ operations: undefined })
+
+			expect(result).toContain("Error:")
+			expect(result).toContain("Missing or empty 'operations' parameter")
+			expect(mockTask.consecutiveMistakeCount).toBe(1)
+		})
+
+		it("returns error when operations is empty array", async () => {
+			const result = await executeSearchAndReplaceTool({ operations: JSON.stringify([]) })
+
+			expect(result).toContain("Error:")
+			expect(result).toContain("Missing or empty 'operations' parameter")
+			expect(mockTask.consecutiveMistakeCount).toBe(1)
+		})
+	})
+
+	describe("file access", () => {
+		it("returns error when file does not exist", async () => {
+			const result = await executeSearchAndReplaceTool({}, { fileExists: false })
+
+			expect(result).toContain("Error:")
+			expect(result).toContain("File not found")
+			expect(mockTask.consecutiveMistakeCount).toBe(1)
+		})
+
+		it("returns error when access is denied", async () => {
+			const result = await executeSearchAndReplaceTool({}, { accessAllowed: false })
+
+			expect(result).toContain("Access denied")
+		})
+	})
+
+	describe("search and replace logic", () => {
+		it("returns error when no match is found", async () => {
+			const result = await executeSearchAndReplaceTool(
+				{ operations: JSON.stringify([{ search: "NonExistent", replace: "New" }]) },
+				{ fileContent: "Line 1\nLine 2\nLine 3" },
+			)
+
+			expect(result).toContain("Error:")
+			expect(result).toContain("No match found")
+			expect(mockTask.consecutiveMistakeCount).toBe(1)
+			expect(mockTask.recordToolError).toHaveBeenCalledWith("search_and_replace", "no_match")
+		})
+
+		it("returns error when multiple matches are found", async () => {
+			const result = await executeSearchAndReplaceTool(
+				{ operations: JSON.stringify([{ search: "Line", replace: "Row" }]) },
+				{ fileContent: "Line 1\nLine 2\nLine 3" },
+			)
+
+			expect(result).toContain("Error:")
+			expect(result).toContain("3 matches")
+			expect(mockTask.consecutiveMistakeCount).toBe(1)
+		})
+
+		it("successfully replaces single unique match", async () => {
+			await executeSearchAndReplaceTool(
+				{ operations: JSON.stringify([{ search: "Line 2", replace: "Modified Line 2" }]) },
+				{ fileContent: "Line 1\nLine 2\nLine 3" },
+			)
+
+			expect(mockTask.consecutiveMistakeCount).toBe(0)
+			expect(mockTask.diffViewProvider.editType).toBe("modify")
+			expect(mockAskApproval).toHaveBeenCalled()
+		})
+	})
+
+	describe("CRLF normalization", () => {
+		it("normalizes CRLF to LF when reading file", async () => {
+			const contentWithCRLF = "Line 1\r\nLine 2\r\nLine 3"
+
+			await executeSearchAndReplaceTool(
+				{ operations: JSON.stringify([{ search: "Line 2", replace: "Modified Line 2" }]) },
+				{ fileContent: contentWithCRLF },
+			)
+
+			expect(mockTask.consecutiveMistakeCount).toBe(0)
+			expect(mockAskApproval).toHaveBeenCalled()
+		})
+
+		it("normalizes CRLF in search string to match LF-normalized file content", async () => {
+			// File has CRLF line endings
+			const contentWithCRLF = "Line 1\r\nLine 2\r\nLine 3"
+			// Search string also has CRLF (simulating what the model might send)
+			const searchWithCRLF = "Line 1\r\nLine 2"
+
+			await executeSearchAndReplaceTool(
+				{ operations: JSON.stringify([{ search: searchWithCRLF, replace: "Modified Lines" }]) },
+				{ fileContent: contentWithCRLF },
+			)
+
+			expect(mockTask.consecutiveMistakeCount).toBe(0)
+			expect(mockAskApproval).toHaveBeenCalled()
+		})
+
+		it("matches LF search string against CRLF file content after normalization", async () => {
+			// File has CRLF line endings
+			const contentWithCRLF = "Line 1\r\nLine 2\r\nLine 3"
+			// Search string has LF (typical model output)
+			const searchWithLF = "Line 1\nLine 2"
+
+			await executeSearchAndReplaceTool(
+				{ operations: JSON.stringify([{ search: searchWithLF, replace: "Modified Lines" }]) },
+				{ fileContent: contentWithCRLF },
+			)
+
+			expect(mockTask.consecutiveMistakeCount).toBe(0)
+			expect(mockAskApproval).toHaveBeenCalled()
+		})
+	})
+
+	describe("approval workflow", () => {
+		it("saves changes when user approves", async () => {
+			mockAskApproval.mockResolvedValue(true)
+
+			await executeSearchAndReplaceTool()
+
+			expect(mockTask.diffViewProvider.saveChanges).toHaveBeenCalled()
