diff --git a/src/core/checkpoints/__tests__/checkpoint.test.ts b/src/core/checkpoints/__tests__/checkpoint.test.ts
index e9e565853f2..299ff823b87 100644
--- a/src/core/checkpoints/__tests__/checkpoint.test.ts
+++ b/src/core/checkpoints/__tests__/checkpoint.test.ts
@@ -2,6 +2,7 @@ import { describe, it, expect, vi, beforeEach, afterEach, Mock } from "vitest"
 import { Task } from "../../task/Task"
 import { ClineProvider } from "../../webview/ClineProvider"
 import { checkpointSave, checkpointRestore, checkpointDiff, getCheckpointService } from "../index"
+import { MessageManager } from "../../message-manager"
 import * as vscode from "vscode"
 
 // Mock vscode
@@ -102,6 +103,7 @@ describe("Checkpoint functionality", () => {
 			overwriteApiConversationHistory: vi.fn(),
 			combineMessages: vi.fn().mockReturnValue([]),
 		}
+		mockTask.messageManager = new MessageManager(mockTask)
 
 		// Update the mock to return our mockCheckpointService
 		const checkpointsModule = await import("../../../services/checkpoints")
diff --git a/src/core/checkpoints/index.ts b/src/core/checkpoints/index.ts
index 3efdb466e66..64a8ad1cfe5 100644
--- a/src/core/checkpoints/index.ts
+++ b/src/core/checkpoints/index.ts
@@ -258,20 +258,20 @@ export async function checkpointRestore(
 		await provider?.postMessageToWebview({ type: "currentCheckpointUpdated", text: commitHash })
 
 		if (mode === "restore") {
-			await task.overwriteApiConversationHistory(task.apiConversationHistory.filter((m) => !m.ts || m.ts < ts))
-
+			// Calculate metrics from messages that will be deleted (must be done before rewind)
 			const deletedMessages = task.clineMessages.slice(index + 1)
 
 			const { totalTokensIn, totalTokensOut, totalCacheWrites, totalCacheReads, totalCost } = getApiMetrics(
 				task.combineMessages(deletedMessages),
 			)
 
-			// For delete operations, exclude the checkpoint message itself
-			// For edit operations, include the checkpoint message (to be edited)
-			const endIndex = operation === "edit" ? index + 1 : index
-			await task.overwriteClineMessages(task.clineMessages.slice(0, endIndex))
+			// Use MessageManager to properly handle context-management events
+			// This ensures orphaned Summary messages and truncation markers are cleaned up
+			await task.messageManager.rewindToTimestamp(ts, {
+				includeTargetMessage: operation === "edit",
+			})
 
