I like to use curl to find out the details of what is breaking.
This is the result of my testing using wireguard on macOS 10.15.3.
I connect wireguard via mobile data to my home router 172.16.4.1.
wireguard.
* Trying 93.184.216.34...
* TCP_NODELAY set
* Connected to example.com (93.184.216.34) port 443 (#0) * ALPN, offering http/1.1
* Cipher selection: ALL:!EXPORT:!EXPORT40:!EXPORT56:!aNULL:!LOW:!RC4:@STRENGTH
* successfully set certificate verify locations:
* CAfile: /opt/local/share/curl/curl-ca-bundle.crt
CApath: none
* TLSv1.2 (OUT), TLS header, Certificate Status (22):
* TLSv1.2 (OUT), TLS handshake, Client hello (1):
* TLSv1.2 (IN), TLS handshake, Server hello (2):
* TLSv1.2 (IN), TLS handshake, Certificate (11):
* TLSv1.2 (IN), TLS handshake, Server key exchange (12):
* TLSv1.2 (IN), TLS handshake, Server finished (14):
* TLSv1.2 (OUT), TLS handshake, Client key exchange (16):
* TLSv1.2 (OUT), TLS change cipher, Client hello (1):
* TLSv1.2 (OUT), TLS handshake, Finished (20):
* TLSv1.2 (IN), TLS change cipher, Client hello (1):
* TLSv1.2 (IN), TLS handshake, Finished (20):
* SSL connection using TLSv1.2 / ECDHE-RSA-AES128-GCM-SHA256
* ALPN, server accepted to use http/1.1
* Server certificate:
* subject: C=US; ST=California; L=Los Angeles; O=Internet Corporation for Assigned Names and Numbers; OU=Technology; CN=www.example.org * start date: Nov 28 00:00:00 2018 GMT
* expire date: Dec 2 12:00:00 2020 GMT
* issuer: C=US; O=DigiCert Inc; CN=DigiCert SHA2 Secure Server CA
* SSL certificate verify ok.
> GET / HTTP/1.1
> User-Agent: curl/7.60.0
> Accept: */*
>
< HTTP/1.1 200 OK
< Accept-Ranges: bytes
< Age: 485981
< Cache-Control: max-age=604800
< Content-Type: text/html; charset=UTF-8
< Date: Sun, 01 Mar 2020 08:36:35 GMT
< Etag: "3147526947"
< Expires: Sun, 08 Mar 2020 08:36:35 GMT
< Last-Modified: Thu, 17 Oct 2019 07:18:26 GMT
< Server: ECS (nyb/1D1E)
< Vary: Accept-Encoding
< X-Cache: HIT
< Content-Length: 1256
<
<!doctype html>
<html>
<head>
<title>Example Domain</title>
<meta charset="utf-8" />
<meta http-equiv="Content-type" content="text/html; charset=utf-8" />
<meta name="viewport" content="width=device-width, initial-scale=1" />
<style type="text/css">
body {
background-color: #f0f0f2;
margin: 0;
padding: 0;
font-family: -apple-system, system-ui, BlinkMacSystemFont, "Segoe UI", "Open Sans", "Helvetica Neue", Helvetica, Arial, sans-serif;
}
div {
width: 600px;
margin: 5em auto;
padding: 2em;
background-color: #fdfdff;
border-radius: 0.5em;
box-shadow: 2px 3px 7px 2px rgba(0,0,0,0.02);
}
a:link, a:visited {
color: #38488f;
text-decoration: none;
}
@media (max-width: 700px) {
div {
margin: 0 auto;
width: auto;
}
}
</style>
</head>
<body>
<div>
<h1>Example Domain</h1>
<p>This domain is for use in illustrative examples in documents. You may use this
domain in literature without prior coordination or asking for permission.</p>
</div>
</body>
</html>