diff --git a/Gemfile b/Gemfile
index 6fdc637b3..5a6c3b6b2 100644
--- a/Gemfile
+++ b/Gemfile
@@ -14,7 +14,7 @@ gem 'rack', '~> 2.2'
 gem 'rack-protection', '~> 3.2.0'
 gem 'em-websocket', '~> 0.5.3' # WebSocket support
 gem 'uglifier', '~> 4.2'
-gem 'mime-types', '~> 3.5'
+gem 'mime-types', '~> 3.6'
 gem 'execjs', '~> 2.9'
 gem 'ansi', '~> 1.5'
 gem 'term-ansicolor', :require => 'term/ansicolor'
@@ -23,7 +23,7 @@ gem 'espeak-ruby', '~> 1.1.0' # Text-to-Voice
 gem 'rake', '~> 13.2'
 gem 'otr-activerecord', '~> 2.2.0'
 gem 'sqlite3', '~> 1.4'
-gem 'rubocop', '~> 1.64.0', require: false
+gem 'rubocop', '~> 1.66.1', require: false
 
 # Geolocation support
 group :geoip do
diff --git a/Gemfile.lock b/Gemfile.lock
index 6d6d85238..9b647a758 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -90,9 +90,10 @@ GEM
     matrix (0.4.2)
     maxmind-db (1.2.0)
     method_source (1.1.0)
-    mime-types (3.5.2)
+    mime-types (3.6.0)
+      logger
       mime-types-data (~> 3.2015)
-    mime-types-data (3.2024.0903)
+    mime-types-data (3.2024.1001)
     mini_mime (1.1.5)
     minitest (5.25.1)
     mojo_magick (0.6.8)
@@ -176,15 +177,14 @@ GEM
       diff-lcs (>= 1.2.0, < 2.0)
       rspec-support (~> 3.13.0)
     rspec-support (3.13.1)
-    rubocop (1.64.1)
+    rubocop (1.66.1)
       json (~> 2.3)
       language_server-protocol (>= 3.17.0)
       parallel (~> 1.10)
       parser (>= 3.3.0.2)
       rainbow (>= 2.2.2, < 4.0)
-      regexp_parser (>= 1.8, < 3.0)
-      rexml (>= 3.2.5, < 4.0)
-      rubocop-ast (>= 1.31.1, < 2.0)
+      regexp_parser (>= 2.4, < 3.0)
+      rubocop-ast (>= 1.32.2, < 2.0)
       ruby-progressbar (~> 1.7)
       unicode-display_width (>= 2.4.0, < 3.0)
     rubocop-ast (1.32.3)
@@ -249,7 +249,7 @@ GEM
     uglifier (4.2.0)
       execjs (>= 0.3.0, < 3)
     unicode-display_width (2.6.0)
-    webrick (1.8.1)
+    webrick (1.8.2)
     websocket (1.2.11)
     websocket-client-simple (0.6.1)
       event_emitter
@@ -283,7 +283,7 @@ DEPENDENCIES
   irb (~> 1.14)
   json
   maxmind-db (~> 1.2)
-  mime-types (~> 3.5)
+  mime-types (~> 3.6)
   msfrpc-client (~> 1.1, >= 1.1.2)
   net-smtp
   otr-activerecord (~> 2.2.0)
@@ -296,7 +296,7 @@ DEPENDENCIES
   rdoc (~> 6.7)
   rest-client (~> 2.1.0)
   rspec (~> 3.13)
-  rubocop (~> 1.64.0)
+  rubocop (~> 1.66.1)
   rubyzip (~> 2.3)
   rushover (~> 0.3.0)
   selenium-webdriver (~> 4.24)
diff --git a/package.json b/package.json
index b7fffe0ae..7b08e8ce8 100644
--- a/package.json
+++ b/package.json
@@ -9,7 +9,7 @@
     "license": "GNU General Public License v2.0",
     "devDependencies": {
         "jsdoc": "^4.0.0",
-        "jsdoc-to-markdown": "^8.0.0"
+        "jsdoc-to-markdown": "^9.0.2"
     },
     "dependencies": {}
 }