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Tor ERR_PROXY_CONNECTION_FAILED when network devices change on Linux

See original GitHub issue

Description

I use Brave on a laptop at home and at work. At home, I use a VPN, at work, I don’t. While the non-Tor windows keep working, the Tor window eventually stops working and all tabs in that window report ERR_PROXY_CONNECTION_FAILED on reload. There appears to be no obvious trigger for the breakage, at some random point it just stops working.

Initially, I thought maybe switching between cable and wifi was causing this, but I’ve been using wifi exclusively for a while and the issue persists.

Steps to Reproduce

Open a Tor window.
Switch networks, or from VPN to non-VPN, or from non-VPN to VPN (not guaranteed to reproduce the problem).
After some time, the Tor connection can no longer be (re)established.

Actual result:

b0rkage.

Expected result:

No b0rkage.

Reproduces how often:

Inconsistently.

Brave version (brave://version info)

Brave	1.2.43 Chromium: 79.0.3945.130 (Official Build) unknown (64-bit)
Revision	e22de67c28798d98833a7137c0e22876237fc40a-refs/branch-heads/3945@{#1047}
OS	Linux
JavaScript	V8 7.9.317.33
Flash	(Disabled)
User Agent	Mozilla/5.0 (X11; Linux x86_64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/79.0.3945.130 Safari/537.36
Command Line	/usr/lib/brave-bin/brave --enable-dom-distiller --disable-domain-reliability --no-pings --extension-content-verification=enforce_strict --extensions-install-verification=enforce --enable-oop-rasterization=Enabled --sync-url=https://no-thanks.invalid --enable-features=PasswordImport,WebUIDarkMode,SimplifyHttpsIndicator --disable-features=AutofillServerCommunication,NotificationTriggers,LookalikeUrlNavigationSuggestionsUI,AudioServiceOutOfProcess,SmsReceiver,WebXR,UnifiedConsent,WebXrGamepadModule,AllowPopupsDuringPageUnload,SyncUSSBookmarks --flag-switches-begin --enable-features=PasswordImport,WebUIDarkMode,SimplifyHttpsIndicator,WebRtcHideLocalIpsWithMdns --disable-features=AutofillServerCommunication,NotificationTriggers,LookalikeUrlNavigationSuggestionsUI,AudioServiceOutOfProcess,SmsReceiver,WebXR,UnifiedConsent,WebXrGamepadModule,AllowPopupsDuringPageUnload,SyncUSSBookmarks,AccountConsistency,WebRTCPipeWireCapturer --flag-switches-end --disable-webrtc-apm-in-audio-service
Executable Path	/usr/lib/brave-bin/brave
Profile Path	/home/redacted/.config/BraveSoftware/Brave-Browser/Default

Brave is installed from an AUR package (PKGBUILD).

Version/Channel Information:

% brave --version
Brave Browser 79.1.2.43 unknown
%

This issue has been present for at least a few versions.

Other Additional Information:

% date
Fri Jan 24 16:35:25 CET 2020
% tail  ~/.config/BraveSoftware/Brave-Browser/tor/data/tor.log
Jan 24 11:26:07.000 [notice] Heartbeat: Tor's uptime is 1 day 23:59 hours, with 8 circuits open. I've sent 34.16 MB and received 66.36 MB.
Jan 24 11:26:07.000 [notice] Average packaged cell fullness: 52.438%. TLS write overhead: 4%
Jan 24 11:30:11.000 [notice] Have tried resolving or connecting to address '[scrubbed]' at 3 different places. Giving up.
Jan 24 11:40:12.000 [notice] Have tried resolving or connecting to address '[scrubbed]' at 3 different places. Giving up.
Jan 24 11:50:14.000 [notice] Have tried resolving or connecting to address '[scrubbed]' at 3 different places. Giving up.
Jan 24 12:00:15.000 [notice] Have tried resolving or connecting to address '[scrubbed]' at 3 different places. Giving up.
Jan 24 12:10:16.000 [notice] Have tried resolving or connecting to address '[scrubbed]' at 3 different places. Giving up.
Jan 24 12:20:16.000 [notice] Have tried resolving or connecting to address '[scrubbed]' at 3 different places. Giving up.
Jan 24 12:30:18.000 [notice] Have tried resolving or connecting to address '[scrubbed]' at 3 different places. Giving up.
Jan 24 12:40:05.000 [notice] Catching signal TERM, exiting cleanly.
%

Miscellaneous Information:

I’m using Arch Linux.

For VPN leak prevention, I use https://github.com/wknapik/vpnfailsafe while the VPN is running and disable it when it’s not running (removing routes, firewall rules, hosts entries).