How to Encrypt a Text file?

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get_g0ing
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How to Encrypt a Text file?

Post by get_g0ing » Mon Nov 05, 2018 6:52 pm

Hi,

Do you use any program or method to encrypt a text file on Widows? Can you please share or recommend something that is free?

use case:
Encrypting a text file containing sensitive data and keeping on cloud (Google drive).

- I know Microsoft Word documents and PDFs can be password protected, but I am asking to encrypt plain text (.txt).
- There are online and offline password managers like LastPass and KeePass, but I'm not looking for those.

Another option is to use 7-zip to create a password protected archive, but I'm looking for something:
that will take a .txt file and use something like OpenSSL to encrypt it with an algorithm like AES-256 and create another .txt file. And then use the same program to decrypt.

Any options? Thank you.
Last edited by get_g0ing on Thu Nov 08, 2018 8:33 am, edited 1 time in total.

ThriftyPhD
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Re: How to Encrypt a Text file?

Post by ThriftyPhD » Mon Nov 05, 2018 6:58 pm


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dm200
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Re: How to Encrypt a Text file?

Post by dm200 » Mon Nov 05, 2018 7:01 pm

Winzip

Silk McCue
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Re: How to Encrypt a Text file?

Post by Silk McCue » Mon Nov 05, 2018 7:06 pm

https://www.comparitech.com/blog/vpn-pr ... _10_8_or_7

The steps do do so in native windows are documented here.

Cheers

supalong52
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Re: How to Encrypt a Text file?

Post by supalong52 » Mon Nov 05, 2018 7:32 pm

When we exchange discovery in litigation, we often use VeraCrypt containers. It's free and open source.

Luke Duke
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Re: How to Encrypt a Text file?

Post by Luke Duke » Mon Nov 05, 2018 7:33 pm

Encrypting a cryptocurrency password?

rkhusky
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Re: How to Encrypt a Text file?

Post by rkhusky » Mon Nov 05, 2018 8:41 pm

get_g0ing wrote:
Mon Nov 05, 2018 6:52 pm
Another option is to use 7-zip to create a password protected archive, but I'm looking for something:
that will take a .txt file and use something like OpenSSL to encrypt it with an algorithm like AES-256 and create another .txt file. And then use the same program to decrypt.
I don't know of an encryption program that produces text files, most produce binary files. There used to be something called UUEncode, which would turn a binary file into a text file.

forevernaive
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Re: How to Encrypt a Text file?

Post by forevernaive » Mon Nov 05, 2018 8:43 pm

Notepad++, a handy text editor for windows, has a plugin called NppCrypt that could do the trick for you.

MathWizard
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Re: How to Encrypt a Text file?

Post by MathWizard » Mon Nov 05, 2018 8:48 pm

BitLocker?

It should be built into windows. It encrypts the entire drive. I believe it is AES.

TravelGeek
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Re: How to Encrypt a Text file?

Post by TravelGeek » Mon Nov 05, 2018 9:39 pm

get_g0ing wrote:
Mon Nov 05, 2018 6:52 pm
... but I'm looking for something:
that will take a .txt file and use something like OpenSSL to encrypt it with an algorithm like AES-256 and create another .txt file. And then use the same program to decrypt.
This seems to be exactly what you want:

https://crypto.stackexchange.com/questi ... ng-openssl

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Mon Nov 05, 2018 10:11 pm

forevernaive wrote:
Mon Nov 05, 2018 8:43 pm
Notepad++, a handy text editor for windows, has a plugin called NppCrypt that could do the trick for you.
Hi,

Thanks. I did come across the NppCrypt plugin before I made this post and tried it out. It encrypted the text fine but it always gave an error when decrypting:
Image

Another concern I have is that it so customizable that I'll forget what options I used to encrypt :)
Image

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JoMoney
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Re: How to Encrypt a Text file?

Post by JoMoney » Mon Nov 05, 2018 10:49 pm

I use a password protected zip file.

However, be aware that when the file is unzipped (even temporarily in the computers memmory) it gets stored unencrypted temporarily on the hard drive and is vulnerable to anyone that might have physical access to the hard drive... maybe even after the unencrypted file is deleted, unless the hard-drive is overwritten it might be vulnerable to recovery.

Password protected Microsoft Word documents remain encrypted even after unlocked/opened, but are weak and the passwords can get bypassed by someone knowledgeable on it, whereas AES 256 password protected ZIP files are very secure (well.. secure as your password... and other than the vulnerability after de-crypted and stored on the drive).
You could combine a password protected word document zipped into a password protected zip file....

Another option, which requires some amount of trust in the provider, is Protonmail.com ... If you store the text in an email to yourself on Protonmail it's stored encrypted on their server and allegedly is only able to be decrypted with your password and is done in your browser when you login so it's not stored decrypted anywhere (just be sure to never email it outside of Protonmail's system).

[Edit] So I went back and re-read the entire post and realized I missed stuff on my first glance over:
...Another option is to use 7-zip to create a password protected archive, but I'm looking for something:
that will take a .txt file and use something like OpenSSL to encrypt it with an algorithm like AES-256 and create another .txt file. And then use the same program to decrypt.
If you use WinZip, you can not only encrypt it with a password using AES-256, but WinZip also has a feature to MIME/UU-encode. MIME/UU-encoding will convert the Zip file to a text file ... I'm not sure if 7-zip offers MIME/UU-enconding.
"To achieve satisfactory investment results is easier than most people realize; to achieve superior results is harder than it looks." - Benjamin Graham

michaeljc70
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Re: How to Encrypt a Text file?

Post by michaeljc70 » Tue Nov 06, 2018 9:18 am

I use 7-zip. You can create a batch file if you want to encrypt/decrypt a whole directory at one time. It is cross platform so I can access and decrypt the files on my phone or Chromebook too. It is a benefit to me that it works on non-text file. I sometimes take a picture (or scan) of something like a passport or other important document and want to encrypt it.

