diff --git a/Gemfile b/Gemfile
index caf5221a..099a1b04 100644
--- a/Gemfile
+++ b/Gemfile
@@ -45,7 +45,7 @@ gem "image_processing", "~> 1.2"
 
 gem "aws-sdk-s3", require: false
 
-gem "tailwindcss-rails", "~> 4.0"
+gem "tailwindcss-rails", "~> 4.4"
 
 # Redis for cache, queue, and Action Cable
 gem "redis", "~> 5.0"
diff --git a/Gemfile.lock b/Gemfile.lock
index 946013be..f2b3603a 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -161,7 +161,7 @@ GEM
       railties (>= 6.1)
     drb (2.2.3)
     ed25519 (1.4.0)
-    erb (5.1.1)
+    erb (5.1.3)
     erb_lint (0.9.0)
       activesupport
       better_html (>= 2.0.1)
@@ -509,15 +509,15 @@ GEM
     stringio (3.1.7)
     tailwind_merge (1.3.1)
       sin_lru_redux (~> 2.5)
-    tailwindcss-rails (4.3.0)
+    tailwindcss-rails (4.4.0)
       railties (>= 7.0.0)
       tailwindcss-ruby (~> 4.0)
-    tailwindcss-ruby (4.1.12)
-    tailwindcss-ruby (4.1.12-aarch64-linux-gnu)
-    tailwindcss-ruby (4.1.12-aarch64-linux-musl)
-    tailwindcss-ruby (4.1.12-arm64-darwin)
-    tailwindcss-ruby (4.1.12-x86_64-linux-gnu)
-    tailwindcss-ruby (4.1.12-x86_64-linux-musl)
+    tailwindcss-ruby (4.1.16)
+    tailwindcss-ruby (4.1.16-aarch64-linux-gnu)
+    tailwindcss-ruby (4.1.16-aarch64-linux-musl)
+    tailwindcss-ruby (4.1.16-arm64-darwin)
+    tailwindcss-ruby (4.1.16-x86_64-linux-gnu)
+    tailwindcss-ruby (4.1.16-x86_64-linux-musl)
     thor (1.4.0)
     thruster (0.1.16)
     thruster (0.1.16-aarch64-linux)
@@ -612,7 +612,7 @@ DEPENDENCIES
   sqlite3 (>= 2.1)
   stimulus-rails
   tailwind_merge (~> 1.3)
-  tailwindcss-rails (~> 4.0)
+  tailwindcss-rails (~> 4.4)
   thruster
   turbo-rails
   tzinfo-data