gpg: decryption failed: No secret key without first encrypting/decrypting a file - gnupg

Okay, this is a very strange case of this "No secret key" error. I've looked at all the other answers related to this and none of them are related to my problem.
On my machine I do this..
gpg --export-secret-keys me#example.com
On a new WSL 2 Linux machine I do this...
gpg --import /tmp/keys.asc
echo 'enter 5 for trust level'
gpg --edit-key me#example.com trust
# I enter '5' trust level and exit
Now I should be ready for my encrypted backup restore, but it fails...
# ssh mount my backup on my NAS to /media/backup
sshfs tdanas:/backup /media/backup/
cat /media/backup/cloud-tar/2021/05/home.0.backupaa | gpg -d | ( cd /; tar -g /dev/null -xvz)
gpg: encrypted with 2048-bit RSA key, ID 465E18C472F84F14, created 2011-01-05
"User Name <me#example.com>"
gpg: public key decryption failed: Inappropriate ioctl for device
gpg: decryption failed: No secret key
If I do the following (decrypt a file and not a stream), it prompts for my password on decryption, and the problem completely vanishes.
gpg -d /media/backup/cloud-tar/2021/05/home.0.backupaa | ( cd /; tar -g /dev/null -xvz)
gpg --list-secret-keys
sec rsa2048 2011-01-05 [SC]
5ABF9709EFF6255C3B9DC4D9F029102596EDB6DB
uid [ultimate] User Name <me#example.com>
ssb rsa2048 2011-01-05 [E]

I'm an idiot, lol. the stdin is already consumed, so it can't prompt for a password at that point, unless I used a gui password prompt

Related

gpg No such file or directory

I'm trying to run gpg from a Bash script designed to backup a website. The command that fails is
gpg --homedir /home/backupuser/.gnupg --verbose --no-tty --recipient {group-name} --trust-model always --output /home/backupuser/backup/{tar-file}.gpg --encrypt /mnt/ramdir/site-backup-backupuser/{tar-file}
It fails with return code 127. The gpg home directory exists, as does the {tar-file}. The output directory exists but the output file does not.
If I repeat the gpg command in the script it fails in exactly the same way. But if I execute it in shell immediately after it has failed in the script it works as expected. The output is:
gpg: using subkey {hhhhhhhhhhhhhhhh} instead of primary key {hhhhhhhhhhhhhhhh}
gpg: automatically retrieved '{email address1}' via Local
gpg: No trust check due to '--trust-model always' option
gpg: using subkey {hhhhhhhhhhhhhhhh} instead of primary key {hhhhhhhhhhhhhhhh}
gpg: automatically retrieved '{email address2}' via Local
gpg: No trust check due to '--trust-model always' option
gpg: reading from '/mnt/ramdir/site-backup-backupuser/{tar-file}'
gpg: writing to '/home/backupuser/backup/{tar-file}.gpg'
gpg: '/mnt/ramdir/site-backup-backupuser/{tar-file}' already compressed
gpg: RSA/AES256 encrypted for: "{hhhhhhhhhhhhhhhh} {Comment} <{email address1}>"
gpg: RSA/AES256 encrypted for: "{hhhhhhhhhhhhhhhh} {Comment} <{email address2}>"
This is Debian "bullseye" 11.6, gpg 2.2.27 and libgcrypt 1.8.8.
I have tried numerous combinations of parameters, always with the above result. With or without --homedir, with or without sudo (I was getting desperate), from a file on disk rather than in RAM, with or without --verbose and several others.

How do you verify an encrypted and signed file with gpg?

