Bug: If a media asset got stuck in the 'processing' state during upload, then it would stay stuck forever and the file couldn't be uploaded again later. Fix: Mark stuck assets as failed before raising the "Upload failed" error. Once the asset is marked as failed, it can be uploaded again later. Also, only wait for assets to finish processing if they were uploaded less than 5 minutes ago. If a processing asset is more than 5 minutes old, consider it stuck and mark it as failed immediately. Assets getting stuck in the processing state is a 'this should never happen' error. Normally if any kind of exception is raised while uploading the asset, the asset will be set to the 'failed' state. The only way an asset can get stuck is if it fails and the exception handler doesn't run, or the exception handler itself fails. This might happen if the process is unexpectedly killed, or possibly if the HTTP request times out and a TimeoutError is raised at an inopportune time. See below for discussion of issues with Timeout. [1]: https://vaneyckt.io/posts/the_disaster_that_is_rubys_timeout_method/ [2]: https://jvns.ca/blog/2015/11/27/why-rubys-timeout-is-dangerous-and-thread-dot-raise-is-terrifying/ [3]: https://adamhooper.medium.com/in-ruby-dont-use-timeout-77d9d4e5a001 [4]: https://ruby-doc.org/core-3.0.2/Thread.html#method-c-handle_interrupt-label-Guarding+from+Timeout-3A-3AError