diff --git a/packages/client/src/jobs/file-download.ts b/packages/client/src/jobs/file-download.ts
index 16876a9b..1568910b 100644
--- a/packages/client/src/jobs/file-download.ts
+++ b/packages/client/src/jobs/file-download.ts
@@ -54,13 +54,6 @@ export class FileDownloadJobHandler implements JobHandler<FileDownloadInput> {
       };
     }
 
-    if (!account.server.isAvailable) {
-      return {
-        type: 'retry',
-        delay: ms('5 seconds'),
-      };
-    }
-
     const workspace = account.getWorkspace(input.workspaceId);
     if (!workspace) {
       return {
@@ -77,7 +70,12 @@ export class FileDownloadJobHandler implements JobHandler<FileDownloadInput> {
 
     const file = await this.fetchNode(workspace, download.file_id);
     if (!file) {
-      await this.deleteDownload(workspace, download.id);
+      await this.updateDownload(workspace, download.id, {
+        status: DownloadStatus.Failed,
+        error_code: 'file_deleted',
+        error_message: 'File has been deleted',
+      });
+
       return {
         type: 'cancel',
       };
@@ -90,6 +88,13 @@ export class FileDownloadJobHandler implements JobHandler<FileDownloadInput> {
       };
     }
 
+    if (!account.server.isAvailable) {
+      return {
+        type: 'retry',
+        delay: ms('5 seconds'),
+      };
+    }
+
     return this.performDownload(workspace, download, file);
   }
 
@@ -230,7 +235,7 @@ export class FileDownloadJobHandler implements JobHandler<FileDownloadInput> {
       .selectFrom('nodes')
       .selectAll()
       .where('id', '=', fileId)
-      .executeTakeFirstOrThrow();
+      .executeTakeFirst();
 
     if (!node) {
       return undefined;
@@ -262,14 +267,4 @@ export class FileDownloadJobHandler implements JobHandler<FileDownloadInput> {
       download: mapDownload(updatedDownload),
     });
   }
-
-  private async deleteDownload(
-    workspace: WorkspaceService,
-    downloadId: string
-  ): Promise<void> {
-    await workspace.database
-      .deleteFrom('downloads')
-      .where('id', '=', downloadId)
-      .execute();
-  }
 }
diff --git a/packages/client/src/jobs/file-upload.ts b/packages/client/src/jobs/file-upload.ts
index 8f8a14a2..f7b307a5 100644
--- a/packages/client/src/jobs/file-upload.ts
+++ b/packages/client/src/jobs/file-upload.ts
@@ -62,13 +62,6 @@ export class FileUploadJobHandler implements JobHandler<FileUploadInput> {
       };
     }
 
-    if (!account.server.isAvailable) {
-      return {
-        type: 'retry',
-        delay: ms('2 seconds'),
-      };
-    }
-
     const workspace = account.getWorkspace(input.workspaceId);
     if (!workspace) {
       return {
@@ -86,6 +79,7 @@ export class FileUploadJobHandler implements JobHandler<FileUploadInput> {
     const file = await this.fetchNode(workspace, upload.file_id);
     if (!file) {
       await this.deleteUpload(workspace, upload.file_id);
+
       return {
         type: 'cancel',
       };
@@ -94,11 +88,19 @@ export class FileUploadJobHandler implements JobHandler<FileUploadInput> {
     const localFile = await this.fetchLocalFile(workspace, file.id);
     if (!localFile) {
       await this.deleteUpload(workspace, upload.file_id);
+
       return {
         type: 'cancel',
       };
     }
 
+    if (!account.server.isAvailable) {
+      return {
+        type: 'retry',
+        delay: ms('2 seconds'),
+      };
+    }
+
     if (!isNodeSynced(file)) {
       return {
         type: 'retry',
@@ -363,7 +365,7 @@ export class FileUploadJobHandler implements JobHandler<FileUploadInput> {
       .selectFrom('nodes')
       .selectAll()
       .where('id', '=', fileId)
-      .executeTakeFirstOrThrow();
+      .executeTakeFirst();
 
     if (!node) {
       return undefined;
@@ -380,7 +382,7 @@ export class FileUploadJobHandler implements JobHandler<FileUploadInput> {
       .selectFrom('local_files')
       .selectAll()
       .where('id', '=', fileId)
-      .executeTakeFirstOrThrow();
+      .executeTakeFirst();
   }
 
