I’ve seen this same issue asked about in different ways in the PLEX Forums and to my knowledge it still is not resolved. Years ago SYNC worked great on PLEX devices, but then they moved to DOWNLOADS and it has been a total mess ever since. I keep thinking an update on an iOS device or on the Server might resolve matters, but the problem has persisted for years now. What am I missing and how is it PLEX isn’t addressing this at all. I would be surprised to hear of anyone that has this working on iOS without employing some kind of weird workaround.
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I fixed it by using VLC 
Yea, I would hate to abandon PLEX, but they sort of force me to when one of the main reasons I purchased it was to take advantage of offline files.
For me, the benefit of PLEX is to stream anywhere to my phone or Roku at any location. Downloads are rare for me, which is why the few time I do d/l, I just use VLC.
Unfortunately, this is the way of Plex and this is only one instance of many things they’re aware of but refuse to do anything about.
Sure, that is your use case, but for many, their use case was to have the benefits you reflected above as well as downloads. The crazy part is, PLEX had this working just fine for some time for almost everyone. Sure, there were exceptions, but now it is failure for everyone. It isn’t like the media it was leveraging changed dramatically overnight. The video files are the same back then as they are now. I don’t know how they can’t just add in the same code that was working in the past. Most developers, big and small, would never dream of having such a failed portion of their program and then allow it to exist for years. They would revert back to what worked or at least better than losing a major function altogether.
Also, VLC isn’t really an “apples to apples” comparison to what PLEX had. I don’t think VLC does any conversion. This was one of the best features about PLEX. If you wanted to download a local file on to your iPhone, you could ask PLEX to convert it down to a much lower resolution. This way it saved a huge amount of space on your iPhone and you certainly didn’t need all the resolution because of how small the screen was compared to your TV or computer display. Ironically, I also found stability issues with VLC. VLC on my desktop computers is rock stable, but when trying to download something with VLC on my iPhone it just continues to crash for some reason. Basically, it isn’t a viable alternative for many reasons.
I agree with you, but I’ve given up on Plex fixing this. 
Man…you are so right…so disappointing to see a company so blatantly ignore the feedback of its customers. I could possibly even understand if they offered a reasonable explanation, but I’m not sure I’ve heard it.
This is not what I want to hear after coming back to Plex and purchasing a plex pass!
have they acknowledged that downloads do not work?
Oh, they definitely know about the issue. As I look through the forum, it has been reported over and over again. Like @Tony_T said, they just seem to have given up on resolving it or even providing updates on what they are doing to resolve the issue.
If you look a few posts lower in this very forum, you’ll see another post regarding the very same issues with DOWNLOADS. After reading it, it appears that refunds are being provided with some success so that might be an avenue. I’m not quite sure how they are going to prorate lifetime members though. Do they somehow know when I’m going to die? 
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