diff --git a/src/core/condense/__tests__/condense.spec.ts b/src/core/condense/__tests__/condense.spec.ts
new file mode 100644
index 00000000000..475b7a1c4f1
--- /dev/null
+++ b/src/core/condense/__tests__/condense.spec.ts
@@ -0,0 +1,260 @@
+// npx vitest src/core/condense/__tests__/condense.spec.ts
+
+import { Anthropic } from "@anthropic-ai/sdk"
+import type { ModelInfo } from "@roo-code/types"
+import { TelemetryService } from "@roo-code/telemetry"
+
+import { BaseProvider } from "../../../api/providers/base-provider"
+import { ApiMessage } from "../../task-persistence/apiMessages"
+import { summarizeConversation, getMessagesSinceLastSummary, N_MESSAGES_TO_KEEP } from "../index"
+
+// Create a mock ApiHandler for testing
+class MockApiHandler extends BaseProvider {
+	createMessage(): any {
+		// Mock implementation for testing - returns an async iterable stream
+		const mockStream = {
+			async *[Symbol.asyncIterator]() {
+				yield { type: "text", text: "Mock summary of the conversation" }
+				yield { type: "usage", inputTokens: 100, outputTokens: 50, totalCost: 0.01 }
+			},
+		}
+		return mockStream
+	}
+
+	getModel(): { id: string; info: ModelInfo } {
+		return {
+			id: "test-model",
+			info: {
+				contextWindow: 100000,
+				maxTokens: 50000,
+				supportsPromptCache: true,
+				supportsImages: false,
+				inputPrice: 0,
+				outputPrice: 0,
+				description: "Test model",
+			},
+		}
+	}
+
+	override async countTokens(content: Array<Anthropic.Messages.ContentBlockParam>): Promise<number> {
+		// Simple token counting for testing
+		let tokens = 0
+		for (const block of content) {
+			if (block.type === "text") {
+				tokens += Math.ceil(block.text.length / 4) // Rough approximation
+			}
+		}
+		return tokens
+	}
+}
+
+const mockApiHandler = new MockApiHandler()
+const taskId = "test-task-id"
+
+describe("Condense", () => {
+	beforeEach(() => {
+		if (!TelemetryService.hasInstance()) {
+			TelemetryService.createInstance([])
+		}
+	})
+
+	describe("summarizeConversation", () => {
+		it("should preserve the first message when summarizing", async () => {
+			const messages: ApiMessage[] = [
+				{ role: "user", content: "First message with /prr command content" },
+				{ role: "assistant", content: "Second message" },
+				{ role: "user", content: "Third message" },
+				{ role: "assistant", content: "Fourth message" },
+				{ role: "user", content: "Fifth message" },
+				{ role: "assistant", content: "Sixth message" },
+				{ role: "user", content: "Seventh message" },
+				{ role: "assistant", content: "Eighth message" },
+				{ role: "user", content: "Ninth message" },
+			]
+
+			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+
+			// Verify the first message is preserved
+			expect(result.messages[0]).toEqual(messages[0])
+			expect(result.messages[0].content).toBe("First message with /prr command content")
+
+			// Verify we have a summary message
+			const summaryMessage = result.messages.find((msg) => msg.isSummary)
+			expect(summaryMessage).toBeTruthy()
+			expect(summaryMessage?.content).toBe("Mock summary of the conversation")
+
+			// Verify we have the expected number of messages
+			// [first message, summary, last N messages]
+			expect(result.messages.length).toBe(1 + 1 + N_MESSAGES_TO_KEEP)
+
+			// Verify the last N messages are preserved
+			const lastMessages = result.messages.slice(-N_MESSAGES_TO_KEEP)
+			expect(lastMessages).toEqual(messages.slice(-N_MESSAGES_TO_KEEP))
+		})
+
+		it("should preserve slash command content in the first message", async () => {
+			const slashCommandContent = "/prr #123 - Fix authentication bug"
+			const messages: ApiMessage[] = [
+				{ role: "user", content: slashCommandContent },
+				{ role: "assistant", content: "I'll help you fix that authentication bug" },
+				{ role: "user", content: "The issue is with JWT tokens" },
+				{ role: "assistant", content: "Let me examine the JWT implementation" },
+				{ role: "user", content: "It's failing on refresh" },
+				{ role: "assistant", content: "I found the issue" },
+				{ role: "user", content: "Great, can you fix it?" },
+				{ role: "assistant", content: "Here's the fix" },
+				{ role: "user", content: "Thanks!" },
+			]
+
+			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+
+			// The first message with slash command should be intact
+			expect(result.messages[0].content).toBe(slashCommandContent)
+			expect(result.messages[0]).toEqual(messages[0])
+		})
+
+		it("should handle complex first message content", async () => {
+			const complexContent: Anthropic.Messages.ContentBlockParam[] = [
+				{ type: "text", text: "/mode code" },
+				{ type: "text", text: "Additional context from the user" },
+			]
+
+			const messages: ApiMessage[] = [
+				{ role: "user", content: complexContent },
+				{ role: "assistant", content: "Switching to code mode" },
+				{ role: "user", content: "Write a function" },
+				{ role: "assistant", content: "Here's the function" },
+				{ role: "user", content: "Add error handling" },
+				{ role: "assistant", content: "Added error handling" },
+				{ role: "user", content: "Add tests" },
+				{ role: "assistant", content: "Tests added" },
