What do you use to send 4GB zip files (taxes) encrypted via email to a non-technical Win10 Home recipient?

[Arlen Holder]

What do you recommend using to send 4GB zip files (taxes) encrypted via
email (i.e., gmail on both sides) to a non-technical Win10 Home recipient?

If you're gonna email it via Gmail, what do you recommend, nowadays, for
password protection for a TurboTax zip attachment of about 4MB in size?
(1) Windows 10 Pro native encryption?
(2) 7-zip encryption? <https://www.7-zip.org/download.html>
(3) Veracrypt encryption? <https://sourceforge.net/projects/veracrypt/>
(4) ?Something better for Windows 10 Home users?

Background:
o The folder will mostly be a combination of PDFs & TurboTax files.
<https://groups.google.com/forum/#!topic/microsoft.public.windowsxp.general/tlh9Bo_p_uw>

The problem isn't encryption - it's encryption so the _user_ can read it!
o I use Veracrypt on Windows 10 Pro to create encrypted file container;
o I have "7-zip" which can encrypt, but again, the user isn't technical;
o I have Windows 10 Pro, which has native encryption by default.

But the recipient user is on a Windows 10 Home system (afaik) which was
converted by me long ago from Windows 10 S (as I recall) - and this
recipient user is not technical.

So I need to make it as easy as possible for this Win10Home recipient.
o How is that best done?

Looking up what Windows 10 Home has to offer by way of native encryption...
o How do I password protect a zipped folder in Microsoft 10
<https://answers.microsoft.com/en-us/windows/forum/windows_10-files/how-do-i-password-protect-a-zipped-folder-in/34f35561-a6a8-492e-96f4-175a218aeb32>

Which says Windows 10 has native file encryption via:
o Right-click on the folder > Properties > [Advanced]
o [x]Encrypt contents to secure data check box > OK > Apply > OK

Which, for me, encrypted with "my" certificate (whatever that is).
o But for this person on Windows 10 Home, that article says:
"File encryption is not available in Windows 10 Home"

Bummer.
o That leaves 7zip or Veracrypt encryption... or.... something easier?

What do you recommend using to send 4GB zip files (taxes) encrypted via
email (i.e., gmail on both sides) to a non-technical Win10 Home recipient?
--
Usenet works best when purposefully helpful adults publicly share ideas.

[Arlen Holder]

On Sat, 13 Jun 2020 16:42:32 -0000 (UTC), Arlen Holder wrote:

> What do you recommend using to send 4GB zip files (taxes) encrypted via
> email (i.e., gmail on both sides) to a non-technical Win10 Home recipient?

Oooops. 4MB

[Paul]

Both you and the recipient can go here.

https://www.7-zip.org/

The 7Z format, when selected, there's a tick box for AES encryption
and a password. Communicate the password to the recipient some
other means than email. Maybe a phone call, or a snail mail, or...

When 7ZIP is asked to open the file, it will prompt for the password.

*******

While you could use WinZIP, I believe the old password scheme on
that is trivially crackable. So much so, that it was an ethics
question as to whether operations like Google would be "scanning"
the innards of ZIP attachments (even ones with password protection).
A later password scheme for ZIP, was less accessible that way.

I'm not saying the above is bulletproof. There is GNU Privacy Guard
and public key encryption if you want it. The software in that
case, will attempt compression of its own, before encrypting,
in an effort to make the smallest file possible. I don't think
the compressor is quite as good as 7ZIP.

*******

Some email systems, do not allow convenient attachments, because
they're "assumed to contain malware" :-/ Don't be surprised if
whatever you attempt to do with attachments, simply won't work.
Welcome to 2020.

You could try pasting 5MB of BASE64 into the body of the
message, but then the recipient would have to be Einstein
to figure out what to do. I just don't know what works today,
to bypass attachment rules...

Paul

[Arlen Holder]

On Sat, 13 Jun 2020 14:28:46 -0400, Paul wrote:

> Both you and the recipient can go here.
> https://www.7-zip.org/

Hi Paul,
Thanks for your purposefully helpful advice, where, this is a question not
of what "can" be done, but what's a "good" way to do it.

For example, on all my systems, both 7-zip & Veracrypt are standard fare;
but this is for someone who is not technical, where it's a complexity to
ask them to install either 7zip or Veracrypt "just" to decrypt a file.

Mainly I was hoping there's something "native" in Windows... so that the
recipient doesn't need to "install" anything.

There is this concept of the native Windows 10 Pro encryption, and I did
find out that the recipient has Windows 10 Pro on their work computer, so
if I could figure out how to pass them the encryption certificate, that
might work best. [They didn't seem fazed when I said they shouldn't do
personal things on a work computer.]

Have you ever sent a recipient a Windows-10-Pro native encrypted file?
o In my tests today, it encrypted with a "certificate" of some sort.

Do I pass the user that certificate?
o Where do I find it?

> While you could use WinZIP, I believe the old password scheme on

> that is trivially crackable....

I agree with you where I have "cracked" my share of supposedly
password-protected files (e.g., PDFs) and where 7-zip has replaced WinZip
for me, many (many) years ago.

And, as you're well aware, we're not hiding from a TLA here; we're just
trying to send a 4MB zip file of tax records, which, if someone is reading
our mail on the Google servers, then we have _bigger_ things to worry about
than tax records which, eventually, are sent to the Feds anyway.

I just wanted to know what's the simplest general-purpose encryption use
model, for prudence, for non technical people.

> Some email systems, do not allow convenient attachments, because
> they're "assumed to contain malware" :-/ Don't be surprised if
> whatever you attempt to do with attachments, simply won't work.
> Welcome to 2020.

I'm well aware that Google Gmail won't send some things, for example,
Android APKs, even when zipped and/or renamed; however I tested both
7zip-encrypted and Veracrypt-encrypted files today and they worked on my
side (I haven't heard from the recipient yet).

So, if the best answer turns out to be either 7Zip or Veracrypt, then I'm
pretty sure it will work as I sent the same format files in the test.

In summary, if I was sending to you, I'd choose either 7Zip or Veracrypt;
but for a non-technical person, I'm hoping that the Windows 10 native file
encryption (or perhaps some other "simple" solution) would work.

In the case of Windows 10 native file encryption, I successfully encrypted
the zipped folder; but it encrypted it with a certificate that it had
(somewhere???) tied, presumably to my username (which certainly isn't
theirs).

SO I'm unsure what the use model is if I use Windows 10 Pro native file
encryption, where I only found out after I posted this thread that teh user
prefers to use their work computer which is Windows 10 Pro.

Has anyone here ever sent a file to someone which was encrypted with
Windows 10 Pro native file encryption? How?
--
Seeking the best answers takes a bit of help from others sometimes.

[Roger Blake]

On 2020-06-13, Arlen Holder <arlen...@newmachine.com> wrote:
> The problem isn't encryption - it's encryption so the _user_ can read it!
> o I use Veracrypt on Windows 10 Pro to create encrypted file container;
> o I have "7-zip" which can encrypt, but again, the user isn't technical;
> o I have Windows 10 Pro, which has native encryption by default.

Again with the f*cking bullet points. Since it is impossible to reason
with you it is time for the killfile.

--
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[Arlen Holder]

UPDATE:

I tested out, as a single user, this native Windows 10 Pro encryption.

Do you have experience with a use model for using this native Microsoft
Windows 10 encryption between two users?

If so, can you expound on any suggestions for improving that use model?

"When encrypting files and folders, Windows will use a self-generated
certificate that contains keys used to encrypt and decrypt the data.
When opening encrypted data when logged into the user account that
generated the certificate, the decryption process is transparent
and the files are opened normally."

"However, if another user or system tries to access those same data files
or if the files are moved to another location, then they cannot be
opened *unless the original certificate is installed*."

. *How to Decrypt Encrypted Windows Files*
<https://www.online-tech-tips.com/computer-tips/decrypt-encrypted-xp-files/>

(1) Open the Windows native certificate manager
. Win+R > certmgr.msc
(2) Select your personal user certificate
. Certificates - Current User > Personal > Certificates > {yourname}
(5) Doublcheck the "Intended Purposes" is "Encrypting File System"
(6) Rightclick the certificate > All Tasks > Export
. Welcome to the Certificate Export Wizard > Next
. (o) Yes, export the private key > Next
. (o) Personal Information Exchange - PKCS #12 (.PFX) > Next
. [x] Password: (enter any desired password twice) > Next
. Filename: my_personal_EFS_information_exchange_certificate.pfx > Next
. Finish > OK
(7) Email that EFS certificate key to the intended recipient.
(8) The recipient can doubleclick on that file which will automatically
open up the "Welcome to the Certificate Import Wizard" which will import
into their machine.
(9) They can then open the files you send them on Windows 10.

Note: The article didn't say whether this is a good practice or not to send
someone else your personal certification key, where I'm not sure if this is
a good use model or not. A lot depends on whether Microsoft generates a new
random key for you each time, or if it's always the same key.

Do you have experience with a use model for using this native Microsoft
Windows 10 encryption between two users?

If so, can you expound on any suggestions for improving that use model?
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