Yes, with the "Mass File Upload" app, you can upload files with the help of a record ID by the use of a CSV file. This CSV file should contain all the record ID's. 

  • In the "Mass File Upload" tab - you have to go to the "CSV" sub-tab.
  • Create the CSV file that contains Record IDs and Actual File Name. The format should be the same as shown in the Below Image. Column A → IDs and Column B → Actual File Name. 
  • Click on the “Upload Files” button or Drag-Drop the selected files that you mentioned in the CSV file Column B. Click on “Done” as shown below.
  • Click on "Upload CSV File" which is under the “Upload File” section and choose a CSV file that you prepared.
  • CSV file can contain record Ids from several different objects, to which you want the file to be attached.
  • Once you upload the CSV file, you will receive a success message. (The CSV file will not be uploaded to your salesforce org, only the record IDs will be extracted from that file.)
  • Note: If there are more than 1999 record IDs present in the CSV file, each file will be uploaded/attached to the first 1999 record IDs present in the CSV file.
  • The data will be shown with the uploaded file name and each record name where the file is going to be uploaded as per the uploaded CSV file data, refer to the below image.
  • Now click on the “Save” button and the files will be uploaded to the records whose record IDs were mentioned in your CSV file.