diff --git a/lib/puppet/indirector/catalog/compiler.rb b/lib/puppet/indirector/catalog/compiler.rb
index 9a6db303d47..f12fc53ca9c 100644
--- a/lib/puppet/indirector/catalog/compiler.rb
+++ b/lib/puppet/indirector/catalog/compiler.rb
@@ -53,12 +53,20 @@ def find(request)
     node.trusted_data = Puppet.lookup(:trusted_information) { Puppet::Context::TrustedInformation.local(node) }.to_h
 
     if node.environment
-      # If the requested environment doesn't match the server specified environment,
-      # as determined by the node terminus, and the request wants us to check for an
+      # If the requested environment name doesn't match the server specified environment
+      # name, as determined by the node terminus, and the request wants us to check for an
       # environment mismatch, then return an empty catalog with the server-specified
       # enviroment.
-      if request.remote? && request.options[:check_environment] && node.environment != request.environment
-        return Puppet::Resource::Catalog.new(node.name, node.environment)
+      if request.remote? && request.options[:check_environment]
+        # The "environment" may be same while environment objects differ. This
+        # is most likely because the environment cache was flushed between the request
+        # processing and node lookup. Environment overrides `==` but requires the
+        # name and modulepath to be the same. When using versioned environment dirs the
+        # same "environment" can have different modulepaths so simply compare names here.
+        if node.environment.name != request.environment.name
+          Puppet.warning _("Requested environment '%{request_env}' did not match server specified environment '%{server_env}'") % {request_env: request.environment.name, server_env: node.environment.name}
+          return Puppet::Resource::Catalog.new(node.name, node.environment)
+        end
       end
 
       node.environment.with_text_domain do
diff --git a/spec/unit/indirector/catalog/compiler_spec.rb b/spec/unit/indirector/catalog/compiler_spec.rb
index 4e883b43b08..4e1a3b07344 100644
--- a/spec/unit/indirector/catalog/compiler_spec.rb
+++ b/spec/unit/indirector/catalog/compiler_spec.rb
@@ -271,6 +271,23 @@ def set_facts(fact_hash)
         expect(catalog).to have_resource('Stage[main]')
       end
 
+      # versioned environment directories can cause this
+      it 'allows environments with the same name but mismatched modulepaths' do
+        envs = Puppet.lookup(:environments)
+        env_server = envs.get!(:env_server)
+        v1_env = env_server.override_with({ modulepath: ['/code-v1/env-v1/'] })
+        v2_env = env_server.override_with({ modulepath: ['/code-v2/env-v2/'] })
+
+        @request.options[:check_environment] = "true"
+        @request.environment = v1_env
+        node.environment = v2_env
+
+        catalog = compiler.find(@request)
+
+        expect(catalog.environment).to eq('env_server')
+        expect(catalog).to have_resource('Stage[main]')
+      end
+
       it 'returns an empty catalog if asked to check the environment and they are mismatched' do
         @request.options[:check_environment] = "true"
         catalog = compiler.find(@request)