+				{ role: "user", content: "Perfect!" },
+			]
+
+			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+
+			// The first message with complex content should be preserved
+			expect(result.messages[0].content).toEqual(complexContent)
+			expect(result.messages[0]).toEqual(messages[0])
+		})
+
+		it("should return error when not enough messages to summarize", async () => {
+			const messages: ApiMessage[] = [
+				{ role: "user", content: "First message with /command" },
+				{ role: "assistant", content: "Second message" },
+				{ role: "user", content: "Third message" },
+				{ role: "assistant", content: "Fourth message" },
+			]
+
+			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+
+			// Should return an error since we have only 4 messages (first + 3 to keep)
+			expect(result.error).toBeDefined()
+			expect(result.messages).toEqual(messages) // Original messages unchanged
+			expect(result.summary).toBe("")
+		})
+
+		it("should not summarize messages that already contain a recent summary", async () => {
+			const messages: ApiMessage[] = [
+				{ role: "user", content: "First message with /command" },
+				{ role: "assistant", content: "Old message" },
+				{ role: "user", content: "Message before summary" },
+				{ role: "assistant", content: "Response" },
+				{ role: "user", content: "Another message" },
+				{ role: "assistant", content: "Previous summary", isSummary: true }, // Summary in last N messages
+				{ role: "user", content: "Final message" },
+			]
+
+			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, 5000, false)
+
+			// Should return an error due to recent summary in last N messages
+			expect(result.error).toBeDefined()
+			expect(result.messages).toEqual(messages)
+			expect(result.summary).toBe("")
+		})
+
+		it("should handle empty summary from API gracefully", async () => {
+			// Mock handler that returns empty summary
+			class EmptyMockApiHandler extends MockApiHandler {
+				override createMessage(): any {
+					const mockStream = {
+						async *[Symbol.asyncIterator]() {
+							yield { type: "text", text: "" }
+							yield { type: "usage", inputTokens: 100, outputTokens: 0, totalCost: 0.01 }
+						},
+					}
+					return mockStream
+				}
+			}
+
+			const emptyHandler = new EmptyMockApiHandler()
+			const messages: ApiMessage[] = [
+				{ role: "user", content: "First message" },
+				{ role: "assistant", content: "Second" },
+				{ role: "user", content: "Third" },
+				{ role: "assistant", content: "Fourth" },
+				{ role: "user", content: "Fifth" },
+				{ role: "assistant", content: "Sixth" },
+				{ role: "user", content: "Seventh" },
+			]
+
+			const result = await summarizeConversation(messages, emptyHandler, "System prompt", taskId, 5000, false)
+
+			expect(result.error).toBeDefined()
+			expect(result.messages).toEqual(messages)
+			expect(result.cost).toBeGreaterThan(0)
+		})
+	})
+
+	describe("getMessagesSinceLastSummary", () => {
+		it("should return all messages when no summary exists", () => {
+			const messages: ApiMessage[] = [
+				{ role: "user", content: "First message" },
+				{ role: "assistant", content: "Second message" },
+				{ role: "user", content: "Third message" },
+			]
+
+			const result = getMessagesSinceLastSummary(messages)
+			expect(result).toEqual(messages)
+		})
+
+		it("should return messages since last summary including the summary", () => {
+			const messages: ApiMessage[] = [
+				{ role: "user", content: "First message" },
+				{ role: "assistant", content: "Second message" },
+				{ role: "assistant", content: "Summary content", isSummary: true },
+				{ role: "user", content: "Message after summary" },
+				{ role: "assistant", content: "Final message" },
+			]
+
+			const result = getMessagesSinceLastSummary(messages)
+
+			// Should include a user message prefix for Bedrock compatibility, the summary, and messages after
+			expect(result[0].role).toBe("user")
+			expect(result[0].content).toBe("Please continue from the following summary:")
+			expect(result[1]).toEqual(messages[2]) // The summary
+			expect(result[2]).toEqual(messages[3])
+			expect(result[3]).toEqual(messages[4])
+		})
+
+		it("should handle multiple summaries and return from the last one", () => {
+			const messages: ApiMessage[] = [
+				{ role: "user", content: "First message" },
+				{ role: "assistant", content: "First summary", isSummary: true },
+				{ role: "user", content: "Middle message" },
+				{ role: "assistant", content: "Second summary", isSummary: true },
+				{ role: "user", content: "Recent message" },
+				{ role: "assistant", content: "Final message" },
+			]
+
+			const result = getMessagesSinceLastSummary(messages)
+
+			// Should only include from the last summary
+			expect(result[0].role).toBe("user")
+			expect(result[0].content).toBe("Please continue from the following summary:")
+			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 11a25a0693e..510d9976738 100644
--- a/src/core/condense/__tests__/index.spec.ts
+++ b/src/core/condense/__tests__/index.spec.ts
@@ -188,11 +188,14 @@ describe("summarizeConversation", () => {
 		expect(maybeRemoveImageBlocks).toHaveBeenCalled()
 
