diff --git a/pkgs/tools/security/metasploit/Gemfile b/pkgs/tools/security/metasploit/Gemfile
index 4e73e39a34e5..edb38fa4e1b5 100644
--- a/pkgs/tools/security/metasploit/Gemfile
+++ b/pkgs/tools/security/metasploit/Gemfile
@@ -1,4 +1,6 @@
 # frozen_string_literal: true
 source "https://rubygems.org"
 
-gem "metasploit-framework", git: "https://github.com/rapid7/metasploit-framework", ref: "refs/tags/6.4.43"
+gem "metasploit-framework", git: "https://github.com/rapid7/metasploit-framework", ref: "refs/tags/6.4.53"
+
+gem "syslog", "~> 0.3.0"
diff --git a/pkgs/tools/security/metasploit/Gemfile.lock b/pkgs/tools/security/metasploit/Gemfile.lock
index 0360b87c4db2..c04ba2f51c90 100644
--- a/pkgs/tools/security/metasploit/Gemfile.lock
+++ b/pkgs/tools/security/metasploit/Gemfile.lock
@@ -1,9 +1,9 @@
 GIT
   remote: https://github.com/rapid7/metasploit-framework
-  revision: 726e819f87e3022dc90232087bf30edb0d149ba5
-  ref: refs/tags/6.4.43
+  revision: ce6990ff84c944186dfa104b3aa1edd98962b468
+  ref: refs/tags/6.4.53
   specs:
-    metasploit-framework (6.4.43)
+    metasploit-framework (6.4.53)
       aarch64
       abbrev
       actionpack (~> 7.0.0)
@@ -17,10 +17,12 @@ GIT
       base64
       bcrypt
       bcrypt_pbkdf
+      benchmark
       bigdecimal
       bootsnap
       bson
       chunky_png
+      concurrent-ruby (= 1.3.4)
       csv
       dnsruby
       drb
@@ -33,6 +35,7 @@ GIT
       faraday-retry
       faye-websocket
       ffi (< 1.17.0)
+      fiddle
       filesize
       getoptlong
       hrr_rb_ssh-ed25519
@@ -62,6 +65,7 @@ GIT
       octokit (~> 4.0)
       openssl-ccm
       openvas-omp
+      ostruct
       packetfu
       patch_finder
       pcaprub
@@ -69,7 +73,7 @@ GIT
       pg
       puma
       railties
-      rasn1 (= 0.13.0)
+      rasn1 (= 0.14.0)
       rb-readline
       recog
       redcarpet
@@ -179,6 +183,7 @@ GEM
     base64 (0.2.0)
     bcrypt (3.1.20)
     bcrypt_pbkdf (1.1.1)
+    benchmark (0.4.0)
     bigdecimal (3.1.8)
     bindata (2.4.15)
     bootsnap (1.18.4)
@@ -223,6 +228,7 @@ GEM
       eventmachine (>= 0.12.0)
       websocket-driver (>= 0.5.1)
     ffi (1.16.3)
+    fiddle (1.1.6)
     filesize (0.2.0)
     getoptlong (0.2.1)
     gssapi (1.3.1)
@@ -249,6 +255,7 @@ GEM
       rkelly-remix
     json (2.7.5)
     little-plugger (1.1.4)
+    logger (1.6.6)
     logging (2.4.0)
       little-plugger (~> 1.1)
       multi_json (~> 1.14)
@@ -322,6 +329,7 @@ GEM
     openssl-ccm (1.2.3)
     openssl-cmac (2.0.2)
     openvas-omp (0.0.4)
+    ostruct (0.6.1)
     packetfu (2.0.0)
       pcaprub (~> 0.13.1)
     patch_finder (1.0.2)
@@ -358,7 +366,7 @@ GEM
       thor (~> 1.0)
       zeitwerk (~> 2.5)
     rake (13.2.1)
-    rasn1 (0.13.0)
+    rasn1 (0.14.0)
       strptime (~> 0.2.5)
     rb-readline (0.5.5)
     recog (3.1.11)
@@ -443,6 +451,8 @@ GEM
     sshkey (3.0.0)
     strptime (0.2.5)
     swagger-blocks (3.0.0)
+    syslog (0.3.0)
+      logger
     thin (1.8.2)
       daemons (~> 1.0, >= 1.0.9)
       eventmachine (~> 1.0, >= 1.0.4)
@@ -487,6 +497,7 @@ PLATFORMS
 
 DEPENDENCIES
   metasploit-framework!
+  syslog (~> 0.3.0)
 
 BUNDLED WITH
    2.5.22
diff --git a/pkgs/tools/security/metasploit/default.nix b/pkgs/tools/security/metasploit/default.nix
index 1406fb4aeff0..3f61d6185e32 100644
--- a/pkgs/tools/security/metasploit/default.nix
+++ b/pkgs/tools/security/metasploit/default.nix
@@ -18,13 +18,13 @@ let
 in
 stdenv.mkDerivation (finalAttrs: {
   pname = "metasploit-framework";
-  version = "6.4.43";
+  version = "6.4.53";
 
   src = fetchFromGitHub {
     owner = "rapid7";
     repo = "metasploit-framework";
     tag = finalAttrs.version;
-    hash = "sha256-1zUt6nInDUIY97fBJa0dQ/hD4WZ1v5LXYdPQhnYKlYw=";
+    hash = "sha256-yHat9U8EZbUWo4j9ut6K9IPtPFm130pfSmIuhtQhFoQ=";
   };
 
