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Episode: 1481
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Title: HPR1481: Encryption and Gmail
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Source: https://hub.hackerpublicradio.org/ccdn.php?filename=/eps/hpr1481/hpr1481.mp3
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Transcribed: 2025-10-18 03:53:35
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---
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Until next time, Pagan.
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Hello, this is Ahuka and welcome to Hacker Public Radio and another in our ongoing series
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on security and privacy.
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And what I want to do this time is pick up from what we did last time.
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Last time we took a look at how to do encryption with email in Thunderbird using an add-on called
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Enigmail.
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What I want to do this time is take on the task of showing how we can also use encryption
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with web-based mail.
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And for this one I'm going to select Gmail because I have to have a Gmail account so that
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makes it easy.
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I think that there are probably similar ways to do this with Yahoo or with Outlook.com or
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what have you.
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I'm going to use a particular example that I happen to be familiar with.
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Now people use web-based mail a lot.
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Gmail is certainly one of the more popular ones.
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The thing that you have to keep in mind is that this is all about encrypting the message
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with your keys that you control before it leaves the computer.
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Steve Gibson calls this pre-internet encryption or PIE.
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Now last time we mentioned LavaBit, LaDar Levison and all of that.
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And the flaw in what they did was that they had keys that the mail provider controlled.
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And these keys could be and were demanded by the government.
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So if you use your own GPG keys that you control, no provider, in this case Google, is
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even capable of giving anything to the government other than a blob of random nonsense.
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Now that I'm not going to get into metadata, that's another discussion and Lord knows
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we will probably get to that one too at some point.
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But what I want to do here is talk about an extension that you can install.
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It's available for both Chrome and Firefox.
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And I'm going to do it with Chrome because that's what I use to access my Gmail account.
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And the extension is called MailVillope, M-A-I-L-V-E-L-O-P-E.
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So it's mail and envelope kind of mashed together.
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And as a Chrome extension, basically you just do what you do with any other Chrome extension.
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You go to the Chrome store, you do a search for MailVillope and you install it.
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Now once you have MailVillope installed, you need to give it your keys.
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We talked about creating keys over a couple of different episodes, how to do it with
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a command line, how to do it with a GUI client.
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Then last time we talked about using your keys with Enigmail in Thunderbird.
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Now one of the things about Enigmail that was really nice was that Enigmail knew where
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to look and would just go grab your keys.
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MailVillope is not quite as user friendly in this respect.
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But it's going to give us a chance to learn something that we're going to need to know.
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And that's all about exporting keys.
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So when you have MailVillope installed, you then in the extensions window in Google Chrome,
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you will see that there's something there that says options.
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It's a link that you click and that opens up the options window for MailVillope.
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And when you take a look at that, you're going to see you've got a number of things you
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can do and one of them sits down a couple on the left.
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You're going to see something that says import keys.
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Now you can import your keys or other people's keys depending on what you have available
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to you.
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But the thing is that it has to be pure ASCII text files.
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Now chances are when GPG created all of this on your hard drive, it was not pure ASCII.
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It was probably a binary file.
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So what you need to do is you need to do an export.
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You can do this in several ways.
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You could do it at the command line, for instance.
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And there's two different commands, one for the private key and one for the public key.
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So for the private key, the command would be GPGspace-export-secret-key-space-a-space-space-a-space.
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And then your username.
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This would be your username, in this case I'm not a Linux box.
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So it would be my Linux username, the name of my home directory, in other words.
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Now this will display your key as ASCII text in the terminal window.
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You can paste it in the mail the loop and away you go.
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Now to get your public key, the public key is the one that's used by other people to
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encrypt messages to you.
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So the command slightly different, GPGspace-Armer, ARMOR, space-export-space, and then the
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email address.
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Remember that when you created your GPG key that the email address was a part of that
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and it's linked to your email address.
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So that's going to get your public key exported.
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And again, this will show up in the window and you can copy and paste what have you.
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Now if you've already set up Thunderbird, we can make this even a little bit simpler.
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Because you can export them both at once.
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In Thunderbird, go to that OpenPGP menu that we talked about last time and this time
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select key management.
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And click on your own key to select it and then go to the file menu and select export
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keys to file.
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You'll then be asked if you wish to include the secret key.
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Say yes and you'll be asked to approve a file name and a location for the exported file.
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Now this will be a dot ASC file.
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In other words, ASCII text.
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And then in MailVolope on the import screen, you can click the import from file, find
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that file.
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So put it in your home directory somewhere where you know how to find it.
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And if all goes well, you're going to see two green lines.
