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At my location, a Sophos RED 50 has been installed. This has compromised my ability to use my VPN (Private Internet Access). This created an internal VPN, and all my internet traffic is now being routed and monitored through another offsite location. This also has compromised my ability to connect to the Tor network. I have tried using a L2TP connection to Private Internet Access (at their recommendation), but that didn't work as well. I am going to set up a whonix VM station, but I doubt that will work as well, since it uses Tor exclusively.

Does anyone have experience with these types of devices or recommendations for keeping my browsing private? Is there any way I can use Tor or a VPN?

Multiple VPNs can be tricky apparently, and I (sys admin locally) do not have control of this device. I know it a place of work, and they have every right, but I can't help myself... keeping myself secure is peace of mind. Link below is pdf of the device in question. I will answer any question I believe won't subvert the security of my company.

https://www.sophos.com/en-us/medialibrary/PDFs/factsheets/sophosreddsna.pdf?la=en

edit: I have two torrc files, tried bridged and not bridged, so I'll post logs of both. 

Bridge obfs3 "IP" "signature"
DataDirectory C:\Users\[######]\Desktop\Tor Browser\Browser\TorBrowse\Data\Tor  
GeoIPFile C:\Users\[######]\Desktop\Tor Browser\Browser\TorBrowser\Data\Tor\geoip  
GeoIPv6File C:\Users\[######]\Desktop\Tor Browser\Browser\TorBrowser\Data\Tor\geoip6  
HiddenServiceStatistics 0  
UseBridges 1

torrc.orig.1 was blank. An example of the logs I get trying to connect directly to tor looks like this:

1/13/2016 8:28:25 AM.600 [NOTICE] DisableNetwork is set. Tor will not make or accept non-control network connections. Shutting down all existing connections.
1/13/2016 8:28:28 AM.900 [NOTICE] Opening Socks listener on 127.0.0.1:9150
1/13/2016 8:28:35 AM.600 [NOTICE] Bootstrapped 5%: Connecting to directory server
1/13/2016 8:28:35 AM.600 [NOTICE] Bootstrapped 10%: Finishing handshake with directory server
1/13/2016 8:28:35 AM.700 [WARN] Proxy Client: unable to connect to "IP address" ("general SOCKS server failure")
1/13/2016 8:28:56 AM.600 [WARN] Proxy Client: unable to connect to "IP address" ("general SOCKS server failure")
1/13/2016 8:28:56 AM.600 [WARN] Proxy Client: unable to connect to "IP address" ("general SOCKS server failure")
1/13/2016 8:28:56 AM.600 [WARN] Proxy Client: unable to connect to "IP address" ("general SOCKS server failure")
1/13/2016 8:32:15 AM.200 [NOTICE] Closing no-longer-configured Socks listener on 127.0.0.1:9150
1/13/2016 8:32:15 AM.200 [NOTICE] DisableNetwork is set. Tor will not make or accept non-control network connections. Shutting down all existing connections.
1/13/2016 8:32:15 AM.200 [NOTICE] Closing old Socks listener on 127.0.0.1:9150

Using obfs3 bridges yields the same log essentially.

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You should try pluggable transports, especially Meek and Obfs4. Of it won't help you, please post a torrc and error log here, I'll be able to help you further

UPDATE 13.1.2016 on your edit: Try to use tor from Git - the latest version, Im using it. Also please paste a log from the very beginnig, i.e. with a shell cmd to execute a binary. Try to use my torrc options in Git-builded tor:

RunAsDaemon 0
PidFile /var/run/tor
FastFirstHop 0
AllowSingleHopCircuits 0
EnforceDistinctSubnets 1
UseEntryGuards 1
DisableAllSwap 1
AvoidDiskWrites 1
NumCPUS 2
ConnLimit 16384
DataDirectory /usr/tor/data
GeoIPFile /usr/tor/share/tor/geoip
GeoIPv6File /usr/tor/share/tor/geoip6
Log notice stdout
SocksListenAddress 127.0.0.1
SocksPort 9050
LongLivedPorts 21,22,80,443,465,554,636,706,873,993,995,1863,2401,3690,4155,5050,5190,5222,5223,5269,5298,6523,6666,6667,6668,6669,6697,6881,6882,6883,6884,6885,6886,6887,6888,6889,7000,8000,8010,8300,8554
ClientOnly 1
DNSPort 53
DNSListenAddress 127.0.0.1
DisableDebuggerAttachment 0
DynamicDHGroups 1
BandwidthRate 1024KBytes
BandwidthBurst 1024KBytes
PublishServerDescriptor 1
ServerTransportPlugin obfs2,obfs3 exec /usr/local/bin/obfsproxy --data-dir /usr/tor/obfsproxy managed
ExtORPort 6699
User tor

Change your path's respectively to your setup and let's take a look what it will do. Also try to seed your instance outside the censored network, i.e. via usb 3g/4g dongle, and then change UseEntryGuards to 0

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  • I have compiled tor using git, but I don't have an etc/tor/torrc. Perhaps I have done this wrong. I can however run tor from terminal. Still doesn't connect. I guess I have some beginner questions that I should have looked for answers for before I tired this leap. Do i need to use git to change its torrc before I compile it? Or can I change it after compiling and installing?
    – Carbide
    Jan 13, 2016 at 21:19
  • @Carbide you should have your own torrc - Git package does not ships it, and for a good reason. Just use -f /path/to/yours
    – Alexey Vesnin ♦
    Jan 13, 2016 at 22:28
  • While I could not find a tor solution yet, (I need to make some changes to VM machine and change how I compiled tor) Upon further research I feel seeding my instance outside the network via usb dongle may be the best solution. Thanks for help... I guess I was looking for an easy solution, and the whole purpose of the RED is to make it difficult. I am sure there may be a solution without exiting the network, but I need to do better research before asking a question broad question like this. I have some learning to do.
    – Carbide
    Jan 14, 2016 at 18:49
  • @Carbide learning is perpetual process! Feel free to ask any questions - I'm glad to help
    – Alexey Vesnin ♦
    Jan 14, 2016 at 22:15
  • Changing UseEntryGuards compromises anonymity. See torproject.org/docs/faq.html.en#EntryGuards.
    – Matt Nordhoff
    May 28, 2016 at 2:13

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