diff --git a/go/plumbing/operations/upload_deploy_function_parameters.go b/go/plumbing/operations/upload_deploy_function_parameters.go
index c35577ef..7ce86435 100644
--- a/go/plumbing/operations/upload_deploy_function_parameters.go
+++ b/go/plumbing/operations/upload_deploy_function_parameters.go
@@ -62,6 +62,8 @@ for the upload deploy function operation typically these are written to a http.R
 */
 type UploadDeployFunctionParams struct {
 
+	/*XNfRetryCount*/
+	XNfRetryCount *int64
 	/*DeployID*/
 	DeployID string
 	/*FileBody*/
@@ -111,6 +113,17 @@ func (o *UploadDeployFunctionParams) SetHTTPClient(client *http.Client) {
 	o.HTTPClient = client
 }
 
+// WithXNfRetryCount adds the xNfRetryCount to the upload deploy function params
+func (o *UploadDeployFunctionParams) WithXNfRetryCount(xNfRetryCount *int64) *UploadDeployFunctionParams {
+	o.SetXNfRetryCount(xNfRetryCount)
+	return o
+}
+
+// SetXNfRetryCount adds the xNfRetryCount to the upload deploy function params
+func (o *UploadDeployFunctionParams) SetXNfRetryCount(xNfRetryCount *int64) {
+	o.XNfRetryCount = xNfRetryCount
+}
+
 // WithDeployID adds the deployID to the upload deploy function params
 func (o *UploadDeployFunctionParams) WithDeployID(deployID string) *UploadDeployFunctionParams {
 	o.SetDeployID(deployID)
@@ -174,6 +187,15 @@ func (o *UploadDeployFunctionParams) WriteToRequest(r runtime.ClientRequest, reg
 	}
 	var res []error
 
+	if o.XNfRetryCount != nil {
+
+		// header param X-Nf-Retry-Count
+		if err := r.SetHeaderParam("X-Nf-Retry-Count", swag.FormatInt64(*o.XNfRetryCount)); err != nil {
+			return err
+		}
+
+	}
+
 	// path param deploy_id
 	if err := r.SetPathParam("deploy_id", o.DeployID); err != nil {
 		return err
diff --git a/go/porcelain/deploy.go b/go/porcelain/deploy.go
index 55ac090c..afe165b9 100644
--- a/go/porcelain/deploy.go
+++ b/go/porcelain/deploy.go
@@ -455,6 +455,8 @@ func (n *Netlify) uploadFile(ctx context.Context, d *models.Deploy, f *FileBundl
 		}
 	}
 
+	var retryCount int64 = 0
+
 	err := backoff.Retry(func() error {
 		sharedErr.mutex.Lock()
 
@@ -485,6 +487,11 @@ func (n *Netlify) uploadFile(ctx context.Context, d *models.Deploy, f *FileBundl
 			}
 		case functionUpload:
 			params := operations.NewUploadDeployFunctionParams().WithDeployID(d.ID).WithName(f.Name).WithFileBody(f).WithRuntime(&f.Runtime)
+
+			if retryCount > 0 {
+				params = params.WithXNfRetryCount(&retryCount)
+			}
+
 			if timeout != 0 {
 				params.SetTimeout(timeout)
 			}
@@ -504,6 +511,9 @@ func (n *Netlify) uploadFile(ctx context.Context, d *models.Deploy, f *FileBundl
 				sharedErr.mutex.Unlock()
 			}
 		}
+
+		retryCount++
+
 		return operationError
 	}, b)
 
diff --git a/go/porcelain/deploy_test.go b/go/porcelain/deploy_test.go
index c0034fc5..65265b84 100644
--- a/go/porcelain/deploy_test.go
+++ b/go/porcelain/deploy_test.go
@@ -262,6 +262,60 @@ func TestUploadFiles_Cancelation(t *testing.T) {
 	require.ErrorIs(t, err, gocontext.Canceled)
 }
 
+func TestUploadFunctions_RetryCountHeader(t *testing.T) {
+	attempts := 0
+	ctx, cancel := gocontext.WithCancel(gocontext.Background())
+	t.Cleanup(cancel)
+
+	server := httptest.NewServer(http.HandlerFunc(func(rw http.ResponseWriter, req *http.Request) {
+		defer func() {
+			attempts++
+		}()
+
+		rw.Header().Set("Content-Type", "application/json; charset=utf-8")
+
+		retryCount := req.Header.Get("X-Nf-Retry-Count")
+
+		if attempts == 0 {
+			require.Empty(t, retryCount)
+		} else {
+			require.Equal(t, fmt.Sprint(attempts), retryCount)
+		}
+
+		if attempts <= 2 {
+			rw.WriteHeader(http.StatusInternalServerError)
+
+			return
+		}
+
+		rw.WriteHeader(http.StatusOK)
+		rw.Write([]byte(`{ "name": "foo" }`))
+	}))
+	defer server.Close()
+
+	hu, _ := url.Parse(server.URL)
+	tr := apiClient.NewWithClient(hu.Host, "/api/v1", []string{"http"}, http.DefaultClient)
+	client := NewRetryable(tr, strfmt.Default, 1)
+	client.uploadLimit = 1
+	apiCtx := context.WithAuthInfo(ctx, apiClient.BearerToken("token"))
+
+	dir, err := ioutil.TempDir("", "deploy")
+	functionsPath := filepath.Join(dir, ".netlify", "functions")
+	os.MkdirAll(functionsPath, os.ModePerm)
+	require.NoError(t, err)
+	defer os.RemoveAll(dir)
+	require.NoError(t, ioutil.WriteFile(filepath.Join(functionsPath, "foo.js"), []byte("module.exports = () => {}"), 0644))
+
+	files, _, err := bundle(ctx, functionsPath, mockObserver{})
+	require.NoError(t, err)
+	d := &models.Deploy{}
+	for _, bundle := range files.Files {
+		d.RequiredFunctions = append(d.RequiredFunctions, bundle.Sum)
+	}
+
+	require.NoError(t, client.uploadFiles(apiCtx, d, files, nil, functionUpload, time.Minute))
+}
+
 func TestBundle(t *testing.T) {
 	functions, schedules, err := bundle(gocontext.Background(), "../internal/data", mockObserver{})
 
diff --git a/swagger.yml b/swagger.yml
index 6d629791..9328a84c 100644
--- a/swagger.yml
+++ b/swagger.yml
@@ -1248,6 +1248,7 @@ paths:
             type: string
             format: binary
           required: true
+        - $ref: '#/parameters/retryCount'
       responses:
         '200':
           description: OK
@@ -3378,6 +3379,10 @@ parameters:
     name: per_page
     required: false
     in: query
+  retryCount:
+    name: X-Nf-Retry-Count
+    type: integer
+    in: header    
 x-tagGroups:
   - name: OAuth
     tags: