diff --git a/src/core/condense/__tests__/index.spec.ts b/src/core/condense/__tests__/index.spec.ts
index ef5af012435..a44a2891cb9 100644
--- a/src/core/condense/__tests__/index.spec.ts
+++ b/src/core/condense/__tests__/index.spec.ts
@@ -482,17 +482,17 @@ describe("getKeepMessagesWithToolBlocks", () => {
 		expect(result.toolUseBlocksToPreserve).toContainEqual(toolUseBlock2)
 	})
 
-	it("should not crash when tool_result references tool_use beyond search boundary", () => {
+	it("should preserve tool_use even when it is far back in the conversation history", () => {
 		const toolResultBlock = {
 			type: "tool_result" as const,
-			tool_use_id: "toolu_beyond_boundary",
+			tool_use_id: "toolu_far_back",
 			content: "result",
 		}
 
-		// Tool_use is at ts:1, but with N_MESSAGES_TO_KEEP=3, we only search back 3 messages
-		// from startIndex-1. StartIndex is 7 (messages.length=10, keepCount=3, startIndex=7).
-		// So we search from index 6 down to index 4 (7-1 down to 7-3).
-		// The tool_use at index 0 (ts:1) is beyond the search boundary.
+		// Tool_use is at ts:1, far back in the conversation.
+		// The search now covers the entire condensed region (from index 0 to startIndex-1),
+		// so the tool_use WILL be found and preserved. This prevents the API error:
+		// "tool_use ids were found without tool_result blocks immediately after"
 		const messages: ApiMessage[] = [
 			{
 				role: "assistant",
@@ -500,7 +500,7 @@ describe("getKeepMessagesWithToolBlocks", () => {
 					{ type: "text" as const, text: "Way back..." },
 					{
 						type: "tool_use" as const,
-						id: "toolu_beyond_boundary",
+						id: "toolu_far_back",
 						name: "old_tool",
 						input: {},
 					},
@@ -522,7 +522,6 @@ describe("getKeepMessagesWithToolBlocks", () => {
 			{ role: "user", content: "Message 10", ts: 10 },
 		]
 
-		// Should not crash
 		const result = getKeepMessagesWithToolBlocks(messages, 3)
 
 		// keepMessages should be the last 3 messages
@@ -531,8 +530,10 @@ describe("getKeepMessagesWithToolBlocks", () => {
 		expect(result.keepMessages[1].ts).toBe(9)
 		expect(result.keepMessages[2].ts).toBe(10)
 
-		// Should not preserve the tool_use since it's beyond the search boundary
-		expect(result.toolUseBlocksToPreserve).toHaveLength(0)
+		// Should NOW preserve the tool_use - this is the fix for the API error
+		// where tool_result blocks were orphaned because their tool_use wasn't found
+		expect(result.toolUseBlocksToPreserve).toHaveLength(1)
+		expect(result.toolUseBlocksToPreserve[0].id).toBe("toolu_far_back")
 	})
 
 	it("should not duplicate tool_use blocks when same tool_result ID appears multiple times", () => {
diff --git a/src/core/condense/index.ts b/src/core/condense/index.ts
index 79bc31ef9fc..01e8b490187 100644
--- a/src/core/condense/index.ts
+++ b/src/core/condense/index.ts
@@ -105,41 +105,54 @@ export function getKeepMessagesWithToolBlocks(messages: ApiMessage[], keepCount:
 	const reasoningBlocksToPreserve: Anthropic.Messages.ContentBlockParam[] = []
 	const preservedToolUseIds = new Set<string>()
 
-	// Check ALL kept messages for tool_result blocks
+	// First, collect all tool_use_ids we need to find from kept messages
+	const toolUseIdsToFind = new Set<string>()
 	for (const keepMsg of keepMessages) {
 		if (!hasToolResultBlocks(keepMsg)) {
 			continue
 		}
+		for (const toolResult of getToolResultBlocks(keepMsg)) {
+			toolUseIdsToFind.add(toolResult.tool_use_id)
+		}
+	}
 
-		const toolResults = getToolResultBlocks(keepMsg)
-
-		for (const toolResult of toolResults) {
-			const toolUseId = toolResult.tool_use_id
+	// Early exit if no tool_results in kept messages
+	if (toolUseIdsToFind.size === 0) {
+		return { keepMessages, toolUseBlocksToPreserve: [], reasoningBlocksToPreserve: [] }
+	}
 
-			// Skip if we've already found this tool_use
-			if (preservedToolUseIds.has(toolUseId)) {
-				continue
+	// Build an index of tool_use ID -> message for the condensed region
+	// This avoids repeated linear searches through the entire history
+	// Only index assistant messages (which contain tool_use blocks)
+	const toolUseIndex = new Map<string, ApiMessage>()
+	for (let i = 0; i < startIndex; i++) {
+		const msg = messages[i]
+		if (msg.role !== "assistant") {
+			continue
+		}
+		for (const toolUse of getToolUseBlocks(msg)) {
+			// Only index IDs we're looking for
+			if (toolUseIdsToFind.has(toolUse.id)) {
+				toolUseIndex.set(toolUse.id, msg)
 			}
+		}
+	}
 
-			// Search backwards through the condensed region (bounded)
-			const searchStart = startIndex - 1
-			const searchEnd = Math.max(0, startIndex - N_MESSAGES_TO_KEEP)
-			const messagesToSearch = messages.slice(searchEnd, searchStart + 1)
-
-			// Find the message containing this tool_use
-			const messageWithToolUse = findLast(messagesToSearch, (msg) => {
-				return findToolUseBlockById(msg, toolUseId) !== undefined
-			})
+	// Now look up each tool_use we need
+	for (const toolUseId of toolUseIdsToFind) {
+		if (preservedToolUseIds.has(toolUseId)) {
+			continue
+		}
 
-			if (messageWithToolUse) {
-				const toolUse = findToolUseBlockById(messageWithToolUse, toolUseId)!
-				toolUseBlocksToPreserve.push(toolUse)
-				preservedToolUseIds.add(toolUseId)
+		const messageWithToolUse = toolUseIndex.get(toolUseId)
+		if (messageWithToolUse) {
+			const toolUse = findToolUseBlockById(messageWithToolUse, toolUseId)!
+			toolUseBlocksToPreserve.push(toolUse)
+			preservedToolUseIds.add(toolUseId)
 
-				// Also preserve reasoning blocks from that message
-				const reasoning = getReasoningBlocks(messageWithToolUse)
-				reasoningBlocksToPreserve.push(...reasoning)
-			}
+			// Also preserve reasoning blocks from that message
+			const reasoning = getReasoningBlocks(messageWithToolUse)
+			reasoningBlocksToPreserve.push(...reasoning)
 		}
 	}