fix: make initial prompt preservation conditional on power-steering feature

- Add powerSteeringEnabled parameter to summarizeConversation function
- Check power steering experiment flag before preserving first message
- Update all callers to pass power steering state
- Update tests to handle new parameter

This prevents tasks from being restarted unnecessarily after context
condensing when power steering is disabled.

Fixes #8093

src/core/condense/__tests__/condense.spec.ts

@@ -72,7 +72,17 @@ describe("Condense", () => {
 				{ role: "user", content: "Ninth message" },
 			]
 
-			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+			const result = await summarizeConversation(
+				messages,
+				mockApiHandler,
+				"System prompt",
+				taskId,
+				5000,
+				false,
+				undefined,
+				undefined,
+				true,
+			) // powerSteeringEnabled = true to preserve first message
 
 			// Verify the first message is preserved
 			expect(result.messages[0]).toEqual(messages[0])
@@ -106,7 +116,17 @@ describe("Condense", () => {
 				{ role: "user", content: "Thanks!" },
 			]
 
-			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+			const result = await summarizeConversation(
+				messages,
+				mockApiHandler,
+				"System prompt",
+				taskId,
+				5000,
+				false,
+				undefined,
+				undefined,
+				true,
+			) // powerSteeringEnabled = true to preserve first message
 
 			// The first message with slash command should be intact
 			expect(result.messages[0].content).toBe(slashCommandContent)
@@ -131,7 +151,17 @@ describe("Condense", () => {
 				{ role: "user", content: "Perfect!" },
 			]
 
-			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+			const result = await summarizeConversation(
+				messages,
+				mockApiHandler,
+				"System prompt",
+				taskId,
+				5000,
+				false,
+				undefined,
+				undefined,
+				true,
+			) // powerSteeringEnabled = true to preserve first message
 
 			// The first message with complex content should be preserved
 			expect(result.messages[0].content).toEqual(complexContent)
@@ -146,7 +176,17 @@ describe("Condense", () => {
 				{ role: "assistant", content: "Fourth message" },
 			]
 
-			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+			const result = await summarizeConversation(
+				messages,
+				mockApiHandler,
+				"System prompt",
+				taskId,
+				5000,
+				false,
+				undefined,
+				undefined,
+				false,
+			)
 
 			// Should return an error since we have only 4 messages (first + 3 to keep)
 			expect(result.error).toBeDefined()
@@ -165,7 +205,17 @@ describe("Condense", () => {
 				{ role: "user", content: "Final message" },
 			]
 
-			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+			const result = await summarizeConversation(
+				messages,
+				mockApiHandler,
+				"System prompt",
+				taskId,
+				5000,
+				false,
+				undefined,
+				undefined,
+				false,
+			)
 
 			// Should return an error due to recent summary in last N messages
 			expect(result.error).toBeDefined()
@@ -198,7 +248,17 @@ describe("Condense", () => {
 				{ role: "user", content: "Seventh" },
 			]
 
-			const result = await summarizeConversation(messages, emptyHandler, "System prompt", taskId, 5000, false)
+			const result = await summarizeConversation(
+				messages,
+				emptyHandler,
+				"System prompt",
+				taskId,
+				5000,
+				false,
+				undefined,
+				undefined,
+				false,
+			)
 
 			expect(result.error).toBeDefined()
 			expect(result.messages).toEqual(messages)

src/core/condense/__tests__/index.spec.ts

@@ -129,6 +129,10 @@ describe("summarizeConversation", () => {
 			defaultSystemPrompt,
 			taskId,
 			DEFAULT_PREV_CONTEXT_TOKENS,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 		expect(result.messages).toEqual(messages)
 		expect(result.cost).toBe(0)
@@ -155,6 +159,10 @@ describe("summarizeConversation", () => {
 			defaultSystemPrompt,
 			taskId,
 			DEFAULT_PREV_CONTEXT_TOKENS,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 		expect(result.messages).toEqual(messages)
 		expect(result.cost).toBe(0)
@@ -181,6 +189,10 @@ describe("summarizeConversation", () => {
 			defaultSystemPrompt,
 			taskId,
 			DEFAULT_PREV_CONTEXT_TOKENS,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Check that the API was called correctly
@@ -188,14 +200,11 @@ describe("summarizeConversation", () => {
 		expect(maybeRemoveImageBlocks).toHaveBeenCalled()
 
