diff --git a/runner/src/server/plugins/engine/pageControllers/PageControllerBase.ts b/runner/src/server/plugins/engine/pageControllers/PageControllerBase.ts
index 6885745b51..94cce40229 100644
--- a/runner/src/server/plugins/engine/pageControllers/PageControllerBase.ts
+++ b/runner/src/server/plugins/engine/pageControllers/PageControllerBase.ts
@@ -606,7 +606,7 @@ export class PageControllerBase {
           path: field.name,
           href: `#${field.name}`,
           name: field.name,
-          text: `The selected file must be smaller than ${config.maxFileSizeStringInMb}MB`,
+          text: `The selected files must be smaller than ${config.maxFileSizeStringInMb}MB`,
         };
       });
 
diff --git a/runner/src/server/plugins/engine/pluginHandlers/files/prehandlers/handleUpload.ts b/runner/src/server/plugins/engine/pluginHandlers/files/prehandlers/handleUpload.ts
index a775ff098c..af902d50a2 100644
--- a/runner/src/server/plugins/engine/pluginHandlers/files/prehandlers/handleUpload.ts
+++ b/runner/src/server/plugins/engine/pluginHandlers/files/prehandlers/handleUpload.ts
@@ -44,16 +44,13 @@ export async function handleUpload(
     }
 
     let response;
-
+    const errors = new Set();
     try {
       response = await uploadService.uploadDocuments(streams);
     } catch (err) {
       if (err.data?.res) {
-        const { error } = uploadService.parsedDocumentUploadResponse(err.data);
-        request.pre.errors = [
-          ...request.pre.errors,
-          parsedError(fieldName, error),
-        ];
+        response = uploadService.parsedDocumentUploadResponse(err.data);
+        errors.add(response.error);
       } else if (err.code === "EPIPE") {
         // ignore this error, it happens when the request is responded to by the doc upload service before the
         // body has finished being sent. A valid response is still received.
@@ -63,10 +60,7 @@ export async function handleUpload(
           { ...loggerIdentifier, err },
           `Error uploading document: ${err.message}`
         );
-        request.pre.errors = [
-          ...(h.request.pre.errors || []),
-          parsedError(fieldName, err),
-        ];
+        errors.add(err);
       }
     }
 
@@ -108,9 +102,13 @@ export async function handleUpload(
         loggerIdentifier,
         `Document upload API responded with an error ${error}`
       );
+      errors.add(error);
+    }
+
+    if(errors){
       request.pre.errors = [
         ...(request.pre.errors || []),
-        parsedError(fieldName, error),
+        ...Array.from(errors).map(e => parsedError(fieldName, String(e)))
       ];
     }
   }
diff --git a/runner/src/server/services/upload/uploadService.ts b/runner/src/server/services/upload/uploadService.ts
index a1e3122f56..9cddda3232 100644
--- a/runner/src/server/services/upload/uploadService.ts
+++ b/runner/src/server/services/upload/uploadService.ts
@@ -26,10 +26,11 @@ const parsedError = (key: string, error?: string) => {
 };
 
 const ERRORS = {
-  fileSizeError: 'The selected file for "%s" is too large',
+  fileSizeError: 'The selected files are too large',
   fileTypeError: "Invalid file type. Upload a PNG, JPG or PDF",
-  virusError: 'The selected file for "%s" contained a virus',
-  default: "There was an error uploading your file",
+  fileCountError: 'You have selected too many files',
+  virusError: 'The selected files contained a virus',
+  default: "There was an error uploading your files",
 };
 
 export class UploadService {
@@ -60,7 +61,7 @@ export class UploadService {
       .join(", ");
     const lastAcceptedTypeName = acceptedTypeNames.slice(-1);
 
-    return `The selected file for "%s" must be a ${acceptedTypesNameWithoutLast} or ${lastAcceptedTypeName}`;
+    return `The selected files must be a ${acceptedTypesNameWithoutLast} or ${lastAcceptedTypeName}`;
   }
 
   get fileSizeLimit() {
@@ -127,7 +128,18 @@ export class UploadService {
   }
 
   parsedDocumentUploadResponse({ res, payload }) {
-    const warning = payload?.toString?.();
+    const payloadString = payload?.toString?.();
+    let payloadJson: any;
+    let warning: string | undefined;
+    let errorCode: string | undefined;
+
+    try {
+      payloadJson = payloadString ? JSON.parse(payloadString) : undefined;
+      errorCode = payloadJson?.errorCode;
+      warning = payloadJson?.warning;
+    } catch (e) {
+      warning = payloadString;
+    }
     let error: string | undefined;
     let location: string | undefined;
     switch (res.statusCode) {
@@ -138,7 +150,15 @@ export class UploadService {
         error = ERRORS.fileTypeError;
         break;
       case 413:
-        error = ERRORS.fileSizeError;
+        if(errorCode === "TOO_MANY_FILES") {
+          if (payloadJson?.maxFilesPerUpload) {
+            error = `You can only select up to ${payloadJson?.maxFilesPerUpload} files at the same time`;
+          } else {
+            error = ERRORS.fileCountError;
+          }
+        } else {
+          error = ERRORS.fileSizeError;
+        }
         break;
       case 422:
         error = ERRORS.virusError;
diff --git a/runner/test/cases/server/upload.test.js b/runner/test/cases/server/upload.test.js
index 981a16b305..f669eeed9c 100644
--- a/runner/test/cases/server/upload.test.js
+++ b/runner/test/cases/server/upload.test.js
@@ -70,7 +70,7 @@ suite("uploads", () => {
 
     stub(UploadService.prototype, "uploadDocuments").callsFake(async () => {
       return {
-        error: 'The selected file for "%s" contained a virus',
+        error: 'The selected files contained a virus',
       };
     });
 
@@ -87,7 +87,7 @@ suite("uploads", () => {
 
     const $ = cheerio.load(response.payload);
     expect($("[href='#file1']").text().trim()).to.equal(
-      'The selected file for "Passport photo" contained a virus'
+      'The selected files contained a virus'
     );
   });
 
@@ -112,7 +112,7 @@ suite("uploads", () => {
     const $ = cheerio.load(response.payload);
 
     expect($("[href='#file1']").text().trim()).to.contain(
-      "The selected file must be smaller than"
+      "The selected files must be smaller than"
     );
   });
 
@@ -150,7 +150,7 @@ suite("uploads", () => {
 
     const $ = cheerio.load(response.payload);
     expect($("[href='#file1']").text().trim()).to.contain(
-      'The selected file for "Passport photo" must be a JPG, JPEG, PNG or PDF'
+      'The selected files must be a JPG, JPEG, PNG or PDF'
     );
   });