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MossySF
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Re: How to Encrypt a Text file?

Post by MossySF » Tue Nov 06, 2018 9:34 am

My recommendation ... if you don't regularly encrypt & decrypt, you WILL FORGET the password ... unless it's so simple as to be easily crackable.

Hence, use something like LastPass. LastPass not only can save your passwords but also can let you write secure notes that require you to enter your password in order to view.

fulltilt
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Re: How to Encrypt a Text file?

Post by fulltilt » Tue Nov 06, 2018 9:41 am

MossySF wrote:
Tue Nov 06, 2018 9:34 am
My recommendation ... if you don't regularly encrypt & decrypt, you WILL FORGET the password ... unless it's so simple as to be easily crackable.

Hence, use something like LastPass. LastPass not only can save your passwords but also can let you write secure notes that require you to enter your password in order to view.
Why not write the password down and store in a secured physical location?

Or use diceware

rich126
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Re: How to Encrypt a Text file?

Post by rich126 » Tue Nov 06, 2018 10:07 am

Ideally any encryption you do, you want to use AES256. Remembering passwords can be tricky and I've used Last Password. Another trick (especially for web sites and not necessarily for file encryption) is to use a complicated password but change a single letter or letters based on the web site name. For example:
Giants!1950!1998!ya
Giants!1950!1998!go

Where Giants may be your favorite sports team (or maybe most hated team), and the two years either represent something like the years they won the WS or something family related to you, and the last 2 letters represent the first 2 letters of the website (yahoo, google).

This way you can have unique, complicated passwords for every web site and not have to store them somewhere (although keeping them in a tool for backup is a good idea). And, of course, you don't want to make things too personal for you to the point where someone that knows you would have an easy time guessing it. Trying to keep it around 16 characters is a good idea although I've run into one bank where the max was 14 characters :(

As others have mentioned, Apple allows you to encrypt the entire drive with AES256 fairly easily, and Microsoft does so with BitLocker (although I'm not sure if it is in every version of windows). One flaw with entire drive encryption is that they only protect you if someone steals your computer with the power off. Once things are up and running, the drive is unencrypted. That is where individual file encryption would be useful.

You can also use openssl to encrypt files individually. (https://gist.github.com/colinstein/de1755d2d7fbe27a0f1e)

Assuming secret.txt is your input file, then secret.txt.enc will be the encrypted file and the command will prompt you for a password phrase:
openssl aes-256-cbc -in secret.txt -out secret.txt.enc

Then to decrypt
openssl aes-256-cbc -d -in secret.txt.enc -out secret.txt.decrypted

This will definitely work on Apple computers and Linux systems, but not windows (at least natively).

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Tue Nov 06, 2018 3:57 pm

ThriftyPhD wrote:
Mon Nov 05, 2018 6:58 pm
https://www.gpg4win.org/
This sounds interesting. gpg4usb looks similar and portable.

So you just encrypt with your own public key (rather than someone else's as normally intended)? Where/how do you safely keep the private key?

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Tue Nov 06, 2018 3:59 pm

supalong52 wrote:
Mon Nov 05, 2018 7:32 pm
When we exchange discovery in litigation, we often use VeraCrypt containers. It's free and open source.
VeraCrypt looks promising. I think it doesn't encrypt individual files. So maybe I can create a small container and put my text file in it.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Tue Nov 06, 2018 3:59 pm

Luke Duke wrote:
Mon Nov 05, 2018 7:33 pm
Encrypting a cryptocurrency password?
Blasphemy :)

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Tue Nov 06, 2018 4:02 pm

MathWizard wrote:
Mon Nov 05, 2018 8:48 pm
BitLocker?

It should be built into windows. It encrypts the entire drive. I believe it is AES.
Yes, it is AES when I looked into it. But it will encrypt your whole drive or partition but not an individual file like I am looking to do.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Tue Nov 06, 2018 4:05 pm

TravelGeek wrote:
Mon Nov 05, 2018 9:39 pm
get_g0ing wrote:
Mon Nov 05, 2018 6:52 pm
... but I'm looking for something:
that will take a .txt file and use something like OpenSSL to encrypt it with an algorithm like AES-256 and create another .txt file. And then use the same program to decrypt.
This seems to be exactly what you want:

https://crypto.stackexchange.com/questi ... ng-openssl
rich126 wrote:
Tue Nov 06, 2018 10:07 am
Ideally any encryption you do, you want to use AES256. Remembering passwords can be tricky and I've used Last Password. Another trick (especially for web sites and not necessarily for file encryption) is to use a complicated password but change a single letter or letters based on the web site name. For example:
Giants!1950!1998!ya
Giants!1950!1998!go

Where Giants may be your favorite sports team (or maybe most hated team), and the two years either represent something like the years they won the WS or something family related to you, and the last 2 letters represent the first 2 letters of the website (yahoo, google).

This way you can have unique, complicated passwords for every web site and not have to store them somewhere (although keeping them in a tool for backup is a good idea). And, of course, you don't want to make things too personal for you to the point where someone that knows you would have an easy time guessing it. Trying to keep it around 16 characters is a good idea although I've run into one bank where the max was 14 characters :(

As others have mentioned, Apple allows you to encrypt the entire drive with AES256 fairly easily, and Microsoft does so with BitLocker (although I'm not sure if it is in every version of windows). One flaw with entire drive encryption is that they only protect you if someone steals your computer with the power off. Once things are up and running, the drive is unencrypted. That is where individual file encryption would be useful.