-			// TODO: Verify that this is working as expected.
+			// Report the deleted API request metrics
 			await task.say(
 				"api_req_deleted",
 				JSON.stringify({
diff --git a/src/core/message-manager/index.spec.ts b/src/core/message-manager/index.spec.ts
new file mode 100644
index 00000000000..84ee10e8956
--- /dev/null
+++ b/src/core/message-manager/index.spec.ts
@@ -0,0 +1,731 @@
+import { MessageManager } from "./index"
+import * as condenseModule from "../condense"
+
+describe("MessageManager", () => {
+	let mockTask: any
+	let manager: MessageManager
+	let cleanupAfterTruncationSpy: any
+
+	beforeEach(() => {
+		mockTask = {
+			clineMessages: [],
+			apiConversationHistory: [],
+			overwriteClineMessages: vi.fn(),
+			overwriteApiConversationHistory: vi.fn(),
+		}
+		manager = new MessageManager(mockTask)
+
+		// Mock cleanupAfterTruncation to track calls and return input by default
+		cleanupAfterTruncationSpy = vi.spyOn(condenseModule, "cleanupAfterTruncation")
+		cleanupAfterTruncationSpy.mockImplementation((messages: any[]) => messages)
+	})
+
+	afterEach(() => {
+		cleanupAfterTruncationSpy.mockRestore()
+	})
+
+	describe("Basic rewind operations", () => {
+		it("should remove messages at and after the target timestamp", async () => {
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+				{ ts: 300, say: "user", text: "Second" },
+				{ ts: 400, say: "assistant", text: "Response 2" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{ ts: 200, role: "assistant", content: [{ type: "text", text: "Response" }] },
+				{ ts: 300, role: "user", content: [{ type: "text", text: "Second" }] },
+				{ ts: 400, role: "assistant", content: [{ type: "text", text: "Response 2" }] },
+			]
+
+			await manager.rewindToTimestamp(300)
+
+			// Should keep messages before ts=300
+			expect(mockTask.overwriteClineMessages).toHaveBeenCalledWith([
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+			])
+
+			// Should keep API messages before ts=300
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			expect(apiCall).toHaveLength(2)
+			expect(apiCall[0].ts).toBe(100)
+			expect(apiCall[1].ts).toBe(200)
+		})
+
+		it("should keep target message when includeTargetMessage is true", async () => {
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+				{ ts: 300, say: "user", text: "Second" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{ ts: 200, role: "assistant", content: [{ type: "text", text: "Response" }] },
+				{ ts: 300, role: "user", content: [{ type: "text", text: "Second" }] },
+			]
+
+			await manager.rewindToTimestamp(300, { includeTargetMessage: true })
+
+			// Should keep messages up to and including ts=300 in clineMessages
+			expect(mockTask.overwriteClineMessages).toHaveBeenCalledWith([
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+				{ ts: 300, say: "user", text: "Second" },
+			])
+
+			// API history uses ts < cutoffTs, so excludes the message at ts=300
+			// This is correct for edit scenarios - keep UI message but truncate API before it
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			expect(apiCall).toHaveLength(2)
+			expect(apiCall[0].ts).toBe(100)
+			expect(apiCall[1].ts).toBe(200)
+		})
+
+		it("should throw error when timestamp not found", async () => {
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+			]
+
+			await expect(manager.rewindToTimestamp(999)).rejects.toThrow(
+				"Message with timestamp 999 not found in clineMessages",
+			)
+		})
+
+		it("should remove messages at and after the target index", async () => {
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+				{ ts: 300, say: "user", text: "Second" },
+				{ ts: 400, say: "assistant", text: "Response 2" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{ ts: 200, role: "assistant", content: [{ type: "text", text: "Response" }] },
+				{ ts: 300, role: "user", content: [{ type: "text", text: "Second" }] },
+				{ ts: 400, role: "assistant", content: [{ type: "text", text: "Response 2" }] },
+			]
+
+			await manager.rewindToIndex(2)
+
+			// Should keep messages [0, 2) - index 0 and 1
+			expect(mockTask.overwriteClineMessages).toHaveBeenCalledWith([
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+			])
+
+			// Should keep API messages before ts=300
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			expect(apiCall).toHaveLength(2)
+		})
+	})
+
+	describe("Condense handling", () => {
+		it("should preserve Summary when condense_context is preserved", async () => {
+			const condenseId = "summary-123"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+				{ ts: 300, say: "condense_context", contextCondense: { condenseId, summary: "Summary" } },
+				{ ts: 400, say: "user", text: "After condense" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{
+					ts: 200,
+					role: "assistant",
+					content: [{ type: "text", text: "Response" }],
+					condenseParent: condenseId,
+				},
+				{
+					ts: 299,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary" }],
+					isSummary: true,
+					condenseId,
+				},
+				{ ts: 400, role: "user", content: [{ type: "text", text: "After condense" }] },
+			]
+
+			// Rewind to ts=400, which preserves condense_context at ts=300
+			await manager.rewindToTimestamp(400)
+
+			// Summary should still exist
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasSummary = apiCall.some((m: any) => m.isSummary && m.condenseId === condenseId)
+			expect(hasSummary).toBe(true)
+		})
+
+		it("should remove Summary when condense_context is removed", async () => {
+			const condenseId = "summary-123"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "assistant", text: "Response" },
+				{ ts: 300, say: "user", text: "Second" },
+				{ ts: 400, say: "condense_context", contextCondense: { condenseId, summary: "Summary" } },
+				{ ts: 500, say: "user", text: "Third" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{
+					ts: 200,
+					role: "assistant",
+					content: [{ type: "text", text: "Response" }],
+					condenseParent: condenseId,
+				},
+				{
+					ts: 299,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary" }],
+					isSummary: true,
+					condenseId,
+				},
+				{ ts: 300, role: "user", content: [{ type: "text", text: "Second" }] },
+				{ ts: 500, role: "user", content: [{ type: "text", text: "Third" }] },
+			]
+
+			// Rewind to ts=300, which removes condense_context at ts=400
+			await manager.rewindToTimestamp(300)
+
+			// Summary should be removed
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasSummary = apiCall.some((m: any) => m.isSummary)
+			expect(hasSummary).toBe(false)
+		})
+
+		it("should clear orphaned condenseParent tags via cleanup", async () => {
+			const condenseId = "summary-123"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "condense_context", contextCondense: { condenseId, summary: "Summary" } },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{
+					ts: 150,
+					role: "assistant",
+					content: [{ type: "text", text: "Response" }],
+					condenseParent: condenseId,
+				},
+				{
+					ts: 199,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary" }],
+					isSummary: true,
+					condenseId,
+				},
+			]
+
+			// Rewind to ts=100, which removes condense_context
+			await manager.rewindToTimestamp(100)
+
+			// cleanupAfterTruncation should be called to remove orphaned tags
+			expect(cleanupAfterTruncationSpy).toHaveBeenCalled()
+		})
+
+		it("should handle multiple condense_context removals", async () => {
+			const condenseId1 = "summary-1"
+			const condenseId2 = "summary-2"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{
+					ts: 200,
+					say: "condense_context",
+					contextCondense: { condenseId: condenseId1, summary: "Summary 1" },
+				},
+				{ ts: 300, say: "user", text: "Second" },
+				{
+					ts: 400,
+					say: "condense_context",
+					contextCondense: { condenseId: condenseId2, summary: "Summary 2" },
+				},
+				{ ts: 500, say: "user", text: "Third" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{
+					ts: 199,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary 1" }],
+					isSummary: true,
+					condenseId: condenseId1,
+				},
+				{ ts: 300, role: "user", content: [{ type: "text", text: "Second" }] },
+				{
+					ts: 399,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary 2" }],
+					isSummary: true,
+					condenseId: condenseId2,
+				},
+				{ ts: 500, role: "user", content: [{ type: "text", text: "Third" }] },
+			]
+
+			// Rewind to ts=200, which removes both condense_context messages
+			await manager.rewindToTimestamp(200)
+
+			// Both summaries should be removed
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasSummary1 = apiCall.some((m: any) => m.condenseId === condenseId1)
+			const hasSummary2 = apiCall.some((m: any) => m.condenseId === condenseId2)
+			expect(hasSummary1).toBe(false)
+			expect(hasSummary2).toBe(false)
+		})
+	})
+
+	describe("Truncation handling", () => {
+		it("should preserve truncation marker when sliding_window_truncation is preserved", async () => {
+			const truncationId = "trunc-123"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "sliding_window_truncation", contextTruncation: { truncationId, reason: "window" } },
+				{ ts: 300, say: "user", text: "After truncation" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }], truncationParent: truncationId },
+				{
+					ts: 199,
+					role: "assistant",
+					content: [{ type: "text", text: "..." }],
+					isTruncationMarker: true,
+					truncationId,
+				},
+				{ ts: 300, role: "user", content: [{ type: "text", text: "After truncation" }] },
+			]
+
+			// Rewind to ts=300, which preserves sliding_window_truncation at ts=200
+			await manager.rewindToTimestamp(300)
+
+			// Truncation marker should still exist
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasMarker = apiCall.some((m: any) => m.isTruncationMarker && m.truncationId === truncationId)
+			expect(hasMarker).toBe(true)
+		})
+
+		it("should remove truncation marker when sliding_window_truncation is removed", async () => {
+			const truncationId = "trunc-123"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "user", text: "Second" },
+				{ ts: 300, say: "sliding_window_truncation", contextTruncation: { truncationId, reason: "window" } },
