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C# and IIS - SSL dropping connections, fine over HTTP

In a testing environment, I self-signed a cert and installed it on a web site in IIS 6. This is using .NET 2.0. Cert seems fine (minus the fact that client services don't fully trust it as one would expect). I can do whatever I want to by hitting the site locally from the server on HTTPS or HTTP.

The problem is coming in when accessing this site remotely. If the page has an exception on it, the connection drops . Not return an error, but just flat-out drops, where the browser says it couldn't find the site (this is after it churns for a few seconds, where I can see TCP traffic from the client IP coming in).

The interesting part is that I can create a blank ASPX page, with nothing on it, and it's fine over HTTPS. But the minute I put throw new Exception(); on the page, it goes back to dropping. By the way, it seems to act completely normal if I hit the same page using HTTP instead.

So I'm a bit stuck. Anyone seen something like this?

My first inclination is to go after the proxy/firewall rules between my remote client machine and the server, but I want to make sure it's not something I could fix before I bug other teams.

EDIT ...looks to be a firewall whitelisting problem. Others on my subnet have the same problem, but people in other locations can hit it just fine.

This is not a proxy or firewall issue, because the Yellow Screen Of Death is just text which transmits through any firewall just fine. Here are a couple things that I would try first.

  1. Make sure that the fact that you are using HTTPS isn't the root cause of the problem, such as the problem isn't caused in your program, by handling HTTPS. Such as some special handling of Error code.

  2. Create a new cert and see if the same issues occures.

  3. Try to reproduce this issue on another machine, it could just be a configuration issue.

  4. Try getting a real cert from GoDaddy, they are only 29.99.

That is all that I can come up with right now. One thing that you didn't mention was which version of IIS you were using, which will be helpful.

Have your thrown the exception and then tested the page using regular HTTP? Is the same thing happening, or does it only happen if you throw an exception and access it using HTTPS?

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