   nativeBuildInputs = [
diff --git a/pkgs/tools/security/metasploit/gemset.nix b/pkgs/tools/security/metasploit/gemset.nix
index ff54d3f154f1..0d7c23000d41 100644
--- a/pkgs/tools/security/metasploit/gemset.nix
+++ b/pkgs/tools/security/metasploit/gemset.nix
@@ -239,6 +239,16 @@
     };
     version = "1.1.1";
   };
+  benchmark = {
+    groups = [ "default" ];
+    platforms = [ ];
+    source = {
+      remotes = [ "https://rubygems.org" ];
+      sha256 = "0jl71qcgamm96dzyqk695j24qszhcc7liw74qc83fpjljp2gh4hg";
+      type = "gem";
+    };
+    version = "0.4.0";
+  };
   bigdecimal = {
     groups = [ "default" ];
     platforms = [ ];
@@ -509,6 +519,16 @@
     };
     version = "1.16.3";
   };
+  fiddle = {
+    groups = [ "default" ];
+    platforms = [ ];
+    source = {
+      remotes = [ "https://rubygems.org" ];
+      sha256 = "1as92bp6pgkab73kj3mh5d1idjr9wykczz7r9i1pkn82wq4xks3r";
+      type = "gem";
+    };
+    version = "1.1.6";
+  };
   filesize = {
     groups = [ "default" ];
     platforms = [ ];
@@ -679,6 +699,16 @@
     };
     version = "1.1.4";
   };
+  logger = {
+    groups = [ "default" ];
+    platforms = [ ];
+    source = {
+      remotes = [ "https://rubygems.org" ];
+      sha256 = "05s008w9vy7is3njblmavrbdzyrwwc1fsziffdr58w9pwqj8sqfx";
+      type = "gem";
+    };
+    version = "1.6.6";
+  };
   logging = {
     groups = [ "default" ];
     platforms = [ ];
@@ -734,12 +764,12 @@
     platforms = [ ];
     source = {
       fetchSubmodules = false;
-      rev = "726e819f87e3022dc90232087bf30edb0d149ba5";
-      sha256 = "134m19v8dl6kc7br5gvmcvhl7y233nnjbhdpywc44397fbm2sdfp";
+      rev = "ce6990ff84c944186dfa104b3aa1edd98962b468";
+      sha256 = "110n47a8cbk299glmpxmb4yfv0zlibgbmzc8lcbbar849zsssxn8";
       type = "git";
       url = "https://github.com/rapid7/metasploit-framework";
     };
-    version = "6.4.43";
+    version = "6.4.53";
   };
   metasploit-model = {
     groups = [ "default" ];
@@ -1025,6 +1055,16 @@
     };
     version = "0.0.4";
   };
+  ostruct = {
+    groups = [ "default" ];
+    platforms = [ ];
+    source = {
+      remotes = [ "https://rubygems.org" ];
+      sha256 = "05xqijcf80sza5pnlp1c8whdaay8x5dc13214ngh790zrizgp8q9";
+      type = "gem";
+    };
+    version = "0.6.1";
+  };
   packetfu = {
     groups = [ "default" ];
     platforms = [ ];
@@ -1180,10 +1220,10 @@
     platforms = [ ];
     source = {
       remotes = [ "https://rubygems.org" ];
-      sha256 = "07dvrv2s9hs2vcbr6lai8vj4vk2i3m4jf468hyvkp9k8xzjvc0fi";
+      sha256 = "1rz96j4jzm02rdxrs70hj5an3kmxrfd77d4hy97b80fasj049992";
       type = "gem";
     };
-    version = "0.13.0";
+    version = "0.14.0";
   };
   rb-readline = {
     groups = [ "default" ];
@@ -1565,6 +1605,16 @@
     };
     version = "3.0.0";
   };
+  syslog = {
+    groups = [ "default" ];
+    platforms = [ ];
+    source = {
+      remotes = [ "https://rubygems.org" ];
+      sha256 = "023lbh48fcn72gwyh1x52ycs1wx1bnhdajmv0qvkidmdsmxnxzjd";
+      type = "gem";
+    };
+    version = "0.3.0";
+  };
   thin = {
     groups = [ "default" ];
     platforms = [ ];
diff --git a/pkgs/tools/security/metasploit/shell.nix b/pkgs/tools/security/metasploit/shell.nix
index 407620581539..f5169e2bb02d 100644
--- a/pkgs/tools/security/metasploit/shell.nix
+++ b/pkgs/tools/security/metasploit/shell.nix
@@ -1,10 +1,11 @@
-# Env to update Gemfile.lock / gemset.nix
 {
   pkgs ? import ../../../.. { },
 }:
-pkgs.stdenv.mkDerivation {
-  name = "env";
-  nativeBuildInputs = [ pkgs.pkg-config ];
+pkgs.mkShell {
+  nativeBuildInputs = [
+    pkgs.pkg-config
+    pkgs.libffi # libffi as native input
+  ];
   buildInputs = with pkgs; [
     bundix
     git
@@ -16,4 +17,9 @@ pkgs.stdenv.mkDerivation {
     ruby.devEnv
     sqlite
   ];
+  # Ensure that pkg-config finds libffi
+  shellHook = ''
+    export PKG_CONFIG_PATH="${pkgs.libffi.out}/lib/pkgconfig:$PKG_CONFIG_PATH"
+    echo "PKG_CONFIG_PATH set to: $PKG_CONFIG_PATH"
+  '';
 }