+				{ ts: 400, say: "user", text: "Third" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }], truncationParent: truncationId },
+				{ ts: 200, role: "user", content: [{ type: "text", text: "Second" }] },
+				{
+					ts: 299,
+					role: "assistant",
+					content: [{ type: "text", text: "..." }],
+					isTruncationMarker: true,
+					truncationId,
+				},
+				{ ts: 400, role: "user", content: [{ type: "text", text: "Third" }] },
+			]
+
+			// Rewind to ts=200, which removes sliding_window_truncation at ts=300
+			await manager.rewindToTimestamp(200)
+
+			// Truncation marker should be removed
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasMarker = apiCall.some((m: any) => m.isTruncationMarker)
+			expect(hasMarker).toBe(false)
+		})
+
+		it("should clear orphaned truncationParent tags via cleanup", async () => {
+			const truncationId = "trunc-123"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "sliding_window_truncation", contextTruncation: { truncationId, reason: "window" } },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }], truncationParent: truncationId },
+				{
+					ts: 199,
+					role: "assistant",
+					content: [{ type: "text", text: "..." }],
+					isTruncationMarker: true,
+					truncationId,
+				},
+			]
+
+			// Rewind to ts=100, which removes sliding_window_truncation
+			await manager.rewindToTimestamp(100)
+
+			// cleanupAfterTruncation should be called to remove orphaned tags
+			expect(cleanupAfterTruncationSpy).toHaveBeenCalled()
+		})
+
+		it("should handle multiple truncation removals", async () => {
+			const truncationId1 = "trunc-1"
+			const truncationId2 = "trunc-2"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{
+					ts: 200,
+					say: "sliding_window_truncation",
+					contextTruncation: { truncationId: truncationId1, reason: "window" },
+				},
+				{ ts: 300, say: "user", text: "Second" },
+				{
+					ts: 400,
+					say: "sliding_window_truncation",
+					contextTruncation: { truncationId: truncationId2, reason: "window" },
+				},
+				{ ts: 500, say: "user", text: "Third" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{
+					ts: 199,
+					role: "assistant",
+					content: [{ type: "text", text: "..." }],
+					isTruncationMarker: true,
+					truncationId: truncationId1,
+				},
+				{ ts: 300, role: "user", content: [{ type: "text", text: "Second" }] },
+				{
+					ts: 399,
+					role: "assistant",
+					content: [{ type: "text", text: "..." }],
+					isTruncationMarker: true,
+					truncationId: truncationId2,
+				},
+				{ ts: 500, role: "user", content: [{ type: "text", text: "Third" }] },
+			]
+
+			// Rewind to ts=200, which removes both truncation messages
+			await manager.rewindToTimestamp(200)
+
+			// Both markers should be removed
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasMarker1 = apiCall.some((m: any) => m.truncationId === truncationId1)
+			const hasMarker2 = apiCall.some((m: any) => m.truncationId === truncationId2)
+			expect(hasMarker1).toBe(false)
+			expect(hasMarker2).toBe(false)
+		})
+	})
+
+	describe("Checkpoint scenarios", () => {
+		it("should preserve Summary when checkpoint restore is BEFORE condense", async () => {
+			const condenseId = "summary-abc"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "Task" },
+				{ ts: 500, say: "condense_context", contextCondense: { condenseId, summary: "Summary" } },
+				{ ts: 600, say: "checkpoint_saved", text: "checkpoint-hash" },
+				{ ts: 700, say: "user", text: "After checkpoint" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "Task" }] },
+				{
+					ts: 200,
+					role: "assistant",
+					content: [{ type: "text", text: "Response 1" }],
+					condenseParent: condenseId,
+				},
+				{
+					ts: 499,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary" }],
+					isSummary: true,
+					condenseId,
+				},
+				{ ts: 700, role: "user", content: [{ type: "text", text: "After checkpoint" }] },
+			]
+
+			// Restore checkpoint at ts=600 (like checkpoint restore does)
+			await manager.rewindToTimestamp(600, { includeTargetMessage: true })
+
+			// Since condense_context (ts=500) is BEFORE checkpoint, it should be preserved
+			const clineCall = mockTask.overwriteClineMessages.mock.calls[0][0]
+			const hasCondenseContext = clineCall.some((m: any) => m.say === "condense_context")
+			expect(hasCondenseContext).toBe(true)
+
+			// And the Summary should still exist
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasSummary = apiCall.some((m: any) => m.isSummary)
+			expect(hasSummary).toBe(true)
+		})
+
+		it("should remove Summary when checkpoint restore is AFTER condense", async () => {
+			const condenseId = "summary-xyz"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "Task" },
+				{ ts: 200, say: "checkpoint_saved", text: "checkpoint-hash" },
+				{ ts: 300, say: "condense_context", contextCondense: { condenseId, summary: "Summary" } },
+				{ ts: 400, say: "user", text: "After condense" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "Task" }] },
+				{
+					ts: 150,
+					role: "assistant",
+					content: [{ type: "text", text: "Response" }],
+					condenseParent: condenseId,
+				},
+				{
+					ts: 299,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary" }],
+					isSummary: true,
+					condenseId,
+				},
+				{ ts: 400, role: "user", content: [{ type: "text", text: "After condense" }] },
+			]
+
+			// Restore checkpoint at ts=200 (before the condense happened)
+			await manager.rewindToTimestamp(200, { includeTargetMessage: true })
+
+			// condense_context (ts=300) is AFTER checkpoint, so it should be removed
+			const clineCall = mockTask.overwriteClineMessages.mock.calls[0][0]
+			const hasCondenseContext = clineCall.some((m: any) => m.say === "condense_context")
+			expect(hasCondenseContext).toBe(false)
+
+			// And the Summary should be removed too
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasSummary = apiCall.some((m: any) => m.isSummary)
+			expect(hasSummary).toBe(false)
+		})
+
+		it("should preserve truncation marker when checkpoint restore is BEFORE truncation", async () => {
+			const truncationId = "trunc-abc"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "Task" },
+				{ ts: 500, say: "sliding_window_truncation", contextTruncation: { truncationId, reason: "window" } },
+				{ ts: 600, say: "checkpoint_saved", text: "checkpoint-hash" },
+				{ ts: 700, say: "user", text: "After checkpoint" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "Task" }], truncationParent: truncationId },
+				{
+					ts: 499,
+					role: "assistant",
+					content: [{ type: "text", text: "..." }],
+					isTruncationMarker: true,
+					truncationId,
+				},
+				{ ts: 700, role: "user", content: [{ type: "text", text: "After checkpoint" }] },
+			]
+
+			// Restore checkpoint at ts=600
+			await manager.rewindToTimestamp(600, { includeTargetMessage: true })
+
+			// Truncation should be preserved
+			const clineCall = mockTask.overwriteClineMessages.mock.calls[0][0]
+			const hasTruncation = clineCall.some((m: any) => m.say === "sliding_window_truncation")
+			expect(hasTruncation).toBe(true)
+
+			// Marker should still exist
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasMarker = apiCall.some((m: any) => m.isTruncationMarker)
+			expect(hasMarker).toBe(true)
+		})
+
+		it("should remove truncation marker when checkpoint restore is AFTER truncation", async () => {
+			const truncationId = "trunc-xyz"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "Task" },
+				{ ts: 200, say: "checkpoint_saved", text: "checkpoint-hash" },
+				{ ts: 300, say: "sliding_window_truncation", contextTruncation: { truncationId, reason: "window" } },
+				{ ts: 400, say: "user", text: "After truncation" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "Task" }], truncationParent: truncationId },
+				{
+					ts: 299,
+					role: "assistant",
+					content: [{ type: "text", text: "..." }],
+					isTruncationMarker: true,
+					truncationId,
+				},
+				{ ts: 400, role: "user", content: [{ type: "text", text: "After truncation" }] },
+			]
+
+			// Restore checkpoint at ts=200 (before truncation happened)
+			await manager.rewindToTimestamp(200, { includeTargetMessage: true })
+
+			// Truncation should be removed
+			const clineCall = mockTask.overwriteClineMessages.mock.calls[0][0]
+			const hasTruncation = clineCall.some((m: any) => m.say === "sliding_window_truncation")
+			expect(hasTruncation).toBe(false)
+
+			// Marker should be removed
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasMarker = apiCall.some((m: any) => m.isTruncationMarker)
+			expect(hasMarker).toBe(false)
+		})
+	})
+
+	describe("Skip cleanup option", () => {
+		it("should NOT call cleanupAfterTruncation when skipCleanup is true", async () => {
+			const condenseId = "summary-123"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "condense_context", contextCondense: { condenseId, summary: "Summary" } },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{
+					ts: 150,
+					role: "assistant",
+					content: [{ type: "text", text: "Response" }],
+					condenseParent: condenseId,
+				},
+				{
+					ts: 199,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary" }],
+					isSummary: true,
+					condenseId,
+				},
+			]
+
+			// Rewind with skipCleanup
+			await manager.rewindToTimestamp(100, { skipCleanup: true })
+
+			// cleanupAfterTruncation should NOT be called
+			expect(cleanupAfterTruncationSpy).not.toHaveBeenCalled()
+		})
+
+		it("should call cleanupAfterTruncation by default", async () => {
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "user", text: "Second" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{ ts: 200, role: "user", content: [{ type: "text", text: "Second" }] },
+			]
+
+			// Rewind without options (skipCleanup defaults to false)
+			await manager.rewindToTimestamp(100)
+
+			// cleanupAfterTruncation should be called
+			expect(cleanupAfterTruncationSpy).toHaveBeenCalled()
+		})
+
+		it("should call cleanupAfterTruncation when skipCleanup is explicitly false", async () => {
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "user", text: "Second" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{ ts: 200, role: "user", content: [{ type: "text", text: "Second" }] },
+			]
+
