diff --git a/packages/js-lib/src/core/DriveData/File/DriveFileTypes.ts b/packages/js-lib/src/core/DriveData/File/DriveFileTypes.ts
index 4bd9f4e77..efb5fee61 100644
--- a/packages/js-lib/src/core/DriveData/File/DriveFileTypes.ts
+++ b/packages/js-lib/src/core/DriveData/File/DriveFileTypes.ts
@@ -89,6 +89,7 @@ export interface PayloadFile {
   payload: File | Blob;
   previewThumbnail?: EmbeddedThumb;
   descriptorContent?: string;
+  skipEncryption?: boolean;
 }
 
 type None = 0;
diff --git a/packages/js-lib/src/core/DriveData/Upload/DriveFileUploadProvider.ts b/packages/js-lib/src/core/DriveData/Upload/DriveFileUploadProvider.ts
index 195d9498a..a9a477614 100644
--- a/packages/js-lib/src/core/DriveData/Upload/DriveFileUploadProvider.ts
+++ b/packages/js-lib/src/core/DriveData/Upload/DriveFileUploadProvider.ts
@@ -36,7 +36,10 @@ export const uploadFile = async (
   thumbnails?: ThumbnailFile[],
   encrypt = true,
   onVersionConflict?: () => Promise<void | UploadResult> | void,
-  axiosConfig?: AxiosRequestConfig
+  options?: {
+    axiosConfig?: AxiosRequestConfig;
+    keyHeader?: KeyHeader | undefined;
+  }
 ): Promise<UploadResult | void> => {
   isDebug &&
     console.debug('request', new URL(`${dotYouClient.getEndpoint()}/drive/files/upload`).pathname, {
@@ -47,9 +50,9 @@ export const uploadFile = async (
     });
 
   // Force isEncrypted on the metadata to match the encrypt flag
-  metadata.isEncrypted = encrypt;
+  metadata.isEncrypted = encrypt || !!options?.keyHeader;
 
-  const keyHeader = encrypt ? GenerateKeyHeader() : undefined;
+  const keyHeader = encrypt ? options?.keyHeader || GenerateKeyHeader() : undefined;
 
   const { systemFileType, ...strippedInstructions } = instructions;
 
@@ -83,7 +86,7 @@ export const uploadFile = async (
     data,
     systemFileType,
     onVersionConflict,
-    axiosConfig
+    options?.axiosConfig
   );
 
   if (!uploadResult) return;
@@ -266,6 +269,8 @@ export const reUploadFile = async (
     thumbnails,
     encrypt,
     undefined,
-    axiosConfig
+    {
+      axiosConfig,
+    }
   );
 };
diff --git a/packages/js-lib/src/core/DriveData/Upload/UploadHelpers.ts b/packages/js-lib/src/core/DriveData/Upload/UploadHelpers.ts
index 55c6013b1..e24bec466 100644
--- a/packages/js-lib/src/core/DriveData/Upload/UploadHelpers.ts
+++ b/packages/js-lib/src/core/DriveData/Upload/UploadHelpers.ts
@@ -119,14 +119,15 @@ export const buildFormData = async (
   if (payloads) {
     for (let i = 0; i < payloads.length; i++) {
       const payload = payloads[i];
-      const encryptedPayload = keyHeader
-        ? await encryptWithKeyheader(payload.payload, {
-            ...keyHeader,
-            iv:
-              manifest?.PayloadDescriptors?.find((p) => p.payloadKey === payload.key)?.iv ||
-              keyHeader.iv,
-          })
-        : payload.payload;
+      const encryptedPayload =
+        keyHeader && !payload.skipEncryption
+          ? await encryptWithKeyheader(payload.payload, {
+              ...keyHeader,
+              iv:
+                manifest?.PayloadDescriptors?.find((p) => p.payloadKey === payload.key)?.iv ||
+                keyHeader.iv,
+            })
+          : payload.payload;
 
       data.append('payload', encryptedPayload, payload.key);
     }