I saw your tweet (
https://twitter.com/ViNull/status/288138271274442752). I can assure you the above answer is the correct diagnosis for the problem you are having.
I looked at the PowerPress code for a possible bug last night before I answered this reply. Here are more specifics so you understand what is happening. Consult an Internet Engineer for confirmation if you do not want accept my expertise on this matter.
PowerPress code uses the WordPress function wp_get_http_headers(), looking at WordPress source code, it will first use cURL library, if that's not enabled on your blog then it will try the fopen functions built into PHP. Either way, this is not my control. It appears WordPress is using the latest HTTP protocol 1.1. In most all cases, this is fine, but if the server it connects to only supports HTTP 1.0 then the server will report the HTTP error 505.
Now some details on the HTTP protocol. The most popular standard is HTTP/1.1, and all web servers support HTTP/1.0 (I Don't know of any web server that does not support 1.0 protocol at minimum). In the RFC for HTTP/1.0 and HTTP/1.1, the HTTP error code 505 is clearly documented, if you get a 505 error from a server, it means that server cannot handle the requested HTTP protocol. In English, if cURL or fopen in PHP use the newer (1.1) version of HTTP and the server doesn't accept it, it will return the 505 error. That is what you indicated above.
Keep in mind the HTTP/1.1 protocol is not new, it was released in 1999. But there are reasons for servers to downgrade themselves to HTTP 1.0, and that's something Microsoft Engineers of the cloud service you are using would be better to answer. My only guess is that once a file has bee in the cloud for more than x days the files are archived on servers that have some HTTP 1.1 features turned off to save on bandwidth costs.
HTTP/1.1 is very important for media and other large files, it includes options for getting extensive header information and more importantly, includes "byte serving" which is required for iTunes, among other applications/phones.
We do not recommend using cloud based services to host podcast media. A cloud storage service is not the same as CDN (Content Delivery Network), cloud services are not concerned about redistributing the files via the web, the primary concern is to store and backup your files that you put in such a service. In most cases, using cloud storage service as a CDN violates the terms of service. The only cloud storage service that I know of that will gladly allow you to host your files and serve them unlimited is Amazon S3, but that service you pay for your bandwidth you consume.