diff --git a/.github/workflows/ci.yaml b/.github/workflows/ci.yaml
index 981ac4b..e8d66b9 100644
--- a/.github/workflows/ci.yaml
+++ b/.github/workflows/ci.yaml
@@ -34,7 +34,7 @@ jobs:
       - uses: actions/checkout@v2
       - uses: ruby/setup-ruby@v1
         with:
-          ruby-version: '2.6'
+          ruby-version: '3.3'
           bundler-cache: true
       - run: bundle exec rubocop
 
@@ -43,7 +43,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ubuntu]
-        ruby: ['2.6', '2.7', '3.0', '3.1', '3.2', 'ruby-head', 'debug', 'truffleruby', 'truffleruby-head']
+        ruby: ['2.7', '3.0', '3.1', '3.2', '3.3', 'ruby-head', 'debug', 'truffleruby', 'truffleruby-head']
     runs-on: ${{ matrix.os }}-latest
     steps:
       - uses: actions/checkout@v2
@@ -58,7 +58,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ubuntu]
-        ruby: ['3.0']
+        ruby: ['3.3']
     runs-on: ${{ matrix.os }}-latest
     env:
       PSYCH_4: "1"
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 6166163..c7e02d8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,6 @@
 # Unreleased
 
+* Fix a compatibility issue with the `prism` library that ships with Ruby 3.3. See #463.
 * Improved the `Kernel#require` decorator to not cause a method redefinition warning. See #461.
 
 # 1.17.0
diff --git a/lib/bootsnap/load_path_cache/core_ext/kernel_require.rb b/lib/bootsnap/load_path_cache/core_ext/kernel_require.rb
index 33540ba..ba4d764 100644
--- a/lib/bootsnap/load_path_cache/core_ext/kernel_require.rb
+++ b/lib/bootsnap/load_path_cache/core_ext/kernel_require.rb
@@ -24,9 +24,7 @@ def require(path) # rubocop:disable Lint/DuplicateMethods
     elsif false == resolved
       return false
     elsif resolved.nil?
-      error = LoadError.new(+"cannot load such file -- #{path}")
-      error.instance_variable_set(:@path, path)
-      raise error
+      return require_without_bootsnap(path)
     else
       # Note that require registers to $LOADED_FEATURES while load does not.
       ret = require_without_bootsnap(resolved)
diff --git a/test/load_path_cache/core_ext/kernel_require_test.rb b/test/load_path_cache/core_ext/kernel_require_test.rb
index b1a7a93..dc120ea 100644
--- a/test/load_path_cache/core_ext/kernel_require_test.rb
+++ b/test/load_path_cache/core_ext/kernel_require_test.rb
@@ -31,6 +31,25 @@ def test_uses_the_same_duck_type_as_require
         cache.unlink
       end
     end
+
+    def test_load_static_libaries
+      skip("Need a working Process.fork to test in isolation") unless Process.respond_to?(:fork)
+      skip("Need some libraries to be compiled statically") unless RUBY_VERSION >= "3.3"
+
+      begin
+        assert_nil LoadPathCache.load_path_cache
+        cache = Tempfile.new("cache")
+        pid = Process.fork do
+          LoadPathCache.setup(cache_path: cache, development_mode: false, ignore_directories: nil)
+          require("prism")
+        end
+        _, status = Process.wait2(pid)
+        assert_predicate status, :success?
+      ensure
+        cache.close
+        cache.unlink
+      end
+    end
   end
 
   class KernelLoadTest < Minitest::Test