diff --git a/src/main/java/com/knowledge/base/application/service/LLMAppServiceImpl.java b/src/main/java/com/knowledge/base/application/service/LLMAppServiceImpl.java
index 00172cd..fabb15c 100644
--- a/src/main/java/com/knowledge/base/application/service/LLMAppServiceImpl.java
+++ b/src/main/java/com/knowledge/base/application/service/LLMAppServiceImpl.java
@@ -110,6 +110,7 @@ public class LLMAppServiceImpl implements LLMAppService {
             log.info("[pinDocsByKeywords] 未查到匹配ES文档，跳过pin操作。");
             return Lists.newArrayList();
         }
+        log.info("[pinDocsByKeywords] 已查询到关键词关联的文档。 {}", JSONUtil.toJsonStr(esFilepaths));
 
         // 将当前问题标注为处理中
         markQuestionProcessing(question);
@@ -122,9 +123,23 @@ public class LLMAppServiceImpl implements LLMAppService {
         }
 
         // 3. 找到需要pin的docPath集合
-        List<WorkspaceAttachment> toPinDocs = attachments.stream()
-                .filter(att -> esFilepaths.stream().anyMatch(f -> att.getUrl().endsWith(f)))
-                .collect(Collectors.toList());
+        List<WorkspaceAttachment> toPinDocs = attachments.stream().filter(att -> {
+            String url = att.getUrl();
+            if (url == null) return false;
+            // .md 文件
+            if (url.endsWith(".md")) {
+                return esFilepaths.stream().anyMatch(f -> url.endsWith(f));
+            }
+            // 其它文件（如 .pptx、.pdf、.docx等）
+            int lastSlash = url.lastIndexOf('/');
+            String fileName = lastSlash != -1 ? url.substring(lastSlash + 1) : url;
+            // esFilepaths 里也提取末尾文件名
+            return esFilepaths.stream().anyMatch(f -> {
+                int esLastSlash = f.lastIndexOf('/');
+                String esName = esLastSlash != -1 ? f.substring(esLastSlash + 1) : f;
+                return fileName.equals(esName);
+            });
+        }).collect(Collectors.toList());
 
         // 4. 只unpin之前已pin的文档
         attachments.stream()