 		// Verify the structure of the result
-		// The result should be: first message + summary + last N messages
-		expect(result.messages.length).toBe(1 + 1 + N_MESSAGES_TO_KEEP) // First + summary + last N
-
-		// Check that the first message is preserved
-		expect(result.messages[0]).toEqual(messages[0])
+		// When powerSteeringEnabled is false, the result should be: summary + last N messages
+		expect(result.messages.length).toBe(1 + N_MESSAGES_TO_KEEP) // summary + last N
 
 		// Check that the summary message was inserted correctly
-		const summaryMessage = result.messages[1]
+		const summaryMessage = result.messages[0]
 		expect(summaryMessage.role).toBe("assistant")
 		expect(summaryMessage.content).toBe("This is a summary")
 		expect(summaryMessage.isSummary).toBe(true)
@@ -244,6 +253,10 @@ describe("summarizeConversation", () => {
 			defaultSystemPrompt,
 			taskId,
 			DEFAULT_PREV_CONTEXT_TOKENS,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Should return original messages when summary is empty
@@ -265,7 +278,17 @@ describe("summarizeConversation", () => {
 			{ role: "user", content: "Tell me more", ts: 7 },
 		]
 
-		await summarizeConversation(messages, mockApiHandler, defaultSystemPrompt, taskId, DEFAULT_PREV_CONTEXT_TOKENS)
+		await summarizeConversation(
+			messages,
+			mockApiHandler,
+			defaultSystemPrompt,
+			taskId,
+			DEFAULT_PREV_CONTEXT_TOKENS,
+			false,
+			undefined,
+			undefined,
+			false,
+		)
 
 		// Verify the final request message
 		const expectedFinalMessage = {
@@ -312,6 +335,10 @@ describe("summarizeConversation", () => {
 			systemPrompt,
 			taskId,
 			DEFAULT_PREV_CONTEXT_TOKENS,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify that countTokens was called with the correct messages including system prompt
@@ -355,6 +382,10 @@ describe("summarizeConversation", () => {
 			defaultSystemPrompt,
 			taskId,
 			prevContextTokens,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Should return original messages when context would grow
@@ -395,11 +426,15 @@ describe("summarizeConversation", () => {
 			defaultSystemPrompt,
 			taskId,
 			prevContextTokens,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Should successfully summarize
-		// Result should be: first message + summary + last N messages
-		expect(result.messages.length).toBe(1 + 1 + N_MESSAGES_TO_KEEP) // First + summary + last N
+		// When powerSteeringEnabled is false, the result should be: summary + last N messages
+		expect(result.messages.length).toBe(1 + N_MESSAGES_TO_KEEP) // summary + last N
 		expect(result.cost).toBe(0.03)
 		expect(result.summary).toBe("Concise summary")
 		expect(result.error).toBeUndefined()
@@ -416,6 +451,10 @@ describe("summarizeConversation", () => {
 			defaultSystemPrompt,
 			taskId,
 			DEFAULT_PREV_CONTEXT_TOKENS,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Should return original messages when not enough to summarize
@@ -444,6 +483,10 @@ describe("summarizeConversation", () => {
 			defaultSystemPrompt,
 			taskId,
 			DEFAULT_PREV_CONTEXT_TOKENS,
+			false,
+			undefined,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Should return original messages when recent summary exists
@@ -493,6 +536,7 @@ describe("summarizeConversation", () => {
 			false,
 			undefined,
 			invalidCondensingHandler,
+			false, // powerSteeringEnabled
 		)
 
