diff --git a/poetry.lock b/poetry.lock
index f8a086d..40f70eb 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -113,11 +113,11 @@
 
 [[package]]
 name = "gitdb"
-version = "4.0.9"
+version = "4.0.10"
 description = "Git Object Database"
 category = "dev"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
 
 [package.dependencies]
 smmap = ">=3.0.1,<6"
@@ -382,7 +382,7 @@
 
 [[package]]
 name = "pymdown-extensions"
-version = "9.8"
+version = "9.9"
 description = "Extension pack for Python Markdown."
 category = "dev"
 optional = false
@@ -497,7 +497,7 @@
 
 [[package]]
 name = "setuptools"
-version = "65.6.0"
+version = "65.6.3"
 description = "Easily download, build, install, upgrade, and uninstall Python packages"
 category = "dev"
 optional = false
@@ -542,11 +542,11 @@
 
 [[package]]
 name = "urllib3"
-version = "1.26.12"
+version = "1.26.13"
 description = "HTTP library with thread-safe connection pooling, file post, and more."
 category = "main"
 optional = false
-python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*, !=3.5.*, <4"
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*, !=3.5.*"
 
 [package.extras]
 brotli = ["brotli (>=1.0.9)", "brotlicffi (>=0.8.0)", "brotlipy (>=0.6.0)"]
@@ -613,8 +613,8 @@
     {file = "ghp_import-2.1.0-py3-none-any.whl", hash = "sha256:8337dd7b50877f163d4c0289bc1f1c7f127550241988d568c1db512c4324a619"},
 ]
 gitdb = [
-    {file = "gitdb-4.0.9-py3-none-any.whl", hash = "sha256:8033ad4e853066ba6ca92050b9df2f89301b8fc8bf7e9324d412a63f8bf1a8fd"},
-    {file = "gitdb-4.0.9.tar.gz", hash = "sha256:bac2fd45c0a1c9cf619e63a90d62bdc63892ef92387424b855792a6cabe789aa"},
+    {file = "gitdb-4.0.10-py3-none-any.whl", hash = "sha256:c286cf298426064079ed96a9e4a9d39e7f3e9bf15ba60701e95f5492f28415c7"},
+    {file = "gitdb-4.0.10.tar.gz", hash = "sha256:6eb990b69df4e15bad899ea868dc46572c3f75339735663b81de79b06f17eb9a"},
 ]
 GitPython = [
     {file = "GitPython-3.1.29-py3-none-any.whl", hash = "sha256:41eea0deec2deea139b459ac03656f0dd28fc4a3387240ec1d3c259a2c47850f"},
@@ -815,8 +815,8 @@
     {file = "pyinstaller_hooks_contrib-2022.13-py2.py3-none-any.whl", hash = "sha256:91ecb30db757a8db8b6661d91d5df99e0998245f05f5cfaade0550922c7030a3"},
 ]
 pymdown-extensions = [
-    {file = "pymdown_extensions-9.8-py3-none-any.whl", hash = "sha256:8e62688a8b1128acd42fa823f3d429d22f4284b5e6dd4d3cd56721559a5a211b"},
-    {file = "pymdown_extensions-9.8.tar.gz", hash = "sha256:1bd4a173095ef8c433b831af1f3cb13c10883be0c100ae613560668e594651f7"},
+    {file = "pymdown_extensions-9.9-py3-none-any.whl", hash = "sha256:ac698c15265680db5eb13cd4342abfcde2079ac01e5486028f47a1b41547b859"},
+    {file = "pymdown_extensions-9.9.tar.gz", hash = "sha256:0f8fb7b74a37a61cc34e90b2c91865458b713ec774894ffad64353a5fce85cfc"},
 ]
 pyparsing = [
     {file = "pyparsing-3.0.9-py3-none-any.whl", hash = "sha256:5026bae9a10eeaefb61dab2f09052b9f4307d44aee4eda64b309723d8d206bbc"},
@@ -893,8 +893,8 @@
     {file = "rich-12.6.0.tar.gz", hash = "sha256:ba3a3775974105c221d31141f2c116f4fd65c5ceb0698657a11e9f295ec93fd0"},
 ]
 setuptools = [
-    {file = "setuptools-65.6.0-py3-none-any.whl", hash = "sha256:6211d2f5eddad8757bd0484923ca7c0a6302ebc4ab32ea5e94357176e0ca0840"},
-    {file = "setuptools-65.6.0.tar.gz", hash = "sha256:d1eebf881c6114e51df1664bc2c9133d022f78d12d5f4f665b9191f084e2862d"},
+    {file = "setuptools-65.6.3-py3-none-any.whl", hash = "sha256:57f6f22bde4e042978bcd50176fdb381d7c21a9efa4041202288d3737a0c6a54"},
+    {file = "setuptools-65.6.3.tar.gz", hash = "sha256:a7620757bf984b58deaf32fc8a4577a9bbc0850cf92c20e1ce41c38c19e5fb75"},
 ]
 six = [
     {file = "six-1.16.0-py2.py3-none-any.whl", hash = "sha256:8abb2f1d86890a2dfb989f9a77cfcfd3e47c2a354b01111771326f8aa26e0254"},
@@ -913,8 +913,8 @@
     {file = "text_unidecode-1.3-py2.py3-none-any.whl", hash = "sha256:1311f10e8b895935241623731c2ba64f4c455287888b18189350b67134a822e8"},
 ]
 urllib3 = [
-    {file = "urllib3-1.26.12-py2.py3-none-any.whl", hash = "sha256:b930dd878d5a8afb066a637fbb35144fe7901e3b209d1cd4f524bd0e9deee997"},
-    {file = "urllib3-1.26.12.tar.gz", hash = "sha256:3fa96cf423e6987997fc326ae8df396db2a8b7c667747d47ddd8ecba91f4a74e"},
+    {file = "urllib3-1.26.13-py2.py3-none-any.whl", hash = "sha256:47cc05d99aaa09c9e72ed5809b60e7ba354e64b59c9c173ac3018642d8bb41fc"},
+    {file = "urllib3-1.26.13.tar.gz", hash = "sha256:c083dd0dce68dbfbe1129d5271cb90f9447dea7d52097c6e0126120c521ddea8"},
 ]
 watchdog = [
     {file = "watchdog-2.1.9-cp310-cp310-macosx_10_9_universal2.whl", hash = "sha256:a735a990a1095f75ca4f36ea2ef2752c99e6ee997c46b0de507ba40a09bf7330"},
diff --git a/requirements.txt b/requirements.txt
index d76d50f..76c413a 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -15,4 +15,4 @@
 rich==12.6.0 ; python_version >= "3.10" and python_version < "3.12"
 soupsieve==2.3.2.post1 ; python_version >= "3.10" and python_version < "3.12"
 text-unidecode==1.3 ; python_version >= "3.10" and python_version < "3.12"
-urllib3==1.26.12 ; python_version >= "3.10" and python_version < "3.12"
+urllib3==1.26.13 ; python_version >= "3.10" and python_version < "3.12"
diff --git a/scripts/install.sh b/scripts/install.sh
index e177d0e..d8b9302 100644
--- a/scripts/install.sh
+++ b/scripts/install.sh
@@ -35,7 +35,7 @@
 function copy() {
   mkdir --parents "$(realpath --canonicalize-missing ${2}/..)"
   cp --force --recursive "${1}" "${2}"
-  success "${1} -> ${2}"
+  success "Copy: ${1} -> ${2}"
 }
 
