diff --git a/packages/core/data-transfer/src/file/providers/source/__tests__/index.test.ts b/packages/core/data-transfer/src/file/providers/source/__tests__/index.test.ts
index 7de7b2f551..edcd1c8f72 100644
--- a/packages/core/data-transfer/src/file/providers/source/__tests__/index.test.ts
+++ b/packages/core/data-transfer/src/file/providers/source/__tests__/index.test.ts
@@ -2,9 +2,10 @@ import { Readable } from 'stream';
 import type { ILocalFileSourceProviderOptions } from '..';
 
 import { createLocalFileSourceProvider } from '..';
+import { isFilePathInDirname, isPathEquivalent, unknownPathToPosix } from '../utils';
 
-describe('Stream assets', () => {
-  test('returns a stream', () => {
+describe('File source provider', () => {
+  test('returns assets stream', () => {
     const options: ILocalFileSourceProviderOptions = {
       file: {
         path: './test-file',
@@ -21,4 +22,108 @@ describe('Stream assets', () => {
 
     expect(stream instanceof Readable).toBeTruthy();
   });
+
+  describe('utils', () => {
+    const unknownConversionCases = [
+      ['some/path/on/posix', 'some/path/on/posix'],
+      ['some/path/on/posix/', 'some/path/on/posix/'],
+      ['some/path/on/posix.jpg', 'some/path/on/posix.jpg'],
+      ['file.jpg', 'file.jpg'],
+      ['noextension', 'noextension'],
+      ['some\\windows\\filename.jpg', 'some/windows/filename.jpg'],
+      ['some\\windows\\noendingslash', 'some/windows/noendingslash'],
+      ['some\\windows\\endingslash\\', 'some/windows/endingslash/'],
+    ];
+    test.each(unknownConversionCases)('unknownPathToPosix: %p -> %p', (input, expected) => {
+      expect(unknownPathToPosix(input)).toEqual(expected);
+    });
+
+    const isFilePathInDirnameCases: [string, string, boolean][] = [
+      // posix paths
+      ['some/path/on/posix', 'some/path/on/posix/file.jpg', true],
+      ['some/path/on/posix/', 'some/path/on/posix/file.jpg', true],
+      ['./some/path/on/posix', 'some/path/on/posix/file.jpg', true],
+      ['some/path/on/posix/', './some/path/on/posix/file.jpg', true],
+      ['some/path/on/posix/', 'some/path/on/posix/', false], // invalid; second method should include a filename
+      ['some/path/on/posix', 'some/path/on/posix', false], // 'posix' in second case should be interpreted as a filename
+      ['', 'file.jpg', true],
+      ['', './file.jpg', true],
+      ['./', './file.jpg', true],
+      ['noextension', 'noextension', false], // second case is a file
+      ['noextension', './noextension/file.jpg', true],
+      ['./noextension', './noextension/file.jpg', true],
+      ['./noextension', 'noextension/file.jpg', true],
+      ['noextension', 'noextension/noextension', true],
+      // win32 paths
+      ['some/path/on/win32', 'some\\path\\on\\win32\\file.jpg', true],
+      ['some/path/on/win32/', 'some\\path\\on\\win32\\file.jpg', true],
+      ['some/path/on/win32/', 'some\\path\\on\\win32\\', false], // invalid; second method should include a filename
+      ['some/path/on/win32', 'some\\path\\on\\win32', false], // 'win32' in second case should be interpreted as a filename
+      ['', 'file.jpg', true],
+      ['', '.\\file.jpg', true],
+      ['./', '.\\file.jpg', true],
+      ['noextension', 'noextension', false], // second case is a file
+      ['noextension', '.\\noextension\\file.jpg', true],
+      ['./noextension', '.\\noextension\\file.jpg', true],
+      ['./noextension', 'noextension\\file.jpg', true],
+      ['noextension', 'noextension\\noextension', true],
+    ];
+    test.each(isFilePathInDirnameCases)(
+      'isFilePathInDirname: %p : %p -> %p',
+      (inputA, inputB, expected) => {
+        expect(isFilePathInDirname(inputA, inputB)).toEqual(expected);
+      }
+    );
+
+    const isPathEquivalentCases: [string, string, boolean][] = [
+      // POSITIVES
+      // root level
+      ['file.jpg', 'file.jpg', true],
+      ['file.jpg', '.\\file.jpg', true],
+      ['file.jpg', './file.jpg', true],
+      // cwd root level (posix)
+      ['./file.jpg', 'file.jpg', true],
+      ['./file.jpg', './file.jpg', true],
+      ['./file.jpg', '.\\file.jpg', true],
+      // cwd root level (win32)
+      ['.\\file.jpg', 'file.jpg', true],
+      ['.\\file.jpg', './file.jpg', true],
+      ['.\\file.jpg', '.\\file.jpg', true],
+      // directory with file (posix)
+      ['one/two/file.jpg', 'one/two/file.jpg', true],
+      ['one/two/file.jpg', './one/two/file.jpg', true],
+      ['one/two/file.jpg', 'one\\two\\file.jpg', true],
+      ['one/two/file.jpg', '.\\one\\two\\file.jpg', true],
+      // cwd with file (posix)
+      ['./one/two/file.jpg', 'one/two/file.jpg', true],
+      ['./one/two/file.jpg', './one/two/file.jpg', true],
+      ['./one/two/file.jpg', 'one\\two\\file.jpg', true],
+      ['./one/two/file.jpg', '.\\one\\two\\file.jpg', true],
+      // directory with file (win32)
+      ['one\\two\\file.jpg', 'one/two/file.jpg', true],
+      ['one\\two\\file.jpg', './one/two/file.jpg', true],
+      ['one\\two\\file.jpg', '.\\one\\two\\file.jpg', true],
+      ['one\\two\\file.jpg', 'one\\two\\file.jpg', true],
+      // cwd with file (win32)
+      ['.\\one\\two\\file.jpg', 'one/two/file.jpg', true],
+      ['.\\one\\two\\file.jpg', './one/two/file.jpg', true],
+      ['.\\one\\two\\file.jpg', '.\\one\\two\\file.jpg', true],
+      ['.\\one\\two\\file.jpg', 'one\\two\\file.jpg', true],
+
+      // NEGATIVES
+      ['file.jpg', 'one/file.jpg', false],
+      ['file.jpg', 'one\\file.jpg', false],
+      ['file.jpg', '/file.jpg', false],
+      ['file.jpg', '\\file.jpg', false],
+      ['one/file.jpg', '\\one\\file.jpg', false],
+      ['one/file.jpg', '/one/file.jpg', false],
+      ['one/file.jpg', 'file.jpg', false],
+    ];
+    test.each(isPathEquivalentCases)(
+      'isPathEquivalent: %p : %p -> %p',
+      (inputA, inputB, expected) => {
+        expect(isPathEquivalent(inputA, inputB)).toEqual(expected);
+      }
+    );
+  });
 });
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 119d527aee..53e5f746bb 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, unknownPathToPosix } from './utils';
+import { isFilePathInDirname, isPathEquivalent, unknownPathToPosix } from './utils';
 
