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 ✅

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

• 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?