Why is this hardcoded?

You can find more clear and meaningful name.

You can also use type annotations.

pathfiles_absolute and pathfiles_relative ?

Even the latter one is not really true, since it's a list of pairs. But clearer name does exist (assuming this is really needed to store pairs, the purpose of this is unclear at this moment).

Never re-purpose variables. Especially if they do change type.

filetuple.endswith

Makes no sense, tuple does not have endswith().

Double space.

buildbot_codesign_config.py ?

Is also a good practice to have buildbot_codesign_config_template.py in the repo which then expected to be copied locally and adjusted to a specific setup.

Don't think this is enough for macOS signing process. That could easily take like 30min.

Brecht will know better though.

Also, PEP8 again, spaces around operator.

allfiles.extend(pathfiles)

self.sign_command ?

pathfiles.extend(path_to_search.rglob(pattern)) to avoid loop to flatten list later.

Also, why to have this Path to str conversions?

Remove prefix rather than replacing basedir as a substring:

• Faster
• More reliable (for rare cases when basedir might be a substring somewhere else)
• More readable and understandable.

Can you finally tackle this one?

I stop my round of review here,

Use namedtuple, or:

@dataclass
class FileAndArchiveName:
  filepath: Path
  archive_name: str

def remove_prefix_if_exists(s: str, prefix: str) -> str:
    if s.startswith(prefix):
        return s[len(prefix):]
    return s

def give_fullpath_and_archive_name(
           basedir: str,
           path: pathlib.PurePath) -> FileAndArchiveName:
   strpath = str(path.resolve())
   return (strpath,
           remove_prefix_if_exists(strpath))

Boring, but more readable.

And again, is there a specific reason to go from Path to str?

Comment is a full sentence, starting with a capital letter and ending with full-stop.

pathlib-ify.

If response_file a Path (as it should be) then simply do response_file.exists().

Generally, just stick to pathlib instead of os.path.

FYI: time.sleep(1) is not guaranteed to sleep for more than 1 second (in fact, it's almost never sleeps exactly 1 sec).

Better to just store a starting time and recompute time passed on every iteration.
Use monotonic clock (time.monotonic()).

Early output, and unindent the entire function.

First of all, what is "140.all" ? dll?

Second, this is too fragile. We might update to a newer compiler which will bump ABI number in the library name.
Even trickier, we might have a transitional period with two different compilers.

self.response_file.unlink(). Similar with zip_with_signed_files.

Just else. Then it will deal with links (junctions on Windows) and sockets and yadi yadi yadi.

Why not to pass as a configuration object?

pathlib-ify.

List of patterns seems to be duplicated. Move to configuration?