Images uploading but not displaying in Media Gallery

I’ve been several extremely frustrating problems uploading images.

1. Images appear to be uploading but are not displaying in the Media Gallery. I can see the images created in my file directory through my host, but they do not show up in WordPress.This only happens with vertically oriented images.

Getting “HHTP error” at lest half the time when uploading images.
Thank you for any assistance!