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I am currently using the Tails OS and am looking to access websites that don't play friendly with Tor by using the configuration Tor > socks5 proxy.

According to the Tails support the recommended method is to create a SSH tunnel and reconfigure the firewall and browser appropriately. Using SSH I am able to do this perfectly fine, but would like to have access to a far wider pool of publicly available proxies and to this end, am looking to configure proxychains appropriately. The previous question How to chain proxy after Tor relates to proxychains and Tor generally, whereas my problem is Tails specific.

Relevant settings of /etc/proxychains.conf are:

proxy_dns
socks5 127.0.0.1 9151
socks5 163.122.18.196 3177 (NB: This IP address has been modified)

Testing with proxychains curl ipecho.net/plain --socks5-hostname 163.122.18.196:3177 shows that proxychains is working fine:

ProxyChains-3.1 (http://proxychains.sf.net)
|S-chain|-<>-127.0.0.1:9151-<>-163.122.18.196:3177-<><>-163.122.18.196:3177-<><>-OK

163.122.18.196

However, running the browser with proxychains iceweasel I'm running into problems.

With default browser settings, I get my Tor IP address. When I manually reconfigure the proxy to point to 163.122.18.196:3177 I get the error message "Proxy server is refusing connections" along with the following error in /var/log/syslog:

Sep 6 11:06:10 localhost kernel: [ 1105.132959] Dropped outbound packet: IN= OUT=wlan0 SRC=192.168.1.3 DST=163.122.18.196 LEN=60 TOS=0x00 PREC=0x00 TTL=64 ID=31261 DF PROTO=TCP SPT=44153 DPT=3177 WINDOW=29200 RES=0x00 SYN URGP=0 UID=1000 GID=1000

So for one reason or another, the firewall is blocking the connection for the browser, but allowing the curl command through.

Without having a full appreciation of the way that Tails is configured, I'm reluctant to mess with my settings blindly -- any suggestions?

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You should run "proxychains iceweasel" and then, in the iceweasel settings disable proxy settings because you "manage" the proxy with proxychains and so iceweasel doesn't have to do anything. Or if you did it all correctly, make sure that the proxy software of the 163.122.18.196 server is properly configured..... last but not least, make sure that proxychains do not change the chain, otherwise Tails will block the connection..

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