diff --git a/.github/upstream-projects.yaml b/.github/upstream-projects.yaml
index eaea19bf..0419bfc2 100644
--- a/.github/upstream-projects.yaml
+++ b/.github/upstream-projects.yaml
@@ -147,8 +147,25 @@ projects:
       - source: enterprise/ai-gateway/docs/operator-guide/management-api.openapi.yaml
         destination: static/api-specs/ai-gateway-management-api.yaml
     public_sources: false
+    helm_version_source: enterprise/stacklok-enterprise-platform/helm/Chart.yaml
     helm:
       - source: enterprise/stacklok-enterprise-platform/helm
+        release_overrides:
+          - since: v0.26.0
+            description_overrides:
+              workspace.production: >-
+                Enforce production requirements for Workspace, including external
+                PostgreSQL and object storage, credentials, and resource limits.
+              workspace.image.repository: Container image repository for Workspace.
+              workspace.postgres.enabled: >-
+                Deploy the development PostgreSQL instance for Workspace.
+                Requires workspace.production to be false.
+              workspace.objectStore.enabled: >-
+                Deploy the development MinIO object store for Workspace.
+                Requires workspace.production to be false.
+              workspace.networkPolicy.cloudUI.enabled: >-
+                Allow console pods to reach Workspace when
+                workspace.networkPolicy.enabled is true.
         page: docs/platform/reference/helm/platform.mdx
         title: Platform Helm values
         description: Values, types, and defaults for the Stacklok Enterprise platform chart.
@@ -209,6 +226,7 @@ projects:
           - label: Deploy the platform
             href: ../../enterprise-platform/deployment.mdx
       - source: enterprise/ai-gateway/helm/operator
+        before: v0.26.0
         page: docs/platform/reference/helm/ai-gateway-operator.mdx
         title: Legacy AI Gateway operator Helm values
         description: Values, types, and defaults for the legacy AI Gateway operator chart in Stacklok Enterprise.
@@ -219,6 +237,7 @@ projects:
           - label: Deploy the platform
             href: ../../enterprise-platform/deployment.mdx
       - source: enterprise/ai-gateway/helm/operator-crds
+        before: v0.26.0
         page: docs/platform/reference/helm/ai-gateway-operator-crds.mdx
         title: Legacy AI Gateway operator CRD Helm values
         description: Values, types, and defaults for the legacy AI Gateway operator CRD chart in Stacklok Enterprise.
@@ -239,6 +258,9 @@ projects:
           - label: Deploy the platform
             href: ../../enterprise-platform/deployment.mdx
       - source: enterprise/sprout/helm
+        release_overrides:
+          - since: v0.26.0
+            source: enterprise/ai-gateway/helm
         page: docs/platform/reference/helm/ai-gateway.mdx
         title: AI Gateway Helm values
         description: Values, types, and defaults for the AI Gateway chart in Stacklok Enterprise.
diff --git a/scripts/upstream-release/generate-helm-reference.mjs b/scripts/upstream-release/generate-helm-reference.mjs
index debc3890..22747b56 100644
--- a/scripts/upstream-release/generate-helm-reference.mjs
+++ b/scripts/upstream-release/generate-helm-reference.mjs
@@ -15,6 +15,68 @@ import yaml from 'yaml';
 
 const repoRoot = fileURLToPath(new URL('../../', import.meta.url));
 
+// Select chart paths from the source release's version, including SHA-based exports.
+export function resolveHelmCharts(project, clone) {
+  const charts = project.helm || [];
+  if (!project.helm_version_source) return charts;
+  const metadata = yaml.parse(
+    fs.readFileSync(path.join(clone, project.helm_version_source), 'utf8')
+  );
+  const version = (value) => {
+    const match = /^v?(\d+)\.(\d+)\.(\d+)(?:-[0-9A-Za-z.-]+)?$/.exec(value);
+    if (!match) throw new Error(`Invalid Helm release version: ${value}`);
+    return match.slice(1, 4).map(Number);
+  };
+  const current = version(metadata.version);
+  const atLeast = (value) => {
+    const target = version(value);
+    for (let i = 0; i < 3; i++) {
+      if (current[i] !== target[i]) return current[i] > target[i];
+    }
+    return true;
+  };
+  return charts
+    .filter((chart) => !chart.before || !atLeast(chart.before))
+    .map((chart) => {
+      const overrides = (chart.release_overrides || [])
+        .filter((override) => atLeast(override.since))
+        .sort((a, b) => {
+          const left = version(a.since);
+          const right = version(b.since);
+          return left[0] - right[0] || left[1] - right[1] || left[2] - right[2];
+        });
+      return overrides.reduce(
+        (resolved, override) => ({
+          ...resolved,
+          ...override,
+          description_overrides: {
+            ...resolved.description_overrides,
+            ...override.description_overrides,
+          },
+        }),
+        chart
+      );
+    });
+}
+
+export function validateHelmInputs(charts, clone) {
+  const missing = charts.flatMap((chart) =>
+    ['Chart.yaml', 'values.yaml']
+      .map((file) => path.join(chart.source, file))
+      .filter((file) => {
+        const input = path.join(clone, file);
+        return (
+          !fs.existsSync(input) ||
+          !fs.statSync(input).isFile() ||
+          !fs.statSync(input).size
+        );
+      })
+  );
+  if (missing.length) {
+    throw new Error(`Missing release Helm inputs:\n${missing.join('\n')}`);
+  }
+}
+
 // Preserve inline code while escaping MDX expressions and JSX in upstream prose.
 export function mdxText(value) {
   return String(value).replace(
@@ -274,11 +336,13 @@ function main(argv) {
   if (!args.clone || (!args.check && !tag))
     throw new Error('Helm generation requires --clone and a release tag');
 