You can also use openssl to encrypt files individually. (https://gist.github.com/colinstein/de1755d2d7fbe27a0f1e)

Assuming secret.txt is your input file, then secret.txt.enc will be the encrypted file and the command will prompt you for a password phrase:
openssl aes-256-cbc -in secret.txt -out secret.txt.enc

Then to decrypt
openssl aes-256-cbc -d -in secret.txt.enc -out secret.txt.decrypted

This will definitely work on Apple computers and Linux systems, but not windows (at least natively).

Thanks for sharing about how to use OpenSSL. Is there a program that automates this with GUI?

ThriftyPhD
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Re: How to Encrypt a Text file?

Post by ThriftyPhD » Tue Nov 06, 2018 7:33 pm

get_g0ing wrote:
Tue Nov 06, 2018 3:57 pm
ThriftyPhD wrote:
Mon Nov 05, 2018 6:58 pm
https://www.gpg4win.org/
This sounds interesting. gpg4usb looks similar and portable.

So you just encrypt with your own public key (rather than someone else's as normally intended)? Where/how do you safely keep the private key?
Yes, you could encrypt with your public key and decrypt with your private key. You could also use symmetric encryption. https://www.gnupg.org/gph/en/manual/x110.html

The private key is stored on your computer, and locked with a passphrase that you remember. https://www.gnupg.org/gph/en/manual/c481.html

You can go extreme and store the private key on a Yubikey.

This probably represents one of the more involved options you have available, but something to consider.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Tue Nov 06, 2018 8:16 pm

ThriftyPhD wrote:
Tue Nov 06, 2018 7:33 pm
get_g0ing wrote:
Tue Nov 06, 2018 3:57 pm
ThriftyPhD wrote:
Mon Nov 05, 2018 6:58 pm
https://www.gpg4win.org/
This sounds interesting. gpg4usb looks similar and portable.

So you just encrypt with your own public key (rather than someone else's as normally intended)? Where/how do you safely keep the private key?
Yes, you could encrypt with your public key and decrypt with your private key. You could also use symmetric encryption. https://www.gnupg.org/gph/en/manual/x110.html

The private key is stored on your computer, and locked with a passphrase that you remember. https://www.gnupg.org/gph/en/manual/c481.html

You can go extreme and store the private key on a Yubikey.

This probably represents one of the more involved options you have available, but something to consider.
I appreciate your knowledge.

I tested the gpg4usb utility a little and I think I have some idea of using the public-private key pair method. Can you tell how to do the symmetric encryption using the gpg4usb GUI? It sounds similar to the "openssl aes-256-cbc" command mentioned above, but I'm not sure how to do it using the GUI.

Thanks.

ThriftyPhD
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Re: How to Encrypt a Text file?

Post by ThriftyPhD » Tue Nov 06, 2018 8:32 pm

Sorry, I can't really help you out. I'm far from an expert, so far I've used it rather sparingly, and everything I've done is from the command line. I've never used the GUI.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Tue Nov 06, 2018 9:04 pm

ThriftyPhD wrote:
Tue Nov 06, 2018 8:32 pm
Sorry, I can't really help you out. I'm far from an expert, so far I've used it rather sparingly, and everything I've done is from the command line. I've never used the GUI.
No problem, you have given me good pointers, and thanks for that.

johnubc
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Re: How to Encrypt a Text file?

Post by johnubc » Tue Nov 06, 2018 9:43 pm

There are plenty of ways to encrypt a file - WinZip has an encrypt option. Word can be used, but make sure the encrypt option is chosen vs just a password protected word file. Just a password on a file does not mean that the file is encrypted.

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dm200
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Re: How to Encrypt a Text file?

Post by dm200 » Wed Nov 07, 2018 9:10 am

johnubc wrote:
Tue Nov 06, 2018 9:43 pm
There are plenty of ways to encrypt a file - WinZip has an encrypt option. Word can be used, but make sure the encrypt option is chosen vs just a password protected word file. Just a password on a file does not mean that the file is encrypted.
Yes - I have used both. When you desire encryption, make sure to select it, have a strong password and ask for the level of encryption you want.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Wed Nov 07, 2018 12:44 pm

forevernaive wrote:
Mon Nov 05, 2018 8:43 pm
Notepad++, a handy text editor for windows, has a plugin called NppCrypt that could do the trick for you.
ThriftyPhD wrote:
Tue Nov 06, 2018 7:33 pm

Yes, you could encrypt with your public key and decrypt with your private key. You could also use symmetric encryption. https://www.gnupg.org/gph/en/manual/x110.html
rich126 wrote:
Tue Nov 06, 2018 10:07 am

You can also use openssl to encrypt files individually. (https://gist.github.com/colinstein/de1755d2d7fbe27a0f1e)

Assuming secret.txt is your input file, then secret.txt.enc will be the encrypted file and the command will prompt you for a password phrase:
openssl aes-256-cbc -in secret.txt -out secret.txt.enc

Then to decrypt
openssl aes-256-cbc -d -in secret.txt.enc -out secret.txt.decrypted

This will definitely work on Apple computers and Linux systems, but not windows (at least natively).
It looks like both NppCrypt (Notepad++ plugin) and OpenSSL can do AES-256 encryption.

Does anyone know what settings to use on NppCrypt to match the output of OpenSSL:
openssl aes-256-cbc -in secret.txt -out secret.txt.enc

Image

TravelGeek
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Re: How to Encrypt a Text file?

