ChatGPT Work with GPT-6 Astra was tasked with structuring a real-world archive of 1,225 files across 97 folders, protecting existing numbering, assigning consecutive numbers to previously unnumbered records, identifying duplicates, and building a verifiable central index. The long-running task became a real-world test of autonomous work, persistent checkpoints, interruption recovery, and state transparency.
I wanted to test GPT-6 Astra on a real task rather than a prepared demo. The challenge was to structure a real-world archive of 1,225 files across 97 folders, preserve existing numbering, assign missing numbers, identify duplicates without deleting them, and build a verifiable central index.
The most interesting part was not just the final result, but what happened during the long-running process. Interruptions, conflicting progress states, temporary results that were no longer available after a restart, and eventually a maximum conversation length made persistent checkpoints essential.
After introducing a persistent checkpoint, the workflow became much more reliable to resume. The project therefore became both an archive workflow and a practical test of autonomous work, recovery, and state transparency with GPT-6 Astra.
The submission documents both what worked and what did not.