[Bug]: dstack `uv` installation fails due to resolution of old pyopenssl

[r4victor]

Steps to reproduce

1. Install dstack with uv: uv pip install 'dstack[all]==0.19.9'
2. dstack server raises and error: AttributeError: module 'lib' has no attribute 'X509_V_FLAG_NOTIFY_POLICY'. Did you mean: 'X509_V_FLAG_EXPLICIT_POLICY'?

This is specific only to uv dependency resolution. Installing dstack with pip works fine.

Actual behaviour

This caused by the old pyopenssl being installed:

├── oci v2.152.0 (extra: all)
│   ├── certifi v2025.4.26
│   ├── circuitbreaker v2.1.3
│   ├── cryptography v45.0.2 (*)
│   ├── pyopenssl v22.0.0
│   │   └── cryptography v45.0.2 (*)
│   ├── python-dateutil v2.9.0.post0 (*)
│   └── pytz v2025.2

The underlying cause seems to be that oci puts an upper limit "pyOpenSSL>=17.5.0,<25.0.0" (https://github.com/oracle/oci-python-sdk/blob/fbefeef0d78a10b38976ddc1c0ea067e0508b0e1/pyproject.toml#L32C5-L32C33). The new release cryptography v45.0.2 is not compatible with the latest pyopenssl v24.3.0 supported by oci. So uv falls back to old pyopenssl v22.0.0, which fails with an exception.

Expected behaviour

No response

dstack version

0.19.9 (and master)

Server logs

Traceback (most recent call last):
  File "/Users/r4victor/Projects/dstack/venvt/bin/dstack", line 4, in <module>
    from dstack._internal.cli.main import main
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/_internal/cli/main.py", line 7, in <module>
    from dstack._internal.cli.commands.apply import ApplyCommand
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/_internal/cli/commands/__init__.py", line 8, in <module>
    from dstack._internal.cli.services.completion import ProjectNameCompleter
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/_internal/cli/services/completion.py", line 11, in <module>
    from dstack.api import Client
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/api/__init__.py", line 23, in <module>
    from dstack.api._public import BackendCollection, Client, RepoCollection, RunCollection
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/api/_public/__init__.py", line 3, in <module>
    import dstack._internal.core.services.api_client as api_client_service
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/_internal/core/services/api_client.py", line 5, in <module>
    from dstack.api.server import APIClient
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/api/server/__init__.py", line 16, in <module>
    from dstack.api.server._backends import BackendsAPIClient
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/api/server/_backends.py", line 5, in <module>
    from dstack._internal.core.backends.models import (
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/_internal/core/backends/__init__.py", line 11, in <module>
    from dstack._internal.core.backends.configurators import list_available_configurator_classes
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/_internal/core/backends/configurators.py", line 10, in <module>
    from dstack._internal.core.backends.aws.configurator import AWSConfigurator
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/dstack/_internal/core/backends/aws/configurator.py", line 5, in <module>
    from boto3.session import Session
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/boto3/__init__.py", line 17, in <module>
    from boto3.session import Session
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/boto3/session.py", line 17, in <module>
    import botocore.session
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/session.py", line 26, in <module>
    import botocore.client
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/client.py", line 15, in <module>
    from botocore import waiter, xform_name
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/waiter.py", line 20, in <module>
    from botocore.docs.docstring import WaiterDocstring
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/docs/__init__.py", line 15, in <module>
    from botocore.docs.service import ServiceDocumenter
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/docs/service.py", line 14, in <module>
    from botocore.docs.client import (
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/docs/client.py", line 18, in <module>
    from botocore.docs.example import ResponseExampleDocumenter
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/docs/example.py", line 13, in <module>
    from botocore.docs.shape import ShapeDocumenter
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/docs/shape.py", line 19, in <module>
    from botocore.utils import is_json_value_header
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/utils.py", line 39, in <module>
    import botocore.httpsession
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/botocore/httpsession.py", line 45, in <module>
    from urllib3.contrib.pyopenssl import (
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/urllib3/contrib/pyopenssl.py", line 43, in <module>
    import OpenSSL.SSL  # type: ignore[import-untyped]
    ^^^^^^^^^^^^^^^^^^
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/OpenSSL/__init__.py", line 8, in <module>
    from OpenSSL import crypto, SSL
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/OpenSSL/crypto.py", line 1570, in <module>
    class X509StoreFlags(object):
  File "/Users/r4victor/Projects/dstack/venvt/lib/python3.12/site-packages/OpenSSL/crypto.py", line 1589, in X509StoreFlags
    NOTIFY_POLICY = _lib.X509_V_FLAG_NOTIFY_POLICY
                    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
AttributeError: module 'lib' has no attribute 'X509_V_FLAG_NOTIFY_POLICY'. Did you mean: 'X509_V_FLAG_EXPLICIT_POLICY'?

Additional information

No response

[r4victor]

Workaround for installing dstack<=0.19.9 with uv:

uv pip install 'pyopenssl>=23.2.0' 'oci>=2.150.0' 'dstack[all]==0.19.9'

[r4victor]

Fixed with 0.19.10