diff --git a/src/core/condense/__tests__/index.spec.ts b/src/core/condense/__tests__/index.spec.ts
index d86b500f90..6a03298aa6 100644
--- a/src/core/condense/__tests__/index.spec.ts
+++ b/src/core/condense/__tests__/index.spec.ts
@@ -283,6 +283,32 @@ describe("summarizeConversation", () => {
 		const mockCallArgs = (maybeRemoveImageBlocks as Mock).mock.calls[0][0] as any[]
 		expect(mockCallArgs[mockCallArgs.length - 1]).toEqual(expectedFinalMessage)
 	})
+	it("should include the original first user message in summarization input", async () => {
+		const messages: ApiMessage[] = [
+			{ role: "user", content: "Initial ask", ts: 1 },
+			{ role: "assistant", content: "Ack", ts: 2 },
+			{ role: "user", content: "Follow-up", ts: 3 },
+			{ role: "assistant", content: "Response", ts: 4 },
+			{ role: "user", content: "More", ts: 5 },
+			{ role: "assistant", content: "Later", ts: 6 },
+			{ role: "user", content: "Newest", ts: 7 },
+		]
+
+		await summarizeConversation(messages, mockApiHandler, defaultSystemPrompt, taskId, DEFAULT_PREV_CONTEXT_TOKENS)
+
+		const mockCallArgs = (maybeRemoveImageBlocks as Mock).mock.calls[0][0] as any[]
+
+		// Expect the original first user message to be present in the messages sent to the summarizer
+		const hasInitialAsk = mockCallArgs.some(
+			(m) =>
+				m.role === "user" &&
+				(typeof m.content === "string"
+					? m.content === "Initial ask"
+					: Array.isArray(m.content) &&
+						m.content.some((b: any) => b.type === "text" && b.text === "Initial ask")),
+		)
+		expect(hasInitialAsk).toBe(true)
+	})
 
 	it("should calculate newContextTokens correctly with systemPrompt", async () => {
 		const messages: ApiMessage[] = [
diff --git a/src/core/condense/index.ts b/src/core/condense/index.ts
index 166a8ba4ca..86cfa7ab1e 100644
--- a/src/core/condense/index.ts
+++ b/src/core/condense/index.ts
@@ -103,8 +103,8 @@ export async function summarizeConversation(
 
 	// 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))
+	// Get messages to summarize, including the first message and excluding the last N messages
+	const messagesToSummarize = getMessagesSinceLastSummary(messages.slice(0, -N_MESSAGES_TO_KEEP))
 
 	if (messagesToSummarize.length <= 1) {
 		const error =