diff --git a/src/app/pfapi/api/sync/providers/webdav/webdav-api.spec.ts b/src/app/pfapi/api/sync/providers/webdav/webdav-api.spec.ts
index 19f133cb36..9ea93e0462 100644
--- a/src/app/pfapi/api/sync/providers/webdav/webdav-api.spec.ts
+++ b/src/app/pfapi/api/sync/providers/webdav/webdav-api.spec.ts
@@ -213,6 +213,121 @@ describe('WebdavApi', () => {
 
       expect(result.rev).toBe('Wed, 15 Jan 2025 10:00:00 GMT');
     });
+
+    it('should add If-None-Match header when localRev is an ETag', async () => {
+      const mockResponse = {
+        status: 200,
+        headers: {
+          etag: '"newrev123"',
+        },
+        data: 'content',
+      };
+      mockHttpAdapter.request.and.returnValue(Promise.resolve(mockResponse));
+      mockXmlParser.validateResponseContent.and.stub();
+
+      await api.download({
+        path: '/test.txt',
+        localRev: 'abc123',
+      });
+
+      expect(mockHttpAdapter.request).toHaveBeenCalledWith(
+        jasmine.objectContaining({
+          headers: jasmine.objectContaining({
+            'If-None-Match': 'abc123',
+          }),
+        }),
+      );
+    });
+
+    it('should add If-Modified-Since header when localRev is a timestamp', async () => {
+      const mockResponse = {
+        status: 200,
+        headers: {
+          etag: '"newrev123"',
+        },
+        data: 'content',
+      };
+      mockHttpAdapter.request.and.returnValue(Promise.resolve(mockResponse));
+      mockXmlParser.validateResponseContent.and.stub();
+
+      const timestamp = '1642248000000'; // 2022-01-15T12:00:00.000Z
+
+      await api.download({
+        path: '/test.txt',
+        localRev: timestamp,
+      });
+
+      expect(mockHttpAdapter.request).toHaveBeenCalledWith(
+        jasmine.objectContaining({
+          headers: jasmine.objectContaining({
+            'If-Modified-Since': 'Sat, 15 Jan 2022 12:00:00 GMT',
+          }),
+        }),
+      );
+    });
+
+    it('should add If-Modified-Since header when localRev is already a date string', async () => {
+      const mockResponse = {
+        status: 200,
+        headers: {
+          etag: '"newrev123"',
+        },
+        data: 'content',
+      };
+      mockHttpAdapter.request.and.returnValue(Promise.resolve(mockResponse));
+      mockXmlParser.validateResponseContent.and.stub();
+
+      const dateString = 'Wed, 15 Jan 2025 10:00:00 GMT';
+
+      await api.download({
+        path: '/test.txt',
+        localRev: dateString,
+      });
+
+      expect(mockHttpAdapter.request).toHaveBeenCalledWith(
+        jasmine.objectContaining({
+          headers: jasmine.objectContaining({
+            'If-Modified-Since': dateString,
+          }),
+        }),
+      );
+    });
+
+    it('should handle 304 Not Modified response', async () => {
+      const mockResponse = {
+        status: 304,
+        headers: {},
+        data: '',
+      };
+      mockHttpAdapter.request.and.returnValue(Promise.resolve(mockResponse));
+
+      const result = await api.download({
+        path: '/test.txt',
+        localRev: 'abc123',
+      });
+
+      expect(result.notModified).toBe(true);
+      expect(result.rev).toBe('abc123');
+      expect(result.dataStr).toBe('');
+    });
+
+    it('should handle 304 response without localRev', async () => {
+      const mockResponse = {
+        status: 304,
+        headers: {},
+        data: '',
+      };
+      mockHttpAdapter.request.and.returnValue(Promise.resolve(mockResponse));
+
+      const result = await api.download({
+        path: '/test.txt',
+        localRev: null,
+      });
+
+      expect(result.notModified).toBe(true);
+      expect(result.rev).toBe('');
+      expect(result.dataStr).toBe('');
+    });
   });
 
   describe('upload', () => {
diff --git a/src/app/pfapi/api/sync/providers/webdav/webdav-api.ts b/src/app/pfapi/api/sync/providers/webdav/webdav-api.ts
index 0a5d05877e..daa5eac646 100644
--- a/src/app/pfapi/api/sync/providers/webdav/webdav-api.ts
+++ b/src/app/pfapi/api/sync/providers/webdav/webdav-api.ts
@@ -5,10 +5,10 @@ import { WebDavHttpAdapter, WebDavHttpResponse } from './webdav-http-adapter';
 import {
   HttpNotOkAPIError,
   InvalidDataSPError,
-  RemoteFileNotFoundAPIError,
   RemoteFileChangedUnexpectedly,
+  RemoteFileNotFoundAPIError,
 } from '../../../errors/errors';
-import { WebDavHttpStatus, WebDavHttpMethod, WebDavHttpHeader } from './webdav.const';
+import { WebDavHttpHeader, WebDavHttpMethod, WebDavHttpStatus } from './webdav.const';
 
 /* eslint-disable @typescript-eslint/naming-convention */
 
@@ -207,11 +207,13 @@ export class WebdavApi {
           );
         }
 
-        // If we get a 409 Conflict, it might be because parent directory doesn't exist
         if (
-          uploadError instanceof HttpNotOkAPIError &&
-          uploadError.response &&
-          uploadError.response.status === WebDavHttpStatus.CONFLICT
+          // if we get a 404 on upload this also indicates that the directory does not exist (for nextcloud)
+          uploadError instanceof RemoteFileNotFoundAPIError ||
+          (uploadError instanceof HttpNotOkAPIError &&
+            uploadError.response &&
+            // If we get a 409 Conflict, it might be because parent directory doesn't exist
+            uploadError.response.status === WebDavHttpStatus.CONFLICT)
         ) {
           PFLog.debug(
             `${WebdavApi.L}.upload() got 409, attempting to create parent directory`,