diff --git a/scripts/validateTokenJson.ts b/scripts/validateTokenJson.ts
index 3d488f90d..23fc55679 100644
--- a/scripts/validateTokenJson.ts
+++ b/scripts/validateTokenJson.ts
@@ -65,15 +65,15 @@ if (getFlag('--silent') === null) {
     // eslint-disable-next-line no-console
     console.log(`\u001b[36;1m\u001b[1m${fail.fileName}\u001b[0m`)
 
-    for (const path of Object.keys(fail.errorsByPath)) {
+    for (const mainPath of Object.keys(fail.errorsByPath)) {
       // eslint-disable-next-line no-console
-      console.log(`\nPath: \u001b[34;1m\u001b[1m${path}\u001b[0m`)
+      console.log(`\nPath: \u001b[34;1m\u001b[1m${mainPath}\u001b[0m`)
       // eslint-disable-next-line no-console
       console.log(
-        fail.errorsByPath[path]
+        fail.errorsByPath[mainPath]
           .map(
-            ({message, code, errors}) =>
-              `${message.replace(/\*\*(.*?)\*\*/g, '- \u001b[31;1m\u001b[1m$1\u001b[0m').replace(/\n(?!-)/g, '\n  ↳ ')}, code: ${code}, errors:\n ${errors
+            ({message, code, errors, ...item}) =>
+              `${message.replace(/\*\*(.*?)\*\*/g, '- \u001b[31;1m\u001b[1m$1\u001b[0m').replace(/\n(?!-)/g, '\n  ↳ ')}, code: ${code}, path: ${item.path}, errors:\n ${errors
                 .map(error => {
                   return `- ${error.issues[0].code}: ${error.issues[0].message}`
                 })
diff --git a/src/schemas/shadowToken.ts b/src/schemas/shadowToken.ts
index 265924472..b78455504 100644
--- a/src/schemas/shadowToken.ts
+++ b/src/schemas/shadowToken.ts
@@ -19,6 +19,12 @@ export const shadowValue = z
   })
   .strict()
 
+const baseShadowToken = baseToken.extend({
+  $value: z.union([shadowValue, referenceValue, z.array(shadowValue)]),
+})
+
+const override = z.union([referenceValue, baseShadowToken]).optional()
+
 export const shadowToken = baseToken
   .extend({
     $value: z.union([shadowValue, z.array(shadowValue), referenceValue]),
@@ -42,6 +48,32 @@ export const shadowToken = baseToken
             group: z.string().optional(),
           })
           .strict(),
+        'org.primer.overrides': z
+          .object(
+            {
+              light: override,
+              'light-tritanopia': override,
+              'light-protanopia-deuteranopia': override,
+              'light-high-contrast': override,
+              dark: override,
+              'dark-tritanopia': override,
+              'dark-protanopia-deuteranopia': override,
+              'dark-high-contrast': override,
+              'dark-dimmed': override,
+            },
+            {
+              errorMap: e => {
+                if (e.code === 'unrecognized_keys') {
+                  return {
+                    message: `Unrecognized key: "${e.keys.join(', ')}", must be one of: light, light-tritanopia, light-protanopia-deuteranopia, light-high-contrast, dark, dark-tritanopia, dark-protanopia-deuteranopia, dark-high-contrast, dark-dimmed`,
+                  }
+                }
+                return {message: `Error: ${e.code}`}
+              },
+            },
+          )
+          .strict()
+          .optional(),
       })
       .optional(),
   })
diff --git a/src/tokens/functional/shadow/shadow.json5 b/src/tokens/functional/shadow/shadow.json5
index b22af96e4..9f972bac0 100644
--- a/src/tokens/functional/shadow/shadow.json5
+++ b/src/tokens/functional/shadow/shadow.json5
@@ -646,6 +646,8 @@
         ],
         $type: 'shadow',
         $extensions: {
+          'org.primer.figma': {
+          },
           'org.primer.overrides': {
             dark: {
               $value: [