diff --git a/packages/types/src/experiment.ts b/packages/types/src/experiment.ts
index 10384db8ed..b455a170b7 100644
--- a/packages/types/src/experiment.ts
+++ b/packages/types/src/experiment.ts
@@ -6,7 +6,7 @@ import type { Keys, Equals, AssertEqual } from "./type-fu.js"
  * ExperimentId
  */
 
-export const experimentIds = ["powerSteering", "multiFileApplyDiff"] as const
+export const experimentIds = ["powerSteering", "multiFileApplyDiff", "readFileDeduplication"] as const
 
 export const experimentIdsSchema = z.enum(experimentIds)
 
@@ -19,6 +19,7 @@ export type ExperimentId = z.infer<typeof experimentIdsSchema>
 export const experimentsSchema = z.object({
 	powerSteering: z.boolean().optional(),
 	multiFileApplyDiff: z.boolean().optional(),
+	readFileDeduplication: z.boolean().optional(),
 })
 
 export type Experiments = z.infer<typeof experimentsSchema>
diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index fe8fd0f68f..a5b0632100 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -353,6 +353,100 @@ export class Task extends EventEmitter<ClineEvents> {
 		}
 	}
 
+	public async deduplicateReadFileHistory(): Promise<void> {
+		// Check if the experimental feature is enabled
+		const state = await this.providerRef.deref()?.getState()
+		const isDeduplicationEnabled = experiments.isEnabled(
+			state?.experiments ?? {},
+			EXPERIMENT_IDS.READ_FILE_DEDUPLICATION,
+		)
+
+		if (!isDeduplicationEnabled) {
+			return
+		}
+
+		// Track which files have been seen (most recent occurrence)
+		const seenFiles = new Set<string>()
+		const cacheWindowMs = 5 * 60 * 1000 // 5 minutes
+		const now = Date.now()
+
+		// Iterate through conversation history in reverse order (newest to oldest)
+		for (let i = this.apiConversationHistory.length - 1; i >= 0; i--) {
+			const message = this.apiConversationHistory[i]
+
+			// Skip if message is within cache window
+			if (message.ts && now - message.ts < cacheWindowMs) {
+				continue
+			}
+
+			// Only process user messages
+			if (message.role !== "user") {
+				continue
+			}
+
+			// Process content blocks
+			if (Array.isArray(message.content)) {
+				const newContent = message.content.filter((block) => {
+					if (block.type !== "text") {
+						return true // Keep non-text blocks
+					}
+
+					// Check if this is a read_file result
+					const readFileMatch = block.text.match(/^\[read_file.*?\] Result:/)
+					if (!readFileMatch) {
+						return true // Keep non-read_file blocks
+					}
+
+					// Extract file paths from the read_file result
+					// Handle both single file and multi-file formats
+					const filePaths: string[] = []
+
+					// Try to match file paths in XML format
+					const filePathMatches = block.text.matchAll(/<file><path>([^<]+)<\/path>/g)
+					for (const match of filePathMatches) {
+						filePaths.push(match[1])
+					}
+
+					// If no paths found in XML, try legacy format
+					if (filePaths.length === 0) {
+						const legacyMatch = block.text.match(/\[read_file for '([^']+)'/)
+						if (legacyMatch) {
+							filePaths.push(legacyMatch[1])
+						}
+					}
+
+					// Check if all files in this result have been seen more recently
+					if (filePaths.length > 0) {
+						const allFilesSeen = filePaths.every((path) => seenFiles.has(path))
+
+						if (allFilesSeen) {
+							// Remove this duplicate read_file result
+							return false
+						} else {
+							// Mark these files as seen
+							filePaths.forEach((path) => seenFiles.add(path))
+							return true
+						}
+					}
+
+					// Keep blocks we couldn't parse
+					return true
+				})
+
+				// Update message content if any blocks were removed
+				if (newContent.length !== message.content.length) {
+					this.apiConversationHistory[i] = {
+						...message,
+						content: newContent,
+					}
+				}
+			}
+		}
+
+		// Save the updated conversation history
+		await this.saveApiConversationHistory()
+	}
+
 	// Cline Messages
 
