Silk Road forums

Discussion => Security => Topic started by: dontek on June 17, 2013, 12:54 am

Title: Mac OS X: VPN -> Parallels -> Tails
Post by: dontek on June 17, 2013, 12:54 am
Maybe some of you guys can offer guidance and assistance.

Using Mac OS X. Can't boot to tails via USB, so have the following:

Log into VPN setup through Private Tunnel (for verification, checked IP addy and confirmed VPN working)
Start Parallels
Boot into Tails
Now have TOR obviously as well.

Few questions here.
How protected am I? I can assume that since my computer is connected through VPN then started tails, that it's running through VPN as well?

Obviously a downside is that I cannot have a persistent state in parallels. Now, I have my tormail addy  and various other addys memorized. What I don't, I have in an email to myself on tormail. Nothing downloads to my computer, nothing is bookmarked, nada. Obviously, whenever you boot tails, it's just like from scratch. If shit ever hits the fan, provable is that I have a VPN, Parallels and Tails that is equipped with tails, but nothing to prove beyond a reasonable doubt that anything is connected to any illicit activities.

The main key piece I see missing is my PGP, which I am still trying to completely figure out, so not sure if it's through OS X i setup or if it has to be within tails.

Anyways...how many of my bases do I have covered? How safe am I from snooping eyes now and snooping eyes should a bad day ever come...
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: dontek on June 17, 2013, 01:10 am
Also, thoughts on PrivNote communication? Don't know how sure I am that once a message is read its "gone forever" and not being logged somewhere.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: Rastaman Vibration on June 17, 2013, 05:20 am
Also, thoughts on PrivNote communication? Don't know how sure I am that once a message is read its "gone forever" and not being logged somewhere.

That's the main problem with using PrivNote. You are trusting a 3rd party with your information. Its really up to you how much you trust them, I personally do not.

Why cant you boot to TAILS via USB?
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: Buttercup. on June 17, 2013, 05:24 am
Isn't it easier to use a DVD to boot Tails on a Mac? I'd try that instead. Otherwise, unless you're a major vendor, a VPN, Tor, and good practices in encrypting (depending on your location, that is) / scrubbing files should be more than sufficient. (Personally I'd worry less about "snooping eyes" than I would what would happen if a bad day came and your computer was seized as evidence.)

I've never used PrivNote. There are quite a few services like it (including  https://quickforget.com/, https://tmwsd.ws/ - which includes the option for an additional password - and http://sms4tor3vcr2geip.onion/) but I prefer PGP. Third party services are convenient only until they're not.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: mbius298074 on June 17, 2013, 09:46 am
Maybe some of you guys can offer guidance and assistance.

Using Mac OS X. Can't boot to tails via USB, so have the following:

Log into VPN setup through Private Tunnel (for verification, checked IP addy and confirmed VPN working)
Start Parallels
Boot into Tails
Now have TOR obviously as well.

Few questions here.
How protected am I? I can assume that since my computer is connected through VPN then started tails, that it's running through VPN as well?

Obviously a downside is that I cannot have a persistent state in parallels. Now, I have my tormail addy  and various other addys memorized. What I don't, I have in an email to myself on tormail. Nothing downloads to my computer, nothing is bookmarked, nada. Obviously, whenever you boot tails, it's just like from scratch. If shit ever hits the fan, provable is that I have a VPN, Parallels and Tails that is equipped with tails, but nothing to prove beyond a reasonable doubt that anything is connected to any illicit activities.

The main key piece I see missing is my PGP, which I am still trying to completely figure out, so not sure if it's through OS X i setup or if it has to be within tails.

Anyways...how many of my bases do I have covered? How safe am I from snooping eyes now and snooping eyes should a bad day ever come...

Don't use Tails in a VM. The Tails project strongly recommend against this as the increase in security is minimal compared to just using the tor browser bundle.

If you can't get it to work from USB/DVD then look for another distribution to use.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: samesamebutdifferent on June 17, 2013, 01:02 pm
Isn't it easier to use a DVD to boot Tails on a Mac? I'd try that instead. Otherwise, unless you're a major vendor, a VPN, Tor, and good practices in encrypting (depending on your location, that is) / scrubbing files should be more than sufficient. (Personally I'd worry less about "snooping eyes" than I would what would happen if a bad day came and your computer was seized as evidence.)