+			// Rewind with skipCleanup explicitly false
+			await manager.rewindToTimestamp(100, { skipCleanup: false })
+
+			// cleanupAfterTruncation should be called
+			expect(cleanupAfterTruncationSpy).toHaveBeenCalled()
+		})
+	})
+
+	describe("Combined scenarios", () => {
+		it("should handle both condense and truncation removal in the same rewind", async () => {
+			const condenseId = "summary-123"
+			const truncationId = "trunc-456"
+
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "condense_context", contextCondense: { condenseId, summary: "Summary" } },
+				{ ts: 300, say: "sliding_window_truncation", contextTruncation: { truncationId, reason: "window" } },
+				{ ts: 400, say: "user", text: "After both" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{
+					ts: 199,
+					role: "assistant",
+					content: [{ type: "text", text: "Summary" }],
+					isSummary: true,
+					condenseId,
+				},
+				{
+					ts: 299,
+					role: "assistant",
+					content: [{ type: "text", text: "..." }],
+					isTruncationMarker: true,
+					truncationId,
+				},
+				{ ts: 400, role: "user", content: [{ type: "text", text: "After both" }] },
+			]
+
+			// Rewind to ts=100, which removes both
+			await manager.rewindToTimestamp(100)
+
+			// Both Summary and marker should be removed
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			const hasSummary = apiCall.some((m: any) => m.isSummary)
+			const hasMarker = apiCall.some((m: any) => m.isTruncationMarker)
+			expect(hasSummary).toBe(false)
+			expect(hasMarker).toBe(false)
+		})
+
+		it("should handle empty clineMessages array", async () => {
+			mockTask.clineMessages = []
+			mockTask.apiConversationHistory = []
+
+			await manager.rewindToIndex(0)
+
+			expect(mockTask.overwriteClineMessages).toHaveBeenCalledWith([])
+			// API history write is skipped when nothing changed (optimization)
+			expect(mockTask.overwriteApiConversationHistory).not.toHaveBeenCalled()
+		})
+
+		it("should handle messages without timestamps in API history", async () => {
+			mockTask.clineMessages = [
+				{ ts: 100, say: "user", text: "First" },
+				{ ts: 200, say: "user", text: "Second" },
+			]
+
+			mockTask.apiConversationHistory = [
+				{ role: "system", content: [{ type: "text", text: "System message" }] }, // No ts
+				{ ts: 100, role: "user", content: [{ type: "text", text: "First" }] },
+				{ ts: 200, role: "user", content: [{ type: "text", text: "Second" }] },
+			]
+
+			await manager.rewindToTimestamp(100)
+
+			// Should keep system message (no ts) and message at ts=100
+			const apiCall = mockTask.overwriteApiConversationHistory.mock.calls[0][0]
+			expect(apiCall).toHaveLength(1)
+			expect(apiCall[0].role).toBe("system")
+		})
+	})
+})
diff --git a/src/core/message-manager/index.ts b/src/core/message-manager/index.ts
new file mode 100644
index 00000000000..b78aa95d681
--- /dev/null
+++ b/src/core/message-manager/index.ts
@@ -0,0 +1,185 @@
+import { Task } from "../task/Task"
+import { ClineMessage } from "@roo-code/types"
+import { ApiMessage } from "../task-persistence/apiMessages"
+import { cleanupAfterTruncation } from "../condense"
+
+export interface RewindOptions {
+	/** Whether to include the target message in deletion (edit=true, delete=false) */
+	includeTargetMessage?: boolean
+	/** Skip cleanup for special cases (default: false) */
+	skipCleanup?: boolean
+}
+
+interface ContextEventIds {
+	condenseIds: Set<string>
+	truncationIds: Set<string>
+}
+
+/**
+ * MessageManager provides centralized handling for all conversation rewind operations.
+ *
+ * This ensures that whenever UI chat history is rewound (delete, edit, checkpoint restore, etc.),
+ * the API conversation history is properly maintained, including:
+ * - Removing orphaned Summary messages when their condense_context is removed
+ * - Removing orphaned truncation markers when their sliding_window_truncation is removed
+ * - Cleaning up orphaned condenseParent/truncationParent tags
+ *
+ * Usage (always access via Task.messageManager getter):
+ * ```typescript
+ * await task.messageManager.rewindToTimestamp(messageTs, { includeTargetMessage: false })
+ * ```
+ *
+ * @see Task.messageManager - The getter that provides lazy-initialized access to this manager
+ */
+export class MessageManager {
+	constructor(private task: Task) {}
+
+	/**
+	 * Rewind conversation to a specific timestamp.
+	 * This is the SINGLE entry point for all message deletion operations.
+	 *
+	 * @param ts - The timestamp to rewind to
+	 * @param options - Rewind options
+	 * @throws Error if timestamp not found in clineMessages
+	 */
+	async rewindToTimestamp(ts: number, options: RewindOptions = {}): Promise<void> {
+		const { includeTargetMessage = false, skipCleanup = false } = options
+
+		// Find the index in clineMessages
+		const clineIndex = this.task.clineMessages.findIndex((m) => m.ts === ts)
+		if (clineIndex === -1) {
+			throw new Error(`Message with timestamp ${ts} not found in clineMessages`)
+		}
+
+		// Calculate the actual cutoff index
+		const cutoffIndex = includeTargetMessage ? clineIndex + 1 : clineIndex
+
+		await this.performRewind(cutoffIndex, ts, { skipCleanup })
+	}
+
+	/**
+	 * Rewind conversation to a specific index in clineMessages.
+	 * Keeps messages [0, toIndex) and removes [toIndex, end].
+	 *
+	 * @param toIndex - The index to rewind to (exclusive)
+	 * @param options - Rewind options
+	 */
+	async rewindToIndex(toIndex: number, options: RewindOptions = {}): Promise<void> {
+		const cutoffTs = this.task.clineMessages[toIndex]?.ts ?? Date.now()
+		await this.performRewind(toIndex, cutoffTs, options)
+	}
+
+	/**
+	 * Internal method that performs the actual rewind operation.
+	 */
+	private async performRewind(toIndex: number, cutoffTs: number, options: RewindOptions): Promise<void> {
+		const { skipCleanup = false } = options
+
+		// Step 1: Collect context event IDs from messages being removed
+		const removedIds = this.collectRemovedContextEventIds(toIndex)
+
+		// Step 2: Truncate clineMessages
+		await this.truncateClineMessages(toIndex)
+
+		// Step 3: Truncate and clean API history (combined with cleanup for efficiency)
+		await this.truncateApiHistoryWithCleanup(cutoffTs, removedIds, skipCleanup)
+	}
+
+	/**
+	 * Collect condenseIds and truncationIds from context-management events
+	 * that will be removed during the rewind.
+	 *
+	 * This is critical for maintaining the linkage between:
+	 * - condense_context (clineMessage) ↔ Summary (apiMessage)
+	 * - sliding_window_truncation (clineMessage) ↔ Truncation marker (apiMessage)
+	 */
+	private collectRemovedContextEventIds(fromIndex: number): ContextEventIds {
+		const condenseIds = new Set<string>()
+		const truncationIds = new Set<string>()
+
+		for (let i = fromIndex; i < this.task.clineMessages.length; i++) {
+			const msg = this.task.clineMessages[i]
+
+			// Collect condenseIds from condense_context events
+			if (msg.say === "condense_context" && msg.contextCondense?.condenseId) {
+				condenseIds.add(msg.contextCondense.condenseId)
+				console.log(`[MessageManager] Found condense_context to remove: ${msg.contextCondense.condenseId}`)
+			}
+
+			// Collect truncationIds from sliding_window_truncation events
+			if (msg.say === "sliding_window_truncation" && msg.contextTruncation?.truncationId) {
+				truncationIds.add(msg.contextTruncation.truncationId)
+				console.log(
+					`[MessageManager] Found sliding_window_truncation to remove: ${msg.contextTruncation.truncationId}`,
+				)
+			}
+		}
+
+		return { condenseIds, truncationIds }
+	}
+
+	/**
+	 * Truncate clineMessages to the specified index.
+	 */
+	private async truncateClineMessages(toIndex: number): Promise<void> {
+		await this.task.overwriteClineMessages(this.task.clineMessages.slice(0, toIndex))
+	}
+
+	/**
+	 * Truncate API history by timestamp, remove orphaned summaries/markers,
+	 * and clean up orphaned tags - all in a single write operation.
+	 *
+	 * This combined approach:
+	 * 1. Avoids multiple writes to API history
+	 * 2. Only writes if the history actually changed
+	 * 3. Handles both truncation and cleanup atomically
+	 */
+	private async truncateApiHistoryWithCleanup(
+		cutoffTs: number,
+		removedIds: ContextEventIds,
+		skipCleanup: boolean,
+	): Promise<void> {
+		const originalHistory = this.task.apiConversationHistory
+		let apiHistory = [...originalHistory]
+
+		// Step 1: Filter by timestamp
+		apiHistory = apiHistory.filter((m) => !m.ts || m.ts < cutoffTs)
+
+		// Step 2: Remove Summaries whose condense_context was removed
+		if (removedIds.condenseIds.size > 0) {
+			apiHistory = apiHistory.filter((msg) => {
+				if (msg.isSummary && msg.condenseId && removedIds.condenseIds.has(msg.condenseId)) {
+					console.log(`[MessageManager] Removing orphaned Summary with condenseId: ${msg.condenseId}`)
+					return false
+				}
+				return true
+			})
+		}
+
+		// Step 3: Remove truncation markers whose sliding_window_truncation was removed
+		if (removedIds.truncationIds.size > 0) {
+			apiHistory = apiHistory.filter((msg) => {
+				if (msg.isTruncationMarker && msg.truncationId && removedIds.truncationIds.has(msg.truncationId)) {
+					console.log(
+						`[MessageManager] Removing orphaned truncation marker with truncationId: ${msg.truncationId}`,
+					)
+					return false
+				}
+				return true
+			})
+		}
+
+		// Step 4: Cleanup orphaned tags (unless skipped)
+		if (!skipCleanup) {
+			apiHistory = cleanupAfterTruncation(apiHistory)
+		}
+
+		// Only write if the history actually changed
+		const historyChanged =
+			apiHistory.length !== originalHistory.length || apiHistory.some((msg, i) => msg !== originalHistory[i])
+
+		if (historyChanged) {
+			await this.task.overwriteApiConversationHistory(apiHistory)
+		}
+	}
+}
diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 493263b9d41..fc3184d8255 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -125,6 +125,7 @@ import { processUserContentMentions } from "../mentions/processUserContentMentio
 import { getMessagesSinceLastSummary, summarizeConversation, getEffectiveApiHistory } from "../condense"
 import { MessageQueueService } from "../message-queue/MessageQueueService"
 import { AutoApprovalHandler, checkAutoApproval } from "../auto-approval"
+import { MessageManager } from "../message-manager"
 