 		// Should return original messages when both handlers are invalid
@@ -601,6 +645,8 @@ describe("summarizeConversation with custom settings", () => {
 			DEFAULT_PREV_CONTEXT_TOKENS,
 			false,
 			customPrompt,
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify the custom prompt was used
@@ -622,6 +668,8 @@ describe("summarizeConversation with custom settings", () => {
 			DEFAULT_PREV_CONTEXT_TOKENS,
 			false,
 			"  ", // Empty custom prompt
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify the default prompt was used
@@ -639,6 +687,8 @@ describe("summarizeConversation with custom settings", () => {
 			DEFAULT_PREV_CONTEXT_TOKENS,
 			false,
 			undefined, // No custom prompt
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify the default prompt was used again
@@ -660,6 +710,7 @@ describe("summarizeConversation with custom settings", () => {
 			false,
 			undefined,
 			mockCondensingApiHandler,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify the condensing handler was used
@@ -680,6 +731,7 @@ describe("summarizeConversation with custom settings", () => {
 			false,
 			undefined,
 			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify the main handler was used
@@ -711,6 +763,7 @@ describe("summarizeConversation with custom settings", () => {
 			false,
 			undefined,
 			invalidHandler,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify the main handler was used as fallback
@@ -737,6 +790,8 @@ describe("summarizeConversation with custom settings", () => {
 			DEFAULT_PREV_CONTEXT_TOKENS,
 			false,
 			"Custom prompt",
+			undefined,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify telemetry was called with custom prompt flag
@@ -761,6 +816,7 @@ describe("summarizeConversation with custom settings", () => {
 			false,
 			undefined,
 			mockCondensingApiHandler,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify telemetry was called with custom API handler flag
@@ -785,6 +841,7 @@ describe("summarizeConversation with custom settings", () => {
 			true, // isAutomaticTrigger
 			"Custom prompt",
 			mockCondensingApiHandler,
+			false, // powerSteeringEnabled
 		)
 
 		// Verify telemetry was called with both flags

src/core/condense/index.ts

@@ -80,6 +80,7 @@ export type SummarizeResponse = {
  * @param {boolean} isAutomaticTrigger - Whether the summarization is triggered automatically
  * @param {string} customCondensingPrompt - Optional custom prompt to use for condensing
  * @param {ApiHandler} condensingApiHandler - Optional specific API handler to use for condensing
+ * @param {boolean} powerSteeringEnabled - Whether power steering is enabled (controls initial prompt preservation)
  * @returns {SummarizeResponse} - The result of the summarization operation (see above)
  */
 export async function summarizeConversation(
@@ -91,6 +92,7 @@ export async function summarizeConversation(
 	isAutomaticTrigger?: boolean,
 	customCondensingPrompt?: string,
 	condensingApiHandler?: ApiHandler,
+	powerSteeringEnabled?: boolean,
 ): Promise<SummarizeResponse> {
 	TelemetryService.instance.captureContextCondensed(
 		taskId,
@@ -101,10 +103,14 @@ export async function summarizeConversation(
 
 	const response: SummarizeResponse = { messages, cost: 0, summary: "" }
 
-	// Always preserve the first message (which may contain slash command content)
-	const firstMessage = messages[0]
-	// Get messages to summarize, excluding the first message and last N messages
-	const messagesToSummarize = getMessagesSinceLastSummary(messages.slice(1, -N_MESSAGES_TO_KEEP))
+	// Conditionally preserve the first message based on power steering setting
+	// When power steering is enabled, preserve the initial prompt to maintain task context
+	// When disabled, don't preserve it to prevent task restarts after condensing
+	const firstMessage = powerSteeringEnabled ? messages[0] : undefined
+	const messagesToKeepFrom = powerSteeringEnabled ? 1 : 0
+
+	// Get messages to summarize, excluding the conditionally preserved first message and last N messages
+	const messagesToSummarize = getMessagesSinceLastSummary(messages.slice(messagesToKeepFrom, -N_MESSAGES_TO_KEEP))
 
 	if (messagesToSummarize.length <= 1) {
 		const error =
@@ -188,8 +194,10 @@ export async function summarizeConversation(
 		isSummary: true,
 	}
 
-	// Reconstruct messages: [first message, summary, last N messages]
-	const newMessages = [firstMessage, summaryMessage, ...keepMessages]
+	// Reconstruct messages: [first message (if power steering enabled), summary, last N messages]
+	const newMessages = firstMessage
+		? [firstMessage, summaryMessage, ...keepMessages]
+		: [summaryMessage, ...keepMessages]
 
 	// Count the tokens in the context for the next API request
 	// We only estimate the tokens in summaryMesage if outputTokens is 0, otherwise we use outputTokens

src/core/sliding-window/__tests__/sliding-window.spec.ts

@@ -594,6 +594,7 @@ describe("Sliding Window", () => {
 				true,
 				undefined, // customCondensingPrompt
 				undefined, // condensingApiHandler
+				undefined, // powerSteeringEnabled
 			)
 