I've never used PrivNote. There are quite a few services like it (including  https://quickforget.com/, https://tmwsd.ws/ - which includes the option for an additional password - and http://sms4tor3vcr2geip.onion/) but I prefer PGP. Third party services are convenient only until they're not.

I have nearly torn all my hair out this evening trying to set up TAILS on my mac, cannot get it to boot via the disc and everything that I have read regarding trying to set up rEFInd has mostly gone right over my head.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: mbius298074 on June 17, 2013, 01:24 pm
Isn't it easier to use a DVD to boot Tails on a Mac? I'd try that instead. Otherwise, unless you're a major vendor, a VPN, Tor, and good practices in encrypting (depending on your location, that is) / scrubbing files should be more than sufficient. (Personally I'd worry less about "snooping eyes" than I would what would happen if a bad day came and your computer was seized as evidence.)

I've never used PrivNote. There are quite a few services like it (including  https://quickforget.com/, https://tmwsd.ws/ - which includes the option for an additional password - and http://sms4tor3vcr2geip.onion/) but I prefer PGP. Third party services are convenient only until they're not.

I have nearly torn all my hair out this evening trying to set up TAILS on my mac, cannot get it to boot via the disc and everything that I have read regarding trying to set up rEFInd has mostly gone right over my head.

USB or DVD should be the same. Did you make it into the bootloader?

If you PM me I can see if I can help.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: samesamebutdifferent on June 17, 2013, 01:29 pm
Isn't it easier to use a DVD to boot Tails on a Mac? I'd try that instead. Otherwise, unless you're a major vendor, a VPN, Tor, and good practices in encrypting (depending on your location, that is) / scrubbing files should be more than sufficient. (Personally I'd worry less about "snooping eyes" than I would what would happen if a bad day came and your computer was seized as evidence.)

I've never used PrivNote. There are quite a few services like it (including  https://quickforget.com/, https://tmwsd.ws/ - which includes the option for an additional password - and http://sms4tor3vcr2geip.onion/) but I prefer PGP. Third party services are convenient only until they're not.

I have nearly torn all my hair out this evening trying to set up TAILS on my mac, cannot get it to boot via the disc and everything that I have read regarding trying to set up rEFInd has mostly gone right over my head.

USB or DVD should be the same. Did you make it into the bootloader?

If you PM me I can see if I can help.

By bootloader I am assuming you mean select the start up destination by holding down the C key during restart? no mate it just loads normally.

Will PM you tomorrow if that's ok, about to crash out now.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: mbius298074 on June 17, 2013, 01:38 pm
Isn't it easier to use a DVD to boot Tails on a Mac? I'd try that instead. Otherwise, unless you're a major vendor, a VPN, Tor, and good practices in encrypting (depending on your location, that is) / scrubbing files should be more than sufficient. (Personally I'd worry less about "snooping eyes" than I would what would happen if a bad day came and your computer was seized as evidence.)

I've never used PrivNote. There are quite a few services like it (including  https://quickforget.com/, https://tmwsd.ws/ - which includes the option for an additional password - and http://sms4tor3vcr2geip.onion/) but I prefer PGP. Third party services are convenient only until they're not.

I have nearly torn all my hair out this evening trying to set up TAILS on my mac, cannot get it to boot via the disc and everything that I have read regarding trying to set up rEFInd has mostly gone right over my head.

USB or DVD should be the same. Did you make it into the bootloader?

If you PM me I can see if I can help.

By bootloader I am assuming you mean select the start up destination by holding down the C key during restart? no mate it just loads normally.

Will PM you tomorrow if that's ok, about to crash out now.

no problem, PM me tomorrow.

The Tails bootloader is a bit different from the BIOS boot menu. If you aren't seeing anything mention Tails when you boot up then you probably haven't hit the tails bootloader.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: ilovelucyshow on June 17, 2013, 08:15 pm
I've never gotten tails to successfully boot from a USB stick, even on my Hackintosh.

But why the insistence on tails? I feel like the TOR browser bundle, running on top of a VPN should be plenty secure.

