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I need to send a file over Email securely. My idea was to use a Disk Image containing the file. Unfortunately, the person who I am sending the file to has a PC running Windows 10.

I need a way (most likely through the command line) to create an Encrypted Disk Image from a folder that is both read and write compatible on both Mac's and PC.

Even better would be an Apple Script Droplet that would take a file (not a folder) create a folder and then create an Encrypted Disk Image from that folder that is both read and write compatible on both Mac's and PC and then remove the original file and folder.

Note: Shell scripts are fine for the Apple Script Droplet.

I have tried creating an encrypted .cdr image and then changing the extension to .iso. Worked on Mac, but "Error...Corrupted" on PC.

I have also tried hdiutil makehybrid -iso -joliet -o [filename].iso [encryptedfile].cdr It worked but it was not encrypted.

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    Zip file with a password is a possible solution. Worked for me sending out exam templates 3 weeks before the exam...
    – Solar Mike
    May 19, 2018 at 18:33
  • @SolarMike Not a bad idea, but I was thinking that a Disk Image encryption was more secure then a Zip file encryption. Am I wrong?
    – JBis
    May 19, 2018 at 18:35
  • I don’t have that answer, but one student out of 125 told me he had cracked the password - kept telling me for 2 weeks ... so, start of the exam I asked him in front of all the other students what the password was .... He had to admit that he didn’t know :) So I said lucky I know it .... :) Don’t they say most stuff is crackable - it depends on the resources you can throw at it...
    – Solar Mike
    May 19, 2018 at 18:38
  • @SolarMike Smart teacher :). Wish we had some of those at my school🤦‍♂️....From my 5min research it appears the only way to crack is brute force. So I may end up using that as our solution. Thanks. Will keep this question open as it is still useful.
    – JBis
    May 19, 2018 at 18:55
  • I used passwords like “dumbledore” well it was topical at the time - I know no real words etc...
    – Solar Mike
    May 19, 2018 at 19:02

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