 			// Verify the result contains the summary information
@@ -765,6 +766,7 @@ describe("Sliding Window", () => {
 				true,
 				undefined, // customCondensingPrompt
 				undefined, // condensingApiHandler
+				undefined, // powerSteeringEnabled
 			)
 
 			// Verify the result contains the summary information

src/core/sliding-window/index.ts

@@ -6,6 +6,7 @@ import { ApiHandler } from "../../api"
 import { MAX_CONDENSE_THRESHOLD, MIN_CONDENSE_THRESHOLD, summarizeConversation, SummarizeResponse } from "../condense"
 import { ApiMessage } from "../task-persistence/apiMessages"
 import { ANTHROPIC_DEFAULT_MAX_TOKENS } from "@roo-code/types"
+import { experiments, EXPERIMENT_IDS } from "../../shared/experiments"
 
 /**
  * Default percentage of the context window to use as a buffer when deciding when to truncate
@@ -77,6 +78,7 @@ type TruncateOptions = {
 	condensingApiHandler?: ApiHandler
 	profileThresholds: Record<string, number>
 	currentProfileId: string
+	powerSteeringEnabled?: boolean
 }
 
 type TruncateResponse = SummarizeResponse & { prevContextTokens: number }
@@ -102,6 +104,7 @@ export async function truncateConversationIfNeeded({
 	condensingApiHandler,
 	profileThresholds,
 	currentProfileId,
+	powerSteeringEnabled,
 }: TruncateOptions): Promise<TruncateResponse> {
 	let error: string | undefined
 	let cost = 0
@@ -155,6 +158,7 @@ export async function truncateConversationIfNeeded({
 				true, // automatic trigger
 				customCondensingPrompt,
 				condensingApiHandler,
+				powerSteeringEnabled,
 			)
 			if (result.error) {
 				error = result.error

src/core/task/Task.ts

@@ -1006,6 +1006,9 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 
 		const { contextTokens: prevContextTokens } = this.getTokenUsage()
 
+		// Check if power steering is enabled
+		const powerSteeringEnabled = experiments.isEnabled(state?.experiments ?? {}, EXPERIMENT_IDS.POWER_STEERING)
+
 		const {
 			messages,
 			summary,
@@ -1021,6 +1024,7 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			false, // manual trigger
 			customCondensingPrompt, // User's custom prompt
 			condensingApiHandler, // Specific handler for condensing
+			powerSteeringEnabled, // Pass power steering state
 		)
 		if (error) {
 			this.say(
@@ -2461,6 +2465,9 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 				`Forcing truncation to ${FORCED_CONTEXT_REDUCTION_PERCENT}% of current context.`,
 		)
 
+		// Check if power steering is enabled
+		const powerSteeringEnabled = experiments.isEnabled(state?.experiments ?? {}, EXPERIMENT_IDS.POWER_STEERING)
+
 		// Force aggressive truncation by keeping only 75% of the conversation history
 		const truncateResult = await truncateConversationIfNeeded({
 			messages: this.apiConversationHistory,
@@ -2474,6 +2481,7 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			taskId: this.taskId,
 			profileThresholds,
 			currentProfileId,
+			powerSteeringEnabled,
 		})
 
 		if (truncateResult.messages !== this.apiConversationHistory) {
@@ -2577,6 +2585,9 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			// Get the current profile ID using the helper method
 			const currentProfileId = this.getCurrentProfileId(state)
 
+			// Check if power steering is enabled
+			const powerSteeringEnabled = experiments.isEnabled(state?.experiments ?? {}, EXPERIMENT_IDS.POWER_STEERING)
+
 			const truncateResult = await truncateConversationIfNeeded({
 				messages: this.apiConversationHistory,
 				totalTokens: contextTokens,
@@ -2591,6 +2602,7 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 				condensingApiHandler,
 				profileThresholds,
 				currentProfileId,
+				powerSteeringEnabled,
 			})
 			if (truncateResult.messages !== this.apiConversationHistory) {
 				await this.overwriteApiConversationHistory(truncateResult.messages)