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  1. #1
    Encrypting Mail and Messages?
    p_rod's Avatar
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    Encrypting Mail and Messages?
    Maybe I am becoming more paranoid as I age, but I think it is time for me to start encrypting both Mail and Messages.

    I know there are email programs offering this (Proton mail comes to mind) but is there a way to accomplish encrypting that is already built into both my Mail and Message programs that I just do not know about without using third party programs?

    As always, thank you for any input you have on this!

    Cheers!

    Pat
    Only two things are infinite, the universe and human stupidity, and I'm not sure about the former.

    Albert Einstein

  2. #2
    Encrypting Mail and Messages?
    ferrarr's Avatar
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    zHere is Apple's Article, Sign or encrypt emails in Mail on Mac - Apple Support, on how to encrypt Mail messages. It looks like you need to create a certificate, for each email address you want to send to. They would also need to get a certificate to then read the email.

    Here's some more info about certificates, Use personal certificates in Mail on Mac - Apple Support.
    -- Bob --
    Please backup. Everything has a life cycle, unexpected and warning free. Nothing will last as long as you want it to.

  3. #3
    Encrypting Mail and Messages?
    chscag's Avatar
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    @Pat:

    Do you really want to do that? It's a lot more complicated than it should be and as Bob stated above it also involves the recipients of the mail and messages.

  4. #4
    Encrypting Mail and Messages?
    p_rod's Avatar
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    ferrarr and chscag!

    Thank you for the replies, gentlemen. The last thing I need is making anything more complicated. I was just hoping that there was an 'easy' way to send emails and messages securely without worrying about "someone" out there monitoring them.

    I appreciate the input!

    Cheers!

    Pat
    Only two things are infinite, the universe and human stupidity, and I'm not sure about the former.

    Albert Einstein

  5. #5
    Encrypting Mail and Messages?
    pm-r's Avatar
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    I was just hoping that there was an 'easy' way to send emails and messages securely without worrying about "someone" out there monitoring them.
    According to this article there is:

    The built-in email client that comes with macOS Sierra actually has encryption capability built into it. Even better, it actually works really well.
    ...
    If you sign up for a CA certificate at StartSSL using Safari, you’ll be up and running with encrypted email on Apple Mail in no time. The only “gotcha” here is that sending encrypted email from the iPhone is mind-bogglingly difficult.
    Encrypting Email on the Mac Is Surprisingly Easy - The Mac Observer

    PS: you might want to check with your recipients and see how they feel like working with encryption.


    - Patrick
    ======

  6. #6
    Encrypting Mail and Messages?
    p_rod's Avatar
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    Thanks, Patrick!

    There are only one or two that I'd do that with in the first place. They've expressed the same concerns I have about being 'more secure'.
    Only two things are infinite, the universe and human stupidity, and I'm not sure about the former.

    Albert Einstein

  7. #7
    Encrypting Mail and Messages?
    krs's Avatar
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    We have used HushMail for years, but it's not free.

    And if you send an encrypted email to a non-HushMail user, they get a link to decrypt it - they don't need anything special.

    Hushmail for Personal Use

  8. #8
    Encrypting Mail and Messages?
    Randy B. Singer's Avatar
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    Quote Originally Posted by p_rod View Post
    I know there are email programs offering this (Proton mail comes to mind) but is there a way to accomplish encrypting that is already built into both my Mail and Message programs that I just do not know about without using third party programs?
    This is a really awesome FREE third party program, and it's good for encrypting ANYTHING that you want to secure.

    Encrypto (free)
    Encrypto: Securely encrypt your files before sending them to friends or coworkers.

    Encrypto: Secure Your Files on the Mac App Store

    Encrypt files, works with Apple’s Mail, cross platform!

    To send an encrypted e-mail, compose your e-mail in something like Apple's TextEdit, save your message as a file, encrypt it by dragging it onto Encrypto, and send the file to Apple's Mail from right within Encrypto. It's easier to do than to explain. There is a version of Encrypto for Windows, so you can even send encrypted files to non-Macintosh users.
    Randy B. Singer
    Co-author of The Macintosh Bible (4th, 5th, and 6th editions)
    Mac OS X Routine Maintenance • http://www.macattorney.com/ts.html

  9. #9
    Encrypting Mail and Messages?
    pm-r's Avatar
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    What about Pretty Good Privacy (PGP)

    It's been in use along with Eudora from years ago, and still seems to active and working:

    Pretty Good Privacy
    How to use PGP on Mac

    How to use PGP on Mac | Set up guide [with images]




    EDIT:
    Speaking of the old Eudora, what about using some of the included encryption tools it used to have such as ROT-13 and quite a few others I've since forgotten about.

    Not earth shattering encryption method but it would often confuse anyone intercepting any such email and easy to implement and translate.

    If I recall correctly, there were also some others that would invert text and jumble the text up and invert in various ways, sort of kids code, but it worked quite well, especially to those who didn't understand what the goofed up text was all about.

    Here's a small text sample using ROT-13:
    Guvf vf n grkg pbzzrag hfvat EBG-13.
    Hint translation:
    This is a text comment using ROT-13.
    Would you have guessed??? ;-)


    - Patrick
    ======
    Last edited by pm-r; 12-04-2019 at 03:24 PM.

  10. #10
    Encrypting Mail and Messages?
    MacInWin's Avatar
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    Patrick, that is a straightforward substitution cipher, the easiest code to break. The letters are shifted 13 backward from their place in the alphabet. Took me about 10 seconds to figure that out.

    For those who didn't:

    G is 13 letters in front of T
    u is 13 letters in front of h
    v is 13 letters in front of a, etc.

    The key is to look at the one letter word "n" in the coded message. There are only three one letter words in English, I, a, and o. If "n" is a, they are 13 apart, which then released all the others.

    So if you are serious about hiding your email, don't use anything at all like that.
    Jake

  11. #11
    Encrypting Mail and Messages?
    pm-r's Avatar
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    Patrick, that is a straightforward substitution cipher, the easiest code to break.

    Sure, but not everyone knows that. If you would rather, you could use the code ring you got with some comic books. ;-)



    - Patrick
    ======

  12. #12
    Encrypting Mail and Messages?
    MacInWin's Avatar
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    Yeah, the ROT probably means rotate, and the 13 is the index of rotation. Just like a decoder ring from Ovaltine, for those who know about that.
    Jake

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