Thumbnail Previews (Roku & iOS) not displaying on 1080P HEVC content / 720P HEVC content and 480P content works

In the Media Info for these items, I assume that “Indexes sd” isn’t present?

Yes, Plex can generate video preview thumbnails for HEVC content.

It does so by extracting keyframes from the video. There are a few scenarios where unusually encoded videos can prevent this process from succeeding.

If you’d like to share a sample file with me, I can confirm or deny that it’s related to the file encoding.

Alternatively, you can try changing a hidden Plex setting. This may slow down all Video Preview Thumbnail generation, but it’s also more reliable.

GenerateBIFKeyframesOnly="0"

Instructions to add hidden settings:
Advanced, Hidden Server Settings | Plex Support

Here’s an alternative way to set the value (customize this for GenerateBIFKeyframesOnly="0"):

Big Media folder? Make smaller video preview thumbnails! - #6 by Volts

One related link & discussion; it includes links to others:

Video Preview Thumbnail Generation Fails for Some Items - #48 by Volts