diff --git a/packages/core/data-transfer/src/file/providers/source/index.ts b/packages/core/data-transfer/src/file/providers/source/index.ts
index e3af20e3b2..119d527aee 100644
--- a/packages/core/data-transfer/src/file/providers/source/index.ts
+++ b/packages/core/data-transfer/src/file/providers/source/index.ts
@@ -15,7 +15,7 @@ import type { IAsset, IMetadata, ISourceProvider, ProviderType } from '../../../
 import { createDecryptionCipher } from '../../../utils/encryption';
 import { collect } from '../../../utils/stream';
 import { ProviderInitializationError, ProviderTransferError } from '../../../errors/providers';
-import { isDirPathEquivalent, isPathEquivalent } from './utils';
+import { isDirPathEquivalent, isPathEquivalent, unknownPathToPosix } from './utils';
 
 type StreamItemArray = Parameters<typeof chain>[0];
 
@@ -143,16 +143,17 @@ class LocalFileSourceProvider implements ISourceProvider {
             if (entry.type !== 'File') {
               return false;
             }
-            console.log(`${filePath} is assets?`, isDirPathEquivalent('assets/uploads', filePath));
             return isDirPathEquivalent('assets/uploads', filePath);
           },
           onentry(entry) {
             // TODO: Check if we need to handle win32 paths here for the assets
             const { path: filePath, size = 0 } = entry;
-            const file = path.basename(filePath);
+            const normalizedPath = unknownPathToPosix(filePath);
+            const file = path.basename(normalizedPath);
+
             const asset: IAsset = {
               filename: file,
-              filepath: filePath,
+              filepath: normalizedPath,
               stats: { size },
               stream: entry as unknown as Readable,
             };
diff --git a/packages/core/data-transfer/src/file/providers/source/utils.ts b/packages/core/data-transfer/src/file/providers/source/utils.ts
index d4470ad66f..e1d25aed0c 100644
--- a/packages/core/data-transfer/src/file/providers/source/utils.ts
+++ b/packages/core/data-transfer/src/file/providers/source/utils.ts
@@ -14,16 +14,30 @@ import path from 'path';
 
 // Check if the directory of a given filePath (which can be either posix or win32) resolves to the same as the given posix-format path posixDirName
 export const isDirPathEquivalent = (posixDirName: string, filePath: string) => {
-  // if win32 convert to posix, then get dirname
-  const normalizedDir = path.posix.dirname(filePath.split(path.win32.sep).join(path.posix.sep));
+  const normalizedDir = path.posix.dirname(unknownPathToPosix(filePath));
   return isPathEquivalent(posixDirName, normalizedDir);
 };
 
 // Check if two paths that can be either in posix or win32 format resolves to the same file
 export const isPathEquivalent = (fileA: string, fileB: string) => {
   // Check if paths appear to be win32 or posix, and if win32 convert to posix
-  const normalizedPathA = fileA.split(path.win32.sep).join(path.posix.sep);
-  const normalizedPathB = fileB.split(path.win32.sep).join(path.posix.sep);
+  const normalizedPathA = unknownPathToPosix(fileA);
+  const normalizedPathB = unknownPathToPosix(fileB);
 
   return !path.posix.relative(normalizedPathB, normalizedPathA).length;
 };
+
+/**
+ *
+ * @param {string} filePath a path that may be either win32 or posix
+ *
+ * @returns {string} a posix path
+ */
+export const unknownPathToPosix = (filePath: string) => {
+  // if it includes a forward slash, it must be posix already -- we will not support win32 with mixed path separators
+  if (filePath.includes(path.posix.sep)) {
+    return filePath;
+  }
+
+  return path.normalize(filePath).split(path.win32.sep).join(path.posix.sep);
+};