different ways and how to sign a file digitally using GnuPG

In his comment on my recent post asking why wordpress.org dev team didn’t opt to sign their popular blog server software package, Barry said it might be cool to actually spell out how to sign a file digitally. With my tax mailed out this afternoon (Yeah,  don’t have to wait in line with all other last-minute losers this year!),  I have some breathing time to actually take a stab using GnuPG as an example. GnuPG is an open-source counterpart of the PGP.

  • To sign a file digitally, you first need to have a pair of keys. If you don’t have one yet, read my earlier post on how to generate one along with best practice recommendations.
  • Quite a few ways to sign a file.  A file named ‘digital.signature.testfile’ has been created for illustration.
    • sign the file to generate a new file containing only its digital signature. The new file is known as the (detached) signature file.
      • in armor text.  The signature file’s name is the original file name appended with a .asc extension. It is reable by human.

                                  gpg –detach-sign -a digital.signature.testfile

      • not in armor text. The signature file’s name is the original file name appended with a .gpg extension. It is NOT readable by human.

                                  gpg –detach-sign digital.signature.testfile

    • sign it to generate a new file containing the original content as well as digital signature. This is known as the signed file.
      • clear-text signing, meaning the the original content can be read as clear text inside the new file. The signed file’s name is the original file name appended with a .asc extension. It is readable by human.

                                   gpg -s –clearsign digital.signature.testfile

      • non-clear-text signing, meaning the the original content can NOT be read as clear text inside the new file. The signed file’s name is the original file name appended with a .gpg extension. It is NOT readable by human.

                                   gpg -s digital.signature.testfile

  • Most software packages need to be unpacked using unzip, tar, 7z, rar or alike, it is obvious the preferred way is not to touch the software packages, but to provide detached signature files in armor text. As a result, you often see on the download page, listed side by side are a package file named  popular.package-1.1.3.tar.gz and its signature file popular.package-1.1.3.tar.gz.asc.
  • The contents of the original file, the signed file by clear-sign, the detached signature file via clear-sign are all appended below for your reference.

/home/experts8$  cat digital.signature.testfile # the original file
Wed Apr 11 23:46:07 EDT 2007
/home/experts8$ cat digital.signature.testfile.asc # the signed file by clear-sign
—–BEGIN PGP SIGNED MESSAGE—–
Hash: SHA1

Wed Apr 11 23:46:07 EDT 2007
—–BEGIN PGP SIGNATURE—–
Version: GnuPG v1.4.1 (Cygwin)

iD8DBQFGHau1qVSbap/EkWYRAkQhAJ98vWY/peeVYW+sQ0JLXm1DWQuB+ACfXHoo
NGV2PrjRiyKJSN5mmmKm3IE=
=Axe4
—–END PGP SIGNATURE—–

/home/experts8$ cat digital.signature.testfile.asc  #detached signature file in armor text
—–BEGIN PGP SIGNATURE—–
Version: GnuPG v1.4.1

iD8DBQBGHbBUqVSbap/EkWYRAtH/AJ9cPHrnz7s1HFIyiJrzxzEPuuPTAwCaAkyi
jvSor1JP4ODC5RW59Hue1f8=
=8+4g
—–END PGP SIGNATURE—–

    229 Comments »

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      April 12, 2007 @ 9:38 am

      I think if you are signing a software package you would want to acquire a code signing certificate from a signing authority or its not very useful.

    2. experts8 said,

      April 12, 2007 @ 7:27 pm

      That’s true for digital certificates, which need to be signed by someone else, being it an official root CA, or your home-made CA. For PGP/GnuPG digital signature, that’s not true. The trustworthiness of the signing key, however, can be boosted by getting your signing key signed by more famous/trustworthy people’s PGP/GnuPG keys. This is called Web of Trust. D&C LUG has an informative page explaining all this.

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