Post by TravelGeek » Wed Nov 07, 2018 12:53 pm

Assuming you are just planning to keep the file to yourself after encryption, it seems there is no value in using asymmetric encryption. You now have two keys to manage, for no good reason. https://en.m.wikipedia.org/wiki/Public-key_cryptography

Depending on what you are actually trying to protect and how computer command line illiterate/savvy you are, I would reconsider the ask for a GUI on top of OpenSSL. The more layers of software you add (from potentially unknown sources, with unknown bugs or “features”), the more you are putting your data at risk (defeating the encryption you are looking for in the first place). The OpenSSL command is pretty simple, and you could probably write a tiny command line wrapper that just saves you a few keystrokes by accepting a single file name as a parameter and defaulting all the other stuff.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Wed Nov 07, 2018 1:30 pm

TravelGeek wrote:
Wed Nov 07, 2018 12:53 pm
Assuming you are just planning to keep the file to yourself after encryption, it seems there is no value in using asymmetric encryption. You now have two keys to manage, for no good reason. https://en.m.wikipedia.org/wiki/Public-key_cryptography

Depending on what you are actually trying to protect and how computer command line illiterate/savvy you are, I would reconsider the ask for a GUI on top of OpenSSL. The more layers of software you add (from potentially unknown sources, with unknown bugs or “features”), the more you are putting your data at risk (defeating the encryption you are looking for in the first place). The OpenSSL command is pretty simple, and you could probably write a tiny command line wrapper that just saves you a few keystrokes by accepting a single file name as a parameter and defaulting all the other stuff.
I'm liking OpenSSL so far. I was able to download it for Windows and play with it a little. Not that difficult to use.
Do you know the defaults used on OpenSSL for key derivation or hashing function? To get a sightly better understanding, I'm trying to get NppCrypt (notepad++ plugin) to generate the same output as: openssl aes-256-cbc -in input.txt -out output.txt

In NppCrypt if I choose AES 256 as the cipher and cbc as the mode, that should match the aes-256-cbc used in the openssl command, but I don't know what to set the rest of the options (see post above for screenshot of options).

ThriftyPhD
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Re: How to Encrypt a Text file?

Post by ThriftyPhD » Wed Nov 07, 2018 7:12 pm

TravelGeek wrote:
Wed Nov 07, 2018 12:53 pm
Depending on what you are actually trying to protect and how computer command line illiterate/savvy you are, I would reconsider the ask for a GUI on top of OpenSSL. The more layers of software you add (from potentially unknown sources, with unknown bugs or “features”), the more you are putting your data at risk (defeating the encryption you are looking for in the first place). The OpenSSL command is pretty simple, and you could probably write a tiny command line wrapper that just saves you a few keystrokes by accepting a single file name as a parameter and defaulting all the other stuff.
Quoting to agree and re-emphasize. Tools like OpenSSL or PGP are open source, simple, and work on more or less every computer you're like to come across. They're likely installed by default on many Linux distributions, and simple to install on Mac or Windows. This means that ten+ years from now, you can reasonable expect to be able to decrypt something you encrypt today. Once you move to 3rd party tools, GUIs, or plugins, that expectation decreases. For example, with NppCrypt, you're relying on the plugin creator to continue supporting it, and you're relying on notepad++ still being around (it's open source, so quite possible, but not as ubiquitous as OpenSSL). Not only do those tools need to be available, but they need to continue to work together. If notepad++ changes such that NppCrypt doesn't continue to work, will you be able to decrypt your files?

MisterMister
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Re: How to Encrypt a Text file?

Post by MisterMister » Thu Nov 08, 2018 12:36 am

get_g0ing wrote:
Wed Nov 07, 2018 1:30 pm

I'm liking OpenSSL so far. I was able to download it for Windows and play with it a little. Not that difficult to use.
Do you know the defaults used on OpenSSL for key derivation or hashing function? To get a sightly better understanding, I'm trying to get NppCrypt (notepad++ plugin) to generate the same output as: openssl aes-256-cbc -in input.txt -out output.txt

In NppCrypt if I choose AES 256 as the cipher and cbc as the mode, that should match the aes-256-cbc used in the openssl command, but I don't know what to set the rest of the options (see post above for screenshot of options).
You didn't make clear what your use cases are. Who are you seeking to protect these files from? Do you need to share them via email or in another way? It makes a big difference in terms of the best program to use.

1. The first order of business is to see to it that your entire computer hard disk is encrypted. If you have a bunch of sensitive text files all over the place you will eventually lose track of them and/or the passwords that enable you to decrypt them. For full disk encryption, BitLocker is by far the best choice but it only works on Windows Pro or above. Depending on what your true use cases are, this one step may be enough and you may not need to encrypted individual files as long as your Windows password is strong. If you can't or don't want to do this, or still want to encrypt at the file level....

2. I agree with another poster who suggested gpg4win. There is a learning curve, but once you're past that it is far less awkward to use for encryption than openssl. It employs the time-tested OpenPGP protocol specification which is far superior to what you are doing with openssl.

The biggest risks to any encryption strategy are a) using too simple a password or b) forgetting the password. Both are major worries if you are dealing with important data.

This forum is not the best place for questions like this; if you do a bit of Googling you'll find a wealth of information.

Oh... it's doubtful you'll get NppCrypt and OpenSSL to produce compatible files. From your questions I assume you're a computer professional of some kind but, even so, this probably won't happen. Unlike OpenPGP and NppCrypt, OpenSSL is not really designed for file encryption; it's just a function someone decided would be easy to add but the methodology is fairly primitive. This results in file format differences that can't be reconciled with a dedicated encryption program.

Good luck.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Thu Nov 08, 2018 9:33 am

MisterMister wrote:
Thu Nov 08, 2018 12:36 am
get_g0ing wrote:
Wed Nov 07, 2018 1:30 pm

I'm liking OpenSSL so far. I was able to download it for Windows and play with it a little. Not that difficult to use.
Do you know the defaults used on OpenSSL for key derivation or hashing function? To get a sightly better understanding, I'm trying to get NppCrypt (notepad++ plugin) to generate the same output as: openssl aes-256-cbc -in input.txt -out output.txt

In NppCrypt if I choose AES 256 as the cipher and cbc as the mode, that should match the aes-256-cbc used in the openssl command, but I don't know what to set the rest of the options (see post above for screenshot of options).
You didn't make clear what your use cases are. Who are you seeking to protect these files from? Do you need to share them via email or in another way? It makes a big difference in terms of the best program to use.

