[BUG]: can not start application with ddtrace.auto

[dawncold]

Tracer Version(s)

not sure

Python Version(s)

3.11.13

Pip Version(s)

not sure

Bug Report

this is azure function app environment (EP1) with the following datadog related variables

it does not work with 4.10.6, but 4.10.5 works fine.

Traceback (most recent call last):
  File "/home/site/wwwroot/function_app.py", line 2, in <module>
    import ddtrace.auto  # this import is required
    ^^^^^^^^^^^^^^^^^^^
  File "/home/site/wwwroot/.python_packages/lib/site-packages/ddtrace/__init__.py", line 9, in <module>
    from ._logger import configure_ddtrace_logger
  File "/home/site/wwwroot/.python_packages/lib/site-packages/ddtrace/_logger.py", line 6, in <module>
    from ddtrace.internal.telemetry import get_config
  File "/home/site/wwwroot/.python_packages/lib/site-packages/ddtrace/internal/telemetry/__init__.py", line 118, in <module>
    from .writer import TelemetryWriter
  File "/home/site/wwwroot/.python_packages/lib/site-packages/ddtrace/internal/telemetry/writer.py", line 29, in <module>
    from ..utils.version import version as tracer_version
  File "/home/site/wwwroot/.python_packages/lib/site-packages/ddtrace/internal/utils/version.py", line 80, in <module>
    version = _pep440_to_semver()
              ^^^^^^^^^^^^^^^^^^^
  File "/home/site/wwwroot/.python_packages/lib/site-packages/ddtrace/internal/utils/version.py", line 73, in _pep440_to_semver
    if "rc" in tracer_version and "-rc" not in tracer_version:
       ^^^^^^^^^^^^^^^^^^^^^^
TypeError: argument of type 'NoneType' is not iterable

here is what i have in site-packages

root@e40b0bae83fa:~/site/wwwroot# ls -adl .python_packages/lib/site-packages/ddtrace*
drwxrwxrwx 2 nobody nogroup 0 Jun 30 08:28 .python_packages/lib/site-packages/ddtrace
drwxrwxrwx 2 nobody nogroup 0 Jun 29 09:53 .python_packages/lib/site-packages/ddtrace-4.10.5.dist-info
drwxrwxrwx 2 nobody nogroup 0 Jun 30 08:28 .python_packages/lib/site-packages/ddtrace-4.10.6.dist-info

here is what I got from importlib.metadata.version('ddtrace')

root@e40b0bae83fa:~/site/wwwroot# python
Python 3.11.13 (main, Jul 22 2025, 01:43:09) [GCC 10.2.1 20210110] on linux
Type "help", "copyright", "credits" or "license" for more information.
>>> import importlib.metadata
>>> importlib.metadata.packages_distributions().get('ddtrace')
['ddtrace']
>>> 
>>> 
>>> importlib.metadata.version('ddtrace')
>>> importlib.metadata.version('ddtrace') is None
True
>>> 

after I moved the 4.10.5-dist-info dir to /tmp, i can get the ddtrace version

root@d4e02ea51b25:~/site/wwwroot/.python_packages/lib/site-packages# mv ddtrace-4.10.5.dist-info/ /tmp
root@d4e02ea51b25:~/site/wwwroot/.python_packages/lib/site-packages# cd 
root@d4e02ea51b25:~# cd /home/site/wwwroot/
root@d4e02ea51b25:~/site/wwwroot# python
Python 3.11.13 (main, Jul 22 2025, 01:43:09) [GCC 10.2.1 20210110] on linux
Type "help", "copyright", "credits" or "license" for more information.
>>> import importlib.metadata
>>> importlib.metadata.version('ddtrace')
'4.10.6'
>>> 

I verified the ddtrace(4.10.6) with the ddtrace-4.10.5.dist-info dir, it's None for the importlib.metadata.version('ddtrace'), it seems there is a verification between code and metadata. this will return 4.10.5 on my local machine, it's a python 3.11.5

Reproduction Code

No response

Error Logs

No response

Libraries in Use

No response

Operating System

No response

[Boksam]

I tried to reproduce this on Azure Function Apps, but I couldn't reproduce it.

What I did:

1. Installed ddtrace==4.10.5 and published it.
2. Bumped ddtrace to 4.10.6 in requirements.txt and republished.
3. Verified site-packages and importlib.metadata.version('ddtrace') again:

root@a021770d821b:~/site/wwwroot/.python_packages/lib/site-packages# ls
__pycache__                       bytecode-0.18.1.dist-info  markupsafe                          typing_extensions.py      wrapt-stubs
azure                             ddtrace                    markupsafe-3.0.3.dist-info          werkzeug
azure_functions-1.24.0.dist-info  ddtrace-4.10.6.dist-info   opentelemetry                       werkzeug-3.1.8.dist-info
bin                               envier                     opentelemetry_api-1.43.0.dist-info  wrapt
bytecode                          envier-0.6.1.dist-info     typing_extensions-4.16.0.dist-info  wrapt-2.2.2.dist-info

root@a021770d821b:~/site/wwwroot/.python_packages/lib/site-packages# python
Python 3.11.13 (main, Jul 22 2025, 01:43:09) [GCC 10.2.1 20210110] on linux
Type "help", "copyright", "credits" or "license" for more information.
>>> import importlib.metadata
>>> importlib.metadata.packages_distributions().get('ddtrace')
['ddtrace', 'ddtrace']
>>> importlib.metadata.version('ddtrace')
'4.10.6'                                           

On my side, only a single ddtrace-*.dist-info directory was present after republish and import ddtrace.auto did not crash.

Could you help me reproduce the same conditions that led to the stale ddtrace-4.10.5.dist-info and ddtrace-4.10.6.dist-info coexisting on your side?
Specifically:

• Did the deployment use Oryx remote build (SCM_DO_BUILD_DURING_DEPLOYMENT / ENABLE_ORYX_BUILD), or was the package pre-built locally and zip-deployed?
• Which deployment method/tooling was used?