Downloaded songs disappear

Hello,
Songs that I have purchased from iTunes and downloaded directly to me my iPhone stop working after one play. When I plug my phone into my Mac, open iTunes, and view "On This iPhone", I see that these unplayable songs are listed in grey with dotted circles on the left. They are also already loaded onto my Mac and play just fine from my computer.
When I go back to my iPhone, the Music app shows an icon next to these songs so that I can re-download them. However, I can't actually re-download them from here - I see a red circle for a moment and then the download icon again.
I can, however, go to the iTunes app on my iPhone and re-download them again there, by going to Puchased/Not On This iPhone.
However, after one play, they go back to the same state.
I've tried to get them to sync instead from iTunes on my Mac and they won't. I've modified the songs so they seem new and they won't sync to the phone.
Thanks in advance for any assistance,
Jimmy
NOTE: I have a huge database of music and don't want to spend hours re-syncing them to my phone

- If you want support from Spotify, you need to get in touch with the support team directly using the online contact form and they will be able to lend a hand. The Spotify community is not an official support channel, it has been set up as a place for user-user help. I would also ask that you try and keep the language respectful here on the community, we are just here to help. Also "begging for money" is a ridiculous thing to say, you pay for a service they don't beg you for money. If you don't like it, you can walk away and they will never bother you again (unlike people who beg for things).
If you get an automated email reply back directing you to the community or help pages, you need to reply directly to that email (even if its from no-reply) and one of the customer services agents will get back to you as soon as possible.
Alternatively, if you prefer support via Twitter, please tweet @SpotifyCares and they will be more than happy to help.

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