python / python/cpython

OSError: [Errno 22] Invalid argument when serving files with last modified time before 1969-12-31 12:00 UTC on windows

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stdlib type-bug
Dominant language
Python
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Description

Bug report

http.server.SimpleHTTPRequestHandler.send_head() does not check if a file's mtime is valid for gmtime() on windows.
An OSError: [Errno 22] Invalid argument exception will be raised which is normal according to the documentation.

https://github.com/python/cpython/blob/ef633e5000222a3dba74473c49d6a81fca0a44ec/Lib/http/server.py#L752
https://github.com/python/cpython/blob/ef633e5000222a3dba74473c49d6a81fca0a44ec/Lib/http/server.py#L766

I encounter this error when using windows built-in unzip functionality to unzip a windows WireGuard client exported zip file.
The zip file does not contain any timestamp information. And windows will not auto fill timestamp information when unzipping.
And win32 api GetFileInformationByHandle will report back a timestamp of -11635213907.559603

Your environment

  • CPython versions tested on: 3.10.9, 3.11.1, 3.12.0a4+
  • Operating system and architecture: windows 11 pro 22h2 OS build 22621.1105 amd64
Linked PRs
  • gh-101036

Contributor guide

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First steps

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  3. Fork the repository and make your change on a branch.
  4. Open a pull request that references the issue number.

Research direction

Start in Lib/http/server.py at http.server.SimpleHTTPRequestHandler.send_head(), especially the file timestamp handling around the referenced gmtime() calls. Reproduce the behavior on Windows with a file whose mtime predates 1969-12-31, then review linked PR gh-101036. Done means serving such a file no longer raises OSError: [Errno 22].

Written by the indexing model from the issue text.

Assessment

Tech stack
python
Domain
web-dev
Issue type
Bug
Difficulty
3/5
Estimated time
1-2 days
Activity status
Stale
Clarity
Mostly clear
Newbie friendliness
25/100

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