 	private async getSavedClineMessages(): Promise<ClineMessage[]> {
diff --git a/src/core/task/__tests__/Task.spec.ts b/src/core/task/__tests__/Task.spec.ts
index 9aa5a8d7a8..28e442bd24 100644
--- a/src/core/task/__tests__/Task.spec.ts
+++ b/src/core/task/__tests__/Task.spec.ts
@@ -1493,5 +1493,331 @@ describe("Cline", () => {
 				expect(noModelTask.apiConfiguration.apiProvider).toBe("openai")
 			})
 		})
+
+		describe("deduplicateReadFileHistory", () => {
+			let mockProvider: any
+			let mockApiConfig: any
+
+			beforeEach(() => {
+				vi.clearAllMocks()
+
+				mockApiConfig = {
+					apiProvider: "anthropic",
+					apiKey: "test-key",
+				}
+
+				mockProvider = {
+					context: {
+						globalStorageUri: { fsPath: "/test/storage" },
+					},
+					getState: vi.fn(),
+					postStateToWebview: vi.fn().mockResolvedValue(undefined),
+					postMessageToWebview: vi.fn().mockResolvedValue(undefined),
+					updateTaskHistory: vi.fn().mockResolvedValue(undefined),
+				}
+			})
+
+			it("should not deduplicate when feature is disabled", async () => {
+				mockProvider.getState.mockResolvedValue({
+					experiments: {
+						[EXPERIMENT_IDS.READ_FILE_DEDUPLICATION]: false,
+					},
+				})
+
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					startTask: false,
+				})
+
+				// Add duplicate read_file results
+				task.apiConversationHistory = [
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file for 'test.ts'] Result:\n<files><file><path>test.ts</path><content>content1</content></file></files>",
+							},
+						],
+						ts: Date.now() - 10 * 60 * 1000, // 10 minutes ago
+					},
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file for 'test.ts'] Result:\n<files><file><path>test.ts</path><content>content2</content></file></files>",
+							},
+						],
+						ts: Date.now() - 8 * 60 * 1000, // 8 minutes ago
+					},
+				]
+
+				const originalLength = task.apiConversationHistory.length
+
+				await task.deduplicateReadFileHistory()
+
+				// Should not remove anything when feature is disabled
+				expect(task.apiConversationHistory.length).toBe(originalLength)
+			})
+
+			it("should deduplicate when feature is enabled", async () => {
+				mockProvider.getState.mockResolvedValue({
+					experiments: {
+						[EXPERIMENT_IDS.READ_FILE_DEDUPLICATION]: true,
+					},
+				})
+
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					startTask: false,
+				})
+
+				// Add duplicate read_file results
+				task.apiConversationHistory = [
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file for 'test.ts'] Result:\n<files><file><path>test.ts</path><content>content1</content></file></files>",
+							},
+						],
+						ts: Date.now() - 10 * 60 * 1000, // 10 minutes ago
+					},
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file for 'test.ts'] Result:\n<files><file><path>test.ts</path><content>content2</content></file></files>",
+							},
+						],
+						ts: Date.now() - 8 * 60 * 1000, // 8 minutes ago
+					},
+				]
+
+				await task.deduplicateReadFileHistory()
+
+				// Should keep only the most recent read_file result
+				expect(task.apiConversationHistory.length).toBe(2)
+				expect(task.apiConversationHistory[0].content).toHaveLength(0) // First one should be empty
+				expect(task.apiConversationHistory[1].content).toHaveLength(1) // Second one should remain
+			})
+
+			it("should not deduplicate messages within cache window", async () => {
+				mockProvider.getState.mockResolvedValue({
+					experiments: {
+						[EXPERIMENT_IDS.READ_FILE_DEDUPLICATION]: true,
+					},
+				})
+
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					startTask: false,
+				})
+
+				const now = Date.now()
+
+				// Add duplicate read_file results
+				task.apiConversationHistory = [
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file for 'test.ts'] Result:\n<files><file><path>test.ts</path><content>content1</content></file></files>",
+							},
+						],
+						ts: now - 10 * 60 * 1000, // 10 minutes ago (outside cache window)
+					},
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file for 'test.ts'] Result:\n<files><file><path>test.ts</path><content>content2</content></file></files>",
+							},
+						],
+						ts: now - 2 * 60 * 1000, // 2 minutes ago (inside cache window)
+					},
+				]
+
+				await task.deduplicateReadFileHistory()
+
+				// Both should remain because the second one is within cache window
+				expect(task.apiConversationHistory.length).toBe(2)
+				expect(task.apiConversationHistory[0].content).toHaveLength(1)
+				expect(task.apiConversationHistory[1].content).toHaveLength(1)
+			})
+
+			it("should handle multi-file read_file results", async () => {
+				mockProvider.getState.mockResolvedValue({
+					experiments: {
+						[EXPERIMENT_IDS.READ_FILE_DEDUPLICATION]: true,
