Password protect many files easily - but not TOO securely?

Software
1

So I have a bunch of documents:

  1. I would like to password protect so that to open them, they require a password.

  2. Ideally they’d also be encrypted on disk & when being backed up by Backblaze.

  3. Finally, though, and this is important – I want the password and decryption process quite reversible if I change computers or anything like that. I use a password manager (1Password) and would store any relevant password there.

I have a bad memory of a time many years ago when I encrypted files using super-strong encryption and then forgot the password! Whoops. I do NOT want that to happen again.

I want to pose a small hurdle in front of people trying to access my files, not fort knox type security that might deny ME the files.

2

With FileVault and Backblaze Encryption then 2 is already done.

If that’s the case a person would need physical access to your machine and therefore in this instance would you get any benefit from adding a password?

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3

I have questions :slight_smile:

Can you describe what kinds of scenarios you’re thinking of?

All files or a selection of files?

Do you want the files to be individually protected or as a group?

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4

One option is to create an encrypted dmg file with Disk Utility. I created and stored a password in 1Password and use it for all my dmg files.

Any security worth using WILL lock you out if you lose the password. Otherwise why bother?

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5

I guess the scenario would be (and this responds to @aardy as well) that someone is at my computer and just using it casually. If they were snooping around a little bit (not anything really nefarious, just a ltitle casual curiosity) I would not want them to be able to access these files.

6

I would (and do) have a very, very strict practice of never granting anyone other than myself access to my computer accounts. Apple makes adding a guest account to a Mac and using it very easy, and that’s what I’d do instead of what you’re looking to do.

If a file isn’t well encypted and you grant access to your account to someone, they can easily just email the file to themselves and remove any password protection. Honestly, I doubt that there’s even a way of password protecting arbitrary files without encrypting them.

(Edit: This reads as being grumily written. Imagine I was smiling when I wrote it :slight_smile: )

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7

While I agree about using security properly, my wife has access to all our systems and our son can get access if we become incapacitated. Always important to have backup options.

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8

That’s a good point and there are ways of dealing with that. I was talking about day to day stuff and the problem scenario being discussed, which is untrusted, casual users of the computer snooping where they shouldn’t be.