diff --git a/web/apps/photos/src/components/WatchFolder.tsx b/web/apps/photos/src/components/WatchFolder.tsx
index a12bb2e49..5715dfb45 100644
--- a/web/apps/photos/src/components/WatchFolder.tsx
+++ b/web/apps/photos/src/components/WatchFolder.tsx
@@ -27,12 +27,11 @@ import {
 } from "@mui/material";
 import { styled } from "@mui/material/styles";
 import { CollectionMappingChoiceModal } from "components/Upload/CollectionMappingChoiceModal";
-import { PICKED_UPLOAD_TYPE } from "constants/upload";
 import { t } from "i18next";
 import { AppContext } from "pages/_app";
 import React, { useContext, useEffect, useState } from "react";
 import watcher from "services/watch";
-import { getImportSuggestion } from "utils/upload";
+import { areAllInSameDirectory } from "utils/upload";
 
 interface WatchFolderProps {
     open: boolean;
@@ -84,15 +83,11 @@ export const WatchFolder: React.FC<WatchFolderProps> = ({ open, onClose }) => {
 
     const selectCollectionMappingAndAddWatch = async (path: string) => {
         const filePaths = await ensureElectron().watch.findFiles(path);
-        const { hasNestedFolders } = getImportSuggestion(
-            PICKED_UPLOAD_TYPE.FOLDERS,
-            filePaths,
-        );
-        if (hasNestedFolders) {
+        if (areAllInSameDirectory(filePaths)) {
+            addWatch(path, "root");
+        } else {
             setSavedFolderPath(path);
             setChoiceModalOpen(true);
-        } else {
-            addWatch(path, "root");
         }
     };
 
diff --git a/web/apps/photos/src/utils/upload/index.ts b/web/apps/photos/src/utils/upload/index.ts
index 935400352..0f3ceb684 100644
--- a/web/apps/photos/src/utils/upload/index.ts
+++ b/web/apps/photos/src/utils/upload/index.ts
@@ -1,3 +1,4 @@
+import { directoryNameFromPOSIXPath } from "@/next/file";
 import { FILE_TYPE } from "constants/file";
 import {
     A_SEC_IN_MICROSECONDS,
@@ -113,46 +114,11 @@ export function areFileWithCollectionsSame(
 /**
  * Return true if all the paths in the given list are items that belong to the
  * same (arbitrary) directory.
+ *
+ * Empty list of paths is considered to be in the same directory.
  */
-export const areInSameDirectory = (
-    uploadType: PICKED_UPLOAD_TYPE,
-    toUploadFiles: File[] | ElectronFile[],
-): ImportSuggestion {
-    if (isElectron() && uploadType === PICKED_UPLOAD_TYPE.FILES) {
-        return DEFAULT_IMPORT_SUGGESTION;
-    }
-
-    const paths: string[] = toUploadFiles.map((file) => file["path"]);
-    const getCharCount = (str: string) => (str.match(/\//g) ?? []).length;
-    paths.sort((path1, path2) => getCharCount(path1) - getCharCount(path2));
-    const firstPath = paths[0];
-    const lastPath = paths[paths.length - 1];
-
-    const L = firstPath.length;
-    let i = 0;
-    const firstFileFolder = firstPath.substring(0, firstPath.lastIndexOf("/"));
-    const lastFileFolder = lastPath.substring(0, lastPath.lastIndexOf("/"));
-
-    while (i < L && firstPath.charAt(i) === lastPath.charAt(i)) i++;
-    let commonPathPrefix = firstPath.substring(0, i);
-
-    if (commonPathPrefix) {
-        commonPathPrefix = commonPathPrefix.substring(
-            0,
-            commonPathPrefix.lastIndexOf("/"),
-        );
-        if (commonPathPrefix) {
-            commonPathPrefix = commonPathPrefix.substring(
-                commonPathPrefix.lastIndexOf("/") + 1,
-            );
-        }
-    }
-    return {
-        rootFolderName: commonPathPrefix || null,
-        hasNestedFolders: firstFileFolder !== lastFileFolder,
-        hasRootLevelFileWithFolder: firstFileFolder === "",
-    };
-}
+export const areAllInSameDirectory = (paths: string[]) =>
+    new Set(paths.map(directoryNameFromPOSIXPath)).size == 1;
 
 export function getImportSuggestion(
     uploadType: PICKED_UPLOAD_TYPE,