diff --git a/CHANGELOG.md b/CHANGELOG.md
index e0f90da..d662d7a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,12 @@
 # `tailwindcss-rails` Changelog
 
+## v4.2.3 / 2025-05-02
+
+### Improved
+
+* The "tailwindcss:upgrade" task now pins to v4.1.4 of the `@tailwindcss/upgrade` tool. #544 @flavorjones
+
+
 ## v4.2.2 / 2025-04-05
 
 ### Improved
diff --git a/Gemfile.lock b/Gemfile.lock
index 08ddee5..9b0500d 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -140,11 +140,11 @@ GEM
       io-console (~> 0.5)
     securerandom (0.4.1)
     stringio (3.1.5)
-    tailwindcss-ruby (4.0.17)
-    tailwindcss-ruby (4.0.17-aarch64-linux-gnu)
-    tailwindcss-ruby (4.0.17-arm64-darwin)
-    tailwindcss-ruby (4.0.17-x86_64-darwin)
-    tailwindcss-ruby (4.0.17-x86_64-linux-gnu)
+    tailwindcss-ruby (4.1.7)
+    tailwindcss-ruby (4.1.7-aarch64-linux-gnu)
+    tailwindcss-ruby (4.1.7-arm64-darwin)
+    tailwindcss-ruby (4.1.7-x86_64-darwin)
+    tailwindcss-ruby (4.1.7-x86_64-linux-gnu)
     thor (1.3.2)
     timeout (0.4.3)
     tzinfo (2.0.6)
diff --git a/README.md b/README.md
index 7188adf..158b175 100644
--- a/README.md
+++ b/README.md
@@ -124,7 +124,7 @@ Then, run `bin/rails tailwindcss:upgrade`. Among other things, this will try to
 - If present, moves `app/assets/stylesheets/application.tailwind.css` to `app/assets/tailwind/application.css`.
 - Removes unnecessary `stylesheet_link_tag "tailwindcss"` tags from the application layout.
 - Removes references to the Inter font from the application layout.
-- Runs the upstream upgrader (note: requires `npx` to run the one-time upgrade, but highly recommended).
+- Runs v4.1.4 of the upstream upgrader (note: requires `npx` to run the one-time upgrade, but highly recommended).
 
 </details>
 
@@ -145,7 +145,7 @@ $ bin/rails tailwindcss:upgrade
       remove    app/assets/stylesheets/application.tailwind.css
 10.9.0
   Running the upstream Tailwind CSS upgrader
-         run    npx @tailwindcss/upgrade --force --config /home/user/myapp/config/tailwind.config.js from "."
+         run    npx @tailwindcss/upgrade@4.1.4 --force --config /home/user/myapp/config/tailwind.config.js from "."
 ≈ tailwindcss v4.0.0
 │ Searching for CSS files in the current directory and its subdirectories…
 │ ↳ Linked `./config/tailwind.config.js` to `./app/assets/tailwind/application.css`
diff --git a/lib/install/upgrade_tailwindcss.rb b/lib/install/upgrade_tailwindcss.rb
index 004d9a8..d6ecada 100644
--- a/lib/install/upgrade_tailwindcss.rb
+++ b/lib/install/upgrade_tailwindcss.rb
@@ -45,8 +45,14 @@
 end
 
 if system("npx --version")
+  # We're pinning to v4.1.4 because v4.1.5 of the upgrade tool introduces a dependency version check
+  # on tailwind and I haven't been able to figure out how to get that to work reliably and I am
+  # extremely frustrated with the whole thing. See #544
+  #
+  # At some point we will probably need to unpin this at which point I am sincerely hoping that
+  # someone else will do it.
   say "Running the upstream Tailwind CSS upgrader"
-  command = Shellwords.join(["npx", "@tailwindcss/upgrade", "--force", "--config", TAILWIND_CONFIG_PATH.to_s])
+  command = Shellwords.join(["npx", "@tailwindcss/upgrade@4.1.4", "--force", "--config", TAILWIND_CONFIG_PATH.to_s])
   success = run(command, abort_on_failure: false)
   unless success
     say "The upgrade tool failed!", :red
diff --git a/lib/tailwindcss/version.rb b/lib/tailwindcss/version.rb
index 8a0f50d..7ab2db8 100644
--- a/lib/tailwindcss/version.rb
+++ b/lib/tailwindcss/version.rb
@@ -1,3 +1,3 @@
 module Tailwindcss
-  VERSION = "4.2.2"
+  VERSION = "4.2.3"
 end