+  const charts = resolveHelmCharts(project, args.clone);
+  validateHelmInputs(charts, args.clone);
   const tmp = fs.mkdtempSync(path.join(os.tmpdir(), 'helm-reference-'));
   try {
     // Copy only documentation inputs: helm-docs must never overwrite upstream READMEs.
     // Prepare every page before replacing outputs, so incomplete annotations fail early.
-    const inputs = project.helm.map((chart, index) => {
+    const inputs = charts.map((chart, index) => {
       const dir = path.join(tmp, String(index));
       fs.mkdirSync(dir);
       for (const file of ['Chart.yaml', 'values.yaml']) {
diff --git a/scripts/upstream-release/generate-helm-reference.test.mjs b/scripts/upstream-release/generate-helm-reference.test.mjs
index c41cf80e..4f4c4732 100644
--- a/scripts/upstream-release/generate-helm-reference.test.mjs
+++ b/scripts/upstream-release/generate-helm-reference.test.mjs
@@ -15,6 +15,8 @@ import {
   renderPage,
   renderDescription,
   validateDescriptions,
+  resolveHelmCharts,
+  validateHelmInputs,
 } from './generate-helm-reference.mjs';
 
 const chart = {
@@ -91,6 +93,80 @@ test('coverage validation reports every missing value across charts', () => {
   );
 });
 
+test('release chart selection supports legacy and current gateway layouts', () => {
+  const root = fs.mkdtempSync(path.join(os.tmpdir(), 'helm-release-layout-'));
+  try {
+    const { projects } = yaml.parse(
+      fs.readFileSync(
+        new URL('../../.github/upstream-projects.yaml', import.meta.url),
+        'utf8'
+      )
+    );
+    const project = projects.find(
+      (p) => p.id === 'stacklok-enterprise-platform'
+    );
+    const metadata = path.join(root, project.helm_version_source);
+    fs.mkdirSync(path.dirname(metadata), { recursive: true });
+    for (const [version, legacy] of [
+      ['0.25.0', true],
+      ['0.26.0', false],
+      ['0.27.0', false],
+      ['0.100.0', false],
+    ]) {
+      fs.writeFileSync(metadata, yaml.stringify({ version }));
+      const charts = resolveHelmCharts(project, root);
+      const sources = charts.map((chart) => chart.source);
+      assert.equal(
+        sources.includes('enterprise/ai-gateway/helm/operator'),
+        legacy
+      );
+      assert.equal(
+        sources.includes('enterprise/ai-gateway/helm/operator-crds'),
+        legacy
+      );
+      assert.equal(sources.includes('enterprise/sprout/helm'), legacy);
+      assert.equal(sources.includes('enterprise/ai-gateway/helm'), !legacy);
+      assert.equal(charts.length, legacy ? 10 : 8);
+      const platform = charts.find((chart) =>
+        chart.page.endsWith('/platform.mdx')
+      );
+      assert.equal(
+        Boolean(platform.description_overrides?.['workspace.production']),
+        !legacy
+      );
+    }
+    fs.writeFileSync(metadata, 'version: invalid\n');
+    assert.throws(
+      () => resolveHelmCharts(project, root),
+      /Invalid Helm release version/
+    );
+  } finally {
+    fs.rmSync(root, { recursive: true, force: true });
+  }
+});
+
+test('missing Helm inputs are reported together before generation', () => {
+  const root = fs.mkdtempSync(path.join(os.tmpdir(), 'helm-missing-inputs-'));
+  try {
+    fs.mkdirSync(path.join(root, 'first'));
+    fs.writeFileSync(path.join(root, 'first/Chart.yaml'), 'name: first\n');
+    fs.writeFileSync(path.join(root, 'first/values.yaml'), '');
+    assert.throws(
+      () =>
+        validateHelmInputs([{ source: 'first' }, { source: 'second' }], root),
+      (error) => {
+        assert.match(error.message, /first\/values.yaml/);
+        assert.match(error.message, /second\/Chart.yaml/);
+        assert.match(error.message, /second\/values.yaml/);
+        assert.doesNotMatch(error.message, /first\/Chart.yaml/);
+        return true;
+      }
+    );
+  } finally {
+    fs.rmSync(root, { recursive: true, force: true });
+  }
+});
+
 test('check mode validates all charts without writing pages or formatting', () => {
   const root = fs.realpathSync(
     fs.mkdtempSync(path.join(os.tmpdir(), 'helm-reference-check-'))