502 Bad Gateway on Roon Download Page for Mac OS (ref#6FQUV4)

Hi! What’s not quite right with Roon?

· None of the above quite fits

None of the above quite fits

· None of these quite match

Tell us what's going on

· I am receiving 502 Bad Gateway when trying to access downloads on your website download page. I need to reinstall my Roon application on Mac OS due to a corrupted database. Please email me the .dmg if this is possible.

Tell us about your home network

· not relevant

The Downloads are working. Did you use this page?

Yes that was exactly where I went. I have tried Chrome and Safari. Have you tried it yourself ?

Hello @John_Tarry

We can confirm that the link is working properly on our end.

Would you kindly clarify the language setting on the Download Roon - Mac, Windows, iOS & Android Apps | Free Download ?

Thank you for confirmation it works

The error message I see happens when I click the link on the Roon website marked ‘install Roon for Mac’. That returns the gateway error. I am at this point logged in to my account.

I hope this information is helpful.

The language on the free trial page is English.

I have have investigated further.

The main Roon website works normally. The problem only occurs when I attempt to download the installer.

When I click the download link I receive SSL certificate warnings followed by HTTP 502 Bad Gateway or HTTP 500 Internal Server Error messages.

I have tested this on two completely independent internet connections:

  • Home broadband

  • iPhone 5G Personal Hotspot

The behaviour is identical on both connections.

DNS resolves download.roonlabs.net successfully.

Running:

curl -Iv https://download.roonlabs.net

shows that the TCP connection succeeds, but the TLS handshake fails with:

SSL certificate problem: self signed certificate

Running:

openssl s_client -connect download.roonlabs.net:443 -servername download.roonlabs.net | openssl x509 -noout -subject -issuer

returns:

Subject:
O = Whalebone
CN = sad.certificate.that.cannot.be.valid.com

Issuer:
O = Whalebone
CN = sad.certificate.that.cannot.be.valid.com

I also checked my macOS Keychain using:

security find-certificate -a | grep -i Whalebone

and could not find a Whalebone certificate installed.

Can a member of the Roon team please confirm whether this is expected behaviour, or whether there is an issue with the download endpoint or its TLS certificate?

Hello @John_Tarry,

Thank you for the excellent diagnostic work - this is very helpful.

The certificate you are seeing (sad.certificate.that.cannot.be.valid.com issued by Whalebone) is not ours. Whalebone is a DNS-based security filtering service used by some ISPs to intercept and inspect HTTPS traffic. It is sitting between your browser and our download server, substituting its own self-signed certificate in place of ours - which is why the TLS handshake fails and you get the 502/500 errors.

The fact that this happens on both your home broadband and your iPhone 5G hotspot suggests Whalebone is enabled at the ISP or carrier level on both connections rather than on your local network.

To work around this:

  1. Try downloading using a VPN - this bypasses your ISP’s traffic inspection entirely
  2. Alternatively, you can download Roon directly from our downloads page at roonlabs.com/downloads using a different network (e.g. a friend’s WiFi)
  3. Contact your ISP and ask them to whitelist download.roonlabs.net in their Whalebone configuration

Our download endpoint is functioning correctly - the issue is specific to how your ISP is handling the connection.

Hi

Many thanks. Purely out of interest, have you seen other customers receiving the specific Whalebone certificate fordownload.roonlabs.net, or is this the first report?

I will try a VPN, or have someone download it for me.

Hi @John_Tarry,

I don’t believe we’ve seen this specific error trace in the past, although it could be possible.

None the less, let us know how the above goes. Thank you!

I used a VPN downloaded and re installed from scratch. Then loaded my backup from a day or two ago. So now I’m thankfully back to where I was.

Note to self and other users - keep an eye on free disk space going forward.

You can close this now . Thanks for your assistance.