Runtime pip installs fail under PEP 668 and what it revealed about SQLAlchemy flushes

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A developer's concurrency reproduction script for an SQLAlchemy autoflush deadlock tried to install a missing dependency at runtime. On a modern Linux system, the install was blocked by PEP 668's externally-managed-environment marker, aborting the script before any database operations ran. The authors argue the failure stemmed from mixing application execution with dependency provisioning rather than from missing packages or bad syntax. PEP 668 lets operating systems mark system Python as externally managed to prevent package conflicts. The post-mortem concludes that dependencies should be declared and installed ahead of time, keeping reproduction scripts focused on the ORM behavior under study.

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