 const MAX_EXPONENTIAL_BACKOFF_SECONDS = 600 // 10 minutes
 const DEFAULT_USAGE_COLLECTION_TIMEOUT_MS = 5000 // 5 seconds
@@ -327,6 +328,9 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 	// Initial status for the task's history item (set at creation time to avoid race conditions)
 	private readonly initialStatus?: "active" | "delegated" | "completed"
 
+	// MessageManager for high-level message operations (lazy initialized)
+	private _messageManager?: MessageManager
+
 	constructor({
 		provider,
 		apiConfiguration,
@@ -4032,6 +4036,35 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		return this.workspacePath
 	}
 
+	/**
+	 * Provides convenient access to high-level message operations.
+	 * Uses lazy initialization - the MessageManager is only created when first accessed.
+	 * Subsequent accesses return the same cached instance.
+	 *
+	 * ## Important: Single Coordination Point
+	 *
+	 * **All MessageManager operations must go through this getter** rather than
+	 * instantiating `new MessageManager(task)` directly. This ensures:
+	 * - A single shared instance for consistent behavior
+	 * - Centralized coordination of all rewind/message operations
+	 * - Ability to add internal state or instrumentation in the future
+	 *
+	 * @example
+	 * ```typescript
+	 * // Correct: Use the getter
+	 * await task.messageManager.rewindToTimestamp(ts)
+	 *
+	 * // Incorrect: Do NOT create new instances directly
+	 * // const manager = new MessageManager(task) // Don't do this!
+	 * ```
+	 */
+	get messageManager(): MessageManager {
+		if (!this._messageManager) {
+			this._messageManager = new MessageManager(this)
+		}
+		return this._messageManager
+	}
+
 	/**
 	 * Broadcast browser session updates to the browser panel (if open)
 	 */
diff --git a/src/core/webview/__tests__/ClineProvider.spec.ts b/src/core/webview/__tests__/ClineProvider.spec.ts
index c3a515b9de2..97fbc43f43f 100644
--- a/src/core/webview/__tests__/ClineProvider.spec.ts
+++ b/src/core/webview/__tests__/ClineProvider.spec.ts
@@ -21,6 +21,7 @@ import { Task, TaskOptions } from "../../task/Task"
 import { safeWriteJson } from "../../../utils/safeWriteJson"
 