1. The first order of business is to see to it that your entire computer hard disk is encrypted. If you have a bunch of sensitive text files all over the place you will eventually lose track of them and/or the passwords that enable you to decrypt them. For full disk encryption, BitLocker is by far the best choice but it only works on Windows Pro or above. Depending on what your true use cases are, this one step may be enough and you may not need to encrypted individual files as long as your Windows password is strong. If you can't or don't want to do this, or still want to encrypt at the file level....

2. I agree with another poster who suggested gpg4win. There is a learning curve, but once you're past that it is far less awkward to use for encryption than openssl. It employs the time-tested OpenPGP protocol specification which is far superior to what you are doing with openssl.

The biggest risks to any encryption strategy are a) using too simple a password or b) forgetting the password. Both are major worries if you are dealing with important data.

This forum is not the best place for questions like this; if you do a bit of Googling you'll find a wealth of information.

Oh... it's doubtful you'll get NppCrypt and OpenSSL to produce compatible files. From your questions I assume you're a computer professional of some kind but, even so, this probably won't happen. Unlike OpenPGP and NppCrypt, OpenSSL is not really designed for file encryption; it's just a function someone decided would be easy to add but the methodology is fairly primitive. This results in file format differences that can't be reconciled with a dedicated encryption program.

Good luck.
Hi,

You sound very knowledgeable, thanks for sharing your advice.

I should have clarified the use case: I'm looking to encrypt a text file with personal info (like passwords, ssn) and store it online (Google drive).
I know something like LastPass can be used also, but I don't want to use it.
I agree with the reminder about whole-disk encryption. It won't help my use case but otherwise it's an important thing to do.

I did do a fair bit of Google searching. That's how I found gpg4usb, which looks like a simpler version of gpg4win. I think gpg4win can also do symmetrical encryption (unlike gpg4usb), which is what I'm looking into right now. I like a earlier poster's advice on not needing the private-public key pair type encryption for my use (so gpg4usb won't be useful to me).
Google also lead me to SafePad.

Regarding NppCrypt, OpenSSL and other tools:
I share the concern posted above that what if I use a particular tool to encrypt but then in the future it becomes unavailable. Which is why I was interested in seeing if I could encrypt with one and decrypt with another.

You mentioned gpg4win: is there another program that can decrypt a file symmetrically encrypted with gpg4win?
Last edited by get_g0ing on Thu Nov 08, 2018 9:58 am, edited 1 time in total.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Thu Nov 08, 2018 9:47 am

ThriftyPhD wrote:
Wed Nov 07, 2018 7:12 pm
TravelGeek wrote:
Wed Nov 07, 2018 12:53 pm
Depending on what you are actually trying to protect and how computer command line illiterate/savvy you are, I would reconsider the ask for a GUI on top of OpenSSL. The more layers of software you add (from potentially unknown sources, with unknown bugs or “features”), the more you are putting your data at risk (defeating the encryption you are looking for in the first place). The OpenSSL command is pretty simple, and you could probably write a tiny command line wrapper that just saves you a few keystrokes by accepting a single file name as a parameter and defaulting all the other stuff.
Quoting to agree and re-emphasize. Tools like OpenSSL or PGP are open source, simple, and work on more or less every computer you're like to come across. They're likely installed by default on many Linux distributions, and simple to install on Mac or Windows. This means that ten+ years from now, you can reasonable expect to be able to decrypt something you encrypt today. Once you move to 3rd party tools, GUIs, or plugins, that expectation decreases. For example, with NppCrypt, you're relying on the plugin creator to continue supporting it, and you're relying on notepad++ still being around (it's open source, so quite possible, but not as ubiquitous as OpenSSL). Not only do those tools need to be available, but they need to continue to work together. If notepad++ changes such that NppCrypt doesn't continue to work, will you be able to decrypt your files?
Yes, I do agree and share the same concern. Even with OpenSSL or PGP:
What if I encrypt with, let's say version 1.x of OpenPGP or OpenSSL and then years later try to decrypt with version 3.x?

Contrary to my initial assumption, doing AES-256 encryption is not just one thing. There are several parameters that go into it, and you'd need the exact same to decrypt (I posted screenshot above).

I'd like to understand this some more but if I don't find a good answer, my backup plan is to save a copy of the tool I used. If I decide on NppCrypt, I'll do a portable install of Notepad++, use NppCrypt, and then zip up that same folder and store it. That's part of why I'm hoping for a portable app :)

MisterMister
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Re: How to Encrypt a Text file?

Post by MisterMister » Thu Nov 08, 2018 10:45 am

get_g0ing wrote:
Thu Nov 08, 2018 9:33 am
I did do a fair bit of Google searching. That's how I found gpg4usb, which looks like a simpler version of gpg4win. I think gpg4win can also do symmetrical encryption (unlike gpg4usb), which is what I'm looking into right now. I like a earlier poster's advice on not needing the private-public key pair type encryption for my use (so gpg4usb won't be useful to me).
Google also lead me to SafePad.

Regarding NppCrypt, OpenSSL and other tools:
I share the concern posted above that what if I use a particular tool to encrypt but then in the future it becomes unavailable. Which is why I was interested in seeing if I could encrypt with one and decrypt with another.

You mentioned gpg4win: is there another program that can decrypt a file symmetrically encrypted with gpg4win?
GPG4Win is a GUI wrapper for the command-line GPG tool. The latter has been around for probably 20 years, works on Windows and Linux. It produces a standard OpenPGP file format that is compatible with a variety of tools on the market, including Symantec's PGP line of (not free) products, and there are various tools popping up all the time that purport to support it (e.g. https://pgptool.github.io, which I have no experience with and cannot vouch for; you could try it). I can't speak to whether symmetric encryption compatibility is there, but I suspect it is. As always use due diligence when downloading software.