As for local storage, I'd just keep the TOR bundle and all my related files and notes (account info etc.) that you don't want to have to remember stored in an encrypted sparsebundle volume. Obviously with a strong password. And don't forget to eject the volume when you aren't using it!

IMO, this strategy protects you from prying eyes, and well as providing protection should your machine get seized. Everything is on the spasebundle, and if you use a good password, your talking super-computer power to crack  it.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: dontek on June 18, 2013, 01:11 am
I can't recall which program it is that I am using on the bootloader...I'd have to reboot and look to know for sure.

Samesamebutdifferent: Are you doing the C button or the command button? Reboot the computer and when it does the startup sound, press command and it should put you into bootloader. At least, that's how mine does.

I can refresh bootloader and I see the USB...I go to boot from it, and the screen goes black and up in the upper right hand corner there's a blinking cursor, where it would say "loading" at any other time. I have let it just sit there and nothing happens.

Maybe I missed a step somewhere. Not like there is an perfect step-by-step tutorial on this, so gathering info from different places and putting it all together. Ultimately, I would like to get the mac itself just to boot tails from the usb of course. I have not yet attempted to use a DVD. However, I am guessing that I wouldn't have a persistent volume with it either which is kinda/sorta where I am at now anyways.

Mentioned above in one of the replies, what are the vulnerabilties with the current setup that I have? I am only accessing Silk Road and TorMail (and possibly privnote) within Tails on the Virtual Machine that's passing through the VPN. Nothing is being stored on the computer memory at all (passwords, keys, urls, nada).


Also of note and on the subject of Tails...I do have a Tails w/ volume usb. I borrowed a friends computer to get it all loaded up and it's working fine on his (windows), but I do have a question about that also: When I went to boot, it was asking about persistence. That's kind of a giveaway to LE if you ever get busted with the USB and they figure it out, they will know that SOMETHING is on that USB, no? Guess that's just a little paranoia on my behalf, as I understand how difficult it would be for them to even think about cracking it, but to me, opens up a few more questions and stares vs having a VPN and Tails installed on your computer, but no saved data on the computer, period.

Also, wouldn't hurt to note that I never have any plans of becoming a vendor, however, I do anticipate doing a substantial amount of shipping transactions with a few select vendors.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: mbius298074 on June 18, 2013, 07:29 am
I've never gotten tails to successfully boot from a USB stick, even on my Hackintosh.

But why the insistence on tails? I feel like the TOR browser bundle, running on top of a VPN should be plenty secure.

As for local storage, I'd just keep the TOR bundle and all my related files and notes (account info etc.) that you don't want to have to remember stored in an encrypted sparsebundle volume. Obviously with a strong password. And don't forget to eject the volume when you aren't using it!

IMO, this strategy protects you from prying eyes, and well as providing protection should your machine get seized. Everything is on the spasebundle, and if you use a good password, your talking super-computer power to crack  it.

People use tails because it doesn't leave the same footprint that the TBB does.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: samesamebutdifferent on June 18, 2013, 08:37 am
I had previously downloaded rEFIt as the boot menu tool for loading a Linux image on Virtual Box however reading the Tails web page it makes reference to rEFInd which I assume does the same thing?

Anyway when I try to access the boot menu by holding down the option key and restart the computer I am not given the option to select Tails, just the normal Mac OS HD.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: dontek on June 18, 2013, 12:29 pm
Well I checked this morning and I am actually using refind. Dont remember it being installed successful but apparently so. 

Anyways, with mine...turn computer off, put usb in, turn on, hold command and get to boot menu.  Initially the only thing thsat shows up is the os x hard drive.  Press ESC and it refreshes the list and shows the usb, which I then select to boot from, and then that takes me to the flashing cursor screen.

FWIW, I have a last gen MacBookPro (about 3 years old)
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: samesamebutdifferent on June 18, 2013, 01:06 pm
Appreciate your help dontek, will try removing rEFIt and replacing with rEFInd and try again tomorrow.
Title: Re: Mac OS X: VPN -> Parallels -> Tails
Post by: dontek on June 18, 2013, 01:52 pm
Please update. Will be interested to see if you run into the same issues that I do.

Guess my last resort would always be got get a cheap netbook. Blah.