diff --git a/web/apps/photos/src/utils/upload/index.ts b/web/apps/photos/src/utils/upload/index.ts
index ca4f5fb22..49f39a676 100644
--- a/web/apps/photos/src/utils/upload/index.ts
+++ b/web/apps/photos/src/utils/upload/index.ts
@@ -1,4 +1,4 @@
-import { directoryNameFromPOSIXPath, fileNameFromPOSIXPath } from "@/next/file";
+import { basename, dirname } from "@/next/file";
 import { FILE_TYPE } from "constants/file";
 import {
     A_SEC_IN_MICROSECONDS,
@@ -118,7 +118,7 @@ export function areFileWithCollectionsSame(
  * Empty list of paths is considered to be in the same directory.
  */
 export const areAllInSameDirectory = (paths: string[]) =>
-    new Set(paths.map(directoryNameFromPOSIXPath)).size == 1;
+    new Set(paths.map(dirname)).size == 1;
 
 export function getImportSuggestion(
     uploadType: PICKED_UPLOAD_TYPE,
@@ -225,5 +225,4 @@ export function isSystemFile(file: File | ElectronFile) {
  *
  * Hidden files are those whose names begin with a "." (dot).
  */
-export const isHiddenFile = (path: string) =>
-    fileNameFromPOSIXPath(path).startsWith(".");
+export const isHiddenFile = (path: string) => basename(path).startsWith(".");
diff --git a/web/packages/next/file.ts b/web/packages/next/file.ts
index dc0bf6108..83b20f2ec 100644
--- a/web/packages/next/file.ts
+++ b/web/packages/next/file.ts
@@ -34,19 +34,35 @@ export const fileNameFromComponents = (components: FileNameComponents) =>
     components.filter((x) => !!x).join(".");
 
 /**
- * Extract the fileName from the given path.
+ * Return the file name portion from the given {@link path}.
+ *
+ * This tries to emulate the UNIX `basename` command. In particular, any
+ * trailing slashes on the path are trimmed, so this function can be used to get
+ * the name of the directory too.
+ *
+ * The path is assumed to use POSIX separators ("/").
  */
-export const fileNameFromPOSIXPath = (path: string) => {
+export const basename = (path: string) => {
     const pathComponents = path.split("/");
-    return pathComponents[pathComponents.length - 1] ?? path;
+    for (let i = pathComponents.length - 1; i >= 0; i--)
+        if (pathComponents[i] !== "") return pathComponents[i];
+    return path;
 };
 
 /**
- * Extract the directory path (leading up to the item) from the given path.
+ * Return the directory portion from the given {@link path}.
+ *
+ * This tries to emulate the UNIX `dirname` command. In particular, any trailing
+ * slashes on the path are trimmed, so this function can be used to get the path
+ * leading up to a directory too.
+ *
+ * The path is assumed to use POSIX separators ("/").
  */
-export const directoryNameFromPOSIXPath = (path: string) => {
+export const dirname = (path: string) => {
     const pathComponents = path.split("/");
-    pathComponents.pop();
+    while (pathComponents.pop() == "") {
+        /* no-op */
+    }
     return pathComponents.join("/");
 };