 		// Verify the structure of the result
-		// The result should be: original messages (except last N) + summary + last N messages
-		expect(result.messages.length).toBe(messages.length + 1) // Original + summary
+		// 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])
 
 		// Check that the summary message was inserted correctly
-		const summaryMessage = result.messages[result.messages.length - N_MESSAGES_TO_KEEP - 1]
+		const summaryMessage = result.messages[1]
 		expect(summaryMessage.role).toBe("assistant")
 		expect(summaryMessage.content).toBe("This is a summary")
 		expect(summaryMessage.isSummary).toBe(true)
@@ -395,7 +398,8 @@ describe("summarizeConversation", () => {
 		)
 
 		// Should successfully summarize
-		expect(result.messages.length).toBe(messages.length + 1) // Original + summary
+		// Result should be: first message + summary + last N messages
+		expect(result.messages.length).toBe(1 + 1 + N_MESSAGES_TO_KEEP) // First + summary + last N
 		expect(result.cost).toBe(0.03)
 		expect(result.summary).toBe("Concise summary")
 		expect(result.error).toBeUndefined()
diff --git a/src/core/condense/index.ts b/src/core/condense/index.ts
index 3b73b1915c6..f50a9550deb 100644
--- a/src/core/condense/index.ts
+++ b/src/core/condense/index.ts
@@ -100,7 +100,11 @@ export async function summarizeConversation(
 	)
 
 	const response: SummarizeResponse = { messages, cost: 0, summary: "" }
-	const messagesToSummarize = getMessagesSinceLastSummary(messages.slice(0, -N_MESSAGES_TO_KEEP))
+
+	// 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))
 
 	if (messagesToSummarize.length <= 1) {
 		const error =
@@ -184,7 +188,8 @@ export async function summarizeConversation(
 		isSummary: true,
 	}
 
-	const newMessages = [...messages.slice(0, -N_MESSAGES_TO_KEEP), summaryMessage, ...keepMessages]
+	// Reconstruct messages: [first message, summary, last N messages]
+	const newMessages = [firstMessage, 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