I am trying to get a better understanding of what is going on with gpg.
If you have a file and sign it: gpg --sign file.txt
you can verify it with: gpg --verify file.txt.gpg
when you get a successful output: gpg: Signature made...
But when you sign AND encrypt a file: gpg --encrypt --sign -r test#email.com file.txt
and then run --verify on the encrypted file I get: gpg: verify signatures failed: Unexpected error
I know that I can just call --decrypt on the file and it will verify and decrypt it, but what if I want to verify only?
I figured out the answer to this and then some. So I am going to add some additional information for clarity.
First of all, I realize based on the last line to this answer that gpg uses SIGN THEN ENCRYPT. Which means calling --verify or any variation to verify on an encrypted file will just output gpg: verify signatures failed: Unexpected error. This happens because the signature is "hidden" in encryption, so when you try to call --verify on the file, it will not see a signature.
Secondly, the --decrypt flag will both decrypt the file AND if the file is signed, verify it too.
Here is what --decrypt is doing. It looks at your default secret keyring secring.kbx in ~/.gnupg to use a secret key for decrypting the file. Then after it is decrypted, it looks at your default public keyring pubring.kbx in the folder ~/.gnupg and tries to verify the signature on the file, if it has one.
If it has no signature, it will just decrypt the file.
If it has a signature, but you don't have the public key, it will decrypt the file but it will fail to verify the signature.
If it has a signature and you have the public key, it will decrypt and verify.
With that said, there is no reason to verify a signed file BEFORE decrypting it.
Thirdly, as an added bonus, you can also specify a keyring you want to use for decrypting and verification. Say you want to use a temporary keyring to verify signatures or for what ever reason you want a temporary keyring to decrypt the message too.
You can specify the keyrings for --decrypt to use with the following command:
gpg --secret-keyring path/to/temp/secring.kbx --keyring path/to/temp/pubring.kbx --decrypt file.txt.gpg
This command will look for the secret ring and public ring at the specified paths in order to use those rings for decryption and verification instead of the default rings found in ~/.gnupg. Want to use a default ring with a temp ring? Just omit the flag and path to the ring you want defaulted.
All in all, for encrypted and signed files, if you want to decrypt and verify that file, you need to make sure that the private key for decryption is in your secret keyring and the public key for verification is in your public keyring.
One thing to understand about GPG encrypt & sign, which isn't very well explained, is that the signature can only be verified by the recipient.
Suppose Alice encrypts a file to send to Bob. She will encrypt with Bob's public key, and sign with her private key.
gpg --output encrypted.gpg --recipient B0B0000000000000000000000000000000000000 --armor --sign --default-key A11CE00000000000000000000000000000000000 --encrypt file-to-encrypt.txt
There's no way now for Alice, or anyone who does not have Bob's private key, to verify the signature.
Now Bob will decrypt the file. If it is signed, he'll see information about the signature in the output:
$ gpg --decrypt encrypted.gpg > decrypted.txt
gpg: encrypted with 2048-bit RSA key, ID D83A4C12B3840EBA, created 2020-09-24
"Alice <alice#example.com>"
gpg: Signature made 09/28/20 13:16:47 Eastern Daylight Time
gpg: using RSA key A11CE00000000000000000000000000000000000
gpg: Good signature from "Alice <alice#example.com>" [ultimate]
Note the Signature made and Good signature lines in the output.
$ gpg --encrypt --sign -r test#email.com file.txt
After file.txt.gpg generated, try the command below:
$ gpg -d file.txt.gpg
or just execute:
$ gpg file.txt.gpg

GPG --gen -key with password in a separate file

I want to encrypt a file using a passphrase, which I did using gpg --gen-key to create a key (I used the default options) in the command line, and I also go this to work in an "automated" way without user interaction.
But, I'd like to specify the passphrase stored in a separate file. This is what I'm running now:
gpg --batch --gen-key "D:\Staging\FileContainingKeySettings.txt"
And what's in the file called "FileContainingKeySettings.txt" is this:
%echo Generating a default key
Key-Type: default
Subkey-Type: default
Name-Real: PBJ
Name-Comment: test
Name-Email: PBJ#pbj.com
Expire-Date: 0
Passphrase:blah
%commit
%echo done
So that works and generates the key.
Then I call this:
gpg --batch --yes -r PBJ --output D:\Staging\newEncryptedFile.txt --encrypt
D:\Staging\textfiletobeencrypted.csv
And this works too.
So now I have 1 problem and 1 question. The problem is that I need to specify the passphrase to reference a file that looks like this (but much longer):
-----BEGIN PGP PUBLIC KEY BLOCK-----
Version: BCPG v1.47
[encoding]
-----END PGP PUBLIC KEY BLOCK-----
instead of using the password where I wrote "blah"^, and I haven't found a way to do this online or from any other team members around me. How can I do that?
Question: I also notice now that the file I was sent containing the encryption key reads at the top
" -----BEGIN PGP PUBLIC KEY BLOCK-----"
...which says it uses PGP (but I am using gpg). I know that gpg and pgp are different and read about them, but can I even do what I'm trying to do using gpg to encrypt a file with a key that was apparently generated with pgp?
(in Windows)
UPDATE: Now I may have gotten this working, although I still have to validate by having the other person decrypt the message (it works fine when I decrypt it). Silly I didn't think of this code change earlier when I've actually tried this before...I simply changed my cmd call from this part:
gpg --batch --gen-key "D:\Staging\FileContainingKeySettings.txt"
to this instead, specifying the passphrase file location here instead:
gpg --batch --passphrase "D:\Staging\FileWithActualKey.txt --gen-key
"D:\Staging\FileContainingKeySettings.txt"
and I took the password line out of the file "FileContainingKeySettings" altogether. I haven't tested this by having the other person decrypt it yet on their end...I hope it worked. At least I didn't get error. But now when I run this line again to actually do encryption, it works:
gpg --batch --yes -r PBJ --output D:\Staging\newEncryptedFile.txt --encrypt
D:\Staging\textfiletobeencrypted.csv