But GPG itself is in wide use, built into many Linux distros, and was funded in part by some national governments (Germany I think). It's not going away and even if it did there are alternatives that should be able to decrypt your file. If you're really concerned you'd need to test those.

You may not need asymmetric encryption but that is the natural way to do things with GPG. It has many advantages, but one downside that you must always have a copy of your key file available (as well as remember the password for the keyfile). I imagine gpg4usb will help with some of that since you can keep some USBs in a safe deposit box. If it were me, I would definitely use the asymmetric variant because it is much more secure.

The best thing you can do to protect your Google Drive data is to ensure you have a secure Google password AND MOST IMPORTANTLY have two-factor authentication turned on. The keys to the kingdom are available if some hacks your email or Google account so you need to protect that. Google drive itself is pretty secure, some might argue that you don't even need to encrypt things stored there. But I don't fault you for wanting to do it, and really GPG / GPG4Win is your best choice.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Thu Nov 08, 2018 12:46 pm

MisterMister wrote:
Thu Nov 08, 2018 10:45 am
get_g0ing wrote:
Thu Nov 08, 2018 9:33 am
I did do a fair bit of Google searching. That's how I found gpg4usb, which looks like a simpler version of gpg4win. I think gpg4win can also do symmetrical encryption (unlike gpg4usb), which is what I'm looking into right now. I like a earlier poster's advice on not needing the private-public key pair type encryption for my use (so gpg4usb won't be useful to me).
Google also lead me to SafePad.

Regarding NppCrypt, OpenSSL and other tools:
I share the concern posted above that what if I use a particular tool to encrypt but then in the future it becomes unavailable. Which is why I was interested in seeing if I could encrypt with one and decrypt with another.

You mentioned gpg4win: is there another program that can decrypt a file symmetrically encrypted with gpg4win?
GPG4Win is a GUI wrapper for the command-line GPG tool. The latter has been around for probably 20 years, works on Windows and Linux. It produces a standard OpenPGP file format that is compatible with a variety of tools on the market, including Symantec's PGP line of (not free) products, and there are various tools popping up all the time that purport to support it (e.g. https://pgptool.github.io, which I have no experience with and cannot vouch for; you could try it). I can't speak to whether symmetric encryption compatibility is there, but I suspect it is. As always use due diligence when downloading software.

But GPG itself is in wide use, built into many Linux distros, and was funded in part by some national governments (Germany I think). It's not going away and even if it did there are alternatives that should be able to decrypt your file. If you're really concerned you'd need to test those.

You may not need asymmetric encryption but that is the natural way to do things with GPG. It has many advantages, but one downside that you must always have a copy of your key file available (as well as remember the password for the keyfile). I imagine gpg4usb will help with some of that since you can keep some USBs in a safe deposit box. If it were me, I would definitely use the asymmetric variant because it is much more secure.

The best thing you can do to protect your Google Drive data is to ensure you have a secure Google password AND MOST IMPORTANTLY have two-factor authentication turned on. The keys to the kingdom are available if some hacks your email or Google account so you need to protect that. Google drive itself is pretty secure, some might argue that you don't even need to encrypt things stored there. But I don't fault you for wanting to do it, and really GPG / GPG4Win is your best choice.
Thanks for the post. I just tested the asymmetric encryption between gpg4usb (which uses GnuPG 1.x) and gpg4win (GnuPG 2.x) and they can decrypt each other. So that's good.

Do you have any recommendation on what program I can use to try to decrypt a filed symmetrically encrypted with gpg4win? i.e. any other app that lets you do a single key encryption with GPG?

Any comments on tools like SafePad (which claims to use AES256) and Encryptpad (which claim to use OpenPGP)?
Do you the difference in using AES vs GPG (symmetric) for encryption? Or does GPG use AES for encryption (just like OpenSSL does)?
[edit: looks like gpg supports different ciphers including AES]

MisterMister
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Re: How to Encrypt a Text file?

Post by MisterMister » Thu Nov 08, 2018 3:00 pm

get_g0ing wrote:
Thu Nov 08, 2018 12:46 pm
Thanks for the post. I just tested the asymmetric encryption between gpg4usb (which uses GnuPG 1.x) and gpg4win (GnuPG 2.x) and they can decrypt each other. So that's good.

Do you have any recommendation on what program I can use to try to decrypt a filed symmetrically encrypted with gpg4win? i.e. any other app that lets you do a single key encryption with GPG?

Any comments on tools like SafePad (which claims to use AES256) and Encryptpad (which claim to use OpenPGP)?
Do you the difference in using AES vs GPG (symmetric) for encryption? Or does GPG use AES for encryption (just like OpenSSL does)?
[edit: looks like gpg supports different ciphers including AES]
I'm not familiar with SafePad or EncryptPad but I encourage you to stay with tools that have stood the test of time.

By default, GPG does use AES for encryption.

I don't know of another tool that supports symmetric encryption but any other tool that supports OpenPGP might (such as the one I posted). Symmetric encryption is not a common use case for gpg, which is another reason to stay away from it. You've already found one tool that supports asymmetric encryption but not symmetric encryption.

But I would rate the odds of GPG going away in the next twenty years to be far less than 1%. Any "backup" tool you might find, well, that's another story. But the OpenPGP format is likely to continue to be around and I wouldn't at all be worried about not being able to decrypt your files (unless you lose your keys or passwords).

TravelGeek
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Re: How to Encrypt a Text file?

