diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 1bdbb55ba94..a588d7db1b1 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -1424,6 +1424,10 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 	}
 
 	public async condenseContext(): Promise<void> {
+		// CRITICAL: Flush any pending tool results before condensing
+		// to ensure tool_use/tool_result pairs are complete in history
+		await this.flushPendingToolResultsToHistory()
+
 		const systemPrompt = await this.getSystemPrompt()
 
 		// Get condensing configuration