 import { ClineProvider } from "../ClineProvider"
+import { MessageManager } from "../../message-manager"
 
 // Mock setup must come before imports.
 vi.mock("../../prompts/sections/custom-instructions")
@@ -208,25 +209,21 @@ vi.mock("../../../integrations/workspace/WorkspaceTracker", () => {
 })
 
 vi.mock("../../task/Task", () => ({
-	Task: vi
-		.fn()
-		.mockImplementation(
-			(_provider, _apiConfiguration, _customInstructions, _diffEnabled, _fuzzyMatchThreshold, _task, taskId) => ({
-				api: undefined,
-				abortTask: vi.fn(),
-				handleWebviewAskResponse: vi.fn(),
-				clineMessages: [],
-				apiConversationHistory: [],
-				overwriteClineMessages: vi.fn(),
-				overwriteApiConversationHistory: vi.fn(),
-				getTaskNumber: vi.fn().mockReturnValue(0),
-				setTaskNumber: vi.fn(),
-				setParentTask: vi.fn(),
-				setRootTask: vi.fn(),
-				taskId: taskId || "test-task-id",
-				emit: vi.fn(),
-			}),
-		),
+	Task: vi.fn().mockImplementation((options: any) => ({
+		api: undefined,
+		abortTask: vi.fn(),
+		handleWebviewAskResponse: vi.fn(),
+		clineMessages: [],
+		apiConversationHistory: [],
+		overwriteClineMessages: vi.fn(),
+		overwriteApiConversationHistory: vi.fn(),
+		getTaskNumber: vi.fn().mockReturnValue(0),
+		setTaskNumber: vi.fn(),
+		setParentTask: vi.fn(),
+		setRootTask: vi.fn(),
+		taskId: options?.historyItem?.id || "test-task-id",
+		emit: vi.fn(),
+	})),
 }))
 
 vi.mock("../../../integrations/misc/extract-text", () => ({
@@ -341,6 +338,32 @@ afterAll(() => {
 })
 
