Why is this no longer working properly… It is seriously unnerving…
Same here, had to remove the entire plex app just to remove a few old downloads and after reinstall no matter what I do nothing syncs to my ipad. 
Recently I’m having same problem. I’ve been using the Plex player new Download feature and it was working for me last month, but now the new Download feature won’t work at all. I always update to latest software, so this change feels like a newly introduced bug. If I switch back to the old Sync method of downloading, it works fine (although I lose playlist support).
Plex Server Version 1.24.2.4973
Plex Player Version iOS 7.23 (deleted and re-installed)
iOS 14.8
I found a workaround to the new Download feature not working. If I start the download in new Download mode it won’t complete…it just stays at 0%. While it’s stuck in 0% and not downloading, I can go to Settings > Downloads and disable new Downloads (enable old Sync). Then the download proceeds. Once complete this new download doesn’t show up in Sync area. When I go back to Settings > Downloads and re-enable new Downloads, then the content is now available in Downloads. I’m hoping a new iOS Plex Player version will fix this behavior.
Plex Server Version 1.24.2.4973
Plex Player Version iOS 7.23 (deleted and re-installed)
iOS 14.8
Similar problem with download with a few extra data points. I tried bermenfam151’s idea, but didn’t work for me.
I used to use Sync with no problem. I switched to download, and no data is downloaded, even after sitting for hours
I switch to Cellular, and the download occurs very fast (about 10 seconds).
I thought this might be a network problem, but interestingly, I can download on the Mac when connect to the same Wifi as the iPhone. The Mac works, but the iPhone doesn’t
Configurations:
iPhone x 14.8 (and same problem on 14.7.1)
IOS Plex Player Version 7.23 (deleted and reinstalled)
Mac OS Big Sur 11.6
Mac Plex player Version - 1.35.1.2632-c6783c78
DS1019 Synology DiskStation Plex server 1.24.3.5033-6000
Both iPhone X and Mac connect to the same Wifi Synology router.
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Try going here on plex web on your host computer.
Top right account icon>users and sharing
On the left side click conversations under status.
Then click resume.
This was my issue after it not working for months.
Ah…my workaround from Sept is no longer working. Now I can’t seem to get any downloads to work on my iPhone, either old Sync or new Downloads. I’ve tried completely deleting PlexApp on my iPhone, deleting the device from Plex Web and then re-installing everything. When I go to download content, it stays at 0%.
Plex Server Version 1.24.5.5173
Plex Player Version iOS 7.24.1 (deleted and re-installed)
iOS 15.0.2
I’m attaching my Plex server logs. Any idea what is going on?
Plex Media Server Logs_2021-11-02_11-10-29.zip (3.0 MB)
I’ve got a Chromebook running Android apps and the Plex downloads run just fine. My download problems appear to be limited to my iPhone 12Pro.
Plex Server Version 1.24.5.5173
Plex Player Version Android 8.25.28703
ChromeOS 94.0.4606.104
I figured it out! Nothing to do with my iPhone or Plex app. I found some other help topics talking about DNS bindings, so I started investigating my network router configuration. Nothing there, but I am using OpenDNS for my Internet filtering. When I pulled up my blocked list on OpenDNS, I saw traffic from ‘plex.direct’ was getting blocked. In OpenDNS > Settings > Web Content Filtering I added ‘plex.direct’ to “Never Block” and applied. After a few minutes, my Plex downloads started working on my iPhone. What a pain, but I’m glad it’s finally working!
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