diff --git a/web/apps/photos/src/utils/upload/index.ts b/web/apps/photos/src/utils/upload/index.ts
index 21531bd38..935400352 100644
--- a/web/apps/photos/src/utils/upload/index.ts
+++ b/web/apps/photos/src/utils/upload/index.ts
@@ -110,14 +110,59 @@ export function areFileWithCollectionsSame(
     return firstFile.localID === secondFile.localID;
 }
 
-export function getImportSuggestion(
+/**
+ * Return true if all the paths in the given list are items that belong to the
+ * same (arbitrary) directory.
+ */
+export const areInSameDirectory = (
     uploadType: PICKED_UPLOAD_TYPE,
-    paths: string[],
+    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 function getImportSuggestion(
+    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];
diff --git a/web/packages/next/file.ts b/web/packages/next/file.ts
index fae9a6d00..b213283b4 100644
--- a/web/packages/next/file.ts
+++ b/web/packages/next/file.ts
@@ -29,6 +29,23 @@ export const nameAndExtension = (fileName: string): FileNameComponents => {
 export const fileNameFromComponents = (components: FileNameComponents) =>
     components.filter((x) => !!x).join(".");
 
+/**
+ * Extract the fileName from the given path.
+ */
+export const fileNameFromPOSIXPath = (path: string) => {
+    const pathComponents = path.split("/");
+    return pathComponents[pathComponents.length - 1] ?? path;
+};
+
+/**
+ * Extract the directory path (leading up to the item) from the given path.
+ */
+export const directoryNameFromPOSIXPath = (path: string) => {
+    const pathComponents = path.split("/");
+    pathComponents.pop();
+    return pathComponents.join("/");
+};
+
 export function getFileNameSize(file: File | ElectronFile) {
     return `${file.name}_${convertBytesToHumanReadable(file.size)}`;
 }