Matt - 2014-08-14

I'm using cntlm 0.92.3 on OS X (installed via Homebrew). Everything works except Adobe's installer/updater program "Adobe Application Manager". This is a standard component Adobe uses with their Creative Suite/Creative Cloud applications. If you're packaging Adobe programs for enterprise deployment, Application Manager downloads full application installers. It also is a central updater utility for all your installed Adobe applications.

When using cntlm, Application Manager is able to download things like lists of available updates. When it downloads the actual installer files through cntlm, it complains that the files failed validation and will not use them. If I route directly through our proxy, everything's fine. I'm reasonably comfortable with Wireshark, but the downloads are all via HTTPS and I can't really see what's going on. A friend speculated that the problem might be related to range headers and partial downloads, because he's had trouble with things like that in other proxy environments. I can tell that even when the errors occur, Application Manager is definitely downloading a bunch of data.

Any ideas how to fix this, or to troubleshoot further?