Imported from this comment #9555 (comment)

This is how things currently work right now:

• Android: Publishing while offline and retrying will lead to the post being uploaded and published
• iOS: Publishing while offline and retrying will lead to the post being uploaded as a draft

I'm not sure which one is right but Android's behavior is scary for me as a user.

Decision

As the user intended to publish the post, retrying should also publish the post
To clarify, we should amend the error state to mention posting. Error message should say "Could not upload media. Post not published." Then its clear that retry relates to posting, not just media.
To make this work we need to differentiate the error state in publishing/saving/scheduling scenarios.

1. User publishes and media upload error (use case in this issue)
   Error Message: "Could not upload media. Post not published."
   Action and behavior: Retry. Retrying publishes the post if media uploads successfully

2. User schedules and media upload error (scheduling rather than publishing)
   Error Message: "Could not upload media. Post not scheduled."
   Action and behavior: Retry. Retrying schedules the post if media uploads successfully

3. User saves and media upload error (user did not intend to publish)
   Error Message: "Could not upload media."
   Action and behavior: Retry. Retrying only retries uploading the media as the user has not changed the post state

Related Issues

wordpress-mobile/WordPress-iOS#11420