When uploading media fails, clicking on Retry button will upload the media and upload the post.
When uploading media fails, clicking on Retry button sometimes uploads the post, but the media are not uploaded. Actually it appears the media got uploaded, as they are displayed in the app, but the path to the file isn't correct -> it contains path to the local file eg. "/storage/emulated/...".

Emulator API 27
Possibly related to #9804.
Possibly related to https://github.com/wordpress-mobile/WordPress-Android/issues/9802
I spent way too much time trying to debug this :)
Some notes:
Theory: that bug can't happen now with #9859 merged because image ids are correctly associated to the failed upload post, so when we hit retry, media uploads are re-tried and the post upload will fail if the media aren't uploaded. This prevent a post to be published with failed media. Prior to #9859 it was possible because image ids were not correctly associated to the post in certain cases (multi selection in the editor).
I'm closing this ticket, but feel free to re-open.
This issue will get most probably fixed in https://github.com/wordpress-mobile/WordPress-Android/pull/10079#issuecomment-510037492