+					},
+				})
+
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					startTask: false,
+				})
+
+				// Add multi-file read_file results
+				task.apiConversationHistory = [
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file] Result:\n<files><file><path>a.ts</path></file><file><path>b.ts</path></file></files>",
+							},
+						],
+						ts: Date.now() - 10 * 60 * 1000,
+					},
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file] Result:\n<files><file><path>a.ts</path></file></files>",
+							},
+						],
+						ts: Date.now() - 8 * 60 * 1000,
+					},
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file] Result:\n<files><file><path>b.ts</path></file><file><path>c.ts</path></file></files>",
+							},
+						],
+						ts: Date.now() - 6 * 60 * 1000,
+					},
+				]
+
+				await task.deduplicateReadFileHistory()
+
+				// First result should be removed (both a.ts and b.ts have been read more recently)
+				expect(task.apiConversationHistory[0].content).toHaveLength(0)
+				// Second result should remain (most recent read of a.ts)
+				expect(task.apiConversationHistory[1].content).toHaveLength(1)
+				// Third result should remain (most recent read of b.ts and c.ts)
+				expect(task.apiConversationHistory[2].content).toHaveLength(1)
+			})
+
+			it("should preserve non-read_file content blocks", async () => {
+				mockProvider.getState.mockResolvedValue({
+					experiments: {
+						[EXPERIMENT_IDS.READ_FILE_DEDUPLICATION]: true,
+					},
+				})
+
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					startTask: false,
+				})
+
+				// Add mixed content
+				task.apiConversationHistory = [
+					{
+						role: "user",
+						content: [
+							{ type: "text", text: "Regular user message" },
+							{
+								type: "text",
+								text: "[read_file for 'test.ts'] Result:\n<files><file><path>test.ts</path></file></files>",
+							},
+							{ type: "image", source: { type: "base64", media_type: "image/png", data: "base64data" } },
+						],
+						ts: Date.now() - 10 * 60 * 1000,
+					},
+					{
+						role: "assistant",
+						content: [{ type: "text", text: "Assistant response" }],
+						ts: Date.now() - 9 * 60 * 1000,
+					},
+					{
+						role: "user",
+						content: [
+							{
+								type: "text",
+								text: "[read_file for 'test.ts'] Result:\n<files><file><path>test.ts</path></file></files>",
+							},
+						],
+						ts: Date.now() - 8 * 60 * 1000,
+					},
+				]
+
+				await task.deduplicateReadFileHistory()
+
+				// First message should have read_file removed but other content preserved
+				expect(task.apiConversationHistory[0].content).toHaveLength(2)
+				const content0 = task.apiConversationHistory[0].content[0]
+				const content1 = task.apiConversationHistory[0].content[1]
+				expect(typeof content0 === "object" && content0 !== null && "type" in content0 && content0.type).toBe(
+					"text",
+				)
+				expect(typeof content0 === "object" && content0 !== null && "text" in content0 && content0.text).toBe(
+					"Regular user message",
+				)
+				expect(typeof content1 === "object" && content1 !== null && "type" in content1 && content1.type).toBe(
+					"image",
+				)
+
+				// Assistant message should remain unchanged
+				expect(task.apiConversationHistory[1].content).toHaveLength(1)
+
+				// Last read_file should remain
+				expect(task.apiConversationHistory[2].content).toHaveLength(1)
+			})
+
+			it("should handle legacy single-file format", async () => {
+				mockProvider.getState.mockResolvedValue({
+					experiments: {
+						[EXPERIMENT_IDS.READ_FILE_DEDUPLICATION]: true,
+					},
+				})
+
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					startTask: false,
+				})
+
+				// Add legacy format read_file results
+				task.apiConversationHistory = [
+					{
+						role: "user",
+						content: [{ type: "text", text: "[read_file for 'test.ts'] Result:\nFile content here" }],
+						ts: Date.now() - 10 * 60 * 1000,
+					},
+					{
+						role: "user",
+						content: [{ type: "text", text: "[read_file for 'test.ts'] Result:\nUpdated file content" }],
+						ts: Date.now() - 8 * 60 * 1000,
+					},
+				]
+
+				await task.deduplicateReadFileHistory()
+
+				// First one should be removed
+				expect(task.apiConversationHistory[0].content).toHaveLength(0)
+				// Second one should remain
+				expect(task.apiConversationHistory[1].content).toHaveLength(1)
+			})
+		})
 	})
 })
diff --git a/src/core/tools/readFileTool.ts b/src/core/tools/readFileTool.ts
index 6de8dd5642..4d6162abd6 100644
--- a/src/core/tools/readFileTool.ts
+++ b/src/core/tools/readFileTool.ts
@@ -609,5 +609,8 @@ export async function readFileTool(
 		const xmlResults = fileResults.filter((result) => result.xmlContent).map((result) => result.xmlContent)
 
