Can't sync to two devices

Plex Media Server Desktops & Laptops
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Server Version#:1.21.1.3830

Hello,

I’ve got Plex Media Server set up on my MacBook.
My main admin account is for me, syncing to my iPhone and I’ve got a managed user for my fiancee syncing to her iPhone. So it’s just two users, two devices, one device per user.

Syncing for me works fine, but I have a lot of trouble syncing to my fiancees phone. Most of the time the sync queue will sit with the spinning circle, or all items will be stuck at Waiting to convert / download.

I’ve tried everything, including a factory reset of my laptop and signing up for a new Plex account. I’ve been trying to fix this for months.

Any ideas please?

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