ubuntu 18.04 failed to connect to some HTTPS sites

Question

I have just formatted my laptop and did a clean install of Ubuntu 18.04. While installing some of my development packages I found issues using both rubygems and python pip. It gives SSL related errors. I cant access their sites either. (Connection reset error message)

Here is the error installing latest version of PIP

Connected to bootstrap.pypa.io (2a04:4e42::175) port 443 (#0)
* ALPN, offering h2
* ALPN, offering http/1.1
* successfully set certificate verify locations:
*   CAfile: /etc/ssl/certs/ca-certificates.crt
  CApath: /etc/ssl/certs
} [5 bytes data]
* TLSv1.2 (OUT), TLS handshake, Client hello (1):
} [215 bytes data]
* TLSv1.2 (IN), TLS handshake, Server hello (2):
{ [112 bytes data]
* TLSv1.2 (IN), TLS handshake, Certificate (11):
{ [3805 bytes data]
* TLSv1.2 (IN), TLS handshake, Server key exchange (12):
{ [300 bytes data]
* TLSv1.2 (IN), TLS handshake, Server finished (14):
{ [4 bytes data]
* TLSv1.2 (OUT), TLS handshake, Client key exchange (16):
} [37 bytes data]
* TLSv1.2 (OUT), TLS change cipher, Client hello (1):
} [1 bytes data]
* TLSv1.2 (OUT), TLS handshake, Finished (20):
} [16 bytes data]
* OpenSSL SSL_connect: SSL_ERROR_SYSCALL in connection to bootstrap.pypa.io:443 
* stopped the pause stream!
  0     0    0     0    0     0      0      0 --:--:--  0:00:01 --:--:--     0
* Closing connection 0
curl: (35) OpenSSL SSL_connect: SSL_ERROR_SYSCALL in connection to bootstrap.pypa.io:443 

And rubygems:

gem update --system
ERROR:  While executing gem ... (Gem::RemoteFetcher::FetchError)
    Errno::ECONNRESET: Connection reset by peer - SSL_connect (https://api.rubygems.org/specs.4.8.gz)

Edit:

I cant even connect to curl website using curl:

➜ curl -v https://curl.haxx.se/mail/archive-2015-08/0015.html
*   Trying 2a04:4e42::561...
* TCP_NODELAY set
* Connected to curl.haxx.se (2a04:4e42::561) port 443 (#0)
* ALPN, offering h2
* ALPN, offering http/1.1
* successfully set certificate verify locations:
*   CAfile: /etc/ssl/certs/ca-certificates.crt
  CApath: /etc/ssl/certs
* 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):
* OpenSSL SSL_connect: SSL_ERROR_SYSCALL in connection to curl.haxx.se:443 
* stopped the pause stream!
* Closing connection 0
curl: (35) OpenSSL SSL_connect: SSL_ERROR_SYSCALL in connection to curl.haxx.se:443 

I tried to update openssl and ca-certificates packages but same issue. Openssl version: OpenSSL 1.1.0g 2 Nov 2017

Does anybody have an idea whats going on? This didn't happen in a VM a couple of days ago.

Edit Tested again in a VM connected to the same network and provisioned the same way and it works!! Something really strange.

Thank you.

Solution

I solved it, by disabling ipv6 on my machine. Dont really know why but it worked.

To disable ipV6 on Ubuntu or Linux Mint, follow this tutorial: https://support.purevpn.com/how-to-disable-ipv6-linuxubuntu

Disabling in network manager was not enough.

Comments

[dobey]

I would suggest grabbing the cert and comparing it against a cert grabbed from a completely different network connection where it verifies just fine. Could be a mitm attempt perhaps?

[brpaz]

I saw a difference between my laptop and VM. it seems that my laptop always try to connect using ipv6, while in my VM it uses ipv4. I disabled ipv6 in network manager but it doesn't seem to work.