 describe("ClineProvider", () => {
+	beforeAll(() => {
+		vi.mocked(Task).mockImplementation((options: any) => {
+			const task: any = {
+				api: undefined,
+				abortTask: vi.fn(),
+				handleWebviewAskResponse: vi.fn(),
+				clineMessages: [],
+				apiConversationHistory: [],
+				overwriteClineMessages: vi.fn(),
+				overwriteApiConversationHistory: vi.fn(),
+				getTaskNumber: vi.fn().mockReturnValue(0),
+				setTaskNumber: vi.fn(),
+				setParentTask: vi.fn(),
+				setRootTask: vi.fn(),
+				taskId: options?.historyItem?.id || "test-task-id",
+				emit: vi.fn(),
+			}
+
+			Object.defineProperty(task, "messageManager", {
+				get: () => new MessageManager(task),
+			})
+
+			return task
+		})
+	})
+
 	let defaultTaskOptions: TaskOptions
 
 	let provider: ClineProvider
diff --git a/src/core/webview/__tests__/webviewMessageHandler.checkpoint.spec.ts b/src/core/webview/__tests__/webviewMessageHandler.checkpoint.spec.ts
index 08e60f3cb1c..a0687d6cc19 100644
--- a/src/core/webview/__tests__/webviewMessageHandler.checkpoint.spec.ts
+++ b/src/core/webview/__tests__/webviewMessageHandler.checkpoint.spec.ts
@@ -2,6 +2,7 @@ import { describe, it, expect, vi, beforeEach } from "vitest"
 import { webviewMessageHandler } from "../webviewMessageHandler"
 import { saveTaskMessages } from "../../task-persistence"
 import { handleCheckpointRestoreOperation } from "../checkpointRestoreHandler"
+import { MessageManager } from "../../message-manager"
 
 // Mock dependencies
 vi.mock("../../task-persistence")
@@ -40,6 +41,7 @@ describe("webviewMessageHandler - checkpoint operations", () => {
 			overwriteClineMessages: vi.fn(),
 			overwriteApiConversationHistory: vi.fn(),
 		}
+		mockCline.messageManager = new MessageManager(mockCline)
 
 		// Setup mock provider
 		mockProvider = {
diff --git a/src/core/webview/__tests__/webviewMessageHandler.delete.spec.ts b/src/core/webview/__tests__/webviewMessageHandler.delete.spec.ts
index 8450ab5d7ab..4d57608e9c7 100644
--- a/src/core/webview/__tests__/webviewMessageHandler.delete.spec.ts
+++ b/src/core/webview/__tests__/webviewMessageHandler.delete.spec.ts
@@ -2,6 +2,7 @@ import { describe, it, expect, beforeEach, vi } from "vitest"
 import { webviewMessageHandler } from "../webviewMessageHandler"
 import * as vscode from "vscode"
 import { ClineProvider } from "../ClineProvider"
+import { MessageManager } from "../../message-manager"
 
 // Mock the saveTaskMessages function
 vi.mock("../../task-persistence", () => ({
@@ -63,6 +64,9 @@ describe("webviewMessageHandler delete functionality", () => {
 			overwriteApiConversationHistory: vi.fn(async () => {}),
 			taskId: "test-task-id",
 		}
+		// Add messageManager using a real MessageManager instance (must be added after object creation
+		// to avoid circular reference issues with 'this')
+		getCurrentTaskMock.messageManager = new MessageManager(getCurrentTaskMock as any)
 
 		// Create mock provider
 		provider = {
@@ -387,8 +391,10 @@ describe("webviewMessageHandler delete functionality", () => {
 				expect(summary1.condenseParent).toBe(condenseId2) // Still tagged
 			})
 
-			it("should prefer non-summary message when timestamps collide for deletion target", async () => {
-				// When multiple messages share the same timestamp, prefer non-summary for targeting
+			it("should use timestamp-based truncation when multiple messages share same timestamp", async () => {
+				// When multiple messages share the same timestamp, timestamp-based truncation
+				// removes ALL messages at or after that timestamp. This is different from
+				// index-based truncation which would preserve earlier array indices.
 				const sharedTs = 1000
 
 				getCurrentTaskMock.clineMessages = [
@@ -405,7 +411,8 @@ describe("webviewMessageHandler delete functionality", () => {
 					{ ts: 1100, role: "assistant", content: "Response" },
 				]
 
-				// Delete at shared timestamp - should target non-summary message (index 2)
+				// Delete at shared timestamp - MessageManager uses ts < cutoffTs, so ALL
+				// messages at ts=1000 are removed (including the Summary)
 				await webviewMessageHandler(provider, {
 					type: "deleteMessageConfirm",
 					messageTs: sharedTs,
@@ -414,12 +421,10 @@ describe("webviewMessageHandler delete functionality", () => {
 				expect(getCurrentTaskMock.overwriteApiConversationHistory).toHaveBeenCalled()
 				const result = getCurrentTaskMock.overwriteApiConversationHistory.mock.calls[0][0]
 
-				// Truncation at index 2 means we keep indices 0-1: previous message and summary
-				expect(result.length).toBe(2)
+				// Timestamp-based truncation keeps only messages with ts < 1000
+				// Both the Summary (ts=1000) and non-summary (ts=1000) are removed
+				expect(result.length).toBe(1)
 				expect(result[0].content).toBe("Previous message")
-				// The summary is kept since it's before truncation point
-				expect(result[1].content).toBe("Summary")
-				expect(result[1].isSummary).toBe(true)
 			})
 
 			it("should remove Summary when its condense_context clineMessage is deleted", async () => {
diff --git a/src/core/webview/__tests__/webviewMessageHandler.edit.spec.ts b/src/core/webview/__tests__/webviewMessageHandler.edit.spec.ts
index d467f5cd92d..dfbce361e45 100644
--- a/src/core/webview/__tests__/webviewMessageHandler.edit.spec.ts
+++ b/src/core/webview/__tests__/webviewMessageHandler.edit.spec.ts
@@ -40,6 +40,7 @@ import { webviewMessageHandler } from "../webviewMessageHandler"
 import type { ClineProvider } from "../ClineProvider"
 import type { ClineMessage } from "@roo-code/types"
 import type { ApiMessage } from "../../task-persistence/apiMessages"
+import { MessageManager } from "../../message-manager"
 
 describe("webviewMessageHandler - Edit Message with Timestamp Fallback", () => {
 	let mockClineProvider: ClineProvider
@@ -57,6 +58,7 @@ describe("webviewMessageHandler - Edit Message with Timestamp Fallback", () => {
 			overwriteApiConversationHistory: vi.fn(),
 			handleWebviewAskResponse: vi.fn(),
 		}
+		mockCurrentTask.messageManager = new MessageManager(mockCurrentTask)
 
