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OpenVPN Client Connection Resets Interface


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I have a PiVPN running at my home and it is tested and working as expected, routing all traffic through the VPN to the home network and then back out. I have tested then on my Android phone, MacBook and Pixel Slate. I feel confident it is getting the job done. I am currently out of the country and I am using my Pineapple TETRA as a gateway onto the hotel network. I have been trying to get OpenVPN on the Pineapple going but when it connects, the wireless interface I am connected to disappears/resets. The light on the front of the TETRA switches from Blue to Amber, the wireless disappears for a short while and then returns. The pineapple uptime indicates that it did not reboot so it appears that the interface(s) reset for some reason. I have tried initiating a connection to ProtonVPN as well with the same results. I used a combination of Hak5 YouTube videos and this documentation - https://openwrt.org/docs/guide-user/services/vpn/openvpn/client to setup the Pineapple.

Pertinent Details:
Firmware: 2.6.2
OpenVPN: openvpn-openssl - 2.4.7-2

Here is a scrubbed copy of the configuration:

#dev tun
proto udp
remote vpn.domain.tld 1194
resolv-retry infinite
remote-cert-tls server
tls-version-min 1.2
verify-x509-name vpn_33b22ab9-0e3d-405a-956c-80e657c57c54 name
cipher AES-256-CBC
auth SHA256
verb 3
# 2048 bit OpenVPN static key
-----BEGIN OpenVPN Static key V1-----
-----END OpenVPN Static key V1-----
user nobody
group nobody
dev tun0

Can anyone else confirm this issue? I have done a good bit of digging but I suspect I am not phrasing my queries succinctly enough to determine if this is a known issue or bug or simply a configuration error. Any assistance or direction is greatly appreciated.

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  • 4 weeks later...

Hi @Foxtrot & @PatriotPaul ,... I am having the exact same problem. Out of country - my vpn is ok but openvpn on my tetra is no longer working.

I am on the latest version of the software on the pineapple and my vpn is no longer working. It was working on a previous version but I have updated recently....


Any troubleshooting or work arounds would be great.. Hate to be on hotel wifi without a vpn on my router :)

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  • 2 weeks later...

Hi there,

Same here, Pineapple nano / last firmware / openvpn, connection resets and ssh session closed...
Tested with Management ap AND with eth1/USB ethernet !
The connection disapears then comes back but the vpn tunnel disconnected.

No error/information/log....

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  • 3 weeks later...


Just received a Tetra for Black Friday and it is doing the same as reported here.
I have two nanos running older firmware, iptables, and an older version of openvpn-openssl.

When I run openvpn --config /etc/openvpn/myconfigfile, it appears to start the connection, then basically power cycles the tetra.
Something has definitely changed and I'm stuck not updating the nanos until a resolution is discovered.  

This is a great feature and it would be nice to get it working again.  Not sure why they seem to deprecate so much.
I have to adjust various code nearly every revision of openvpn and receive zero additional benefits. 

I've listed the versions that are currently working for the nano.

openvpn-openssl - 2.3.6-5
iptables - 1.4.21-1
iptables-mod-ipopt - 1.4.21-1
iptables-mod-nat-extra - 1.4.21-1

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  • 1 month later...
  • 3 weeks later...
  • 11 months later...

Having the same issue on Pineapple Tetra's running 2.7.0. Please check in to this as the issue listed in the release notes for 2.7.0 doens't seem to be resolved!

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  • 2 weeks later...

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