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Use an older Python for cqlsh. The maintainer's fix: downgrade to Python 3.11 with brew uninstall --ignore-dependencies python && brew install python@3.11 (the reporter also confirmed the macOS builtin python interpreter worked). The root cause is the cqlsh bundle's incompatibility with Python 3.12, not your Astra setup. In Astra CLI v1.x and later this is handled automatically: the CLI patches the cqlsh runner script to try python3.11, python3.10, python3.9 before the default python3, so upgrading the CLI is the durable fix. Source: https://github.com/datastax/astra-cli/issues/225