+			expect(mockTask.didEditFile).toBe(true)
+			expect(mockTask.recordToolUsage).toHaveBeenCalledWith("search_and_replace")
+		})
+
+		it("reverts changes when user rejects", async () => {
+			mockAskApproval.mockResolvedValue(false)
+
+			const result = await executeSearchAndReplaceTool()
+
+			expect(mockTask.diffViewProvider.revertChanges).toHaveBeenCalled()
+			expect(mockTask.diffViewProvider.saveChanges).not.toHaveBeenCalled()
+			expect(result).toContain("rejected")
+		})
+	})
+
+	describe("partial block handling", () => {
+		it("handles partial block without errors", async () => {
+			await executeSearchAndReplaceTool({}, { isPartial: true })
+
+			expect(mockTask.ask).toHaveBeenCalled()
+		})
+	})
+
+	describe("error handling", () => {
+		it("handles file read errors gracefully", async () => {
+			mockedFsReadFile.mockRejectedValueOnce(new Error("Read failed"))
+
+			const toolUse: ToolUse = {
+				type: "tool_use",
+				name: "search_and_replace",
+				params: {
+					path: testFilePath,
+					operations: JSON.stringify([{ search: "Line 2", replace: "Modified" }]),
+				},
+				partial: false,
+			}
+
+			let capturedResult: ToolResponse | undefined
+			const localPushToolResult = vi.fn((result: ToolResponse) => {
+				capturedResult = result
+			})
+
+			await searchAndReplaceTool.handle(mockTask, toolUse as ToolUse<"search_and_replace">, {
+				askApproval: mockAskApproval,
+				handleError: mockHandleError,
+				pushToolResult: localPushToolResult,
+				removeClosingTag: mockRemoveClosingTag,
+				toolProtocol: "native",
+			})
+
+			expect(capturedResult).toContain("Error:")
+			expect(capturedResult).toContain("Failed to read file")
+			expect(mockTask.consecutiveMistakeCount).toBe(1)
+		})
+
+		it("handles general errors and resets diff view", async () => {
+			mockTask.diffViewProvider.open.mockRejectedValueOnce(new Error("General error"))
+
+			await executeSearchAndReplaceTool()
+
+			expect(mockHandleError).toHaveBeenCalledWith("search and replace", expect.any(Error))
+			expect(mockTask.diffViewProvider.reset).toHaveBeenCalled()
+		})
+	})
+
+	describe("file tracking", () => {
+		it("tracks file context after successful edit", async () => {
+			await executeSearchAndReplaceTool()
+
+			expect(mockTask.fileContextTracker.trackFileContext).toHaveBeenCalledWith(testFilePath, "roo_edited")
+		})
+	})
+})
diff --git a/src/core/tools/__tests__/searchReplaceTool.spec.ts b/src/core/tools/__tests__/searchReplaceTool.spec.ts
index b9b1e453d4..984808e971 100644
--- a/src/core/tools/__tests__/searchReplaceTool.spec.ts
+++ b/src/core/tools/__tests__/searchReplaceTool.spec.ts
@@ -379,4 +379,48 @@ describe("searchReplaceTool", () => {
 			expect(mockCline.fileContextTracker.trackFileContext).toHaveBeenCalledWith(testFilePath, "roo_edited")
 		})
 	})
+
+	describe("CRLF normalization", () => {
+		it("normalizes CRLF to LF when reading file", async () => {
+			const contentWithCRLF = "Line 1\r\nLine 2\r\nLine 3"
+
+			await executeSearchReplaceTool(
+				{ old_string: "Line 2", new_string: "Modified Line 2" },
+				{ fileContent: contentWithCRLF },
+			)
+
+			expect(mockCline.consecutiveMistakeCount).toBe(0)
+			expect(mockAskApproval).toHaveBeenCalled()
+		})
+
+		it("normalizes CRLF in old_string to match LF-normalized file content", async () => {
+			// File has CRLF line endings
+			const contentWithCRLF = "Line 1\r\nLine 2\r\nLine 3"
+			// Search string also has CRLF (simulating what the model might send)
+			const searchWithCRLF = "Line 1\r\nLine 2"
+
+			await executeSearchReplaceTool(
+				{ old_string: searchWithCRLF, new_string: "Modified Lines" },
+				{ fileContent: contentWithCRLF },
+			)
+
+			expect(mockCline.consecutiveMistakeCount).toBe(0)
+			expect(mockAskApproval).toHaveBeenCalled()
+		})
+
+		it("matches LF old_string against CRLF file content after normalization", async () => {
+			// File has CRLF line endings
+			const contentWithCRLF = "Line 1\r\nLine 2\r\nLine 3"
+			// Search string has LF (typical model output)
+			const searchWithLF = "Line 1\nLine 2"
+
+			await executeSearchReplaceTool(
+				{ old_string: searchWithLF, new_string: "Modified Lines" },
+				{ fileContent: contentWithCRLF },
+			)
+
+			expect(mockCline.consecutiveMistakeCount).toBe(0)
+			expect(mockAskApproval).toHaveBeenCalled()
+		})
+	})
 })