diff --git a/src/core/condense/__tests__/condense.spec.ts b/src/core/condense/__tests__/condense.spec.ts
index 475b7a1c4f..5eb97b3e8a 100644
--- a/src/core/condense/__tests__/condense.spec.ts
+++ b/src/core/condense/__tests__/condense.spec.ts
@@ -229,9 +229,9 @@ describe("Condense", () => {
 
 			const result = getMessagesSinceLastSummary(messages)
 
-			// Should include a user message prefix for Bedrock compatibility, the summary, and messages after
+			// Should include the original first user message for context preservation, the summary, and messages after
 			expect(result[0].role).toBe("user")
-			expect(result[0].content).toBe("Please continue from the following summary:")
+			expect(result[0].content).toBe("First message") // Preserves original first message
 			expect(result[1]).toEqual(messages[2]) // The summary
 			expect(result[2]).toEqual(messages[3])
 			expect(result[3]).toEqual(messages[4])
@@ -249,9 +249,9 @@ describe("Condense", () => {
 
 			const result = getMessagesSinceLastSummary(messages)
 
-			// Should only include from the last summary
+			// Should only include from the last summary with original first message preserved
 			expect(result[0].role).toBe("user")
-			expect(result[0].content).toBe("Please continue from the following summary:")
+			expect(result[0].content).toBe("First message") // Preserves original first message
 			expect(result[1]).toEqual(messages[3]) // Second summary
 			expect(result[2]).toEqual(messages[4])
 			expect(result[3]).toEqual(messages[5])
diff --git a/src/core/condense/__tests__/index.spec.ts b/src/core/condense/__tests__/index.spec.ts
index 510d997673..d86b500f90 100644
--- a/src/core/condense/__tests__/index.spec.ts
+++ b/src/core/condense/__tests__/index.spec.ts
@@ -36,7 +36,7 @@ describe("getMessagesSinceLastSummary", () => {
 		expect(result).toEqual(messages)
 	})
 
-	it("should return messages since the last summary with prepended user message", () => {
+	it("should return messages since the last summary with original first user message", () => {
 		const messages: ApiMessage[] = [
 			{ role: "user", content: "Hello", ts: 1 },
 			{ role: "assistant", content: "Hi there", ts: 2 },
@@ -47,14 +47,14 @@ describe("getMessagesSinceLastSummary", () => {
 
 		const result = getMessagesSinceLastSummary(messages)
 		expect(result).toEqual([
-			{ role: "user", content: "Please continue from the following summary:", ts: 0 },
+			{ role: "user", content: "Hello", ts: 1 },
 			{ role: "assistant", content: "Summary of conversation", ts: 3, isSummary: true },
 			{ role: "user", content: "How are you?", ts: 4 },
 			{ role: "assistant", content: "I'm good", ts: 5 },
 		])
 	})
 
-	it("should handle multiple summary messages and return since the last one with prepended user message", () => {
+	it("should handle multiple summary messages and return since the last one with original first user message", () => {
 		const messages: ApiMessage[] = [
 			{ role: "user", content: "Hello", ts: 1 },
 			{ role: "assistant", content: "First summary", ts: 2, isSummary: true },
@@ -65,7 +65,7 @@ describe("getMessagesSinceLastSummary", () => {
 
 		const result = getMessagesSinceLastSummary(messages)
 		expect(result).toEqual([
-			{ role: "user", content: "Please continue from the following summary:", ts: 0 },
+			{ role: "user", content: "Hello", ts: 1 },
 			{ role: "assistant", content: "Second summary", ts: 4, isSummary: true },
 			{ role: "user", content: "What's new?", ts: 5 },
 		])
diff --git a/src/core/condense/index.ts b/src/core/condense/index.ts
index f50a9550de..166a8ba4ca 100644
--- a/src/core/condense/index.ts
+++ b/src/core/condense/index.ts
@@ -223,11 +223,24 @@ export function getMessagesSinceLastSummary(messages: ApiMessage[]): ApiMessage[
 	const messagesSinceSummary = messages.slice(lastSummaryIndex)
 
 	// Bedrock requires the first message to be a user message.
+	// We preserve the original first message to maintain context.
 	// See https://github.com/RooCodeInc/Roo-Code/issues/4147
-	const userMessage: ApiMessage = {
-		role: "user",
-		content: "Please continue from the following summary:",
-		ts: messages[0]?.ts ? messages[0].ts - 1 : Date.now(),
+	if (messagesSinceSummary.length > 0 && messagesSinceSummary[0].role !== "user") {
+		// Get the original first message (should always be a user message with the task)
+		const originalFirstMessage = messages[0]
+		if (originalFirstMessage && originalFirstMessage.role === "user") {
+			// Use the original first message unchanged to maintain full context
+			return [originalFirstMessage, ...messagesSinceSummary]
+		} else {
+			// Fallback to generic message if no original first message exists (shouldn't happen)
+			const userMessage: ApiMessage = {
+				role: "user",
+				content: "Please continue from the following summary:",
+				ts: messages[0]?.ts ? messages[0].ts - 1 : Date.now(),
+			}
+			return [userMessage, ...messagesSinceSummary]
+		}
 	}
-	return [userMessage, ...messagesSinceSummary]
+
+	return messagesSinceSummary
 }