diff --git a/web/apps/photos/src/services/ffmpeg.ts b/web/apps/photos/src/services/ffmpeg.ts
index dbdc53a3c..4dfdb3f64 100644
--- a/web/apps/photos/src/services/ffmpeg.ts
+++ b/web/apps/photos/src/services/ffmpeg.ts
@@ -10,7 +10,11 @@ import {
 import { NULL_LOCATION } from "constants/upload";
 import type { ParsedExtractedMetadata } from "types/metadata";
 import type { DedicatedFFmpegWorker } from "worker/ffmpeg.worker";
-import type { UploadItem } from "./upload/types";
+import {
+    toDataOrPathOrZipEntry,
+    type DesktopUploadItem,
+    type UploadItem,
+} from "./upload/types";
 
 /**
  * Generate a thumbnail for the given video using a wasm FFmpeg running in a web
@@ -59,12 +63,12 @@ const _generateVideoThumbnail = async (
  */
 export const generateVideoThumbnailNative = async (
     electron: Electron,
-    dataOrPath: Uint8Array | string,
+    desktopUploadItem: DesktopUploadItem,
 ) =>
     _generateVideoThumbnail((seekTime: number) =>
         electron.ffmpegExec(
             makeGenThumbnailCommand(seekTime),
-            dataOrPath,
+            toDataOrPathOrZipEntry(desktopUploadItem),
             "jpeg",
             0,
         ),
@@ -104,21 +108,16 @@ export const extractVideoMetadata = async (
     const outputData =
         uploadItem instanceof File
             ? await ffmpegExecWeb(command, uploadItem, "txt", 0)
-            : await electron.ffmpegExec(command, forE(uploadItem), "txt", 0);
+            : await electron.ffmpegExec(
+                  command,
+                  toDataOrPathOrZipEntry(uploadItem),
+                  "txt",
+                  0,
+              );
 
     return parseFFmpegExtractedMetadata(outputData);
 };
 
-/**
- * For each of cases of {@link UploadItem} that apply when we're running in the
- * context of our desktop app, return a value that can be passed to
- * {@link Electron}'s {@link ffmpegExec} over IPC.
- */
-const forE = (desktopUploadItem: Exclude<UploadItem, File>) =>
-    typeof desktopUploadItem == "string" || Array.isArray(desktopUploadItem)
-        ? desktopUploadItem
-        : desktopUploadItem.path;
-
 // Options:
 //
 // - `-c [short for codex] copy`
diff --git a/web/apps/photos/src/services/upload/thumbnail.ts b/web/apps/photos/src/services/upload/thumbnail.ts
index 9cd9a339c..1dd448376 100644
--- a/web/apps/photos/src/services/upload/thumbnail.ts
+++ b/web/apps/photos/src/services/upload/thumbnail.ts
@@ -4,6 +4,7 @@ import { type Electron } from "@/next/types/ipc";
 import { withTimeout } from "@ente/shared/utils";
 import * as ffmpeg from "services/ffmpeg";
 import { heicToJPEG } from "services/heic-convert";
+import { toDataOrPathOrZipEntry, type DesktopUploadItem } from "./types";
 
 /** Maximum width or height of the generated thumbnail */
 const maxThumbnailDimension = 720;
@@ -189,16 +190,16 @@ const percentageSizeDiff = (
  */
 export const generateThumbnailNative = async (
     electron: Electron,
-    dataOrPath: Uint8Array | string,
+    desktopUploadItem: DesktopUploadItem,
     fileTypeInfo: FileTypeInfo,
 ): Promise<Uint8Array> =>
     fileTypeInfo.fileType === FILE_TYPE.IMAGE
         ? await electron.generateImageThumbnail(
-              dataOrPath,
+              toDataOrPathOrZipEntry(desktopUploadItem),
               maxThumbnailDimension,
               maxThumbnailSize,
           )
-        : ffmpeg.generateVideoThumbnailNative(electron, dataOrPath);
+        : ffmpeg.generateVideoThumbnailNative(electron, desktopUploadItem);
 
 /**
  * A fallback, black, thumbnail for use in cases where thumbnail generation
diff --git a/web/apps/photos/src/services/upload/types.ts b/web/apps/photos/src/services/upload/types.ts
index 25a79de1a..05ad332d4 100644
--- a/web/apps/photos/src/services/upload/types.ts
+++ b/web/apps/photos/src/services/upload/types.ts
@@ -29,3 +29,19 @@ import type { ZipItem } from "@/next/types/ipc";
  * Also see: [Note: Reading a UploadItem].
  */
 export type UploadItem = File | FileAndPath | string | ZipItem;
+
+/**
+ * The of cases of {@link UploadItem} that apply when we're running in the
+ * context of our desktop app.
+ */
+export type DesktopUploadItem = Exclude<UploadItem, File>;
+
+/**
+ * For each of cases of {@link UploadItem} that apply when we're running in the
+ * context of our desktop app, return a value that can be passed to
+ * {@link Electron} functions over IPC.
+ */
+export const toDataOrPathOrZipEntry = (desktopUploadItem: DesktopUploadItem) =>
+    typeof desktopUploadItem == "string" || Array.isArray(desktopUploadItem)
+        ? desktopUploadItem
+        : desktopUploadItem.path;
diff --git a/web/apps/photos/src/services/upload/uploadService.ts b/web/apps/photos/src/services/upload/uploadService.ts
index 8c042ccaf..6dc1bbd49 100644
--- a/web/apps/photos/src/services/upload/uploadService.ts
+++ b/web/apps/photos/src/services/upload/uploadService.ts
@@ -1012,14 +1012,12 @@ const withThumbnail = async (
         fileTypeInfo.fileType == FILE_TYPE.IMAGE &&
         moduleState.isNativeImageThumbnailGenerationNotAvailable;
 
-    // 1. Native thumbnail generation using file's path.
-    if (electron && !notAvailable) {
+    // 1. Native thumbnail generation using items's (effective) path.
+    if (electron && !notAvailable && !(uploadItem instanceof File)) {
         try {
-            // When running in the context of our desktop app, File paths will
-            // be absolute. See: [Note: File paths when running under Electron].
             thumbnail = await generateThumbnailNative(
                 electron,
-                uploadItem instanceof File ? uploadItem["path"] : uploadItem,
+                uploadItem,
                 fileTypeInfo,
             );
         } catch (e) {
@@ -1051,12 +1049,14 @@ const withThumbnail = async (
             // The fallback in this case involves reading the entire stream into
             // memory, and passing that data across the IPC boundary in a single
             // go (i.e. not in a streaming manner). This is risky for videos of
-            // unbounded sizes, plus that isn't the expected scenario. So
-            // instead of trying to cater for arbitrary exceptions, we only run
-            // this fallback to cover for the case where thumbnail generation
-            // was not available for an image file on Windows. If/when we add
-            // support of native thumbnailing on Windows too, this entire branch
-            // can be removed.
+            // unbounded sizes, plus we shouldn't even be getting here unless
+            // something went wrong.
+            //
+            // So instead of trying to cater for arbitrary exceptions, we only
+            // run this fallback to cover for the case where thumbnail
+            // generation was not available for an image file on Windows.
+            // If/when we add support of native thumbnailing on Windows too,
+            // this entire branch can be removed.
 
             if (fileTypeInfo.fileType == FILE_TYPE.IMAGE) {
                 const data = await readEntireStream(fileStream.stream);