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I believe this client was on Ubuntu at the time, and a physical machine. I created a Server 2008 R2 VM and it has worked perfectly since. Somewhere along the line the Ubuntu instance just got hosed.

Greetings, This morning I noticed my downloads were failing and came to find that I was getting this error for both the newshosting and easynews servers (partner account for easynews). [Errno 10061] Failed to connect: Server news.newshosting.com uses an untrusted certificate [[SSL: CERTIFICATE_VERIF...