Feed Causes "PDB does not match image." Error

We have several feeds in our ProGet server (one for each business unit) and we've had historical problems with debugging NuGet packages from all the feeds. After taking over the project, I was able to get one feed working correctly where symbols files are correctly indexed and source files are being downloaded without any issue.

Taking the exact same steps I created for that feed, I moved onto the next feed and I'm still running into issues. Visual Studio correctly downloads the symbols file (verified this with Fiddler) and I see in the symbols cache the PDB file. When I debug, however, Visual Studio 2013 gives me a "PDB does not match image." When I look at the symbol load information, I that it went to the feed correct feed and downloaded the correct PDB file.

Here is where it gets interesting. I take the exact same NuGet package and push into a different feed that is currently working, I have no issues debugging with symbols.

Here are the settings for the feed that works:

Feed Type: NuGet
Disk path override: Default
Buil import drop path: Default
NuGet API key: Default
Options:

Active -> Checked

Cache packages from this feed's connectors -> Checked

Enable symbol and source server for this feed -> Checked

Automatically strip PDB files when downloading packages -> Checked

Here are the settings for the feed that does not work:

Feed Type: NuGet
Disk path override: Default
Buil import drop path: Default
NuGet API key: Default
Options:

Active -> Checked

Cache packages from this feed's connectors -> Checked

Enable symbol and source server for this feed -> Checked

Automatically strip PDB files when downloading packages -> Checked

As you can see, they are identical. The only difference is the broken feed does have connectors setup for it. The ProGet UI does not show any indexing errors (a few JSON errors for an NPM feed I'm not currently working on) and nothing shows up in the event viewer. If you have an suggestions or thoughts on what the issue might be or a way to get more details to find the issue, it would be most appreciative.

Thanks in advance for your help.

Product: ProGet
Version: 3.5.5

There have been a few modifications since the version you're running to the symbol/source server that will likely fix the behavior you're experiencing.

There is one issue in particular that involved reverse sorting of the symbol file's age value that I believe is related. When you upgrade to the latest, it should resolve the issues.