The issue here, IIUC is the fact that the CF cache is colo-local only (every CF data center has its

The issue here, IIUC is the fact that the CF cache is colo-local only (every CF data center has its own independent cache). Uploading a new picture and forcing cache to update does what you expect in the colo nearest to the uploader, but this change does not automatically propagate to other colos around the world. Omar’s solution works too, but since you’re already using Workers, check this out to see if it helps? https://developers.cloudflare.com/workers/learning/how-the-cache-works/#single-file-purge--assets-cached-by-a-worker

This also explains single-file purge: https://developers.cloudflare.com/cache/how-to/purge-cache/purge-by-single-file/
With purge by single-file, cached resources are immediately removed from the stored assets in your Content Delivery Network (CDN) across all data
How Workers interacts with the Cloudflare cache.
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