Post by TravelGeek » Thu Nov 08, 2018 3:44 pm

MisterMister wrote:
Thu Nov 08, 2018 3:00 pm
But I would rate the odds of GPG going away in the next twenty years to be far less than 1%. Any "backup" tool you might find, well, that's another story. But the OpenPGP format is likely to continue to be around and I wouldn't at all be worried about not being able to decrypt your files (unless you lose your keys or passwords).
I’d rate the chances of Google Drive going away (as we know it) higher than basic open source encryption tools going away. And if the community stops supporting them, there will always be time to use the currently working version to decrypt the files and then switch to something else.

MisterMister
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Re: How to Encrypt a Text file?

Post by MisterMister » Thu Nov 08, 2018 5:06 pm

TravelGeek wrote:
Thu Nov 08, 2018 3:44 pm
MisterMister wrote:
Thu Nov 08, 2018 3:00 pm
But I would rate the odds of GPG going away in the next twenty years to be far less than 1%. Any "backup" tool you might find, well, that's another story. But the OpenPGP format is likely to continue to be around and I wouldn't at all be worried about not being able to decrypt your files (unless you lose your keys or passwords).
I’d rate the chances of Google Drive going away (as we know it) higher than basic open source encryption tools going away. And if the community stops supporting them, there will always be time to use the currently working version to decrypt the files and then switch to something else.
I definitely agree with you.

But, to the OP: I don't usually recommend encryption tools to lay people, as I think the odds of their losing their encrypted data through misuse or accident can be sometimes be greater than it can be for it to fall in the wrong hands.

Make sure you have a back up unencrypted version in a secure location. I'm a professional, and some of these tools can give me trouble from time to time. I have a safe deposit box, and in there is a printed document with financial information, log in credentials, passwords, etc. If something happens to me, I don't have to worry about whether my wife is fluent with the use of encryption tools.

As TravelGeek points out, even Google Drive could go away at some stage.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Thu Nov 08, 2018 5:52 pm

MisterMister wrote:
Thu Nov 08, 2018 5:06 pm
TravelGeek wrote:
Thu Nov 08, 2018 3:44 pm
MisterMister wrote:
Thu Nov 08, 2018 3:00 pm
But I would rate the odds of GPG going away in the next twenty years to be far less than 1%. Any "backup" tool you might find, well, that's another story. But the OpenPGP format is likely to continue to be around and I wouldn't at all be worried about not being able to decrypt your files (unless you lose your keys or passwords).
I’d rate the chances of Google Drive going away (as we know it) higher than basic open source encryption tools going away. And if the community stops supporting them, there will always be time to use the currently working version to decrypt the files and then switch to something else.
I definitely agree with you.

But, to the OP: I don't usually recommend encryption tools to lay people, as I think the odds of their losing their encrypted data through misuse or accident can be sometimes be greater than it can be for it to fall in the wrong hands.

Make sure you have a back up unencrypted version in a secure location. I'm a professional, and some of these tools can give me trouble from time to time. I have a safe deposit box, and in there is a printed document with financial information, log in credentials, passwords, etc. If something happens to me, I don't have to worry about whether my wife is fluent with the use of encryption tools.

As TravelGeek points out, even Google Drive could go away at some stage.
You share sensible, balanced advice. Thanks for assisting me.

For completeness sake (if anyone else is interested), I figured out how to use GPG to do symmetric encryption:

To encrypt:
gpg --cipher-algo AES256 -c -a unencrypted.txt
-c = symmetric
-a = base64/ascii, if you want that
You'll be asked for password.

To decrypt:
gpg -d -o unencrypted.txt encrypted.gpg
-d = decrypt
The neat thing is you don't need to give it any other options, it knows what to do :)

The other option is to use asymmetric encryption where you yourself are the recipient (i.e. use your own public key as the recipient).

I think symmetric is simpler and easier for one person use.

TravelGeek
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Re: How to Encrypt a Text file?

Post by TravelGeek » Thu Nov 08, 2018 7:23 pm

MisterMister wrote:
Thu Nov 08, 2018 5:06 pm
Make sure you have a back up unencrypted version in a secure location. I'm a professional, and some of these tools can give me trouble from time to time. I have a safe deposit box, and in there is a printed document with financial information, log in credentials, passwords, etc. If something happens to me, I don't have to worry about whether my wife is fluent with the use of encryption tools.
One other thing to keep in mind is that if you die, your wife should probably not log into financial accounts with your credentials. Assuming the accounts have PoD set up, she should just contact the financial institutions. Knowing where the accounts are would probably helpful. And I agree, that information should be easily accessible, without use of command line encryption tools after pulling the file from some Google Drive account.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Thu Nov 08, 2018 9:33 pm

MisterMister wrote:
Thu Nov 08, 2018 5:06 pm
TravelGeek wrote:
Thu Nov 08, 2018 3:44 pm
MisterMister wrote:
Thu Nov 08, 2018 3:00 pm
But I would rate the odds of GPG going away in the next twenty years to be far less than 1%. Any "backup" tool you might find, well, that's another story. But the OpenPGP format is likely to continue to be around and I wouldn't at all be worried about not being able to decrypt your files (unless you lose your keys or passwords).
I’d rate the chances of Google Drive going away (as we know it) higher than basic open source encryption tools going away. And if the community stops supporting them, there will always be time to use the currently working version to decrypt the files and then switch to something else.
I definitely agree with you.

But, to the OP: I don't usually recommend encryption tools to lay people, as I think the odds of their losing their encrypted data through misuse or accident can be sometimes be greater than it can be for it to fall in the wrong hands.

Make sure you have a back up unencrypted version in a secure location. I'm a professional, and some of these tools can give me trouble from time to time. I have a safe deposit box, and in there is a printed document with financial information, log in credentials, passwords, etc. If something happens to me, I don't have to worry about whether my wife is fluent with the use of encryption tools.

