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I have posted the same inquiry to the Jetpack subreddit. It’s a very tiny subreddit with small membership so I am posting here to the WordPress community as well.
When using the Jetpack app on iOS, New images uploaded through media upload just fine – but new media uploaded while creating a new post always fail.
The weird thing, though, the failed image that did not get uploaded while creating a new post does show up in the media uploads section of Jetpack along with a failed version.
Why is this?
Is this a common occurrence?
Is there a straightforward solution?
It could be a bug in their app. I would report this to the link/email in their App Store listing (most apps usually have a way to report issues). I would personally just use the dashboard in the browser. wp-admin is responsive and everything works as it should, even though it doesn’t look as nice as the native app.