diff --git a/desktop/src/main/ipc.ts b/desktop/src/main/ipc.ts
index 97d7b36569..fc70be1a92 100644
--- a/desktop/src/main/ipc.ts
+++ b/desktop/src/main/ipc.ts
@@ -56,8 +56,8 @@ import {
 import {
     clearPendingUploads,
     listZipItems,
-    markUploadedFiles,
-    markUploadedZipItems,
+    markUploadedFile,
+    markUploadedZipItem,
     pathOrZipItemSize,
     pendingUploads,
     setPendingUploads,
@@ -211,13 +211,15 @@ export const attachIPCHandlers = () => {
     );
 
     ipcMain.handle(
-        "markUploadedFiles",
-        (_, paths: PendingUploads["filePaths"]) => markUploadedFiles(paths),
+        "markUploadedFile",
+        (_, path: string, associatedPath: string | undefined) =>
+            markUploadedFile(path, associatedPath),
     );
 
     ipcMain.handle(
-        "markUploadedZipItems",
-        (_, items: PendingUploads["zipItems"]) => markUploadedZipItems(items),
+        "markUploadedZipItem",
+        (_, item: ZipItem, associatedItem: ZipItem | undefined) =>
+            markUploadedZipItem(item, associatedItem),
     );
 
     ipcMain.handle("clearPendingUploads", () => clearPendingUploads());
diff --git a/desktop/src/main/services/upload.ts b/desktop/src/main/services/upload.ts
index 4c20529da4..7786deb45d 100644
--- a/desktop/src/main/services/upload.ts
+++ b/desktop/src/main/services/upload.ts
@@ -135,22 +135,34 @@ export const setPendingUploads = ({
     });
 };
 
-export const markUploadedFiles = (paths: string[]) => {
+export const markUploadedFile = (
+    path: string,
+    associatedPath: string | undefined,
+) => {
     const existing = uploadStatusStore.get("filePaths") ?? [];
-    const updated = existing.filter((p) => !paths.includes(p));
+    const updated = existing.filter((p) => p != path && p != associatedPath);
     uploadStatusStore.set("filePaths", updated);
+    return fs.stat(path).then((st) => st.mtime.getTime());
 };
 
-export const markUploadedZipItems = (
-    items: [zipPath: string, entryName: string][],
+export const markUploadedZipItem = (
+    item: ZipItem,
+    associatedItem: ZipItem | undefined,
 ) => {
     const existing = uploadStatusStore.get("zipItems") ?? [];
-    const updated = existing.filter(
-        (z) => !items.some((e) => z[0] == e[0] && z[1] == e[1]),
+    const updated = exceptZipItem(
+        exceptZipItem(existing, item),
+        associatedItem,
     );
     uploadStatusStore.set("zipItems", updated);
+    return fs.stat(item[0]).then((st) => st.mtime.getTime());
 };
 
+const exceptZipItem = (items: ZipItem[], item: ZipItem | undefined) =>
+    item
+        ? items.filter((zi) => !(zi[0] == item[0] && zi[1] == item[1]))
+        : items;
+
 export const clearPendingUploads = () => {
     uploadStatusStore.clear();
     clearOpenZipCache();
diff --git a/desktop/src/preload.ts b/desktop/src/preload.ts
index 0c96d61b30..2199535457 100644
--- a/desktop/src/preload.ts
+++ b/desktop/src/preload.ts
@@ -290,11 +290,13 @@ const pendingUploads = () => ipcRenderer.invoke("pendingUploads");
 const setPendingUploads = (pendingUploads: PendingUploads) =>
     ipcRenderer.invoke("setPendingUploads", pendingUploads);
 
-const markUploadedFiles = (paths: PendingUploads["filePaths"]) =>
-    ipcRenderer.invoke("markUploadedFiles", paths);
+const markUploadedFile = (path: string, associatedPath: string | undefined) =>
+    ipcRenderer.invoke("markUploadedFile", path, associatedPath);
 
-const markUploadedZipItems = (items: PendingUploads["zipItems"]) =>
-    ipcRenderer.invoke("markUploadedZipItems", items);
+const markUploadedZipItem = (
+    item: ZipItem,
+    associatedItem: ZipItem | undefined,
+) => ipcRenderer.invoke("markUploadedZipItem", item, associatedItem);
 
 const clearPendingUploads = () => ipcRenderer.invoke("clearPendingUploads");
 
@@ -411,7 +413,7 @@ contextBridge.exposeInMainWorld("electron", {
     pathOrZipItemSize,
     pendingUploads,
     setPendingUploads,
-    markUploadedFiles,
-    markUploadedZipItems,
+    markUploadedFile,
+    markUploadedZipItem,
     clearPendingUploads,
 });