As TravelGeek points out, even Google Drive could go away at some stage.
Do you have any thoughts or comments on AxCrypt and AES Crypt?

MisterMister
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Re: How to Encrypt a Text file?

Post by MisterMister » Thu Nov 08, 2018 10:27 pm

get_g0ing wrote:
Thu Nov 08, 2018 9:33 pm
Do you have any thoughts or comments on AxCrypt and AES Crypt?
I've used and like both. But AxCrypt is not free, if I recall correctly. AESCrypt is fine but it's user base is much smaller I'm sure than GPG and also the file format, while it is documented, is not standardized as is OpenPGP.

So if you want something you'll be able to download and use 20 years from now I'd only feel comfortable with GPG. If you want something you can use now any of these will work and all will have the same level of security. But if you have an encrypted file, and no program to decrypt it (as might happen 20 years from now), data goes bye-bye.

palaheel
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Re: How to Encrypt a Text file?

Post by palaheel » Thu Nov 08, 2018 10:34 pm

Is veracrypt still around? It was good for presenting itself as a file system to windows.
Markets crash. Markets recover. Inflation takes your money FOREVER.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Thu Nov 08, 2018 11:18 pm

MisterMister wrote:
Thu Nov 08, 2018 10:27 pm
get_g0ing wrote:
Thu Nov 08, 2018 9:33 pm
Do you have any thoughts or comments on AxCrypt and AES Crypt?
I've used and like both. But AxCrypt is not free, if I recall correctly. AESCrypt is fine but it's user base is much smaller I'm sure than GPG and also the file format, while it is documented, is not standardized as is OpenPGP.

So if you want something you'll be able to download and use 20 years from now I'd only feel comfortable with GPG. If you want something you can use now any of these will work and all will have the same level of security. But if you have an encrypted file, and no program to decrypt it (as might happen 20 years from now), data goes bye-bye.
Thanks for this.

rgs92
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Re: How to Encrypt a Text file?

Post by rgs92 » Fri Nov 09, 2018 1:21 am

Thanks for the tip on Notepad++!
I was looking for a notepad app that would recognize Regular Expressions.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Sun Nov 11, 2018 9:42 pm

MisterMister wrote:
Thu Nov 08, 2018 3:00 pm
I'm not familiar with SafePad or EncryptPad but I encourage you to stay with tools that have stood the test of time.

By default, GPG does use AES for encryption.

I don't know of another tool that supports symmetric encryption but any other tool that supports OpenPGP might (such as the one I posted). Symmetric encryption is not a common use case for gpg, which is another reason to stay away from it. You've already found one tool that supports asymmetric encryption but not symmetric encryption.

But I would rate the odds of GPG going away in the next twenty years to be far less than 1%. Any "backup" tool you might find, well, that's another story. But the OpenPGP format is likely to continue to be around and I wouldn't at all be worried about not being able to decrypt your files (unless you lose your keys or passwords).
ThriftyPhD wrote:
Mon Nov 05, 2018 6:58 pm
https://www.gpg4win.org/
Question for you:

gpg4win can output encrypted data in two forms: binary with .gpg extension, or base64 with .asc extension.

I can take the binary .gpg file and convert it to base64/ascii (using Notepad++ option "Base64 Encode"). gpg4win can read and decrypt this converted form.

But is there a way to convert the .asc base64 encrypted output of gpg4win into binary? (I tried the "Base64 Decode" option in Notepad++ but that didn't work).

[I know doing this is not necessary, just asking out of curiosity. I can convert gpg4win's binary to ascii and have that decrypted successfully, so I was wondering if I could convert gpg4win's ascii to binary]

MisterMister
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Re: How to Encrypt a Text file?

Post by MisterMister » Sun Nov 11, 2018 10:11 pm

Yes, but I will leave it as an exercise for you to determine what the options might be for actually doing that.

In any case, these days there is no point in using the ASCII format; there are some obscure use cases that might need it, but certainly not if you're going to upload your encrypted file to Google Drive. It just makes your file bigger without providing any real benefit.

get_g0ing
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Re: How to Encrypt a Text file?

Post by get_g0ing » Sun Nov 11, 2018 11:27 pm

MisterMister wrote:
Sun Nov 11, 2018 10:11 pm
Yes, but I will leave it as an exercise for you to determine what the options might be for actually doing that.

In any case, these days there is no point in using the ASCII format; there are some obscure use cases that might need it, but certainly not if you're going to upload your encrypted file to Google Drive. It just makes your file bigger without providing any real benefit.
I was able to encode gpg4win's binary output to ascii, using Notepad++'s MIME Tools plugin.

But I can't figure out how to do the reverse, i.e. convert ascii produced by gpg4win to a binary file. Notepad++ does have a "Base64 Decode", but it does not work for me.

Any idea please?

I suspect the utility of converting binary to ascii (despite the size increase) would be that you can copy paste it as text, or email it.

MisterMister
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Re: How to Encrypt a Text file?

Post by MisterMister » Sun Nov 11, 2018 11:50 pm

get_g0ing wrote:
Sun Nov 11, 2018 11:27 pm

But I can't figure out how to do the reverse, i.e. convert ascii produced by gpg4win to a binary file. Notepad++ does have a "Base64 Decode", but it does not work for me.

Any idea please?

I suspect the utility of converting binary to ascii (despite the size increase) would be that you can copy paste it as text, or email it.
You need to strip the first line and last two lines of the ASC file, then save the resulting decoded file with the file GPG extension.

As far why you'd use ASCII, you are correct, but those scenarios are not in your use case and are unlikely to be something you need to do.

You might consider taking some basic computer programming training (I'm assuming you are not already a programmer!). The Internet has a wealth of information for free if this is of interest to you.

I probably won't be able to help you beyond this point, but I do hope your original question is answered and you've learned a few tricks along the way.

Good luck!

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