diff --git a/app.py b/app.py
index 8b2fe76..aa1b978 100644
--- a/app.py
+++ b/app.py
@@ -10,6 +10,7 @@ import random
 import string
 from io import BytesIO
 import zipfile
+import shutil
 from pypinyin import pinyin, Style
 import uuid
 
@@ -1119,7 +1120,6 @@ def delete_ca(ca_id):
 
     return render_template('confirm_delete_ca.html', ca=ca)
 
-
 @app.route('/certificates/<int:cert_id>/delete', methods=['GET', 'POST'])
 @login_required
 def delete_certificate(cert_id):
@@ -1136,19 +1136,38 @@ def delete_certificate(cert_id):
     if request.method == 'POST':
         # 删除文件
         try:
-            if os.path.exists(cert['cert_path']):
-                os.remove(cert['cert_path'])
-            if os.path.exists(cert['key_path']):
-                os.remove(cert['key_path'])
-            if os.path.exists(cert['csr_path']):
-                os.remove(cert['csr_path'])
-            # 删除证书目录
+            # 确保所有文件路径都存在
+            files_to_delete = [
+                cert['cert_path'],
+                cert['key_path'],
+                cert['csr_path']
+            ]
+
+            # 删除所有指定文件
+            for file_path in files_to_delete:
+                if file_path and os.path.exists(file_path):
+                    os.remove(file_path)
+
+            # 删除证书目录及其所有内容
             cert_dir = os.path.dirname(cert['cert_path'])
             if os.path.exists(cert_dir):
+                # 删除目录中的所有文件
+                for filename in os.listdir(cert_dir):
+                    file_path = os.path.join(cert_dir, filename)
+                    try:
+                        if os.path.isfile(file_path) or os.path.islink(file_path):
+                            os.unlink(file_path)
+                        elif os.path.isdir(file_path):
+                            shutil.rmtree(file_path)
+                    except Exception as e:
+                        print(f'Failed to delete {file_path}. Reason: {e}')
+
+                # 现在删除空目录
                 os.rmdir(cert_dir)
+
         except OSError as e:
             print(f"文件删除错误: {e}")
-            flash('删除文件时出错', 'danger')
+            flash(f'删除文件时出错: {str(e)}', 'danger')
             return redirect(url_for('certificate_detail', cert_id=cert_id))
 
         # 删除数据库记录
@@ -1170,7 +1189,6 @@ def delete_certificate(cert_id):
                     conn.close()
 
     return render_template('confirm_delete_certificate.html', cert=cert)
-
 def generate_separate_files_zip(cert, cert_ext, zip_suffix):
     """生成包含分开文件的ZIP包通用函数"""
     memory_file = BytesIO()