 		// Create mock provider
 		mockClineProvider = {
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index c1c8e6aa204..f9bc7a85cda 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -21,7 +21,6 @@ import { TelemetryService } from "@roo-code/telemetry"
 
 import { type ApiMessage } from "../task-persistence/apiMessages"
 import { saveTaskMessages } from "../task-persistence"
-import { cleanupAfterTruncation } from "../condense"
 
 import { ClineProvider } from "./ClineProvider"
 import { BrowserSessionPanelManager } from "./BrowserSessionPanelManager"
@@ -111,85 +110,6 @@ export const webviewMessageHandler = async (
 		)
 	}
 
-	/**
-	 * Removes the target message and all subsequent messages.
-	 * After truncation, cleans up orphaned condenseParent and truncationParent references for any
-	 * summaries or truncation markers that were removed by the truncation.
-	 *
-	 * Design: Rewind/delete operations preserve earlier condense and truncation states.
-	 * Only summaries and truncation markers that are removed by the truncation (i.e., were created
-	 * after the rewind point) have their associated tags cleared.
-	 * This allows nested condensing and multiple truncations to work correctly - rewinding past the
-	 * second condense restores visibility of messages condensed by it, while keeping the first condense intact.
-	 * Same applies to truncation markers.
-	 */
-	const removeMessagesThisAndSubsequent = async (
-		currentCline: any,
-		messageIndex: number,
-		apiConversationHistoryIndex: number,
-	) => {
-		// Step 1: Collect condenseIds from condense_context messages being removed.
-		// These IDs link clineMessages to their corresponding Summaries in apiConversationHistory.
-		const removedCondenseIds = new Set<string>()
-		// Step 1b: Collect truncationIds from sliding_window_truncation messages being removed.
-		// These IDs link clineMessages to their corresponding truncation markers in apiConversationHistory.
-		const removedTruncationIds = new Set<string>()
-
-		for (let i = messageIndex; i < currentCline.clineMessages.length; i++) {
-			const msg = currentCline.clineMessages[i]
-			if (msg.say === "condense_context" && msg.contextCondense?.condenseId) {
-				removedCondenseIds.add(msg.contextCondense.condenseId)
-			}
-			if (msg.say === "sliding_window_truncation" && msg.contextTruncation?.truncationId) {
-				removedTruncationIds.add(msg.contextTruncation.truncationId)
-			}
-		}
-
-		// Step 2: Delete this message and all that follow
-		await currentCline.overwriteClineMessages(currentCline.clineMessages.slice(0, messageIndex))
-
-		if (apiConversationHistoryIndex !== -1) {
-			// Step 3: Truncate API history by timestamp/index
-			let truncatedApiHistory = currentCline.apiConversationHistory.slice(0, apiConversationHistoryIndex)
-
-			// Step 4: Remove Summaries whose condenseId was in a removed condense_context message.
-			// This handles the case where Summary.ts < truncation point but condense_context.ts > truncation point.
-			// Without this, the Summary would survive truncation but its corresponding UI event would be gone.
-			if (removedCondenseIds.size > 0) {
-				truncatedApiHistory = truncatedApiHistory.filter((msg: ApiMessage) => {
-					if (msg.isSummary && msg.condenseId && removedCondenseIds.has(msg.condenseId)) {
-						console.log(
-							`[removeMessagesThisAndSubsequent] Removing orphaned Summary with condenseId=${msg.condenseId}`,
-						)
-						return false
-					}
-					return true
-				})
-			}
-
-			// Step 4b: Remove truncation markers whose truncationId was in a removed sliding_window_truncation message.
-			// Same logic as condense - without this, the marker would survive but its UI event would be gone.
-			if (removedTruncationIds.size > 0) {
-				truncatedApiHistory = truncatedApiHistory.filter((msg: ApiMessage) => {
-					if (msg.isTruncationMarker && msg.truncationId && removedTruncationIds.has(msg.truncationId)) {
-						console.log(
-							`[removeMessagesThisAndSubsequent] Removing orphaned truncation marker with truncationId=${msg.truncationId}`,
-						)
-						return false
-					}
-					return true
-				})
-			}
-
-			// Step 5: Clean up orphaned condenseParent and truncationParent references for messages whose
-			// summary or truncation marker was removed by the truncation. Summaries, truncation markers, and messages
-			// from earlier condense/truncation operations are preserved.
-			const cleanedApiHistory = cleanupAfterTruncation(truncatedApiHistory)
-
-			await currentCline.overwriteApiConversationHistory(cleanedApiHistory)
-		}
-	}
-
 	/**
 	 * Handles message deletion operations with user confirmation
 	 */
@@ -281,8 +201,8 @@ export const webviewMessageHandler = async (
 					}
 				}
 
-				// Delete this message and all subsequent messages
-				await removeMessagesThisAndSubsequent(currentCline, messageIndex, apiIndexToUse)
+				// Delete this message and all subsequent messages using MessageManager
+				await currentCline.messageManager.rewindToTimestamp(targetMessage.ts!, { includeTargetMessage: false })
 
 				// Restore checkpoint associations for preserved messages
 				for (const [ts, checkpoint] of preservedCheckpoints) {
@@ -448,8 +368,11 @@ export const webviewMessageHandler = async (
 				}
 			}
 
-			// Delete the original (user) message and all subsequent messages
-			await removeMessagesThisAndSubsequent(currentCline, deleteFromMessageIndex, deleteFromApiIndex)
+			// Delete the original (user) message and all subsequent messages using MessageManager
+			const rewindTs = currentCline.clineMessages[deleteFromMessageIndex]?.ts
+			if (rewindTs) {
+				await currentCline.messageManager.rewindToTimestamp(rewindTs, { includeTargetMessage: false })
+			}
 
 			// Restore checkpoint associations for preserved messages
 			for (const [ts, checkpoint] of preservedCheckpoints) {