Message Authentication Code for gpg

The gpg software supports symmetric encryption out of the box. That means, it works with a password. But apart from protecting the content it is also important to ensure the Authentication of a message. The idea is to create a hashsum of the file itself together with the password used for encryption. According to [1] a popular “Message Authentication Code” is HMAC. After entering:
gpg --hmac --armor --symmetric --passphrase pwd1 file.txt
gpg: Invalid option "--hmac"
an error message occurs that the switch is not known by the software. How can i use the MAC authentication the right way?
You can't. The reason for the error message is that type of signature is not available with GPG. You'd be better off simply signing and encrypting the file with the standard GPG method. Even if you wanted to use symmetric encryption only, then the recipient would still need to use GPG to decrypt the file. The correct command would be:
gpg -o filename.txt.asc -sear $recipient_key filename.txt
This assumes you also always encrypt to your own key, otherwise the command would be:
gpg -o filename.txt.asc -sear $recipient_key -r $your_key filename.txt
If they don't have a key, you could still sign and encrypt to your own key only and then extract the session key so you could provide that for them to decrypt the file with it:
gpg -o filename.txt --show-session-key -d filename.txt.asc
Then the recipient would be able to decrypt with:
gpg -o filename.txt --override-session-key $session_key -d filename.txt.asc
If you really must use symmetric encryption only, however, you can do it in two setps.
First sign the file:
gpg -o filename.txt.asc -sa filename.txt
Then symmetrically encrypt that file:
gpg -o newfilename.asc -a -c filename.txt.asc
The recipient would then need to run the decryption command twice; first on the symmetrically encrypted file and then a second time on the file it decrypts.
The normal --verify option is only used for checking clearsigned files or files with detached signatures.

GNUPG - stdin encrypted file and passphrase on windows

How can I pipe the passphrase and encrypted file in gpg.exe?
I have tried a few different combinations but I can't get it to work.
Here is my attempt,
C:\>gpg.exe --output [OUTPUT_FILE] --batch --passphrase-fd 0 --decrypt < [INPUT_FILE] < [PASSPHRASE_FILE]
from this I get error
gpg: decrypt_message failed: eof
Swapping the input and passphrase around I get the error
gpg: no valid OpenPGP data found.
gpg: decrypt_message failed: eof
If I don't try and send the encrypted file via stdin then the decryption works fine.
Ultimately what I want to do is decrypt a file based on a file mask with the date timestamp in the file name. Outlined below,
C:\>gpg.exe --output yyyyMMdd.csv --batch --passphrase-fd 0 --decrypt < *_yyyyMMdd_*.txt < [PASSPHRASE_FILE]
I'm not sure if this will work because I can't get the basic scenario working, I would also appreciate if someone could advise me of the best way to achieve this.
Don't use redirection for the file you want to decrypt, only for the file containing your passphrase:
C:\>gpg.exe --output [OUTPUT_FILE] --batch --passphrase-fd 0 --decrypt [INPUT_FILE] < [PASSPHRASE_FILE]
But honestly, it might be easier for you to remove the passphrase from your key. After all, storing your passphrase in a file is not very secure. Just change your passphrase to a blank and protect your gpg home directory to deny access to any process other than your own.

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