How can I resolve the tailscale HTTPS error "SSL_ERROR_RX_RECORD_TOO_LONG"

Question

I just setup MagicDNS and HTTPS on my tailscale account. Then I ssh'ed into my nas and issued a tls certificate with

sudo tailscale cert "machinename.tailnetalias.ts.net"

Response was:

Wrote private key to machinename.tailnetalias.ts.net.crt
Wrote private key to machinename.tailnetalias.ts.net.key

Now when I try to access the web interface of my nas via https:// in a browser, I get an error. Firefox for example says "SSL_ERROR_RX_RECORD_TOO_LONG".

What can I do about this?

Answer 1

The tailscale cert command doesn't know where the certificate files should be installed (it doesn't even know what you were planning to do with them). So the first question is: did you move those files somewhere to install them? If not, the certificate getting SSL_ERROR_RX_RECORD_TOO_LONG is likely some other cert file which was already there.

If the tailscale cert files did get installed, I think the next step would be to click on the lock icon in Firefox on the left side of the URL. It will have a bunch of information about the TLS connection, in particular:

• if the certificate had something wrong with it
• in the Technical Details section, it will say what TLS version was used (SSL2, SSL3, TLS1.0, TLS1.1, TLS1.2, TLS1.3).

The SSL_ERROR_RX_RECORD_TOO_LONG error was mostly a problem in older versions of TLS like 1.1 and before. If the TLS version is one of those, it may be necessary to figure out how to get the NAS to stop offering the older versions and only offer 1.2 and 1.3.