diff --git a/.github/workflows/security.yml b/.github/workflows/security.yml
index 80789d1b..cbd8e5e2 100644
--- a/.github/workflows/security.yml
+++ b/.github/workflows/security.yml
@@ -93,6 +93,8 @@ jobs:
         with:
           go-version-file: 'go/go.mod'
           cache-dependency-path: 'go/go.sum'
+          # Scan against the newest 1.26.x, not whatever patch the runner has cached.
+          check-latest: true
 
       - name: Install govulncheck
         run: go install golang.org/x/vuln/cmd/govulncheck@latest
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index e1dbe096..71df687e 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -146,12 +146,22 @@ jobs:
           persist-credentials: false
 
       - name: Set up Ruby
+        if: matrix.ruby != 'head'
         uses: ruby/setup-ruby@7372622e62b60b3cb750dcd2b9e32c247ffec26a # v1.302.0
         with:
           ruby-version: ${{ matrix.ruby }}
           bundler-cache: true
           working-directory: ruby
 
+      - name: Set up Ruby head
+        if: matrix.ruby == 'head'
+        uses: ruby/setup-ruby@7372622e62b60b3cb750dcd2b9e32c247ffec26a # v1.302.0
+        with:
+          ruby-version: ${{ matrix.ruby }}
+          bundler: default
+          bundler-cache: true
+          working-directory: ruby
+
       - name: Lint
         if: matrix.ruby == '3.3'
         run: bundle exec rubocop
diff --git a/ruby/Gemfile.lock b/ruby/Gemfile.lock
index 4eb6c846..a1ab555a 100644
--- a/ruby/Gemfile.lock
+++ b/ruby/Gemfile.lock
@@ -136,7 +136,6 @@ GEM
       addressable (>= 2.8.0)
       crack (>= 0.3.2)
       hashdiff (>= 0.4.0, < 2.0.0)
-    webrick (1.9.2)
     yard (0.9.44)
     zeitwerk (2.8.2)
 
@@ -153,7 +152,6 @@ DEPENDENCIES
   rubocop-37signals
   simplecov (~> 0.22)
   webmock (~> 3.24)
-  webrick (~> 1.9)
   yard (~> 0.9)
 
 CHECKSUMS
@@ -216,7 +214,6 @@ CHECKSUMS
   unicode-emoji (4.2.0) sha256=519e69150f75652e40bf736106cfbc8f0f73aa3fb6a65afe62fefa7f80b0f80f
   uri (1.1.1) sha256=379fa58d27ffb1387eaada68c749d1426738bd0f654d812fcc07e7568f5c57c6
   webmock (3.26.2) sha256=774556f2ea6371846cca68c01769b2eac0d134492d21f6d0ab5dd643965a4c90
-  webrick (1.9.2) sha256=beb4a15fc474defed24a3bda4ffd88a490d517c9e4e6118c3edce59e45864131
   yard (0.9.44) sha256=eb087e9b631ccd887b049f303d489963945452d5e2a7eb49a5a74a7cf6887f28
   zeitwerk (2.8.2) sha256=7212a61311083c604184b1ea2574b9aa05cd14f855a0841c06985cabe9181d12
 
diff --git a/ruby/basecamp-sdk.gemspec b/ruby/basecamp-sdk.gemspec
index 159a1144..becd75df 100644
--- a/ruby/basecamp-sdk.gemspec
+++ b/ruby/basecamp-sdk.gemspec
@@ -41,6 +41,5 @@ Gem::Specification.new do |spec|
   spec.add_development_dependency 'webmock', '~> 3.24'
   spec.add_development_dependency 'irb', '~> 1.15'
   spec.add_development_dependency 'rdoc', '~> 7.1'
-  spec.add_development_dependency 'webrick', '~> 1.9'
   spec.add_development_dependency 'yard', '~> 0.9'
 end