You can add your proxy into the local certs being used
Try setting the variable SSL_CERT_FILE to a file that includes your proxy
certificate.

Alvaro.


On Thu, Dec 14, 2017 at 2:44 PM, Alex Drawbond <[email protected]> wrote:

> Hello,
>
> I am trying to run:
> vagrant box update --box ubuntu/trusty64
>
> from a macOS machine running behind Websense. I am taking the following
> error:
>
> There was an error while downloading the metadata for this box.
> The error message is shown below:
> SSL certificate problem: unable to get local issuer certificate
> More details here: https://curl.haxx.se/docs/sslcerts.html
> curl performs SSL certificate verification by default, using a "bundle"
> of Certificate Authority (CA) public keys (CA certs). If the default
> bundle file isn't adequate, you can specify an alternate file using the
> --cacert option. If this HTTPS server uses a certificate signed by a CA
> represented in the bundle, the certificate verification probably failed due
> to a problem with the certificate (it might be expired, or the name might
> not match the domain name in the URL). If you'd like to turn off curl's
> verification of the certificate, use the -k (or --insecure) option.
> HTTPS-proxy has similar options --proxy-cacert and --proxy-insecure.
>
> We assume the issue is that Websense is terminating SSL, inspecting the
> traffic and then injecting it's own certificate before passing the traffic
> along. Websense's certificate isn't recognized by curl and rejected. Using
> the --insecure option does resolve the problem. I would prefer to not use
> --insecure, and adding Websense's cert to the list of trusted certs isn't
> an option either. What I can do is have IP's whitelisted in Websense so
> that their SSL isn't interfered with. I am having a hard time tracking down
> all the IP's Vagrant is hitting behind scenes, and was hoping there was
> some documentation somewhere detailing which IP's need to be whitelisted to
> work with Websense?
>
> Thanks,
> Alex
>
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-- 
Alvaro

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