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neutrino17

macrumors regular
Original poster
Jun 25, 2022
105
114
I just spoke with Apple support and there is not an encryption function for file level encryption in the Finder.

Preview can password PDFs (and apparently encrypt them) but there is no information about how the level of encryption.

I rarely need this, but now I need to email a couple of PDF files with some sensitive information. What is normally done in this case?

I'm emailing a PDF to a lawyer and I assume they are using Windows so I need a cross platform solution. Otherwise I could make an encrypted volume.

Thanks.
 

njvm

macrumors regular
Jul 17, 2018
206
61
I use WinZip for Mac - I currently have Version 8 (Version 9 is the latest). It allows you to set the Encryption method to:

  • WinZip 2.0
  • AES 128-bit
  • AES 256-bit
As it is across platform application, its files can be opened on Windows.

I often use it for sending sensitive information and I have not encountered any issues.

1683586440921.png
 

Slartibart

macrumors 68030
Aug 19, 2020
2,912
2,627
Preview can password PDFs (and apparently encrypt them) but there is no information about how the level of encryption.

The level of encryption depends on the PDF version. You can see the version level of the PDF document in Get Info.

Early versions of MacOS saved with PDF v1.4, giving RCA-128bit encryptions. Newer versions save as PDF v1.6, giving AES-128 encryption. The encrypted PDFs made by Preview are valid PDFs that can be opened (when the password is provided) by any PDF app that follows the spec on any platform.
 

MacBH928

macrumors G3
May 17, 2008
8,359
3,739
are the .zip files encrypted or password protected? as i believe password protection can be broken
 

bogdanw

macrumors 603
Mar 10, 2009
5,732
2,763
are the .zip files encrypted or password protected? as i believe password protection can be broken
Zip 2.0=ZipCrypto
"You should not rely on Zip 2.0 encryption to provide strong security for your data."
https://kb.winzip.com/help/help_encryption.htm
"ZipCrypto, for legacy compatibility purpose only as the algorithm is considered weak under today's standards, not recommended to protect sensitive data"
https://peazip.github.io/encrypt-files.html
Keka - Password protected and encrypted files
https://github.com/aonez/Keka/wiki/Compressing-with-Keka#password-protected-and-encrypted-files
 
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DominikHoffmann

macrumors 6502
Jan 15, 2007
482
470
Indiana

Creates and decompresses 7z, zip, tar and a bunch of other formats.
You can also encrypt 7z and zip files. For zip there is even an AES256 Option.
I just purchased it and tried it. It works reasonably well. My question is, whether a Windows 10/11 user receiving an encrypted 7z archive from me will be able to decrypt it without requiring him to install any utility software not part of the out-of-the-box Windows distribution.

Also, I found that Apple’s own Archive Utility
Archive Utility.png

which launches, when double-clicking a .7z file will ask for the decryption password but then pops up the password dialog again:
Screenshot 2023-08-31 at 11.30.59 AM.png

It evidently cannot handle the particular encryption format that Keka used. Keka itself can decrypt the file successfully.
 

svenmany

macrumors demi-god
Jun 19, 2011
2,064
1,339
You can do this with a free proton mail account. That has the advantage that the email itself is encrypted.
 

neutrino17

macrumors regular
Original poster
Jun 25, 2022
105
114
FYI, my solution was that the office I was communicating with setup a link to a secure portal for uploading files. I didn’t have to use email.
 

tonmischa

macrumors regular
Apr 22, 2007
149
197
I just purchased it and tried it. It works reasonably well. My question is, whether a Windows 10/11 user receiving an encrypted 7z archive from me will be able to decrypt it without requiring him to install any utility software not part of the out-of-the-box Windows distribution.

Also, I found that Apple’s own Archive Utility
View attachment 2253270
which launches, when double-clicking a .7z file will ask for the decryption password but then pops up the password dialog again:
View attachment 2253271
It evidently cannot handle the particular encryption format that Keka used. Keka itself can decrypt the file successfully.
7z is a 3rd-Party-Format, which requires 3rd-Party Software.
Win and Mac do not support 7z out-of-the box.
Mac also does not support encrypted Zips out-of-the-box.
That’s why I recommended Keka.

BTW: Keka is free software.
 

DominikHoffmann

macrumors 6502
Jan 15, 2007
482
470
Indiana
Mac also does not support encrypted Zips out-of-the-box.
macOS can generated encrypted ZIP files from the command line. Those can be opened by double-clicking in the Finder, which will put up a dialog asking for the encryption password.
BTW: Keka is free software.
Absolutely correct! I opted to purchase the software for the convenience of receiving updates through the App Store.
 
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