Indexing stuck in loop of failures, with no explanation

When using Cursor with a remote SSH project (basically running a Docker dev container on a Mac) - Indexing hangs and fails with no clear error. it takes deleting the index and re-computing the index multiple times until it can complete indexing.
Logs simply say Bad unexpected error on random files.

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:white_check_mark: Checked the forum for similar cases - found none
:counterclockwise_arrows_button: Unknown how to reproduce
:laptop: Running Cursor 0.48.7 on Mac OS Sequoia

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