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The first one says success, public key was imported blah, blah, blah and the second one
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to be success private key was imported blah, blah, blah.
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And you know in each case saying that's been added to your key ring.
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And then you can take a look at your key ring in MailVolope and you should see your name
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and the ID of your key and you'll actually see two keys, two keys in the icon on the left
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because that's going to indicate that it got both the public and the private.
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Now if you then later on import the public key of some other people, people that you might
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want to correspond with, when you look, you would see their name and their key identifier,
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but you'd only see a single key on the left because you obviously would not have their
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private key.
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Now I said it was worth learning this import export business with keys because it's really
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the best way to move your keys to other computers.
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Now I've seen stuff that says, oh just copy your .gpg directory and if you're going to
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another Linux machine, that'll probably work, but what if you're a cross-platform person?
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What if you're like our friend night-wise who makes a whole big fetish out of being cross-platform?
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And let me just face a lot of people, there are times they want to use Linux, other times
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I have to use Windows when I'm at work, some people may have a Macintosh around that they
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want to use.
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So understanding how you can export your key files and then in any other computer you just
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use the import like we just did with MailVolo and that's going to be a good way to get your
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keys moved around.
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Now that you've imported this, let's say you wanted to send a message in Gmail, if the
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only key you have is your own you have to send something to yourself, you can actually
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do that.
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But what you're going to see now because of MailVolope is that when you click the compose and in
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Gmail, I'm going to assume you all know how this works.
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When you click the compose button, a window opens up in the lower right and it's got a black
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bar across the top and you start typing your message.
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What you're going to see now is something has changed and what has changed is that there
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is an additional icon that is on that window and the icon is an edit icon and it's got the
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yellow pencil on top of a sheet of paper.
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And if you click that, another window opens for you to create your encrypted message.
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So you just type your message in that window.
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So it's going to say at the very top Chrome extension and a bunch of blah, blah, blah,
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yes, because the extension is MailVolope that you installed that's taking over this process.
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And then you compose your mail and now what?
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If you simply click the transfer button, you get to pop up warning you, you're trying
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to send unencrypted data, right?
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So just because you've composed it in this window, you haven't finished the process yet.
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But if you take a look, there's an icon of a padlock, ah, the lock icon.
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So you click that and what happens.
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Now another window is going to open, remember that when you send encrypted mail, you encrypt
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it using the public key of the recipient.
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Now right now you may only have your own public key in there because we just imported it
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a moment ago.
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But at some point you're going to start accumulating public keys of other people.
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And so what you need to do is select the recipient for whom you have a public key.
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Now I think I mentioned last time, I'm setting up something with Tony Beaness from the Sunday
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Morning Linux review that I think the two of us are going to do a little program talking
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about how you do all of the obtaining keys of other people and things like that.
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So you know, that should be fun.
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We're going to get there.
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It's like everything else you got to take it one step at a time.
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So anyway, at this point, you know, you click that maybe the only name you see up there
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is your own.
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So highlight that and click the add button.
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And when you do that, everything gets encrypted.
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Then when you click the transfer, what's going to get transferred is an encrypted message.
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And so in your Gmail window, your compose window now, it's just going to say begin PGP message
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and then all sorts of gobbledygook and then at the end, it's going to say end PGP message.
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So you have a completely encrypted message, but so far not a thing has left your computer.
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And that's the important part.
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So if you now click the send button, your message will be sent, but Google will have no idea
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what it says and neither will anyone else if they do not have the private key of the recipient.
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Ideally, they wouldn't.
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Now, suppose you receive a message that has been encrypted and that means that you have a correspondent
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out there who has your public key and they use that to encrypt a message to send to you.
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Well, when that comes in, mail the loop is going to notice, oh, wait a minute, this is encrypted.
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Isn't it?
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I'm supposed to do something.
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So it'll throw an overlay on top of the message with the icon of an envelope and lock.
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Your cursor will turn into a key and if you click on the icon, you will be asked to provide your passphrase.
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And assuming you can do this successfully, the message will decrypt.
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Let's hope you know your passphrase.
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Now, the last thing, digital signing.
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And I'd have to tell you at this point, now I'm recording this now in towards the end of February of 2014,
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but I'm recording it ahead of time and it's going to go out later on this year.
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At the time I'm recording this, mail the loop does not support digital signing,
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but it's clear that they're working on it and I hope it will be added soon.
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Obviously, they put the priority on ensuring that you could securely encrypt messages
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and that's not really a terribly bad priority to have when you think about it.
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So with that, this is Huka signing off for Hacker Public Radio
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and reminding everyone, please support FreeSoftware.
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Bye.
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