A frustrating issue that we’ve run into at my organization is that iTunes doesn’t support LE. I’ve talked to them about this, and they have replied with:
Talking to a friend that works at Apple, the best way to fix this is to file bugs at https://bugreport.apple.com. To do this you need a developer account, but that’s free and easy to set up if you go to https://developer.apple.com. Each bug filed counts as a vote towards getting this fixed, so if you want this to work, please go file more bugs.
Here’s the bug I filed:
If you try to set up a podcast that is available on HTTPS it will only work if the HTTPS certificate was provided by one of a few special providers, as documented in the attached screenshot.
This list of providers does not include Let’s Encrypt, a fairly new provider of HTTPS certificates. This is frustrating because Let’s Encrypt is supported by all modern browsers and is a perfectly legitimate certificate. The only issue that we have run into using a certificate from Let’s Encrypt is that it cannot be used in iTunes.
Here is an example url that does not work:
Steps to Reproduce:
Try to set up a new podcast that is encrypted with a Let’s Encrypt certificate.
The iTunes backend should support the same truststore as Safari or as other browsers, including supporting Let’s Encrypt.
You get a curt and useless error message.