ubuntu 20.04 https misconfiguration?

[999null 0]

Hi, 

I have installed ubuntu server 20.04 on a new Intel Nuc.

My issue is that with Wireguard connected on my nuc, I cannot get to install from pipx command (and potentially others, I don't know how to check)

nuc@usss:~$ pipx install --force pycowsay
Installing to existing directory '/home/nuc/.local/pipx/venvs/pycowsay'
WARNING: Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'ReadTimeoutError("HTTPSConnectionPool(host='pypi.org', port=443): Read timed out. (read timeout=15)")': /simple/pip/
^CERROR: Operation cancelled by user

It works with wireguard off  (  sudo wg-quick down vpn  and then pipx install pycowsay )

Another thing to note, is the with wireguard on, I can install from pipx command on another laptop with same vpn exit point. (but different keys). 

Any advice how to find out the root of this issue? I am not sure where to start.


sysctl.conf  as follows on new NUC (some rtorrent tuning and bbr mode)
 

net.ipv6.conf.all.disable_ipv6=1
net.ipv6.conf.default.disable_ipv6=1
net.ipv6.conf.lo.disable_ipv6=1

## net.ipv4.ip_forward = 1
## disabled now, coz using nuc is a client


#### some new valus ###
# Maximum Socket Receive Buffer. 16MB per socket - which sounds like a lot, but will virtually never consume that much. Default: 212992
net.core.rmem_max = 16777216
# Maximum Socket Send Buffer. 16MB per socket - which sounds like a lot, but will virtually never consume that much. Default: 212992
net.core.wmem_max = 16777216
# Increase the write-buffer-space allocatable: min 4KB, def 12MB, max 16MB. Default: 4096 16384 4194304
net.ipv4.tcp_wmem = 4096 12582912 16777216
# Increase the read-buffer-space allocatable: min 4KB, def 12MB, max 16MB. Default: 4096 16384 4194304
net.ipv4.tcp_rmem = 4096 12582912 16777216

# Tells the system whether it should start at the default window size only for new TCP connections or also for existing TCP connections that have been idle for too long. Default: 1
net.ipv4.tcp_slow_start_after_idle = 0
# Allow reuse of sockets in TIME_WAIT state for new connections only when it is safe from the network stack’s perspective. Default: 0
net.ipv4.tcp_tw_reuse = 1

##Setting BBR as the default is simple. Open up a terminal window and issue the command sudo nano /etc/sysctl.conf. At the bottom of this file, add the following two lines:
net.core.default_qdisc=fq
net.ipv4.tcp_congestion_control=bbr

routing works fine - 
https://i.ibb.co/270nTnx/image.png
 

[999null 0]

UPDATE on this. 

I Change my "Device" key ( i used a different wireguard private public key on my nuc )  and IT WORKED !! wth?