tomsonoda
The concept of per-user key wrapping is interesting.
I learned this the hard way... just because a wrapped key exists on the server doesn't guarantee the recipient can actually unwrap it—for instance, if the recipient's identity key has changed due to a re-installation. Implementing a mechanism to verify successful decryption on the client side before discarding the old key helped prevent situations where users would lose access to their own data.
EXIF Orientation: If you decode an image without applying the orientation information, the resulting embeddings will be calculated based on the rotated image. CLIP is surprisingly sensitive to this, and OCR generally fails to work on text rotated by 90 degrees.
1. When a new client joins but fails to retrieve the workspace key (due to temporary network issues or a 404 error from the server, for example), does it ever generate a new key locally? We encountered exactly this scenario: a device "helpfully" created its own key and encrypted data with it, rendering the message unreadable to other members (without any error notification). We ended up changing the server behavior so that instead of returning a "key missing" response, it signals that the key exists and the client should wait for it.
2. How do you handle key revocation? If you invite someone and later remove them, do you rotate (update) the workspace key and re-wrap it for the remaining members, or does the old key still allow access to past content?