 cd "$(git rev-parse --show-toplevel || echo .)"
diff --git a/thu_learn_downloader/downloader.py b/thu_learn_downloader/downloader.py
index 936612d..dd2d2c3 100644
--- a/thu_learn_downloader/downloader.py
+++ b/thu_learn_downloader/downloader.py
@@ -18,7 +18,7 @@
     console: rich.console.Console = rich.console.Console(),
     progress: rich.progress.Progress = rich.progress.Progress(),
     task_id: rich.progress.TaskID = rich.progress.TaskID(0),
-) -> None:
+) -> bool:
     res = (session or requests).get(url=url, stream=True)
     raw_size = int(res.headers.get("Content-Length", 0)) or raw_size
     if os.path.exists(file):
@@ -27,7 +27,7 @@
                 mtime = os.path.getmtime(filename=file)
                 mtime = datetime.datetime.fromtimestamp(mtime)
                 if mtime >= upload_time:
-                    return
+                    return False
     os.makedirs(name=os.path.dirname(file), exist_ok=True)
     progress.reset(task_id=task_id, total=raw_size)
     with open(file=file, mode="wb") as fp:
@@ -40,6 +40,7 @@
     if upload_time:
         mtime = int(upload_time.timestamp())
         os.utime(path=file, times=(mtime, mtime))
+    return True
 
 
 def download(
@@ -60,7 +61,7 @@
                     f"Retry {i}: {progress.tasks[task_id].description}",
                     style="bold bright_blue",
                 )
-            download_once(
+            ret = download_once(
                 url=url,
                 file=file,
                 raw_size=raw_size,
@@ -76,10 +77,16 @@
                 style="bold bright_red",
             )
         else:
-            console.log(
-                f"Download Success: {progress.tasks[task_id].description}",
-                style="bold bright_green",
-            )
+            if ret:
+                console.log(
+                    f"Download Success: {progress.tasks[task_id].description}",
+                    style="bold bright_green",
+                )
+            else:
+                console.log(
+                    f"Download Skipped: {progress.tasks[task_id].description}",
+                    style="dim",
+                )
             progress.update(task_id=task_id, visible=False)
             return
 
diff --git a/thu_learn_downloader/sync.py b/thu_learn_downloader/sync.py
index 5756732..b499b8c 100644
--- a/thu_learn_downloader/sync.py
+++ b/thu_learn_downloader/sync.py
@@ -190,7 +190,7 @@
     with open(file=file, mode="w") as fp:
         fp.write(readme.dump_work(work))
     if shutil.which(cmd="prettier"):
-        os.system(f"prettier --write {file}")
+        os.system(f"prettier --write {file} > /dev/null")
 
 
 def sync_work_attachment(
@@ -214,6 +214,13 @@
         for p in ["attach", "ans", "submit", "comment"]:
             title = title.removeprefix(p + "-")
         title = attachment_type + "-" + title
+        upload_time = None
+        if attachment_type == "submit":
+            upload_time = work.submit_time
+        elif attachment_type == "comment":
+            upload_time = work.grade_time
+        else:
+            upload_time = None
         downloader.schedule_download(
             url=attachment.download_url,
             file=os.path.join(
@@ -223,6 +230,7 @@
                 utils.slugify(work.title),
                 utils.slugify(title),
             ),
+            upload_time=upload_time,
             session=helper,
             console=console,
             description=f"[bold bright_blue]{course.name} > {title}",