diff --git a/node-src/lib/upload.ts b/node-src/lib/upload.ts
index 51bebdabf..f5ad83571 100644
--- a/node-src/lib/upload.ts
+++ b/node-src/lib/upload.ts
@@ -2,6 +2,8 @@ import makeZipFile from './compress';
 import { Context, FileDesc, TargetInfo } from '../types';
 import { uploadZip, waitForUnpack } from './uploadZip';
 import { uploadFiles } from './uploadFiles';
+import { maxFileCountExceeded } from '../ui/messages/errors/maxFileCountExceeded';
+import { maxFileSizeExceeded } from '../ui/messages/errors/maxFileSizeExceeded';
 
 const UploadBuildMutation = `
   mutation UploadBuildMutation($buildId: ObjID!, $files: [FileUploadInput!]!, $zip: Boolean) {
@@ -24,6 +26,7 @@ const UploadBuildMutation = `
         }
       }
       userErrors {
+        __typename
         ... on UserError {
           message
         }
@@ -46,13 +49,24 @@ interface UploadBuildMutationResult {
       targets: TargetInfo[];
       zipTarget?: TargetInfo & { sentinelUrl: string };
     };
-    userErrors: {
-      message: string;
-      maxFileCount?: number;
-      maxFileSize?: number;
-      fileCount?: number;
-      filePaths?: string[];
-    }[];
+    userErrors: (
+      | {
+          __typename: 'UserError';
+          message: string;
+        }
+      | {
+          __typename: 'MaxFileCountExceededError';
+          message: string;
+          maxFileCount: number;
+          fileCount: number;
+        }
+      | {
+          __typename: 'MaxFileSizeExceededError';
+          message: string;
+          maxFileSize: number;
+          filePaths: string[];
+        }
+    )[];
   };
 }
 
@@ -79,8 +93,16 @@ export async function uploadBuild(
   );
 
   if (uploadBuild.userErrors.length) {
-    uploadBuild.userErrors.forEach((e) => ctx.log.error(e.message));
-    return options.onError?.(new Error('Upload does not meet requirements'));
+    uploadBuild.userErrors.forEach((e) => {
+      if (e.__typename === 'MaxFileCountExceededError') {
+        ctx.log.error(maxFileCountExceeded(e));
+      } else if (e.__typename === 'MaxFileSizeExceededError') {
+        ctx.log.error(maxFileSizeExceeded(e));
+      } else {
+        ctx.log.error(e.message);
+      }
+    });
+    return options.onError?.(new Error('Upload rejected due to user error'));
   }
 
   const targets = uploadBuild.info.targets.map((target) => {
diff --git a/node-src/ui/messages/errors/maxFileCountExceeded.stories.ts b/node-src/ui/messages/errors/maxFileCountExceeded.stories.ts
new file mode 100644
index 000000000..41b67cade
--- /dev/null
+++ b/node-src/ui/messages/errors/maxFileCountExceeded.stories.ts
@@ -0,0 +1,11 @@
+import { maxFileCountExceeded } from './maxFileCountExceeded';
+
+export default {
+  title: 'CLI/Messages/Errors',
+};
+
+export const MaxFileCountExceeded = () =>
+  maxFileCountExceeded({
+    fileCount: 54_321,
+    maxFileCount: 20_000,
+  });
diff --git a/node-src/ui/messages/errors/maxFileCountExceeded.ts b/node-src/ui/messages/errors/maxFileCountExceeded.ts
new file mode 100644
index 000000000..6487599c8
--- /dev/null
+++ b/node-src/ui/messages/errors/maxFileCountExceeded.ts
@@ -0,0 +1,19 @@
+import chalk from 'chalk';
+import { dedent } from 'ts-dedent';
+
+import { error } from '../../components/icons';
+
+export const maxFileCountExceeded = ({
+  fileCount,
+  maxFileCount,
+}: {
+  fileCount: number;
+  maxFileCount: number;
+}) =>
+  dedent(chalk`
+    ${error} {bold Attempted to upload too many files}
+    You're not allowed to upload more than ${maxFileCount} files per build.
+    Your Storybook contains ${fileCount} files. This is a very high number.
+    Do you have files in a static/public directory that shouldn't be there?
+    Contact customer support if you need to increase this limit.
+  `);
diff --git a/node-src/ui/messages/errors/maxFileSizeExceeded.stories.ts b/node-src/ui/messages/errors/maxFileSizeExceeded.stories.ts
new file mode 100644
index 000000000..a7cb75430
--- /dev/null
+++ b/node-src/ui/messages/errors/maxFileSizeExceeded.stories.ts
@@ -0,0 +1,8 @@
+import { maxFileSizeExceeded } from './maxFileSizeExceeded';
+
+export default {
+  title: 'CLI/Messages/Errors',
+};
+
+export const MaxFileSizeExceeded = () =>
+  maxFileSizeExceeded({ filePaths: ['index.js', 'main.js'], maxFileSize: 12345 });
diff --git a/node-src/ui/messages/errors/maxFileSizeExceeded.ts b/node-src/ui/messages/errors/maxFileSizeExceeded.ts
new file mode 100644
index 000000000..6e619607e
--- /dev/null
+++ b/node-src/ui/messages/errors/maxFileSizeExceeded.ts
@@ -0,0 +1,18 @@
+import chalk from 'chalk';
+import { dedent } from 'ts-dedent';
+
+import { error } from '../../components/icons';
+
+export const maxFileSizeExceeded = ({
+  filePaths,
+  maxFileSize,
+}: {
+  filePaths: string[];
+  maxFileSize: number;
+}) =>
+  dedent(chalk`
+    ${error} {bold Attempted to exceed maximum file size}
+    You're attempting to upload files that exceed the maximum file size of ${maxFileSize} bytes.
+    Contact customer support if you need to increase this limit.
+    - ${filePaths.map((path) => path).join('\n- ')}
+  `);