   private async updateUpload(
@@ -411,9 +413,19 @@ export class FileUploadJobHandler implements JobHandler<FileUploadInput> {
     workspace: WorkspaceService,
     fileId: string
   ): Promise<void> {
-    await workspace.database
+    const deletedUpload = await workspace.database
       .deleteFrom('uploads')
       .where('file_id', '=', fileId)
-      .execute();
+      .returningAll()
+      .executeTakeFirst();
+
+    if (deletedUpload) {
+      eventBus.publish({
+        type: 'upload.deleted',
+        accountId: workspace.accountId,
+        workspaceId: workspace.id,
+        upload: mapUpload(deletedUpload),
+      });
+    }
   }
 }
diff --git a/packages/client/src/services/workspaces/node-service.ts b/packages/client/src/services/workspaces/node-service.ts
index 2ac96ab3..adf46ab1 100644
--- a/packages/client/src/services/workspaces/node-service.ts
+++ b/packages/client/src/services/workspaces/node-service.ts
@@ -4,13 +4,19 @@ import {
   SelectNodeReference,
 } from '@colanode/client/databases/workspace';
 import { eventBus } from '@colanode/client/lib/event-bus';
-import { mapNode, mapNodeReference } from '@colanode/client/lib/mappers';
+import {
+  mapDownload,
+  mapNode,
+  mapNodeReference,
+  mapUpload,
+} from '@colanode/client/lib/mappers';
 import {
   applyMentionUpdates,
   checkMentionChanges,
 } from '@colanode/client/lib/mentions';
 import { deleteNodeRelations, fetchNodeTree } from '@colanode/client/lib/utils';
 import { WorkspaceService } from '@colanode/client/services/workspaces/workspace-service';
+import { DownloadStatus } from '@colanode/client/types';
 import {
   generateId,
   IdType,
@@ -488,22 +494,63 @@ export class NodeService {
         return { deletedNode, createdMutation };
       });
 
-    if (deletedNode) {
-      debug(`Deleted node ${deletedNode.id} with type ${deletedNode.type}`);
-
-      eventBus.publish({
-        type: 'node.deleted',
-        accountId: this.workspace.accountId,
-        workspaceId: this.workspace.id,
-        node: mapNode(deletedNode),
-      });
-    } else {
-      debug(`Failed to delete node ${nodeId}`);
+    if (!deletedNode || !createdMutation) {
+      return;
     }
 
-    if (createdMutation) {
-      this.workspace.mutations.scheduleSync();
+    debug(`Deleted node ${deletedNode.id} with type ${deletedNode.type}`);
+
+    eventBus.publish({
+      type: 'node.deleted',
+      accountId: this.workspace.accountId,
+      workspaceId: this.workspace.id,
+      node: mapNode(deletedNode),
+    });
+
+    if (deletedNode.type === 'file') {
+      const deletedUpload = await this.workspace.database
+        .deleteFrom('uploads')
+        .where('file_id', '=', deletedNode.id)
+        .returningAll()
+        .executeTakeFirst();
+
+      if (deletedUpload) {
+        eventBus.publish({
+          type: 'upload.deleted',
+          accountId: this.workspace.accountId,
+          workspaceId: this.workspace.id,
+          upload: mapUpload(deletedUpload),
+        });
+      }
+
+      const updatedDownloads = await this.workspace.database
+        .updateTable('downloads')
+        .set({
+          status: DownloadStatus.Failed,
+          error_code: 'file_deleted',
+          error_message: 'File has been deleted',
+        })
+        .where('file_id', '=', deletedNode.id)
+        .where('status', 'in', [
+          DownloadStatus.Pending,
+          DownloadStatus.Downloading,
+        ])
+        .returningAll()
+        .execute();
+
+      if (updatedDownloads.length > 0) {
+        for (const updatedDownload of updatedDownloads) {
+          eventBus.publish({
+            type: 'download.updated',
+            accountId: this.workspace.accountId,
+            workspaceId: this.workspace.id,
+            download: mapDownload(updatedDownload),
+          });
+        }
+      }
     }
+
+    this.workspace.mutations.scheduleSync();
   }
 
   public async syncServerNodeUpdate(update: SyncNodeUpdateData) {
@@ -821,7 +868,48 @@ export class NodeService {
     await this.workspace.nodeCounters.checkCountersForDeletedNode(deletedNode);
 