 type StreamItemArray = Parameters<typeof chain>[0];
 
@@ -143,7 +143,7 @@ class LocalFileSourceProvider implements ISourceProvider {
             if (entry.type !== 'File') {
               return false;
             }
-            return isDirPathEquivalent('assets/uploads', filePath);
+            return isFilePathInDirname('assets/uploads', filePath);
           },
           onentry(entry) {
             // TODO: Check if we need to handle win32 paths here for the assets
@@ -203,7 +203,7 @@ class LocalFileSourceProvider implements ISourceProvider {
               return false;
             }
 
-            return isDirPathEquivalent(directory, filePath);
+            return isFilePathInDirname(directory, filePath);
           },
 
           async onentry(entry) {
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 ced1cf0f7d..60111f5da3 100644
--- a/packages/core/data-transfer/src/file/providers/source/utils.ts
+++ b/packages/core/data-transfer/src/file/providers/source/utils.ts
@@ -12,23 +12,37 @@ 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
-// We must be able to assume the first argument is a path, otherwise path.dirname will interpret a path without any slashes as the filename
-export const isDirPathEquivalent = (posixDirName: string, filePath: string) => {
+/**
+ * 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
+ * We must be able to assume the first argument is a path to a directory and the second is a path to a file, otherwise path.dirname will interpret a path without any slashes as the filename
+ *
+ * @param {string} posixDirName A posix path pointing to a directory
+ * @param {string} filePath an unknown filesystem path pointing to a file
+ * @returns {boolean} is the file located in the given directory
+ */
+export const isFilePathInDirname = (posixDirName: string, filePath: string) => {
   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 two paths that can be either in posix or win32 format resolves to the same file
+ *
+ * @param {string} pathA a path that may be either win32 or posix
+ * @param {string} pathB a path that may be either win32 or posix
+ *
+ * @returns {boolean} do paths point to the same place
+ */
+export const isPathEquivalent = (pathA: string, pathB: string) => {
   // Check if paths appear to be win32 or posix, and if win32 convert to posix
-  const normalizedPathA = unknownPathToPosix(fileA);
-  const normalizedPathB = unknownPathToPosix(fileB);
+  const normalizedPathA = path.posix.normalize(unknownPathToPosix(pathA));
+  const normalizedPathB = path.posix.normalize(unknownPathToPosix(pathB));
 
   return !path.posix.relative(normalizedPathB, normalizedPathA).length;
 };
 
 /**
+ *  Convert an unknown format path (win32 or posix) to a posix path
  *
  * @param {string} filePath a path that may be either win32 or posix
  *