User profile for user: BusyGuy
BusyGuy Author
User level: Level 1
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Zipping and encrypting a file for delivery to a person without the same uti

I am routinely security-conscious. Today, I wanted to encrypt a file before sending it as an email attachment. (If it had been a big file, i might've also wanted to zip it. But, on this occasion, it was not necessary.)

I have PGP. My correspondent does not, but I have had no problems in the past using PGP in "conventional encrypt" mode to ask PGP to encrypt a file with a password (i.e. instead of using a pair of PGP keys). So I chose that option and, to my surprise, he could not decrypt the file, using the password I sent him by another method. Either he screwed up somehow or there is a shortcoming with PGP (that I had not realised before.

He begged me to use Zip or RAR. A lengthy search for a utility that would encrypt, was fruitless. To my amazement, I could not find any Mac utility that would enable compressing (in case I ever wanted it) and encryption in circumstances where the recipient could decrypt the file without having the same utility on his (Windows) computer.

I found this too amazing for words!

First, PGP is a wonderful tool but the company is a lame bunch of morons with an opaque web site and useless support. I did find this in the manual for pgpDesktopMac"

" If you prefer to encrypt to a passphrase...you can specify conventional encryption and encrypt the archive using a passphrase...The recipients must have PGP Desktop installed." Dead end therefore.

Does anyone know of a utility that is self-decrypting?

G5 dual, Intel iMac, Intel MacBook Pro, others, Mac OS X (10.6.2)

Posted on Sep 22, 2010 7:29 PM

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14 replies
User profile for user: babowa
babowa
User level: Level 9
78,556 points

Sep 22, 2010 7:44 PM in response to BusyGuy

How about making your file(s) a .pdf. That is a universal format and can be opened with any OS. And you can encrypt PDF's with Preview. Here is how:

Open a .pdf document in Preview
Choose File -> Save as
Choose a name
Click "Encrypt"
Choose a password
Done
Send the password to your recipient in a separate email
Send the encrypted .pdf as an attachment
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User profile for user: jsd2
jsd2
User level: Level 5
6,245 points

Sep 23, 2010 5:25 AM in response to BusyGuy

I could not find any Mac utility that would enable compressing (in case I ever
wanted it) and encryption in circumstances where the recipient could decrypt the
file without having the same utility on his (Windows) computer.


Does anyone know of a utility that is self-decrypting?


I don't see how this would work. It seems to me that a true self-decrypting archive, one that does not require ANY additional application that resides on the recipient's computer, would itself have to behave as an application - it would have to execute the code that does the decrypting. And running executable code is OS-specific - a Mac application will not directly run under Windows, and vice-versa.
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User profile for user: BusyGuy
BusyGuy Author
User level: Level 1
0 points

Sep 25, 2010 11:39 AM in response to jsd2

jsd2, in a former life, my job required me to compress often before delivery of, say, a folder of files. I used to use a utility (if my memory serves, it was one of the Stuffit suite of tools) that, indeed, would create an executable that would open on any platform. In other words, on a PC or a Mac, it would self-expand without the user owning any compander utility. If I then wanted to encrypt it, I used a separate utility but I forget now, what it was. Most unfortunate and, when I come to do it again after years away from that need, I am totally surprised that I can find no useful tools today. Hence my post.

Maybe I must explore the Stuffit scene again but, the last time I did, the suite of tools was a train wreck.
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User profile for user: etresoft
etresoft
User level: Level 9
56,146 points

Sep 25, 2010 11:58 AM in response to BusyGuy

BusyGuy wrote:
I am routinely security-conscious. Today, I wanted to encrypt a file before sending it as an email attachment. (If it had been a big file, i might've also wanted to zip it. But, on this occasion, it was not necessary.)


You can send secure e-mail with Apple Mail: http://support.apple.com/kb/TA22353

He begged me to use Zip or RAR. A lengthy search for a utility that would encrypt, was fruitless.


The best place to find Mac software these days is: http://osx.iusethis.com. There are a number of ZIP and RAR utilities.

To my amazement, I could not find any Mac utility that would enable compressing (in case I ever wanted it) and encryption in circumstances where the recipient could decrypt the file without having the same utility on his (Windows) computer.


Windows will open encrypted ZIP files without any additional utilities.
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User profile for user: BusyGuy
BusyGuy Author
User level: Level 1
0 points

Sep 25, 2010 12:02 PM in response to babowa

Barbara, files that can't be turned into a PDF might include music, applications, videos, and even picture files if it's important to keep them in their original format for further treatment in their creator's application or for high-fidelity printing. I don't use Illustrator, animation, 3D or rendering apps but how about those, too? Files from a digital audio workstation? Databases? Fonts? Games? Keynote files? QuarkXPress files in need of future work?

Although I'm grumpy with Adobe over several issues, I'm certainly grateful to them for the PDF format and Apple's Preview just makes a winning combination and I'm surprised it isn't ubiquitous. Every time my wife applies for a job online, some moron sends a mangled, ugly and barely-legible Word document. Oh well.

The whole computer scene still needs to progress considerably. I'm alarmed that some categories of application still mysteriously lack members that are stable, fully-featured, professionally-designed, Mac-UI-compliant, and costing money to justify support and further development. Typical examples that make me grumpy include email (I don't think Apple's Mail is up to Eudora's standard yet), scan, OCR, fax, font management (yes, I've tried many, all disappointing) and the very situation that sent me here to ask for a compress-encrypt-reverse utility. Where are the developers?
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User profile for user: babowa
babowa
User level: Level 9
78,556 points

Sep 25, 2010 12:47 PM in response to BusyGuy

Well, I didn't realize what kinds of apps/files you are sending - a lot of ISPs have size limits, so I wouldn't send a video (but upload it to a site where they can look or even download it), nor an entire application - the recipient can download/purchase an app, so unless you've created that app, there are copyright issues involved besides the fact that the files would be huge. Unless you've created it, why would you a) send a font the recipient can get elsewhere, and b) encrypt it? I agree that the music and, say, RAW images should be sent in the original format, but I can't see the need for encryption - unless you are in a security sensitive job situation, but then you'd have your employer's security measures already in place.

Sorry, but I just don't quite get it; unless it is financial or personal health information which has to reach the recipient immediately (and which I would email as an encrypted PDF), I would probably resort to the old fashioned snail mail (or even overnight delivery service), insured with delivery confirmation, to send a priceless created-by-me masterpiece.
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User profile for user: BusyGuy
BusyGuy Author
User level: Level 1
0 points

Sep 25, 2010 1:00 PM in response to etresoft

Etresoft, thanks for the input.

The best place to find Mac software these days is: http://osx.iusethis.com. There are a number of ZIP and RAR utilities.


Very helpful. My daily routine was upset hen cnet screwed up VersionTracker.


Windows will open encrypted ZIP files without any additional utilities.


Yes that's what i understood. My problem is finding a utility these days that will both zip and encrypt.

Here's an off-topic tip: I decided to visit the Stuffit web site. I googled and was sent to <http://www.stuffit.com/dr/aus/stuffit2010_aus.html> Appalling! Unbelievable! Not a single link to anywhere. No opportunity to ask them a question.

Further exploration produced <http://www.stuffit.com/mac-home.html> which is a totally-different page with links.

There, I discovered that, as I was wondering, Stuffit Deluxe claims to be able to create self-opening zipped, encrypted archives. Looks like I've answered my own enquiry, which is never good. Shows that I did inadequate research before posting. sorry.
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Zipping and encrypting a file for delivery to a person without the same uti

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