diff --git a/apps/api/plane/settings/storage.py b/apps/api/plane/settings/storage.py
index e4a978bd2b1..97b74028465 100644
--- a/apps/api/plane/settings/storage.py
+++ b/apps/api/plane/settings/storage.py
@@ -63,9 +63,34 @@ def __init__(self, request=None):
             )
 
     def generate_presigned_post(self, object_name, file_type, file_size, expiration=None):
-        """Generate a presigned URL to upload an S3 object"""
         if expiration is None:
             expiration = self.signed_url_expiration
+            
+        # Check if we are using Cloudflare R2 (which doesn't support S3 Presigned POST nicely)
+        is_r2 = self.aws_s3_endpoint_url and "r2.cloudflarestorage" in self.aws_s3_endpoint_url
+        if is_r2:
+            try:
+                response_url = self.s3_client.generate_presigned_url(
+                    ClientMethod="put_object",
+                    Params={
+                        "Bucket": self.aws_storage_bucket_name,
+                        "Key": object_name,
+                        "ContentType": file_type,
+                        "ContentLength": file_size,
+                    },
+                    ExpiresIn=expiration,
+                )
+                return {
+                    "url": response_url,
+                    "fields": {
+                        "_method": "PUT",
+                        "Content-Type": file_type
+                    }
+                }
+            except ClientError as e:
+                print(f"Error generating presigned PUT URL for R2: {e}")
+                return None
+
         fields = {"Content-Type": file_type}
 
         conditions = [
diff --git a/apps/api/plane/tests/unit/settings/test_storage.py b/apps/api/plane/tests/unit/settings/test_storage.py
index 00856aeecb6..a6ce6a18cc7 100644
--- a/apps/api/plane/tests/unit/settings/test_storage.py
+++ b/apps/api/plane/tests/unit/settings/test_storage.py
@@ -116,6 +116,46 @@ def test_generate_presigned_post_uses_custom_expiration(self, mock_boto3):
         call_kwargs = mock_s3_client.generate_presigned_post.call_args[1]
         assert call_kwargs["ExpiresIn"] == 60
 
+    @patch.dict(
+        os.environ,
+        {
+            "AWS_ACCESS_KEY_ID": "test-key",
+            "AWS_SECRET_ACCESS_KEY": "test-secret",
+            "AWS_S3_BUCKET_NAME": "test-bucket",
+            "AWS_REGION": "us-east-1",
+            "AWS_S3_ENDPOINT_URL": "https://test.r2.cloudflarestorage.com",
+        },
+        clear=True,
+    )
+    @patch("plane.settings.storage.boto3")
+    def test_generate_presigned_post_with_cloudflare_r2(self, mock_boto3):
+        """Test that Cloudflare R2 endpoints generate presigned PUT URLs instead of POST"""
+        # Mock the boto3 client and its response
+        mock_s3_client = Mock()
+        mock_s3_client.generate_presigned_url.return_value = "https://r2-test-url.com"
+        mock_boto3.client.return_value = mock_s3_client
+
+        # Create S3Storage instance 
+        storage = S3Storage()
+
+        # Call generate_presigned_post
+        result = storage.generate_presigned_post("test-object", "image/png", 1024)
+
+        # Assert that the boto3 method generate_presigned_url was called with put_object
+        mock_s3_client.generate_presigned_url.assert_called_once()
+        call_kwargs = mock_s3_client.generate_presigned_url.call_args[1]
+        assert call_kwargs["ClientMethod"] == "put_object"
+        assert call_kwargs["Params"]["Bucket"] == "test-bucket"
+        assert call_kwargs["Params"]["Key"] == "test-object"
+        assert call_kwargs["Params"]["ContentType"] == "image/png"
+        assert call_kwargs["Params"]["ContentLength"] == 1024
+        
+        # Verify the returned object structure
+        assert result["url"] == "https://r2-test-url.com"
+        assert result["fields"]["_method"] == "PUT"
+        assert result["fields"]["Content-Type"] == "image/png"
+
+
     @patch.dict(
         os.environ,
         {
diff --git a/apps/web/core/services/file-upload.service.ts b/apps/web/core/services/file-upload.service.ts
index f8f49396799..32d791ec54f 100644
--- a/apps/web/core/services/file-upload.service.ts
+++ b/apps/web/core/services/file-upload.service.ts
@@ -5,7 +5,7 @@
  */
 
 import type { AxiosRequestConfig } from "axios";
-import axios from "axios";
+import { CancelToken, isCancel } from "axios";
 // services
 import { APIService } from "@/services/api.service";
 
@@ -21,10 +21,22 @@ export class FileUploadService extends APIService {
     data: FormData,
     uploadProgressHandler?: AxiosRequestConfig["onUploadProgress"]
   ): Promise<void> {
-    this.cancelSource = axios.CancelToken.source();
-    return this.post(url, data, {
+    this.cancelSource = CancelToken.source();
+
+    const isPut = data.has("_method") && data.get("_method") === "PUT";
+    const requestMethod = isPut ? "put" : "post";
+    // For PUT (Cloudflare R2), we send the raw File blob, not FormData. The helper appended it as 'file'
+    const requestData = isPut ? data.get("file") : data;
+
+    if (isPut && !(requestData instanceof Blob)) {
+      return Promise.reject(new Error("Invalid or missing file data for upload."));
+    }
+
+    const contentType = isPut ? data.get("Content-Type") || "application/octet-stream" : "multipart/form-data";
+
+    return this[requestMethod](url, requestData, {
       headers: {
-        "Content-Type": "multipart/form-data",
+        "Content-Type": contentType as string,
       },
       cancelToken: this.cancelSource.token,
       withCredentials: false,
@@ -32,7 +44,7 @@ export class FileUploadService extends APIService {
     })
       .then((response) => response?.data)
       .catch((error) => {
-        if (axios.isCancel(error)) {
+        if (isCancel(error)) {
           console.log(error.message);
         } else {
           throw error?.response?.data;