diff --git a/docker/lib/dependabot/shared/utils/helpers.rb b/docker/lib/dependabot/shared/utils/helpers.rb
index 09bbf5daca6..796b7d7096d 100644
--- a/docker/lib/dependabot/shared/utils/helpers.rb
+++ b/docker/lib/dependabot/shared/utils/helpers.rb
@@ -6,7 +6,7 @@
 module Dependabot
   module Shared
     module Utils
-      HELM_REGEXP = /values[\-a-zA-Z_0-9]*\.ya?ml$/i
+      HELM_REGEXP = %r{(^|/)values(?:\.[\w-]+)?\.ya?ml$}i
 
       extend T::Sig
 
diff --git a/helm/lib/dependabot/helm/file_parser.rb b/helm/lib/dependabot/helm/file_parser.rb
index 0dbcb1bbfd2..91230edbbdc 100644
--- a/helm/lib/dependabot/helm/file_parser.rb
+++ b/helm/lib/dependabot/helm/file_parser.rb
@@ -12,7 +12,7 @@ class FileParser < Dependabot::Shared::SharedFileParser
 
       CHART_YAML = /.*chart\.ya?ml$/i
       CHART_LOCK = /.*chart\.lock$/i
-      VALUES_YAML = /.*values\.ya?ml$/i
+      VALUES_YAML = %r{.*(^|/)values(?:\.[\w-]+)?\.ya?ml$}i
       DEFAULT_REPOSITORY = "https://charts.helm.sh/stable"
 
       sig { returns(Ecosystem) }
diff --git a/helm/spec/dependabot/helm/file_parser_spec.rb b/helm/spec/dependabot/helm/file_parser_spec.rb
index 94258de4dc7..7fbfff00797 100644
--- a/helm/spec/dependabot/helm/file_parser_spec.rb
+++ b/helm/spec/dependabot/helm/file_parser_spec.rb
@@ -191,6 +191,34 @@
           expect(dependency.version).to eq("1.25.3")
         end
       end
+
+      context "with environment-specific values file (values.cass.yaml)" do
+        let(:helmfile_fixture_name) { "values_environment_specific.yaml" }
+        let(:helmfile) do
+          Dependabot::DependencyFile.new(
+            name: "values.cass.yaml",
+            content: helmfile_body
+          )
+        end
+
+        it "is able to parse environment-specific values files" do
+          expect(dependencies.length).to eq(3)
+
+          mdsd_dependency = dependencies.find { |d| d.name == "linuxgeneva-microsoft.azurecr.io/distroless/genevamdsd" }
+          expect(mdsd_dependency).to be_a(Dependabot::Dependency)
+          expect(mdsd_dependency.version).to eq("1.35.9-20250722-2")
+
+          mdm_dependency = dependencies.find { |d| d.name == "linuxgeneva-microsoft.azurecr.io/distroless/genevamdm" }
+          expect(mdm_dependency).to be_a(Dependabot::Dependency)
+          expect(mdm_dependency.version).to eq("2.202507220956.0-20250722-1")
+
+          fluentd_dependency = dependencies.find do |d|
+            d.name == "linuxgeneva-microsoft.azurecr.io/distroless/genevafluentd"
+          end
+          expect(fluentd_dependency).to be_a(Dependabot::Dependency)
+          expect(fluentd_dependency.version).to eq("1.18.0-20250722-2")
+        end
+      end
     end
   end
 
diff --git a/helm/spec/fixtures/helm/v3/values_environment_specific.yaml b/helm/spec/fixtures/helm/v3/values_environment_specific.yaml
new file mode 100644
index 00000000000..49608865786
--- /dev/null
+++ b/helm/spec/fixtures/helm/v3/values_environment_specific.yaml
@@ -0,0 +1,15 @@
+# Test fixture for environment-specific values file like values.cass.yaml
+mdsd:
+  image:
+    repository: linuxgeneva-microsoft.azurecr.io/distroless/genevamdsd
+    tag: 1.35.9-20250722-2
+
+mdm:
+  image:
+    repository: linuxgeneva-microsoft.azurecr.io/distroless/genevamdm
+    tag: 2.202507220956.0-20250722-1
+
+fluentd:
+  image:
+    repository: linuxgeneva-microsoft.azurecr.io/distroless/genevafluentd
+    tag: 1.18.0-20250722-2
\ No newline at end of file