 		pushToolResult(`<files>\n${xmlResults.join("\n")}\n</files>`)
+
+		// Deduplicate read_file history after successful reads
+		await cline.deduplicateReadFileHistory()
 	}
 }
diff --git a/src/shared/experiments.ts b/src/shared/experiments.ts
index 1edadf654f..f5f490c228 100644
--- a/src/shared/experiments.ts
+++ b/src/shared/experiments.ts
@@ -3,6 +3,7 @@ import type { AssertEqual, Equals, Keys, Values, ExperimentId, Experiments } fro
 export const EXPERIMENT_IDS = {
 	MULTI_FILE_APPLY_DIFF: "multiFileApplyDiff",
 	POWER_STEERING: "powerSteering",
+	READ_FILE_DEDUPLICATION: "readFileDeduplication",
 } as const satisfies Record<string, ExperimentId>
 
 type _AssertExperimentIds = AssertEqual<Equals<ExperimentId, Values<typeof EXPERIMENT_IDS>>>
@@ -16,6 +17,7 @@ interface ExperimentConfig {
 export const experimentConfigsMap: Record<ExperimentKey, ExperimentConfig> = {
 	MULTI_FILE_APPLY_DIFF: { enabled: false },
 	POWER_STEERING: { enabled: false },
+	READ_FILE_DEDUPLICATION: { enabled: false },
 }
 
 export const experimentDefault = Object.fromEntries(
diff --git a/webview-ui/src/context/__tests__/ExtensionStateContext.spec.tsx b/webview-ui/src/context/__tests__/ExtensionStateContext.spec.tsx
index 1e5867d3fc..f89bf2c4c1 100644
--- a/webview-ui/src/context/__tests__/ExtensionStateContext.spec.tsx
+++ b/webview-ui/src/context/__tests__/ExtensionStateContext.spec.tsx
@@ -222,10 +222,8 @@ describe("mergeExtensionState", () => {
 			apiConfiguration: { modelMaxThinkingTokens: 456, modelTemperature: 0.3 },
 			experiments: {
 				powerSteering: true,
-				marketplace: false,
-				disableCompletionCommand: false,
-				concurrentFileReads: true,
 				multiFileApplyDiff: true,
+				readFileDeduplication: false,
 			} as Record<ExperimentId, boolean>,
 		}