Automation triggering but "0 Files" showing despite multiple items in board

Hi everyone,

I’m having an issue with my Gmail + Extract AI automations. Here’s what’s happening:

Setup:

  • Using Gmail & Extract AI integration

  • Board: MIF Tenders with multiple groups (76 and 117 tender subject lines)

  • Automations configured:

    • “When a new item is created using email, save Text and Email and Files (Gmail Only)”

    • “When an email is received, create an item in Group Title”

Issue:

  • Automations show “Success” in Run History

  • Email converts to an update with file attachment :white_check_mark:

  • BUT the file does NOT upload to the Files column of that row :cross_mark:

  • Board shows “0 Files” at the bottom despite multiple items

The confusing part:

  • When my boss follows the exact same process, it works perfectly

  • I’ve replicated the methodology across multiple boards - none work for me

  • His files upload to the column, mine don’t

Questions:

  1. Could this be a permissions issue even though the automation runs successfully?

  2. Is there a specific Gmail or Monday.com permission needed for file uploads?

  3. Has anyone else experienced files saving to updates but not to the Files column?

if it’s working for your boss and not for you that it must be a permission issue or maybe your gmail is not properly connected

also today there is monday was down so that’s might also might be the issuse, my automations are not working so I guess we have to wait for things to be normal

The app is working the way its suppose to but it is not finishing the last 5% of the job. Which is putting the files from the update chat to the files column. I am not sure if its a permissions thing

I guess then support is the best option here you should reach out to them