diff --git a/pkgs/tools/security/whatweb/Gemfile b/pkgs/tools/security/whatweb/Gemfile
new file mode 100644
index 00000000000..a376a3baae3
--- /dev/null
+++ b/pkgs/tools/security/whatweb/Gemfile
@@ -0,0 +1,6 @@
+source 'https://rubygems.org'
+gem 'ipaddr'
+gem 'addressable'
+gem 'json'
+gem 'mongo'
+gem 'rchardet'
diff --git a/pkgs/tools/security/whatweb/Gemfile.lock b/pkgs/tools/security/whatweb/Gemfile.lock
new file mode 100644
index 00000000000..7bfd24112b1
--- /dev/null
+++ b/pkgs/tools/security/whatweb/Gemfile.lock
@@ -0,0 +1,25 @@
+GEM
+  remote: https://rubygems.org/
+  specs:
+    addressable (2.8.0)
+      public_suffix (>= 2.0.2, < 5.0)
+    bson (4.14.1)
+    ipaddr (1.2.4)
+    json (2.6.1)
+    mongo (2.17.1)
+      bson (>= 4.8.2, < 5.0.0)
+    public_suffix (4.0.6)
+    rchardet (1.8.0)
+
+PLATFORMS
+  ruby
+
+DEPENDENCIES
+  addressable
+  ipaddr
+  json
+  mongo
+  rchardet
+
+BUNDLED WITH
+   2.1.4
diff --git a/pkgs/tools/security/whatweb/default.nix b/pkgs/tools/security/whatweb/default.nix
new file mode 100644
index 00000000000..30d866da869
--- /dev/null
+++ b/pkgs/tools/security/whatweb/default.nix
@@ -0,0 +1,50 @@
+{ lib, stdenv, fetchFromGitHub, bundlerEnv, ruby }:
+
+let
+  gems = bundlerEnv {
+    name = "whatweb-env";
+    inherit ruby;
+    gemdir = ./.;
+  };
+
+in stdenv.mkDerivation rec {
+  pname = "whatweb";
+  version = "0.5.5";
+
+  src = fetchFromGitHub {
+    owner = "urbanadventurer";
+    repo = "whatweb";
+    rev = "v${version}";
+    sha256 = "sha256-HLF55x4C8n8aPO4SI0d6Z9wZe80krtUaGUFmMaYRBIE=";
+  };
+
+  prePatch = ''
+    substituteInPlace Makefile \
+      --replace "/usr/local" "$out" \
+      --replace "/usr" "$out"
+  '';
+
+  buildInputs = [ gems ];
+
+  installPhase = ''
+    runHook preInstall
+
+    raw=$out/share/whatweb/whatweb
+    rm $out/bin/whatweb
+    cat << EOF >> $out/bin/whatweb
+    #!/bin/sh -e
+    exec ${gems}/bin/bundle exec ${ruby}/bin/ruby "$raw" "\$@"
+    EOF
+    chmod +x $out/bin/whatweb
+
+    runHook postInstall
+  '';
+
+  meta = with lib; {
+    description = "Next generation web scanner";
+    homepage = "https://github.com/urbanadventurer/whatweb";
+    license = licenses.gpl2Only;
+    maintainers = with maintainers; [ wolfangaukang ];
+    platforms = platforms.unix;
+  };
+}
diff --git a/pkgs/tools/security/whatweb/gemset.nix b/pkgs/tools/security/whatweb/gemset.nix
new file mode 100644
index 00000000000..22d469b53e2
--- /dev/null
+++ b/pkgs/tools/security/whatweb/gemset.nix
@@ -0,0 +1,74 @@
+{
+  addressable = {
+    dependencies = ["public_suffix"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "022r3m9wdxljpbya69y2i3h9g3dhhfaqzidf95m6qjzms792jvgp";
+      type = "gem";
+    };
+    version = "2.8.0";
+  };
+  bson = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "03n3w96vpblaxvk1qk8hq7sbsmg4nv7qdkdr8f7nfvalgpakp5i5";
+      type = "gem";
+    };
+    version = "4.14.1";
+  };
+  ipaddr = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "13qd34nzpgp3fxfjbvaqg3dcnfr0cgl5vjvcqy0hfllbvfcklnbq";
+      type = "gem";
+    };
+    version = "1.2.4";
+  };
+  json = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1z9grvjyfz16ag55hg522d3q4dh07hf391sf9s96npc0vfi85xkz";
+      type = "gem";
+    };
+    version = "2.6.1";
+  };
+  mongo = {
+    dependencies = ["bson"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "19sihy8ihi3hmdg3gxbf4qvzmjnzx8xygg9534012j9z0wmhs7h1";
+      type = "gem";
+    };
+    version = "2.17.1";
+  };
+  public_suffix = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1xqcgkl7bwws1qrlnmxgh8g4g9m10vg60bhlw40fplninb3ng6d9";
+      type = "gem";
+    };
+    version = "4.0.6";
+  };
+  rchardet = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1isj1b3ywgg2m1vdlnr41lpvpm3dbyarf1lla4dfibfmad9csfk9";
+      type = "gem";
+    };
+    version = "1.8.0";
+  };
+}
diff --git a/pkgs/top-level/all-packages.nix b/pkgs/top-level/all-packages.nix
index a330618c6a1..2496bc3765c 100644
--- a/pkgs/top-level/all-packages.nix
+++ b/pkgs/top-level/all-packages.nix
@@ -11106,6 +11106,8 @@ with pkgs;
 
   wf-recorder = callPackage ../applications/video/wf-recorder { };
 
+  whatweb = callPackage ../tools/security/whatweb { };
+
   whipper = callPackage ../applications/audio/whipper { };
 
   whitebophir = callPackage ../servers/web-apps/whitebophir { };