     if (deletedNode.type === 'file') {
-      this.workspace.files.deleteFile(deletedNode);
+      await this.workspace.files.deleteFile(deletedNode);
+
+      const deletedUpload = await this.workspace.database
+        .deleteFrom('uploads')
+        .where('file_id', '=', deletedNode.id)
+        .returningAll()
+        .executeTakeFirst();
+
+      if (deletedUpload) {
+        eventBus.publish({
+          type: 'upload.deleted',
+          accountId: this.workspace.accountId,
+          workspaceId: this.workspace.id,
+          upload: mapUpload(deletedUpload),
+        });
+      }
+
+      const updatedDownloads = await this.workspace.database
+        .updateTable('downloads')
+        .set({
+          status: DownloadStatus.Failed,
+          error_code: 'file_deleted',
+          error_message: 'File has been deleted',
+        })
+        .where('file_id', '=', deletedNode.id)
+        .where('status', 'in', [
+          DownloadStatus.Pending,
+          DownloadStatus.Downloading,
+        ])
+        .returningAll()
+        .execute();
+
+      if (updatedDownloads.length > 0) {
+        for (const updatedDownload of updatedDownloads) {
+          eventBus.publish({
+            type: 'download.updated',
+            accountId: this.workspace.accountId,
+            workspaceId: this.workspace.id,
+            download: mapDownload(updatedDownload),
+          });
+        }
+      }
     }
 
     eventBus.publish({
diff --git a/packages/ui/src/components/workspaces/downloads/workspace-download-file.tsx b/packages/ui/src/components/workspaces/downloads/workspace-download-file.tsx
index 5c23e099..4eac9b1b 100644
--- a/packages/ui/src/components/workspaces/downloads/workspace-download-file.tsx
+++ b/packages/ui/src/components/workspaces/downloads/workspace-download-file.tsx
@@ -2,6 +2,7 @@ import { Folder } from 'lucide-react';
 
 import { LocalFileNode, Download } from '@colanode/client/types';
 import { formatBytes, timeAgo } from '@colanode/core';
+import { FileIcon } from '@colanode/ui/components/files/file-icon';
 import { FileThumbnail } from '@colanode/ui/components/files/file-thumbnail';
 import {
   Tooltip,
@@ -30,19 +31,22 @@ export const WorkspaceDownloadFile = ({
     nodeId: download.fileId,
   });
 
-  const file = fileQuery.data as LocalFileNode;
-  if (!file) {
-    return null;
-  }
+  const file = fileQuery.data as LocalFileNode | undefined;
 
   return (
     <div
       className="border rounded-lg p-4 bg-card hover:bg-accent/50 transition-colors flex items-center gap-6 cursor-pointer"
       onClick={() => {
-        layout.previewLeft(file.id, true);
+        if (file) {
+          layout.previewLeft(file.id, true);
+        }
       }}
     >
-      <FileThumbnail file={file} className="size-10 text-muted-foreground" />
+      {file ? (
+        <FileThumbnail file={file} className="size-10 text-muted-foreground" />
+      ) : (
+        <FileIcon mimeType={download.mimeType} className="size-10" />
+      )}
 
       <div className="flex-grow flex flex-col gap-2 justify-center items-start min-w-0">
         <p className="font-medium text-sm truncate">{download.name}</p>
diff --git a/packages/ui/src/components/workspaces/uploads/workspace-upload-file.tsx b/packages/ui/src/components/workspaces/uploads/workspace-upload-file.tsx
index 99289001..145c6de1 100644
--- a/packages/ui/src/components/workspaces/uploads/workspace-upload-file.tsx
+++ b/packages/ui/src/components/workspaces/uploads/workspace-upload-file.tsx
@@ -1,3 +1,5 @@
+import { BadgeAlert } from 'lucide-react';
+
 import { Upload, LocalFileNode } from '@colanode/client/types';
 import { formatBytes, timeAgo } from '@colanode/core';
 import { FileThumbnail } from '@colanode/ui/components/files/file-thumbnail';
@@ -24,7 +26,28 @@ export const WorkspaceUploadFile = ({ upload }: WorkspaceUploadFileProps) => {
   const file = fileQuery.data as LocalFileNode;
 
   if (!file) {
-    return null;
+    return (
+      <div className="border rounded-lg p-4 bg-card hover:bg-accent/50 transition-colors flex items-center gap-6 cursor-pointer">
+        <BadgeAlert className="size-10 text-muted-foreground" />
+
+        <div className="flex-grow flex flex-col gap-2 justify-center items-start min-w-0">
+          <p className="font-medium text-sm truncate w-full">
+            File not found or has been deleted
+          </p>
+          {upload.errorMessage && (
+            <p className="text-xs text-red-500">{upload.errorMessage}</p>
+          )}
+        </div>
+        <div className="flex items-center gap-2 flex-shrink-0">
+          <div className="w-10 flex items-center justify-center">
+            <WorkspaceUploadStatus
+              status={upload.status}
+              progress={upload.progress}
+            />
+          </div>
+        </div>
+      </div>
+    );
   }
 
   return (